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<div class="vector-toc-text"> <span class="vector-toc-numb">2</span> <span>Polymers (peptides and oligonucleotides)</span> </div> </a> <button aria-controls="toc-Polymers_(peptides_and_oligonucleotides)-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Polymers (peptides and oligonucleotides) subsection</span> </button> <ul id="toc-Polymers_(peptides_and_oligonucleotides)-sublist" class="vector-toc-list"> <li id="toc-Combinatorial_split-mix_(split_and_pool)_synthesis" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Combinatorial_split-mix_(split_and_pool)_synthesis"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.1</span> <span>Combinatorial split-mix (split and pool) synthesis</span> </div> </a> <ul id="toc-Combinatorial_split-mix_(split_and_pool)_synthesis-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Small_molecules" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Small_molecules"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Small molecules</span> </div> </a> <ul id="toc-Small_molecules-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Deconvolution_and_screening" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Deconvolution_and_screening"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Deconvolution and screening</span> </div> </a> <button aria-controls="toc-Deconvolution_and_screening-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Deconvolution and screening subsection</span> </button> <ul id="toc-Deconvolution_and_screening-sublist" class="vector-toc-list"> <li id="toc-Combinatorial_libraries" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Combinatorial_libraries"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.1</span> <span>Combinatorial libraries</span> </div> </a> <ul id="toc-Combinatorial_libraries-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Deconvolution_of_libraries_cleaved_from_the_solid_support" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Deconvolution_of_libraries_cleaved_from_the_solid_support"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.2</span> <span>Deconvolution of libraries cleaved from the solid support</span> </div> </a> <ul id="toc-Deconvolution_of_libraries_cleaved_from_the_solid_support-sublist" class="vector-toc-list"> <li id="toc-Recursive_deconvolution" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Recursive_deconvolution"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.2.1</span> <span>Recursive deconvolution</span> </div> </a> <ul id="toc-Recursive_deconvolution-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Positional_scanning" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Positional_scanning"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.2.2</span> <span>Positional scanning</span> </div> </a> <ul id="toc-Positional_scanning-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Omission_libraries" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Omission_libraries"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.2.3</span> <span>Omission libraries</span> </div> </a> <ul id="toc-Omission_libraries-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Deconvolution_of_tethered_combinatorial_libraries" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Deconvolution_of_tethered_combinatorial_libraries"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.3</span> <span>Deconvolution of tethered combinatorial libraries</span> </div> </a> <ul id="toc-Deconvolution_of_tethered_combinatorial_libraries-sublist" class="vector-toc-list"> <li id="toc-Encoded_combinatorial_libraries" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Encoded_combinatorial_libraries"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.3.1</span> <span>Encoded combinatorial libraries</span> </div> </a> <ul id="toc-Encoded_combinatorial_libraries-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> </ul> </li> <li id="toc-Materials_science" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Materials_science"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Materials science</span> </div> </a> <ul id="toc-Materials_science-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Diversity-oriented_libraries" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Diversity-oriented_libraries"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>Diversity-oriented libraries</span> </div> </a> <ul id="toc-Diversity-oriented_libraries-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Patent_classification_subclass" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Patent_classification_subclass"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>Patent classification subclass</span> </div> </a> <ul id="toc-Patent_classification_subclass-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-See_also" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#See_also"> <div class="vector-toc-text"> <span class="vector-toc-numb">8</span> <span>See also</span> </div> </a> <ul id="toc-See_also-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-References" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> <span class="vector-toc-numb">9</span> <span>References</span> </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-External_links" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#External_links"> <div class="vector-toc-text"> <span class="vector-toc-numb">10</span> <span>External links</span> </div> </a> <ul id="toc-External_links-sublist" class="vector-toc-list"> </ul> </li> </ul> </div> </div> </nav> </div> </div> <div class="mw-content-container"> <main id="content" class="mw-body"> <header class="mw-body-header 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<h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">Combinatorial chemistry</span></h1> <div id="p-lang-btn" class="vector-dropdown mw-portlet mw-portlet-lang" > <input type="checkbox" id="p-lang-btn-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-p-lang-btn" class="vector-dropdown-checkbox mw-interlanguage-selector" aria-label="Go to an article in another language. Available in 20 languages" > <label id="p-lang-btn-label" for="p-lang-btn-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--action-progressive mw-portlet-lang-heading-20" aria-hidden="true" ><span class="vector-icon mw-ui-icon-language-progressive mw-ui-icon-wikimedia-language-progressive"></span> <span class="vector-dropdown-label-text">20 languages</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D9%83%D9%8A%D9%85%D9%8A%D8%A7%D8%A1_%D8%AA%D9%88%D8%A7%D9%81%D9%82%D9%8A%D8%A9" title="كيمياء توافقية – Arabic" lang="ar" hreflang="ar" data-title="كيمياء توافقية" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Qu%C3%ADmica_combinat%C3%B2ria" title="Química combinatòria – Catalan" lang="ca" hreflang="ca" data-title="Química combinatòria" data-language-autonym="Català" data-language-local-name="Catalan" class="interlanguage-link-target"><span>Català</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Kombinatorische_Chemie" title="Kombinatorische Chemie – German" lang="de" hreflang="de" data-title="Kombinatorische Chemie" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Qu%C3%ADmica_combinacional" title="Química combinacional – Spanish" lang="es" hreflang="es" data-title="Química combinacional" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D8%B4%DB%8C%D9%85%DB%8C_%D8%AA%D8%B1%DA%A9%DB%8C%D8%A8%DB%8C" title="شیمی ترکیبی – Persian" lang="fa" hreflang="fa" data-title="شیمی ترکیبی" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target"><span>فارسی</span></a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/Chimie_combinatoire" title="Chimie combinatoire – French" lang="fr" hreflang="fr" data-title="Chimie combinatoire" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-hy mw-list-item"><a href="https://hy.wikipedia.org/wiki/%D4%BF%D5%B8%D5%B4%D5%A2%D5%AB%D5%B6%D5%A1%D5%BF%D5%B8%D6%80%D5%A1%D5%B5%D5%AB%D5%B6_%D6%84%D5%AB%D5%B4%D5%AB%D5%A1" title="Կոմբինատորային քիմիա – Armenian" lang="hy" hreflang="hy" data-title="Կոմբինատորային քիմիա" data-language-autonym="Հայերեն" data-language-local-name="Armenian" class="interlanguage-link-target"><span>Հայերեն</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Kimia_kombinatorial" title="Kimia kombinatorial – Indonesian" lang="id" hreflang="id" data-title="Kimia kombinatorial" data-language-autonym="Bahasa Indonesia" data-language-local-name="Indonesian" class="interlanguage-link-target"><span>Bahasa Indonesia</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Chimica_combinatoria" title="Chimica combinatoria – Italian" lang="it" hreflang="it" data-title="Chimica combinatoria" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-he mw-list-item"><a href="https://he.wikipedia.org/wiki/%D7%9B%D7%99%D7%9E%D7%99%D7%94_%D7%A7%D7%95%D7%9E%D7%91%D7%99%D7%A0%D7%98%D7%95%D7%A8%D7%99%D7%AA" title="כימיה קומבינטורית – Hebrew" lang="he" hreflang="he" data-title="כימיה קומבינטורית" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target"><span>עברית</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Kombinatorikus_k%C3%A9mia" title="Kombinatorikus kémia – Hungarian" lang="hu" hreflang="hu" data-title="Kombinatorikus kémia" data-language-autonym="Magyar" data-language-local-name="Hungarian" class="interlanguage-link-target"><span>Magyar</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%82%B3%E3%83%B3%E3%83%93%E3%83%8A%E3%83%88%E3%83%AA%E3%82%A2%E3%83%AB%E3%82%B1%E3%83%9F%E3%82%B9%E3%83%88%E3%83%AA%E3%83%BC" title="コンビナトリアルケミストリー – Japanese" lang="ja" hreflang="ja" data-title="コンビナトリアルケミストリー" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%9A%D0%BE%D0%BC%D0%B1%D0%B8%D0%BD%D0%B0%D1%82%D0%BE%D1%80%D0%BD%D0%B0%D1%8F_%D1%85%D0%B8%D0%BC%D0%B8%D1%8F" title="Комбинаторная химия – Russian" lang="ru" hreflang="ru" data-title="Комбинаторная химия" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-simple mw-list-item"><a href="https://simple.wikipedia.org/wiki/Combinatorial_chemistry" title="Combinatorial chemistry – Simple English" lang="en-simple" hreflang="en-simple" data-title="Combinatorial chemistry" data-language-autonym="Simple English" data-language-local-name="Simple English" class="interlanguage-link-target"><span>Simple English</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Kombinatorna_hemija" title="Kombinatorna hemija – Serbian" lang="sr" hreflang="sr" data-title="Kombinatorna hemija" data-language-autonym="Српски / srpski" data-language-local-name="Serbian" class="interlanguage-link-target"><span>Српски / srpski</span></a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Kombinatoriaalinen_kemia" title="Kombinatoriaalinen kemia – Finnish" lang="fi" hreflang="fi" data-title="Kombinatoriaalinen kemia" data-language-autonym="Suomi" data-language-local-name="Finnish" class="interlanguage-link-target"><span>Suomi</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%9A%D0%BE%D0%BC%D0%B1%D1%96%D0%BD%D0%B0%D1%82%D0%BE%D1%80%D0%BD%D0%B0_%D1%85%D1%96%D0%BC%D1%96%D1%8F" title="Комбінаторна хімія – Ukrainian" lang="uk" hreflang="uk" data-title="Комбінаторна хімія" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link interwiki-vi mw-list-item"><a href="https://vi.wikipedia.org/wiki/H%C3%B3a_h%E1%BB%8Dc_t%E1%BB%95_h%E1%BB%A3p" title="Hóa học tổ hợp – Vietnamese" lang="vi" hreflang="vi" data-title="Hóa học tổ hợp" data-language-autonym="Tiếng Việt" data-language-local-name="Vietnamese" class="interlanguage-link-target"><span>Tiếng Việt</span></a></li><li class="interlanguage-link interwiki-zh-yue mw-list-item"><a href="https://zh-yue.wikipedia.org/wiki/%E7%B5%84%E5%90%88%E5%8C%96%E5%AD%B8" title="組合化學 – Cantonese" lang="yue" hreflang="yue" data-title="組合化學" data-language-autonym="粵語" data-language-local-name="Cantonese" class="interlanguage-link-target"><span>粵語</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E7%BB%84%E5%90%88%E5%8C%96%E5%AD%A6" title="组合化学 – Chinese" lang="zh" hreflang="zh" data-title="组合化学" data-language-autonym="中文" data-language-local-name="Chinese" class="interlanguage-link-target"><span>中文</span></a></li> </ul> <div class="after-portlet after-portlet-lang"><span class="wb-langlinks-edit wb-langlinks-link"><a href="https://www.wikidata.org/wiki/Special:EntityPage/Q899212#sitelinks-wikipedia" title="Edit interlanguage links" class="wbc-editpage">Edit links</a></span></div> </div> </div> </div> </header> <div class="vector-page-toolbar"> <div class="vector-page-toolbar-container"> <div id="left-navigation"> <nav aria-label="Namespaces"> <div id="p-associated-pages" class="vector-menu vector-menu-tabs mw-portlet mw-portlet-associated-pages" > <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="ca-nstab-main" class="selected vector-tab-noicon mw-list-item"><a href="/wiki/Combinatorial_chemistry" title="View the content page [c]" accesskey="c"><span>Article</span></a></li><li id="ca-talk" 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</div> </div> </div> </nav> </div> </div> </div> <div class="vector-column-end"> <div class="vector-sticky-pinned-container"> <nav class="vector-page-tools-landmark" aria-label="Page tools"> <div id="vector-page-tools-pinned-container" class="vector-pinned-container"> </div> </nav> <nav class="vector-appearance-landmark" aria-label="Appearance"> <div id="vector-appearance-pinned-container" class="vector-pinned-container"> <div id="vector-appearance" class="vector-appearance vector-pinnable-element"> <div class="vector-pinnable-header vector-appearance-pinnable-header vector-pinnable-header-pinned" data-feature-name="appearance-pinned" data-pinnable-element-id="vector-appearance" data-pinned-container-id="vector-appearance-pinned-container" data-unpinned-container-id="vector-appearance-unpinned-container" > <div class="vector-pinnable-header-label">Appearance</div> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-pin-button" data-event-name="pinnable-header.vector-appearance.pin">move to sidebar</button> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-unpin-button" data-event-name="pinnable-header.vector-appearance.unpin">hide</button> </div> </div> </div> </nav> </div> </div> <div id="bodyContent" class="vector-body" aria-labelledby="firstHeading" data-mw-ve-target-container> <div class="vector-body-before-content"> <div class="mw-indicators"> </div> <div id="siteSub" class="noprint">From Wikipedia, the free encyclopedia</div> </div> <div id="contentSub"><div id="mw-content-subtitle"></div></div> <div id="mw-content-text" class="mw-body-content"><div class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Compound library-based chemical synthesis method</div> <p><b>Combinatorial chemistry</b> comprises <a href="/wiki/Chemical_synthesis" title="Chemical synthesis">chemical synthetic methods</a> that make it possible to prepare a large number (tens to thousands or even millions) of compounds in a single process. These <a href="/wiki/Compound_library" class="mw-redirect" title="Compound library">compound libraries</a> can be made as mixtures, sets of individual compounds or chemical structures generated by computer software.<sup id="cite_ref-1" class="reference"><a href="#cite_note-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> Combinatorial chemistry can be used for the synthesis of small molecules and for peptides. </p><p>Strategies that allow identification of useful components of the libraries are also part of combinatorial chemistry. The methods used in combinatorial chemistry are applied outside chemistry, too. </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Introduction">Introduction</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Combinatorial_chemistry&action=edit&section=1" title="Edit section: Introduction"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The basic principle of combinatorial chemistry is to prepare <a href="/wiki/Compound_library" class="mw-redirect" title="Compound library">libraries</a> of a very large number of compounds and identify those which are useful as potential drugs or agrochemicals. This relies on <a href="/wiki/High-throughput_screening" title="High-throughput screening">high-throughput screening</a> which is capable of assessing the output at sufficient scale.<sup id="cite_ref-Warr1997_2-0" class="reference"><a href="#cite_note-Warr1997-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </p><p>Although combinatorial chemistry has only really been taken up by industry since the 1990s,<sup id="cite_ref-3" class="reference"><a href="#cite_note-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> its roots can be seen as far back as the 1960s when a researcher at <a href="/wiki/Rockefeller_University" title="Rockefeller University">Rockefeller University</a>, <a href="/wiki/Bruce_Merrifield" class="mw-redirect" title="Bruce Merrifield">Bruce Merrifield</a>, started investigating the <a href="/wiki/Solid-phase_synthesis" title="Solid-phase synthesis">solid-phase synthesis</a> of <a href="/wiki/Peptide" title="Peptide">peptides</a>. Synthesis of peptides in a <a href="/wiki/Combinatorial" class="mw-redirect" title="Combinatorial">combinatorial</a> fashion quickly leads to large numbers of molecules. Using the twenty natural <a href="/wiki/Amino_acids" class="mw-redirect" title="Amino acids">amino acids</a>, for example, in a <a href="/wiki/Tripeptide" title="Tripeptide">tripeptide</a> creates 8,000 (20<sup>3</sup>) possibilities. Solid-phase methods for small molecules were later introduced and Furka devised a "split and mix" approach<sup id="cite_ref-Warr1997_2-1" class="reference"><a href="#cite_note-Warr1997-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Furka_4-0" class="reference"><a href="#cite_note-Furka-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </p><p>In its modern form, combinatorial chemistry has probably had its biggest impact in the <a href="/wiki/Pharmaceutical" class="mw-redirect" title="Pharmaceutical">pharmaceutical</a> industry.<sup id="cite_ref-5" class="reference"><a href="#cite_note-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> Researchers attempting to optimize the activity profile of a compound create a 'library' of many different but related compounds.<sup id="cite_ref-6" class="reference"><a href="#cite_note-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-7" class="reference"><a href="#cite_note-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> Advances in <a href="/wiki/Robotics" title="Robotics">robotics</a> have led to an industrial approach to combinatorial synthesis, enabling companies to routinely produce over 100,000 new and unique compounds per year.<sup id="cite_ref-8" class="reference"><a href="#cite_note-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> </p><p>In order to handle the vast number of structural possibilities, researchers often create a 'virtual library', a computational enumeration of all possible structures of a given <a href="/wiki/Pharmacophore" title="Pharmacophore">pharmacophore</a> with all available <a href="/wiki/Reactant" class="mw-redirect" title="Reactant">reactants</a>.<sup id="cite_ref-9" class="reference"><a href="#cite_note-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> Such a library can consist of thousands to millions of 'virtual' compounds. The researcher will select a subset of the 'virtual library' for actual synthesis, based upon various calculations and criteria (see <a href="/wiki/ADME" title="ADME">ADME</a>, <a href="/wiki/Computational_chemistry" title="Computational chemistry">computational chemistry</a>, and <a href="/wiki/Quantitative_structure%E2%80%93activity_relationship" title="Quantitative structure–activity relationship">QSAR</a>). </p> <div class="mw-heading mw-heading2"><h2 id="Polymers_(peptides_and_oligonucleotides)"><span id="Polymers_.28peptides_and_oligonucleotides.29"></span>Polymers (peptides and oligonucleotides)</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Combinatorial_chemistry&action=edit&section=2" title="Edit section: Polymers (peptides and oligonucleotides)"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Cycle_3,4_v%C3%A1gott.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/e/ee/Cycle_3%2C4_v%C3%A1gott.jpg/250px-Cycle_3%2C4_v%C3%A1gott.jpg" decoding="async" width="250" height="278" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/e/ee/Cycle_3%2C4_v%C3%A1gott.jpg 1.5x" data-file-width="262" data-file-height="291" /></a><figcaption> Peptides forming in cycles 3 and 4</figcaption></figure> <div class="mw-heading mw-heading3"><h3 id="Combinatorial_split-mix_(split_and_pool)_synthesis"><span id="Combinatorial_split-mix_.28split_and_pool.29_synthesis"></span>Combinatorial split-mix (split and pool) synthesis</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Combinatorial_chemistry&action=edit&section=3" title="Edit section: Combinatorial split-mix (split and pool) synthesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1236090951">.mw-parser-output .hatnote{font-style:italic}.mw-parser-output div.hatnote{padding-left:1.6em;margin-bottom:0.5em}.mw-parser-output .hatnote i{font-style:normal}.mw-parser-output .hatnote+link+.hatnote{margin-top:-0.5em}@media print{body.ns-0 .mw-parser-output .hatnote{display:none!important}}</style><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Split_and_pool_synthesis" title="Split and pool synthesis">Split and pool synthesis</a></div> <p>Combinatorial split-mix (split and pool) synthesis <sup id="cite_ref-10" class="reference"><a href="#cite_note-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-11" class="reference"><a href="#cite_note-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> is based on the <a href="/wiki/Solid-phase_synthesis" title="Solid-phase synthesis">solid-phase synthesis</a> developed by <a href="/wiki/Robert_Bruce_Merrifield" title="Robert Bruce Merrifield">Merrifield</a>.<sup id="cite_ref-12" class="reference"><a href="#cite_note-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> If a combinatorial peptide library is synthesized using 20 <a href="/wiki/Amino_acid" title="Amino acid">amino acids</a> (or other kinds of building blocks) the bead form solid support is divided into 20 equal portions. This is followed by coupling a different amino acid to each portion. The third step is the mixing of all portions. These three steps comprise a cycle. Elongation of the peptide chains can be realized by simply repeating the steps of the cycle. </p> <figure class="mw-halign-left" typeof="mw:File/Thumb"><a href="/wiki/File:Split-mix_synthesis.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/0/0f/Split-mix_synthesis.jpg/200px-Split-mix_synthesis.jpg" decoding="async" width="200" height="286" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/0/0f/Split-mix_synthesis.jpg 1.5x" data-file-width="250" data-file-height="358" /></a><figcaption>Flow diagram of the split-mix combinatorial synthesis</figcaption></figure> <p>The procedure is illustrated by the synthesis of a <a href="/wiki/Dipeptide" title="Dipeptide">dipeptide</a> library using the same three amino acids as building blocks in both cycles. Each component of this library contains two amino acids arranged in different orders. The amino acids used in couplings are represented by yellow, blue and red circles in the figure. Divergent arrows show dividing solid support resin (green circles) into equal portions, vertical arrows mean coupling and convergent arrows represent mixing and homogenizing the portions of the support. </p><p>The figure shows that in the two synthetic cycles 9 dipeptides are formed. In the third and fourth cycles, 27 tripeptides and 81 tetrapeptides would form, respectively. </p><p>The "split-mix synthesis" has several outstanding features: </p> <ul><li>It is highly efficient. As the figure demonstrates the number of peptides formed in the synthetic process (3, 9, 27, 81) increases exponentially with the number of executed cycles. Using 20 amino acids in each synthetic cycle the number of formed peptides are: 400, 8,000, 160,000 and 3,200,000, respectively. This means that the number of peptides increases exponentially with the number of the executed cycles.</li> <li>All peptide sequences are formed in the process that can be deduced by a combination of the amino acids used in the cycles.</li> <li>Portioning of the support into equal samples assures formation of the components of the library in nearly equal molar quantities.</li> <li>Only a single peptide forms on each bead of the support. This is the consequence of using only one amino acid in the coupling steps. It is completely unknown, however, which is the peptide that occupies a selected bead.</li> <li>The split-mix method can be used for the synthesis of organic or any other kind of library that can be prepared from its building blocks in a stepwise process.</li></ul> <p>In 1990 three groups described methods for preparing peptide libraries by biological methods<sup id="cite_ref-13" class="reference"><a href="#cite_note-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-14" class="reference"><a href="#cite_note-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-15" class="reference"><a href="#cite_note-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> and one year later Fodor et al. published a remarkable method for synthesis of peptide arrays on small glass slides.<sup id="cite_ref-16" class="reference"><a href="#cite_note-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> </p><p>A "parallel synthesis" method was developed by Mario Geysen and his colleagues for preparation of peptide arrays.<sup id="cite_ref-17" class="reference"><a href="#cite_note-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> They synthesized 96 peptides on plastic rods (pins) coated at their ends with the solid support. The pins were immersed into the solution of reagents placed in the wells of a <a href="/wiki/Microtiter_plate" class="mw-redirect" title="Microtiter plate">microtiter plate</a>. The method is widely applied particularly by using automatic parallel synthesizers. Although the parallel method is much slower than the real combinatorial one, its advantage is that it is exactly known which peptide or other compound forms on each pin. </p><p>Further procedures were developed to combine the advantages of both split-mix and parallel synthesis. In the method described by two groups<sup id="cite_ref-18" class="reference"><a href="#cite_note-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-19" class="reference"><a href="#cite_note-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> the solid support was enclosed into permeable plastic capsules together with a radiofrequency tag that carried the code of the compound to be formed in the capsule. The procedure was carried out similar to the split-mix method. In the split step, however, the capsules were distributed among the reaction vessels according to the codes read from the radiofrequency tags of the capsules. </p><p>A different method for the same purpose was developed by Furka et al.<sup id="cite_ref-20" class="reference"><a href="#cite_note-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> is named "string synthesis". In this method, the capsules carried no code. They are strung like the pearls in a necklace and placed into the reaction vessels in stringed form. The identity of the capsules, as well as their contents, are stored by their position occupied on the strings. After each coupling step, the capsules are redistributed among new strings according to definite rules. </p> <div class="mw-heading mw-heading2"><h2 id="Small_molecules">Small molecules</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Combinatorial_chemistry&action=edit&section=4" title="Edit section: Small molecules"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1251242444">.mw-parser-output .ambox{border:1px solid #a2a9b1;border-left:10px solid #36c;background-color:#fbfbfb;box-sizing:border-box}.mw-parser-output .ambox+link+.ambox,.mw-parser-output .ambox+link+style+.ambox,.mw-parser-output .ambox+link+link+.ambox,.mw-parser-output .ambox+.mw-empty-elt+link+.ambox,.mw-parser-output .ambox+.mw-empty-elt+link+style+.ambox,.mw-parser-output .ambox+.mw-empty-elt+link+link+.ambox{margin-top:-1px}html body.mediawiki .mw-parser-output .ambox.mbox-small-left{margin:4px 1em 4px 0;overflow:hidden;width:238px;border-collapse:collapse;font-size:88%;line-height:1.25em}.mw-parser-output .ambox-speedy{border-left:10px solid #b32424;background-color:#fee7e6}.mw-parser-output .ambox-delete{border-left:10px solid #b32424}.mw-parser-output .ambox-content{border-left:10px solid #f28500}.mw-parser-output .ambox-style{border-left:10px solid #fc3}.mw-parser-output .ambox-move{border-left:10px solid #9932cc}.mw-parser-output .ambox-protection{border-left:10px solid #a2a9b1}.mw-parser-output .ambox .mbox-text{border:none;padding:0.25em 0.5em;width:100%}.mw-parser-output .ambox .mbox-image{border:none;padding:2px 0 2px 0.5em;text-align:center}.mw-parser-output .ambox .mbox-imageright{border:none;padding:2px 0.5em 2px 0;text-align:center}.mw-parser-output .ambox .mbox-empty-cell{border:none;padding:0;width:1px}.mw-parser-output .ambox .mbox-image-div{width:52px}@media(min-width:720px){.mw-parser-output .ambox{margin:0 10%}}@media print{body.ns-0 .mw-parser-output .ambox{display:none!important}}</style><table class="box-Review plainlinks metadata ambox ambox-style" role="presentation"><tbody><tr><td class="mbox-image"><div class="mbox-image-div"><span typeof="mw:File"><span><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/f/f2/Edit-clear.svg/40px-Edit-clear.svg.png" decoding="async" width="40" height="40" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/f2/Edit-clear.svg/60px-Edit-clear.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/f2/Edit-clear.svg/80px-Edit-clear.svg.png 2x" data-file-width="48" data-file-height="48" /></span></span></div></td><td class="mbox-text"><div class="mbox-text-span">This section <b>is written like a <a href="/wiki/Wikipedia:What_Wikipedia_is_not#SOAPBOX" title="Wikipedia:What Wikipedia is not">review</a></b>.<span class="hide-when-compact"> Please help <a class="external text" href="https://en.wikipedia.org/w/index.php?title=Combinatorial_chemistry&action=edit">improve this article</a> by rewriting it in <a href="/wiki/Wikipedia:Encyclopedic_style" class="mw-redirect" title="Wikipedia:Encyclopedic style">encyclopedic style</a>.</span> <span class="date-container"><i>(<span class="date">July 2018</span>)</i></span></div></td></tr></tbody></table> <p>In the drug discovery process, the synthesis and biological evaluation of <a href="/wiki/Small_molecule" title="Small molecule">small molecules</a> of interest have typically been a long and laborious process. Combinatorial chemistry has emerged in recent decades as an approach to quickly and efficiently synthesize large numbers of potential small molecule drug candidates. In a typical synthesis, only a single target molecule is produced at the end of a synthetic scheme, with each step in a synthesis producing only a single product. In a <a href="/wiki/Combinatorial_synthesis" class="mw-redirect" title="Combinatorial synthesis">combinatorial synthesis</a>, when using only single starting material, it is possible to synthesize a large library of molecules using identical reaction conditions that can then be screened for their <a href="/wiki/Biological_activity" title="Biological activity">biological activity</a>. This pool of products is then split into three equal portions containing each of the three products, and then each of the three individual pools is then reacted with another unit of reagent B, C, or D, producing 9 unique compounds from the previous 3. This process is then repeated until the desired number of building blocks is added, generating many compounds. When synthesizing a library of compounds by a multi-step synthesis, efficient reaction methods must be employed, and if traditional purification methods are used after each reaction step, yields and efficiency will suffer. </p><p>Solid-phase synthesis offers potential solutions to obviate the need for typical quenching and purification steps often used in synthetic chemistry. In general, a starting molecule is adhered to a solid support (typically an <a href="/w/index.php?title=Insoluble_polymer&action=edit&redlink=1" class="new" title="Insoluble polymer (page does not exist)">insoluble polymer</a>), then additional reactions are performed, and the final product is purified and then cleaved from the solid support. Since the molecules of interest are attached to a solid support, it is possible to reduce the purification after each reaction to a single filtration/wash step, eliminating the need for tedious liquid-liquid extraction and solvent evaporation steps that most synthetic chemistry involves. Furthermore, by using heterogeneous reactants, excess reagents can be used to drive sluggish reactions to completion, which can further improve yields. Excess reagents can simply be washed away without the need for additional purification steps such as <a href="/wiki/Chromatography" title="Chromatography">chromatography</a>. </p> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Use_of_a_solid-supported_polyamine_that_is_used_to_scavenge_excess_reagent.tif" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/d/d6/Use_of_a_solid-supported_polyamine_that_is_used_to_scavenge_excess_reagent.tif/lossless-page1-220px-Use_of_a_solid-supported_polyamine_that_is_used_to_scavenge_excess_reagent.tif.png" decoding="async" width="220" height="101" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/d6/Use_of_a_solid-supported_polyamine_that_is_used_to_scavenge_excess_reagent.tif/lossless-page1-330px-Use_of_a_solid-supported_polyamine_that_is_used_to_scavenge_excess_reagent.tif.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/d6/Use_of_a_solid-supported_polyamine_that_is_used_to_scavenge_excess_reagent.tif/lossless-page1-440px-Use_of_a_solid-supported_polyamine_that_is_used_to_scavenge_excess_reagent.tif.png 2x" data-file-width="1823" data-file-height="840" /></a><figcaption>Use of a solid-supported polyamine to scavenge excess reagent</figcaption></figure> <p>Over the years, a variety of methods have been developed to refine the use of solid-phase organic synthesis in combinatorial chemistry, including efforts to increase the ease of synthesis and purification, as well as non-traditional methods to characterize intermediate products. Although the majority of the examples described here will employ heterogeneous reaction media in every reaction step, Booth and Hodges provide an early example of using solid-supported reagents only during the purification step of traditional solution-phase syntheses.<sup id="cite_ref-21" class="reference"><a href="#cite_note-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> In their view, solution-phase chemistry offers the advantages of avoiding attachment and cleavage reactions necessary to anchor and remove molecules to resins as well as eliminating the need to recreate solid-phase analogues of established solution-phase reactions. </p><p>The single purification step at the end of a synthesis allows one or more impurities to be removed, assuming the chemical structure of the offending impurity is known. While the use of solid-supported reagents greatly simplifies the synthesis of compounds, many combinatorial syntheses require multiple steps, each of which still requires some form of purification. Armstrong, et al. describe a one-pot method for generating combinatorial libraries, called multiple-component condensations (MCCs).<sup id="cite_ref-22" class="reference"><a href="#cite_note-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> In this scheme, three or more reagents react such that each reagent is incorporated into the final product in a single step, eliminating the need for a multi-step synthesis that involves many purification steps. In MCCs, there is no deconvolution required to determine which compounds are biologically active because each synthesis in an array has only a single product, thus the identity of the compound should be unequivocally known. </p> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Example_of_a_solid-phase_supported_dye_indicating_ligand_binding.tif" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/1/12/Example_of_a_solid-phase_supported_dye_indicating_ligand_binding.tif/lossless-page1-220px-Example_of_a_solid-phase_supported_dye_indicating_ligand_binding.tif.png" decoding="async" width="220" height="64" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/12/Example_of_a_solid-phase_supported_dye_indicating_ligand_binding.tif/lossless-page1-330px-Example_of_a_solid-phase_supported_dye_indicating_ligand_binding.tif.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/12/Example_of_a_solid-phase_supported_dye_indicating_ligand_binding.tif/lossless-page1-440px-Example_of_a_solid-phase_supported_dye_indicating_ligand_binding.tif.png 2x" data-file-width="563" data-file-height="163" /></a><figcaption>Example of a solid-phase supported dye to signal ligand binding</figcaption></figure> <p>In another array synthesis, Still generated a large library of <a href="/wiki/Oligopeptides" class="mw-redirect" title="Oligopeptides">oligopeptides</a> by split synthesis.<sup id="cite_ref-23" class="reference"><a href="#cite_note-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup> The drawback to making many thousands of compounds is that it is difficult to determine the structure of the formed compounds. Their solution is to use molecular tags, where a tiny amount (1 pmol/bead) of a dye is attached to the beads, and the identity of a certain bead can be determined by analyzing which tags are present on the bead. Despite how easy attaching tags makes identification of receptors, it would be quite impossible to individually screen each compound for its receptor binding ability, so a dye was attached to each receptor, such that only those receptors that bind to their substrate produce a color change. </p><p>When many reactions need to be run in an array (such as the 96 reactions described in one of Armstrong's MCC arrays), some of the more tedious aspects of synthesis can be automated to improve efficiency. This work, the "<a href="/w/index.php?title=DIVERSOMER_method&action=edit&redlink=1" class="new" title="DIVERSOMER method (page does not exist)">DIVERSOMER method</a>" was pioneered at <a href="/wiki/Parke-Davis" title="Parke-Davis">Parke-Davis</a> in the early 1990s to run up to 40 chemical reactions in parallel. These efforts led to the first commercially available equipment for combinatorial chemistry (Diversomer synthesizer which was sold by Chemglass) and the first use of liquid handling robotics within a chemistry labortory.<sup id="cite_ref-24" class="reference"><a href="#cite_note-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-25" class="reference"><a href="#cite_note-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> This method uses a device that automates the resin loading and wash cycles, as well as the reaction cycle monitoring and purification, and demonstrates the feasibility of their method and apparatus by using it to synthesize a variety of molecule classes, such as <a href="/wiki/Hydantoins" class="mw-redirect" title="Hydantoins">hydantoins</a> and <a href="/wiki/Benzodiazepines" class="mw-redirect" title="Benzodiazepines">benzodiazepines</a>, running 8 or 40 individual reactions in parallel. This and several other pioneering efforts in combinatorial chemistry were featured as "classical" papers in the field in 1999.<sup id="cite_ref-26" class="reference"><a href="#cite_note-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup> </p><p>Oftentimes, it is not possible to use expensive equipment, and Schwabacher, et al. describe a simple method of combining parallel synthesis of library members and evaluation of entire libraries of compounds.<sup id="cite_ref-27" class="reference"><a href="#cite_note-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup> In their method, a thread that is partitioned into different regions is wrapped around a cylinder, where a different reagent is then coupled to each region which bears only a single species. The thread is then re-divided and wrapped around a cylinder of a different size, and this process is then repeated. The beauty of this method is that the identity of each product can be known simply by its location along the thread, and the corresponding biological activity is identified by <a href="/wiki/Fourier_transformation" class="mw-redirect" title="Fourier transformation">Fourier transformation</a> of fluorescence signals. </p> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Using_a_traceless_linker_as_described_by_Ellman.tif" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/9e/Using_a_traceless_linker_as_described_by_Ellman.tif/lossless-page1-220px-Using_a_traceless_linker_as_described_by_Ellman.tif.png" decoding="async" width="220" height="56" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/9e/Using_a_traceless_linker_as_described_by_Ellman.tif/lossless-page1-330px-Using_a_traceless_linker_as_described_by_Ellman.tif.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/9e/Using_a_traceless_linker_as_described_by_Ellman.tif/lossless-page1-440px-Using_a_traceless_linker_as_described_by_Ellman.tif.png 2x" data-file-width="1595" data-file-height="403" /></a><figcaption>Use of a traceless linker</figcaption></figure> <p>In most of the syntheses described here, it is necessary to attach and remove the starting reagent to/from a solid support. This can lead to the generation of a hydroxyl group, which can potentially affect the biological activity of a target compound. Ellman uses solid phase supports in a multi-step synthesis scheme to obtain 192 individual 1,4-benzodiazepine derivatives, which are well-known therapeutic agents.<sup id="cite_ref-28" class="reference"><a href="#cite_note-28"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup> To eliminate the possibility of potential hydroxyl group interference, a novel method using silyl-aryl chemistry is used to link the molecules to the solid support which cleaves from the support and leaves no trace of the linker. </p> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Products_that_can_be_synthesized_from_imines.tif" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/9e/Products_that_can_be_synthesized_from_imines.tif/lossless-page1-220px-Products_that_can_be_synthesized_from_imines.tif.png" decoding="async" width="220" height="86" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/9e/Products_that_can_be_synthesized_from_imines.tif/lossless-page1-330px-Products_that_can_be_synthesized_from_imines.tif.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/9e/Products_that_can_be_synthesized_from_imines.tif/lossless-page1-440px-Products_that_can_be_synthesized_from_imines.tif.png 2x" data-file-width="1462" data-file-height="570" /></a><figcaption>Compounds that can be synthesized from solid-phase bound imines</figcaption></figure> <p>When anchoring a molecule to a solid support, intermediates cannot be isolated from one another without cleaving the molecule from the resin. Since many of the traditional characterization techniques used to track reaction progress and confirm product structure are solution-based, different techniques must be used. Gel-phase <sup>13</sup>C NMR spectroscopy, MALDI mass spectrometry, and IR spectroscopy have been used to confirm structure and monitor the progress of solid-phase reactions.<sup id="cite_ref-accounts_29-0" class="reference"><a href="#cite_note-accounts-29"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup> Gordon et al., describe several case studies that utilize imines and peptidyl phosphonates to generate combinatorial libraries of small molecules.<sup id="cite_ref-accounts_29-1" class="reference"><a href="#cite_note-accounts-29"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup> To generate the imine library, an amino acid tethered to a resin is reacted in the presence of an aldehyde. The authors demonstrate the use of fast <sup>13</sup>C gel phase NMR spectroscopy and magic angle spinning 1 H NMR spectroscopy to monitor the progress of reactions and showed that most imines could be formed in as little as 10 minutes at room temperature when trimethyl orthoformate was used as the solvent. The formed imines were then derivatized to generate 4-thiazolidinones, B-lactams, and pyrrolidines. </p><p>The use of solid-phase supports greatly simplifies the synthesis of large combinatorial libraries of compounds. This is done by anchoring a starting material to a solid support and then running subsequent reactions until a sufficiently large library is built, after which the products are cleaved from the support. The use of solid-phase purification has also been demonstrated for use in solution-phase synthesis schemes in conjunction with standard liquid-liquid extraction purification techniques. </p> <div class="mw-heading mw-heading2"><h2 id="Deconvolution_and_screening">Deconvolution and screening</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Combinatorial_chemistry&action=edit&section=5" title="Edit section: Deconvolution and screening"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Combinatorial_libraries">Combinatorial libraries</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Combinatorial_chemistry&action=edit&section=6" title="Edit section: Combinatorial libraries"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Combinatorial libraries are special multi-component mixtures of small-molecule chemical compounds that are synthesized in a single stepwise process. They differ from collection of individual compounds as well as from series of compounds prepared by parallel synthesis. It is an important feature that mixtures are used in their synthesis. The use of mixtures ensures the very high efficiency of the process. Both reactants can be mixtures and in this case the procedure would be even more efficient. For practical reasons however, it is advisable to use the split-mix method in which one of two mixtures is replaced by single building blocks (BBs). The mixtures are so important that there are no combinatorial libraries without using mixture in the synthesis, and if a mixture is used in a process inevitably combinatorial library forms. The split-mix synthesis is usually realized using solid support but it is possible to apply it in solution, too. Since he structures the components are unknown deconvolution methods need to be used in screening. One of the most important features of combinatorial libraries is that the whole mixture can be screened in a single process. This makes these libraries very useful in pharmaceutical research. Partial libraries of full combinatorial libraries can also be synthesized. Some of them can be used in deconvolution<sup id="cite_ref-30" class="reference"><a href="#cite_note-30"><span class="cite-bracket">[</span>30<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Deconvolution_of_libraries_cleaved_from_the_solid_support">Deconvolution of libraries cleaved from the solid support</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Combinatorial_chemistry&action=edit&section=7" title="Edit section: Deconvolution of libraries cleaved from the solid support"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>If the synthesized molecules of a combinatorial library are cleaved from the solid support a soluble mixture forms. In such solution, millions of different compounds may be found. When this synthetic method was developed, it first seemed impossible to identify the molecules, and to find molecules with useful properties. Strategies for identification of the useful components had been developed, however, to solve the problem. All these strategies are based on synthesis and testing of partial libraries. An early iterative strategy was devised by Furka in 1982.<sup id="cite_ref-Furka_4-1" class="reference"><a href="#cite_note-Furka-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> The method was later independently published by Erb et al. under the name "Recursive deconvolution"<sup id="cite_ref-31" class="reference"><a href="#cite_note-31"><span class="cite-bracket">[</span>31<span class="cite-bracket">]</span></a></sup> </p> <figure class="mw-halign-left" typeof="mw:File/Thumb"><a href="/wiki/File:Recursive_deconvolution.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/f/f3/Recursive_deconvolution.png/350px-Recursive_deconvolution.png" decoding="async" width="350" height="216" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/f3/Recursive_deconvolution.png/525px-Recursive_deconvolution.png 1.5x, //upload.wikimedia.org/wikipedia/commons/f/f3/Recursive_deconvolution.png 2x" data-file-width="555" data-file-height="342" /></a><figcaption>Recursive deconvolution. Blue, yellow and red circles: amino acids, Green circle: solid support</figcaption></figure> <div class="mw-heading mw-heading4"><h4 id="Recursive_deconvolution">Recursive deconvolution</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Combinatorial_chemistry&action=edit&section=8" title="Edit section: Recursive deconvolution"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The method is made understandable by the figure. A 27-member peptide library is synthesized from three amino acids. After the first (A) and second (B) cycles samples were set aside before mixing them. The products of the third cycle (C) are cleaved down before mixing then are tested for activity. Suppose the group labeled by + sign is active. All members have the red amino acid at the last coupling position (CP). Consequently, the active member also has the red amino acid at the last CP. Then the red amino acid is coupled to the three samples set aside after the second cycle (B) to get samples D. After cleaving, the three E samples are formed. If after testing the sample marked by + is the active one it shows that the blue amino acid occupies the second CP in the active component. Then to the three A samples first the blue then the red amino acid is coupled (F) then tested again after cleaving (G). If the + component proves to be active, the sequence of the active component is determined and shown in H. </p> <div class="mw-heading mw-heading4"><h4 id="Positional_scanning">Positional scanning</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Combinatorial_chemistry&action=edit&section=9" title="Edit section: Positional scanning"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Positional scanning was introduced independently by Furka et al.<sup id="cite_ref-32" class="reference"><a href="#cite_note-32"><span class="cite-bracket">[</span>32<span class="cite-bracket">]</span></a></sup> and Pinilla et al.<sup id="cite_ref-33" class="reference"><a href="#cite_note-33"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup> The method is based on the synthesis and testing of series of sublibraries. in which a certain sequence position is occupied by the same amino acid. The figure shows the nine sublibraries (B1-D3) of a full peptide trimer library (A) made from three amino acids. In sublibraries there is a position which is occupied by the same amino acid in all components. In the synthesis of a sublibrary the support is not divided and only one amino acid is coupled to the whole sample. As a result, one position is really occupied by the same amino acid in all components. For example, in the B2 sublibrary position 2 is occupied by the "yellow" amino acid in all the nine components. If in a screening test this sublibrary gives positive answer it means that position 2 in the active peptide is also occupied by the "yellow" amino acid. The amino acid sequence can be determined by testing all the nine (or sometime less) sublibraries. </p> <figure class="mw-halign-left" typeof="mw:File/Thumb"><a href="/wiki/File:Positional_scanning.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/c/cc/Positional_scanning.png/400px-Positional_scanning.png" decoding="async" width="400" height="362" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/cc/Positional_scanning.png/600px-Positional_scanning.png 1.5x, //upload.wikimedia.org/wikipedia/commons/c/cc/Positional_scanning.png 2x" data-file-width="752" data-file-height="681" /></a><figcaption>Positional scanning. Full trimer peptide library made from 3 amino acids and its 9 sublibraries. The first row shows the coupling positions.</figcaption></figure> <figure class="mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Full_and_omission_libraries.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/4/44/Full_and_omission_libraries.png" decoding="async" width="239" height="326" class="mw-file-element" data-file-width="239" data-file-height="326" /></a><figcaption>A 27-member tripeptide full library and the three omission libraries. The color circles are amino acids.</figcaption></figure> <div class="mw-heading mw-heading4"><h4 id="Omission_libraries">Omission libraries</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Combinatorial_chemistry&action=edit&section=10" title="Edit section: Omission libraries"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In omission libraries<sup id="cite_ref-34" class="reference"><a href="#cite_note-34"><span class="cite-bracket">[</span>34<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-35" class="reference"><a href="#cite_note-35"><span class="cite-bracket">[</span>35<span class="cite-bracket">]</span></a></sup> a certain amino acid is missing from all peptides of the mixture. The figure shows the full library and the three omission libraries. At the top the omitted amino acids are shown. If the omission library gives a negative test the omitted amino acid is present in the active component. </p> <div class="mw-heading mw-heading3"><h3 id="Deconvolution_of_tethered_combinatorial_libraries">Deconvolution of tethered combinatorial libraries</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Combinatorial_chemistry&action=edit&section=11" title="Edit section: Deconvolution of tethered combinatorial libraries"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>If the peptides are not cleaved from the solid support we deal with a mixture of beads, each bead containing a single peptide. Smith and his colleagues<sup id="cite_ref-36" class="reference"><a href="#cite_note-36"><span class="cite-bracket">[</span>36<span class="cite-bracket">]</span></a></sup> showed earlier that peptides could be tested in tethered form, too. This approach was also used in screening peptide libraries. The tethered peptide library was tested with a dissolved target protein. The beads to which the protein was attached were picked out, removed the protein from the bead then the tethered peptide was identified by sequencing. A somewhat different approach was followed by Taylor and Morken.<sup id="cite_ref-37" class="reference"><a href="#cite_note-37"><span class="cite-bracket">[</span>37<span class="cite-bracket">]</span></a></sup> They used infrared thermography to identify catalysts in non-peptide tethered libraries. The method is based on the heat that is evolved in the beads that contain a catalyst when the tethered library immersed into a solution of a substrate. When the beads are examined through an infrared microscope the catalyst containing beads appear as bright spots and can be picked out. </p> <div class="mw-heading mw-heading4"><h4 id="Encoded_combinatorial_libraries">Encoded combinatorial libraries</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Combinatorial_chemistry&action=edit&section=12" title="Edit section: Encoded combinatorial libraries"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>If we deal with a non-peptide organic libraries library it is not as simple to determine the identity of the content of a bead as in the case of a peptide one. In order to circumvent this difficulty methods had been developed to attach to the beads, in parallel with the synthesis of the library, molecules that encode the structure of the compound formed in the bead. Ohlmeyer and his colleagues published a binary encoding method<sup id="cite_ref-38" class="reference"><a href="#cite_note-38"><span class="cite-bracket">[</span>38<span class="cite-bracket">]</span></a></sup> They used mixtures of 18 tagging molecules that after cleaving them from the beads could be identified by Electron Capture Gas Chromatography. Sarkar et al. described chiral oligomers of pentenoic amides (COPAs) that can be used to construct mass encoded OBOC libraries.<sup id="cite_ref-39" class="reference"><a href="#cite_note-39"><span class="cite-bracket">[</span>39<span class="cite-bracket">]</span></a></sup> Kerr et al. introduced an innovative encoding method<sup id="cite_ref-40" class="reference"><a href="#cite_note-40"><span class="cite-bracket">[</span>40<span class="cite-bracket">]</span></a></sup> An orthogonally protected removable bifunctional linker was attached to the beads. One end of the linker was used to attach the non-natural building blocks of the library while to the other end encoding amino acid triplets were linked. The building blocks were non-natural amino acids and the series of their encoding amino acid triplets could be determined by Edman degradation. The important aspect of this kind of encoding was the possibility to cleave down from the beads the library members together with their attached encoding tags forming a soluble library. The same approach was used by Nikolajev et al. for encoding with peptides.<sup id="cite_ref-41" class="reference"><a href="#cite_note-41"><span class="cite-bracket">[</span>41<span class="cite-bracket">]</span></a></sup> In 1992 by Brenner and Lerner introduced DNA sequences to encode the beads of the solid support that proved to be the most successful encoding method.<sup id="cite_ref-42" class="reference"><a href="#cite_note-42"><span class="cite-bracket">[</span>42<span class="cite-bracket">]</span></a></sup> Nielsen, Brenner and Janda also used the Kerr approach for implementing the DNA encoding<sup id="cite_ref-43" class="reference"><a href="#cite_note-43"><span class="cite-bracket">[</span>43<span class="cite-bracket">]</span></a></sup> In the latest period of time there were important advancements in DNA sequencing. The next generation techniques make it possible to sequence large number of samples in parallel that is very important in screening of DNA encoded libraries. There was another innovation that contributed to the success of DNA encoding. In 2000 Halpin and Harbury omitted the solid support in the split-mix synthesis of the DNA encoded combinatorial libraries and replaced it by the encoding DNA oligomers. In solid phase split and pool synthesis the number of components of libraries can't exceed the number of the beads of the support. By the novel approach of the authors, this restraint was eliminated and made it possible to prepare new compounds in practically unlimited number.<sup id="cite_ref-44" class="reference"><a href="#cite_note-44"><span class="cite-bracket">[</span>44<span class="cite-bracket">]</span></a></sup> The Danish company Nuevolution for example synthesized a DNA encoded library containing 40 trillion! components<sup id="cite_ref-45" class="reference"><a href="#cite_note-45"><span class="cite-bracket">[</span>45<span class="cite-bracket">]</span></a></sup> The DNA encoded libraries are soluble that makes possible to apply the efficient affinity binding in screening. Some authors apply the DEL for acromim of DNA encoded combinatorial libraries others are using DECL. The latter seems better since in this name the combinatorial nature of these libraries is clearly expressed. Several types of DNA encoded combinatorial libraries had been introduced and described in the first decade of the present millennium. These libraries are very successfully applied in drug research. </p> <ul><li>DNA templated synthesis of combinatorial libraries described in 2001 by Gartner et al.<sup id="cite_ref-46" class="reference"><a href="#cite_note-46"><span class="cite-bracket">[</span>46<span class="cite-bracket">]</span></a></sup></li> <li>Dual pharmacophore DNA encoded combinatorial libraries invented in 2004 by Mlecco et al.<sup id="cite_ref-47" class="reference"><a href="#cite_note-47"><span class="cite-bracket">[</span>47<span class="cite-bracket">]</span></a></sup></li> <li>Sequence encoded routing published by Harbury Halpin and Harbury in 2004.<sup id="cite_ref-48" class="reference"><a href="#cite_note-48"><span class="cite-bracket">[</span>48<span class="cite-bracket">]</span></a></sup></li> <li>Single pharmacophore DNA encoded combinatorial libraries introduced in 2008 by Manocci et al.<sup id="cite_ref-49" class="reference"><a href="#cite_note-49"><span class="cite-bracket">[</span>49<span class="cite-bracket">]</span></a></sup></li> <li>DNA encoded combinatorial libraries formed by using yoctoliter-scale reactor published by Hansen et al. in 2009<sup id="cite_ref-50" class="reference"><a href="#cite_note-50"><span class="cite-bracket">[</span>50<span class="cite-bracket">]</span></a></sup></li></ul> <p>Details are found about their synthesis and application in the page <a href="/wiki/DNA-encoded_chemical_library" title="DNA-encoded chemical library">DNA-encoded chemical library</a>. The DNA encoded soluble combinatorial libraries have drawbacks, too. First of all the advantage coming from the use of solid support is completely lost. In addition, the polyionic character of DNA encoding chains limits the utility of non-aqueous solvents in the synthesis. For this reason many laboratories choose to develop DNA compatible reactions for use in the synthesis of DECLs. Quite a few of available ones are already described<sup id="cite_ref-51" class="reference"><a href="#cite_note-51"><span class="cite-bracket">[</span>51<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-52" class="reference"><a href="#cite_note-52"><span class="cite-bracket">[</span>52<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-53" class="reference"><a href="#cite_note-53"><span class="cite-bracket">[</span>53<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Materials_science">Materials science</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Combinatorial_chemistry&action=edit&section=13" title="Edit section: Materials science"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Materials_science" title="Materials science">Materials science</a> has applied the techniques of combinatorial chemistry to the discovery of new materials. This work was pioneered by <a href="/wiki/Peter_G._Schultz" title="Peter G. Schultz">P.G. Schultz</a> et al. in the mid-nineties <sup id="cite_ref-54" class="reference"><a href="#cite_note-54"><span class="cite-bracket">[</span>54<span class="cite-bracket">]</span></a></sup> in the context of luminescent materials obtained by co-deposition of elements on a silicon substrate. His work was preceded by J. J. Hanak in 1970<sup id="cite_ref-55" class="reference"><a href="#cite_note-55"><span class="cite-bracket">[</span>55<span class="cite-bracket">]</span></a></sup> but the computer and robotics tools were not available for the method to spread at the time. Work has been continued by several academic groups<sup id="cite_ref-56" class="reference"><a href="#cite_note-56"><span class="cite-bracket">[</span>56<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-57" class="reference"><a href="#cite_note-57"><span class="cite-bracket">[</span>57<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-58" class="reference"><a href="#cite_note-58"><span class="cite-bracket">[</span>58<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-59" class="reference"><a href="#cite_note-59"><span class="cite-bracket">[</span>59<span class="cite-bracket">]</span></a></sup> as well as companies with large research and development programs (<a href="/wiki/Symyx_Technologies" title="Symyx Technologies">Symyx Technologies</a>, <a href="/wiki/General_Electric" title="General Electric">GE</a>, <a href="/wiki/Dow_Chemical" class="mw-redirect" title="Dow Chemical">Dow Chemical</a> etc.). The technique has been used extensively for catalysis,<sup id="cite_ref-60" class="reference"><a href="#cite_note-60"><span class="cite-bracket">[</span>60<span class="cite-bracket">]</span></a></sup> coatings,<sup id="cite_ref-61" class="reference"><a href="#cite_note-61"><span class="cite-bracket">[</span>61<span class="cite-bracket">]</span></a></sup> electronics,<sup id="cite_ref-62" class="reference"><a href="#cite_note-62"><span class="cite-bracket">[</span>62<span class="cite-bracket">]</span></a></sup> and many other fields.<sup id="cite_ref-63" class="reference"><a href="#cite_note-63"><span class="cite-bracket">[</span>63<span class="cite-bracket">]</span></a></sup> The application of appropriate informatics tools is critical to handle, administer, and store the vast volumes of data produced.<sup id="cite_ref-64" class="reference"><a href="#cite_note-64"><span class="cite-bracket">[</span>64<span class="cite-bracket">]</span></a></sup> New types of <a href="/wiki/Design_of_experiments" title="Design of experiments">design of experiments</a> methods have also been developed to efficiently address the large experimental spaces that can be tackled using combinatorial methods.<sup id="cite_ref-65" class="reference"><a href="#cite_note-65"><span class="cite-bracket">[</span>65<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Diversity-oriented_libraries">Diversity-oriented libraries</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Combinatorial_chemistry&action=edit&section=14" title="Edit section: Diversity-oriented libraries"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Even though combinatorial chemistry has been an essential part of early drug discovery for more than two decades, so far only one de novo combinatorial chemistry-synthesized chemical has been approved for clinical use by FDA (<a href="/wiki/Sorafenib" title="Sorafenib">sorafenib</a>, a multikinase inhibitor indicated for advanced renal cancer).<sup id="cite_ref-66" class="reference"><a href="#cite_note-66"><span class="cite-bracket">[</span>66<span class="cite-bracket">]</span></a></sup> The analysis of the poor success rate of the approach has been suggested to connect with the rather limited <a href="/wiki/Chemical_space" title="Chemical space">chemical space</a> covered by products of combinatorial chemistry.<sup id="cite_ref-pubs.acs.org_67-0" class="reference"><a href="#cite_note-pubs.acs.org-67"><span class="cite-bracket">[</span>67<span class="cite-bracket">]</span></a></sup> When comparing the properties of compounds in combinatorial chemistry libraries to those of approved drugs and natural products, Feher and Schmidt<sup id="cite_ref-pubs.acs.org_67-1" class="reference"><a href="#cite_note-pubs.acs.org-67"><span class="cite-bracket">[</span>67<span class="cite-bracket">]</span></a></sup> noted that combinatorial chemistry libraries suffer particularly from the lack of <a href="/wiki/Chirality_(chemistry)" title="Chirality (chemistry)">chirality</a>, as well as structure rigidity, both of which are widely regarded as drug-like properties. Even though natural product <a href="/wiki/Drug_discovery" title="Drug discovery">drug discovery</a> has not probably been the most fashionable trend in the pharmaceutical industry in recent times,<sup id="cite_ref-Warr1997_2-2" class="reference"><a href="#cite_note-Warr1997-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> a large proportion of new chemical entities still are nature-derived compounds,<sup id="cite_ref-68" class="reference"><a href="#cite_note-68"><span class="cite-bracket">[</span>68<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-69" class="reference"><a href="#cite_note-69"><span class="cite-bracket">[</span>69<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-70" class="reference"><a href="#cite_note-70"><span class="cite-bracket">[</span>70<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-71" class="reference"><a href="#cite_note-71"><span class="cite-bracket">[</span>71<span class="cite-bracket">]</span></a></sup> and thus, it has been suggested that effectiveness of combinatorial chemistry could be improved by enhancing the chemical diversity of screening libraries.<sup id="cite_ref-72" class="reference"><a href="#cite_note-72"><span class="cite-bracket">[</span>72<span class="cite-bracket">]</span></a></sup> As chirality and rigidity are the two most important features distinguishing approved drugs and natural products from compounds in combinatorial chemistry libraries, these are the two issues emphasized in so-called diversity oriented libraries, i.e. compound collections that aim at coverage of the chemical space, instead of just huge numbers of compounds.<sup id="cite_ref-73" class="reference"><a href="#cite_note-73"><span class="cite-bracket">[</span>73<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-74" class="reference"><a href="#cite_note-74"><span class="cite-bracket">[</span>74<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-75" class="reference"><a href="#cite_note-75"><span class="cite-bracket">[</span>75<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-76" class="reference"><a href="#cite_note-76"><span class="cite-bracket">[</span>76<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-77" class="reference"><a href="#cite_note-77"><span class="cite-bracket">[</span>77<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-78" class="reference"><a href="#cite_note-78"><span class="cite-bracket">[</span>78<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Patent_classification_subclass">Patent classification subclass</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Combinatorial_chemistry&action=edit&section=15" title="Edit section: Patent classification subclass"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In the 8th edition of the <a href="/wiki/International_Patent_Classification" title="International Patent Classification">International Patent Classification</a> (IPC), which entered into force on January 1, 2006, a special subclass has been created for <a href="/wiki/Patent_application" title="Patent application">patent applications</a> and <a href="/wiki/Patent" title="Patent">patents</a> related to <a href="/wiki/Invention" title="Invention">inventions</a> in the domain of combinatorial chemistry: "C40B". </p> <div class="mw-heading mw-heading2"><h2 id="See_also">See also</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Combinatorial_chemistry&action=edit&section=16" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Combinatorics" title="Combinatorics">Combinatorics</a></li> <li><a href="/wiki/Cheminformatics" title="Cheminformatics">Cheminformatics</a></li> <li><a href="/wiki/Combinatorial_biology" title="Combinatorial biology">Combinatorial biology</a></li> <li><a href="/wiki/Drug_discovery" title="Drug discovery">Drug discovery</a></li> <li><a href="/wiki/Dynamic_combinatorial_chemistry" title="Dynamic combinatorial chemistry">Dynamic combinatorial chemistry</a></li> <li><a href="/wiki/High-throughput_screening" title="High-throughput screening">High-throughput screening</a></li> <li><a href="/wiki/Mathematical_chemistry" title="Mathematical chemistry">Mathematical chemistry</a></li> <li><a href="/wiki/Molecular_modeling" class="mw-redirect" title="Molecular modeling">Molecular modeling</a></li></ul> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Combinatorial_chemistry&action=edit&section=17" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist"> <div class="mw-references-wrap mw-references-columns"><ol 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New Jersey: John Wiley & Sons, Inc. pp. 40–63.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Combinatorial+Chemistry+Library+Design%2C+in%2C+Plant+Chemical+Biology%2C+Audenaert%2C+D.%3B+Overvoorde%2C+P.%3B+Eds.&rft.place=New+Jersey&rft.pages=40-63&rft.pub=John+Wiley+%26+Sons%2C+Inc.&rft.date=2014&rft.aulast=Klein&rft.aufirst=R.&rft.au=Lindell%2C+S.D.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACombinatorial+chemistry" class="Z3988"></span></span> </li> </ol></div></div> <div class="mw-heading mw-heading2"><h2 id="External_links">External links</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Combinatorial_chemistry&action=edit&section=18" title="Edit section: External links"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a rel="nofollow" class="external text" href="http://www.iupac.org/publications/pac/1999/pdf/7112x2349.pdf">IUPAC's "Glossary of Terms Used in Combinatorial Chemistry"</a></li> <li><a rel="nofollow" class="external text" href="http://pubs.acs.org/journals/jcchff/index.html">ACS Combinatorial Science</a> (formerly <a href="/wiki/Journal_of_Combinatorial_Chemistry" class="mw-redirect" title="Journal of Combinatorial Chemistry">Journal of Combinatorial Chemistry</a>)</li> <li><a rel="nofollow" class="external text" href="http://www.combichemistry.com">Combinatorial Chemistry Review</a></li> <li><a rel="nofollow" class="external text" href="http://arquivo.pt/wayback/20160515025842/http://springerlink.metapress.com/openurl.asp?genre=journal&eissn=1573-501X">Molecular Diversity</a></li> <li><a rel="nofollow" class="external text" href="https://web.archive.org/web/20050627080008/http://www.bentham.org/cchts/">Combinatorial Chemistry and High Throughput Screening</a></li> <li><a rel="nofollow" class="external text" href="http://www.sciencedirect.com/science/journal/14643383">Combinatorial Chemistry: an Online Journal</a></li> <li><a rel="nofollow" class="external text" href="https://web.archive.org/web/20090105154339/http://gecco.org.chemie.uni-frankfurt.de/smilib/">SmiLib - A free open-source software for combinatorial library enumeration</a></li> <li><a rel="nofollow" class="external text" href="http://glare.sourceforge.net/">GLARE - A free open-source software for combinatorial library design</a></li></ul> <div class="navbox-styles"><style data-mw-deduplicate="TemplateStyles:r1129693374">.mw-parser-output .hlist dl,.mw-parser-output .hlist ol,.mw-parser-output .hlist ul{margin:0;padding:0}.mw-parser-output .hlist dd,.mw-parser-output .hlist dt,.mw-parser-output .hlist li{margin:0;display:inline}.mw-parser-output .hlist.inline,.mw-parser-output .hlist.inline dl,.mw-parser-output .hlist.inline ol,.mw-parser-output .hlist.inline ul,.mw-parser-output .hlist dl dl,.mw-parser-output .hlist dl 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style="width:1%"><a href="/wiki/Analytical_chemistry" title="Analytical chemistry">Analytical</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Instrumental_chemistry" title="Instrumental chemistry">Instrumental chemistry</a></li> <li><a href="/wiki/Electroanalytical_methods" title="Electroanalytical methods">Electroanalytical methods</a></li> <li><a href="/wiki/Spectroscopy" title="Spectroscopy">Spectroscopy</a> <ul><li><a href="/wiki/Infrared_spectroscopy" title="Infrared spectroscopy">IR</a></li> <li><a href="/wiki/Raman_spectroscopy" title="Raman spectroscopy">Raman</a></li> <li><a href="/wiki/Ultraviolet%E2%80%93visible_spectroscopy" title="Ultraviolet–visible spectroscopy">UV-Vis</a></li> <li><a href="/wiki/Nuclear_magnetic_resonance_spectroscopy" title="Nuclear magnetic resonance spectroscopy">NMR</a></li></ul></li> <li><a href="/wiki/Mass_spectrometry" title="Mass spectrometry">Mass spectrometry</a> <ul><li><a href="/wiki/Electron_ionization" title="Electron ionization">EI</a></li> <li><a href="/wiki/Inductively_coupled_plasma_mass_spectrometry" title="Inductively coupled plasma mass spectrometry">ICP</a></li> <li><a href="/wiki/Matrix-assisted_laser_desorption/ionization" title="Matrix-assisted laser desorption/ionization">MALDI</a></li></ul></li> <li><a href="/wiki/Separation_process" title="Separation process">Separation process</a></li> <li><a href="/wiki/Chromatography" title="Chromatography">Chromatography</a> <ul><li><a href="/wiki/Gas_chromatography" title="Gas chromatography">GC</a></li> <li><a href="/wiki/High-performance_liquid_chromatography" title="High-performance liquid chromatography">HPLC</a></li></ul></li> <li><a href="/wiki/Crystallography" title="Crystallography">Crystallography</a></li> <li><a href="/wiki/Characterization_(materials_science)" title="Characterization (materials science)">Characterization</a></li> <li><a href="/wiki/Titration" title="Titration">Titration</a></li> <li><a href="/wiki/Wet_chemistry" title="Wet chemistry">Wet chemistry</a></li> <li><a href="/wiki/Calorimetry" title="Calorimetry">Calorimetry</a></li> <li><a href="/wiki/Elemental_analysis" title="Elemental analysis">Elemental analysis</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Theoretical_chemistry" title="Theoretical chemistry">Theoretical</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Quantum_chemistry" title="Quantum chemistry">Quantum chemistry</a></li> <li><a href="/wiki/Computational_chemistry" title="Computational chemistry">Computational chemistry</a> <ul><li><a href="/wiki/Mathematical_chemistry" title="Mathematical chemistry">Mathematical chemistry</a></li></ul></li> <li><a href="/wiki/Molecular_modelling" title="Molecular modelling">Molecular modelling</a></li> <li><a href="/wiki/Molecular_mechanics" title="Molecular mechanics">Molecular mechanics</a></li> <li><a href="/wiki/Molecular_dynamics" title="Molecular dynamics">Molecular dynamics</a></li> <li><a href="/wiki/Molecular_geometry" title="Molecular geometry">Molecular geometry</a> <ul><li><a href="/wiki/VSEPR_theory" title="VSEPR theory">VSEPR theory</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Physical_chemistry" title="Physical chemistry">Physical</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Electrochemistry" title="Electrochemistry">Electrochemistry</a> <ul><li><a href="/wiki/Spectroelectrochemistry" title="Spectroelectrochemistry">Spectroelectrochemistry</a></li> <li><a href="/wiki/Photoelectrochemistry" title="Photoelectrochemistry">Photoelectrochemistry</a></li></ul></li> <li><a href="/wiki/Thermochemistry" title="Thermochemistry">Thermochemistry</a></li> <li><a href="/wiki/Chemical_thermodynamics" title="Chemical thermodynamics">Chemical thermodynamics</a></li> <li><a href="/wiki/Surface_science" title="Surface science">Surface science</a></li> <li><a href="/wiki/Interface_and_colloid_science" title="Interface and colloid science">Interface and colloid science</a> <ul><li><a href="/wiki/Micromeritics" title="Micromeritics">Micromeritics</a></li></ul></li> <li><a href="/wiki/Cryochemistry" title="Cryochemistry">Cryochemistry</a></li> <li><a href="/wiki/Sonochemistry" title="Sonochemistry">Sonochemistry</a></li> <li><a href="/wiki/Structural_chemistry" title="Structural chemistry">Structural chemistry</a></li> <li><a href="/wiki/Chemical_physics" title="Chemical physics">Chemical physics</a> <ul><li><a href="/wiki/Molecular_physics" title="Molecular physics">Molecular physics</a></li></ul></li> <li><a href="/wiki/Femtochemistry" title="Femtochemistry">Femtochemistry</a></li> <li><a href="/wiki/Chemical_kinetics" title="Chemical kinetics">Chemical kinetics</a></li> <li><a href="/wiki/Spectroscopy" title="Spectroscopy">Spectroscopy</a></li> <li><a href="/wiki/Photochemistry" title="Photochemistry">Photochemistry</a></li> <li><a href="/wiki/Spin_chemistry" title="Spin chemistry">Spin chemistry</a></li> <li><a href="/wiki/Microwave_chemistry" title="Microwave chemistry">Microwave chemistry</a></li> <li><a href="/wiki/Equilibrium_chemistry" title="Equilibrium chemistry">Equilibrium chemistry</a></li> <li><a href="/wiki/Mechanochemistry" title="Mechanochemistry">Mechanochemistry</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Inorganic_chemistry" title="Inorganic chemistry">Inorganic</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Coordination_complex" title="Coordination complex">Coordination chemistry</a></li> <li><a href="/wiki/Magnetochemistry" title="Magnetochemistry">Magnetochemistry</a></li> <li><a href="/wiki/Organometallic_chemistry" title="Organometallic chemistry">Organometallic chemistry</a> <ul><li><a href="/wiki/Organolanthanide_chemistry" title="Organolanthanide chemistry">Organolanthanide chemistry</a></li></ul></li> <li><a href="/wiki/Atom_cluster" class="mw-redirect" title="Atom cluster">Cluster chemistry</a></li> <li><a href="/wiki/Solid-state_chemistry" title="Solid-state chemistry">Solid-state chemistry</a></li> <li><a href="/wiki/Ceramic_chemistry" class="mw-redirect" title="Ceramic chemistry">Ceramic chemistry</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Organic_chemistry" title="Organic chemistry">Organic</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Stereochemistry" title="Stereochemistry">Stereochemistry</a> <ul><li><a href="/wiki/Alkane_stereochemistry" class="mw-redirect" title="Alkane stereochemistry">Alkane stereochemistry</a></li></ul></li> <li><a href="/wiki/Physical_organic_chemistry" title="Physical organic chemistry">Physical organic chemistry</a></li> <li><a href="/wiki/Organic_reactions" class="mw-redirect" title="Organic reactions">Organic reactions</a></li> <li><a href="/wiki/Organic_synthesis" title="Organic synthesis">Organic synthesis</a></li> <li><a href="/wiki/Retrosynthetic_analysis" title="Retrosynthetic analysis">Retrosynthetic analysis</a></li> <li><a href="/wiki/Enantioselective_synthesis" title="Enantioselective synthesis">Enantioselective synthesis</a></li> <li><a href="/wiki/Total_synthesis" title="Total synthesis">Total synthesis</a> / <a href="/wiki/Semisynthesis" title="Semisynthesis">Semisynthesis</a></li> <li><a href="/wiki/Fullerene_chemistry" title="Fullerene chemistry">Fullerene chemistry</a></li> <li><a href="/wiki/Polymer_chemistry" title="Polymer chemistry">Polymer chemistry</a></li> <li><a href="/wiki/Petrochemistry" class="mw-redirect" title="Petrochemistry">Petrochemistry</a></li> <li><a href="/wiki/Dynamic_covalent_chemistry" title="Dynamic covalent chemistry">Dynamic covalent chemistry</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Biochemistry" title="Biochemistry">Biological</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Biochemistry" title="Biochemistry">Biochemistry</a> <ul><li><a href="/wiki/Molecular_biology" title="Molecular biology">Molecular biology</a></li> <li><a href="/wiki/Cell_biology" title="Cell biology">Cell biology</a></li></ul></li> <li><a href="/wiki/Chemical_biology" title="Chemical biology">Chemical biology</a> <ul><li><a href="/wiki/Bioorthogonal_chemistry" title="Bioorthogonal chemistry">Bioorthogonal chemistry</a></li></ul></li> <li><a href="/wiki/Medicinal_chemistry" title="Medicinal chemistry">Medicinal chemistry</a> <ul><li><a href="/wiki/Pharmacology" title="Pharmacology">Pharmacology</a></li></ul></li> <li><a href="/wiki/Clinical_chemistry" title="Clinical chemistry">Clinical chemistry</a></li> <li><a href="/wiki/Neurochemistry" title="Neurochemistry">Neurochemistry</a></li> <li><a href="/wiki/Bioorganic_chemistry" title="Bioorganic chemistry">Bioorganic chemistry</a></li> <li><a href="/wiki/Bioorganometallic_chemistry" title="Bioorganometallic chemistry">Bioorganometallic chemistry</a></li> <li><a href="/wiki/Bioinorganic_chemistry" title="Bioinorganic chemistry">Bioinorganic chemistry</a></li> <li><a href="/wiki/Biophysical_chemistry" title="Biophysical chemistry">Biophysical chemistry</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Interdisciplinarity" title="Interdisciplinarity">Interdisciplinarity</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Nuclear_chemistry" title="Nuclear chemistry">Nuclear chemistry</a> <ul><li><a href="/wiki/Radiochemistry" title="Radiochemistry">Radiochemistry</a></li> <li><a href="/wiki/Radiation_chemistry" title="Radiation chemistry">Radiation chemistry</a></li> <li><a href="/wiki/Actinide_chemistry" title="Actinide chemistry">Actinide chemistry</a></li></ul></li> <li><a href="/wiki/Cosmochemistry" title="Cosmochemistry">Cosmochemistry</a> / <a href="/wiki/Astrochemistry" title="Astrochemistry">Astrochemistry</a> / <a href="/wiki/Stellar_chemistry" title="Stellar chemistry">Stellar chemistry</a></li> <li><a href="/wiki/Geochemistry" title="Geochemistry">Geochemistry</a> <ul><li><a href="/wiki/Biogeochemistry" title="Biogeochemistry">Biogeochemistry</a></li> <li><a href="/wiki/Photogeochemistry" title="Photogeochemistry">Photogeochemistry</a></li></ul></li></ul> <ul><li><a href="/wiki/Environmental_chemistry" title="Environmental chemistry">Environmental chemistry</a> <ul><li><a href="/wiki/Atmospheric_chemistry" title="Atmospheric chemistry">Atmospheric chemistry</a></li> <li><a href="/wiki/Ocean_chemistry" class="mw-redirect" title="Ocean chemistry">Ocean chemistry</a></li></ul></li> <li><a href="/wiki/Clay_chemistry" title="Clay chemistry">Clay chemistry</a></li> <li><a href="/wiki/Carbochemistry" title="Carbochemistry">Carbochemistry</a></li> <li><a href="/wiki/Food_chemistry" title="Food chemistry">Food chemistry</a> <ul><li><a href="/wiki/Carbohydrate_chemistry" class="mw-redirect" title="Carbohydrate chemistry">Carbohydrate chemistry</a></li> <li><a href="/wiki/Food_physical_chemistry" title="Food physical chemistry">Food physical chemistry</a></li></ul></li> <li><a href="/wiki/Agricultural_chemistry" title="Agricultural chemistry">Agricultural chemistry</a> <ul><li><a href="/wiki/Soil_chemistry" title="Soil chemistry">Soil chemistry</a></li></ul></li></ul> <ul><li><a href="/wiki/Chemistry_education" title="Chemistry education">Chemistry education</a> <ul><li><a href="/wiki/Amateur_chemistry" title="Amateur chemistry">Amateur chemistry</a></li> <li><a href="/wiki/General_chemistry" title="General chemistry">General chemistry</a></li></ul></li> <li><a href="/wiki/Clandestine_chemistry" title="Clandestine chemistry">Clandestine chemistry</a></li> <li><a href="/wiki/Forensic_chemistry" title="Forensic chemistry">Forensic chemistry</a> <ul><li><a href="/wiki/Forensic_toxicology" title="Forensic toxicology">Forensic toxicology</a></li> <li><a href="/wiki/Post-mortem_chemistry" title="Post-mortem chemistry">Post-mortem chemistry</a></li></ul></li></ul> <ul><li><a href="/wiki/Nanochemistry" title="Nanochemistry">Nanochemistry</a> <ul><li><a href="/wiki/Supramolecular_chemistry" title="Supramolecular chemistry">Supramolecular chemistry</a></li></ul></li> <li><a href="/wiki/Chemical_synthesis" title="Chemical synthesis">Chemical synthesis</a> <ul><li><a href="/wiki/Green_chemistry" title="Green chemistry">Green chemistry</a></li> <li><a href="/wiki/Click_chemistry" title="Click chemistry">Click chemistry</a></li> <li><a class="mw-selflink selflink">Combinatorial chemistry</a></li> <li><a href="/wiki/Biosynthesis" title="Biosynthesis">Biosynthesis</a></li></ul></li> <li><a href="/wiki/Chemical_engineering" title="Chemical engineering">Chemical engineering</a> <ul><li><a href="/wiki/Stoichiometry" title="Stoichiometry">Stoichiometry</a></li></ul></li> <li><a href="/wiki/Materials_science" title="Materials science">Materials science</a> <ul><li><a href="/wiki/Metallurgy" title="Metallurgy">Metallurgy</a></li> <li><a href="/wiki/Ceramic_engineering" title="Ceramic engineering">Ceramic engineering</a></li> <li><a href="/wiki/Polymer_science" title="Polymer science">Polymer science</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">See also</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/History_of_chemistry" title="History of chemistry">History of chemistry</a></li> <li><a href="/wiki/Nobel_Prize_in_Chemistry" title="Nobel Prize in Chemistry">Nobel Prize in Chemistry</a></li> <li><a href="/wiki/Timeline_of_chemistry" title="Timeline of chemistry">Timeline of chemistry</a> <ul><li><a href="/wiki/Discovery_of_chemical_elements" title="Discovery of chemical elements">of element discoveries</a></li></ul></li> <li>"<a href="/wiki/The_central_science" title="The central science">The central science</a>"</li> <li><a href="/wiki/Chemical_reaction" title="Chemical reaction">Chemical reaction</a> <ul><li><a href="/wiki/Catalysis" title="Catalysis">Catalysis</a></li></ul></li> <li><a href="/wiki/Chemical_element" title="Chemical element">Chemical element</a></li> <li><a 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