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</div> </div> </div> </nav> <h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">Heptose</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. 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href="https://bn.wikipedia.org/wiki/%E0%A6%B9%E0%A7%87%E0%A6%AA%E0%A7%8D%E0%A6%9F%E0%A7%8B%E0%A6%9C" title="হেপ্টোজ – Bangla" lang="bn" hreflang="bn" data-title="হেপ্টোজ" data-language-autonym="বাংলা" data-language-local-name="Bangla" class="interlanguage-link-target"><span>বাংলা</span></a></li><li class="interlanguage-link interwiki-bg mw-list-item"><a href="https://bg.wikipedia.org/wiki/%D0%A5%D0%B5%D0%BF%D1%82%D0%BE%D0%B7%D0%B0" title="Хептоза – Bulgarian" lang="bg" hreflang="bg" data-title="Хептоза" data-language-autonym="Български" data-language-local-name="Bulgarian" class="interlanguage-link-target"><span>Български</span></a></li><li class="interlanguage-link interwiki-bs mw-list-item"><a href="https://bs.wikipedia.org/wiki/Heptoza" title="Heptoza – Bosnian" lang="bs" hreflang="bs" data-title="Heptoza" data-language-autonym="Bosanski" data-language-local-name="Bosnian" class="interlanguage-link-target"><span>Bosanski</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Heptosa" title="Heptosa – Catalan" lang="ca" hreflang="ca" data-title="Heptosa" data-language-autonym="Català" data-language-local-name="Catalan" class="interlanguage-link-target"><span>Català</span></a></li><li class="interlanguage-link interwiki-cs mw-list-item"><a href="https://cs.wikipedia.org/wiki/Hept%C3%B3zy" title="Heptózy – Czech" lang="cs" hreflang="cs" data-title="Heptózy" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Heptosen" title="Heptosen – German" lang="de" hreflang="de" data-title="Heptosen" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-el mw-list-item"><a href="https://el.wikipedia.org/wiki/%CE%95%CF%80%CF%84%CF%8C%CE%B6%CE%B7" title="Επτόζη – Greek" lang="el" hreflang="el" data-title="Επτόζη" data-language-autonym="Ελληνικά" data-language-local-name="Greek" class="interlanguage-link-target"><span>Ελληνικά</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Heptosa" title="Heptosa – Spanish" lang="es" hreflang="es" data-title="Heptosa" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-eu mw-list-item"><a href="https://eu.wikipedia.org/wiki/Heptosa" title="Heptosa – Basque" lang="eu" hreflang="eu" data-title="Heptosa" data-language-autonym="Euskara" data-language-local-name="Basque" class="interlanguage-link-target"><span>Euskara</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D9%87%D9%BE%D8%AA%D9%88%D8%B2" title="هپتوز – Persian" lang="fa" hreflang="fa" data-title="هپتوز" 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/Heptose" title="Heptose – French" lang="fr" hreflang="fr" data-title="Heptose" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-gl mw-list-item"><a href="https://gl.wikipedia.org/wiki/Heptosa" title="Heptosa – Galician" lang="gl" hreflang="gl" data-title="Heptosa" data-language-autonym="Galego" data-language-local-name="Galician" class="interlanguage-link-target"><span>Galego</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%EC%B9%A0%ED%83%84%EB%8B%B9" title="칠탄당 – Korean" lang="ko" hreflang="ko" data-title="칠탄당" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-hr mw-list-item"><a href="https://hr.wikipedia.org/wiki/Heptoza" title="Heptoza – Croatian" lang="hr" hreflang="hr" data-title="Heptoza" data-language-autonym="Hrvatski" data-language-local-name="Croatian" class="interlanguage-link-target"><span>Hrvatski</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Eptoso" title="Eptoso – Italian" lang="it" hreflang="it" data-title="Eptoso" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Hept%C3%B3z" title="Heptóz – Hungarian" lang="hu" hreflang="hu" data-title="Heptóz" 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%83%98%E3%83%97%E3%83%88%E3%83%BC%E3%82%B9" title="ヘプトース – Japanese" lang="ja" hreflang="ja" data-title="ヘプトース" 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-nn mw-list-item"><a href="https://nn.wikipedia.org/wiki/Heptose" title="Heptose – Norwegian Nynorsk" lang="nn" hreflang="nn" data-title="Heptose" data-language-autonym="Norsk nynorsk" data-language-local-name="Norwegian Nynorsk" class="interlanguage-link-target"><span>Norsk nynorsk</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Heptozy" title="Heptozy – Polish" lang="pl" hreflang="pl" data-title="Heptozy" data-language-autonym="Polski" data-language-local-name="Polish" class="interlanguage-link-target"><span>Polski</span></a></li><li class="interlanguage-link interwiki-pt mw-list-item"><a href="https://pt.wikipedia.org/wiki/Heptose" title="Heptose – Portuguese" lang="pt" hreflang="pt" data-title="Heptose" data-language-autonym="Português" data-language-local-name="Portuguese" class="interlanguage-link-target"><span>Português</span></a></li><li class="interlanguage-link interwiki-ro mw-list-item"><a href="https://ro.wikipedia.org/wiki/Heptoz%C4%83" title="Heptoză – Romanian" lang="ro" hreflang="ro" data-title="Heptoză" data-language-autonym="Română" data-language-local-name="Romanian" class="interlanguage-link-target"><span>Română</span></a></li><li class="interlanguage-link interwiki-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%93%D0%B5%D0%BF%D1%82%D0%BE%D0%B7%D1%8B" title="Гептозы – Russian" lang="ru" hreflang="ru" data-title="Гептозы" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sk mw-list-item"><a href="https://sk.wikipedia.org/wiki/Hept%C3%B3za" title="Heptóza – Slovak" lang="sk" hreflang="sk" data-title="Heptóza" data-language-autonym="Slovenčina" data-language-local-name="Slovak" class="interlanguage-link-target"><span>Slovenčina</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Heptoza" title="Heptoza – Serbian" lang="sr" hreflang="sr" data-title="Heptoza" 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-sh mw-list-item"><a href="https://sh.wikipedia.org/wiki/Heptoza" title="Heptoza – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Heptoza" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="Serbo-Croatian" class="interlanguage-link-target"><span>Srpskohrvatski / српскохрватски</span></a></li><li class="interlanguage-link interwiki-sv mw-list-item"><a href="https://sv.wikipedia.org/wiki/Heptos" title="Heptos – Swedish" lang="sv" hreflang="sv" data-title="Heptos" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-ta mw-list-item"><a href="https://ta.wikipedia.org/wiki/%E0%AE%8E%E0%AE%B4%E0%AF%81%E0%AE%95%E0%AE%B0%E0%AE%BF%E0%AE%9A%E0%AF%8D%E0%AE%9A%E0%AE%B0%E0%AF%8D%E0%AE%95%E0%AF%8D%E0%AE%95%E0%AE%B0%E0%AF%88" title="எழுகரிச்சர்க்கரை – Tamil" lang="ta" hreflang="ta" data-title="எழுகரிச்சர்க்கரை" data-language-autonym="தமிழ்" data-language-local-name="Tamil" class="interlanguage-link-target"><span>தமிழ்</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Heptoz" title="Heptoz – Turkish" lang="tr" hreflang="tr" data-title="Heptoz" data-language-autonym="Türkçe" data-language-local-name="Turkish" class="interlanguage-link-target"><span>Türkçe</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%93%D0%B5%D0%BF%D1%82%D0%BE%D0%B7%D0%B8" title="Гептози – Ukrainian" lang="uk" hreflang="uk" data-title="Гептози" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link interwiki-zh-yue mw-list-item"><a href="https://zh-yue.wikipedia.org/wiki/%E5%BA%9A%E9%86%A3" title="庚醣 – Cantonese" lang="yue" hreflang="yue" data-title="庚醣" 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/%E5%BA%9A%E9%86%A3" title="庚醣 – Chinese" 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class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Class of carbohydrate</div> <p>A <b>heptose</b> is a <a href="/wiki/Monosaccharide" title="Monosaccharide">monosaccharide</a> with seven <a href="/wiki/Carbon" title="Carbon">carbon</a> atoms. </p><p>They have either an <a href="/wiki/Aldehyde" title="Aldehyde">aldehyde</a> <a href="/wiki/Functional_group" title="Functional group">functional group</a> in position 1 (<b>aldoheptoses</b>) or a <a href="/wiki/Ketone" title="Ketone">ketone</a> functional group in position 2, 3 or 4 (<b>ketoheptoses</b>). Ketoheptoses have 4 chiral centers, whereas aldoheptoses have 5. </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Examples">Examples</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Heptose&action=edit&section=1" title="Edit section: Examples"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>There are few examples of seven-carbon sugars in nature, among which are: </p> <ul><li><a href="/wiki/Sedoheptulose" title="Sedoheptulose">sedoheptulose</a> or <small>D</small>-<i>altro</i>-heptulose (a ketose), an intermediate in the <a href="/wiki/Calvin_cycle" title="Calvin cycle">Calvin cycle</a> and in <a href="/wiki/Lipid_A" title="Lipid A">lipid A</a> biosynthesis<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><sup id="cite_ref-2" class="reference"><a href="#cite_note-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup></li> <li><a href="/wiki/Mannoheptulose" title="Mannoheptulose">mannoheptulose</a> (a ketose), found in <a href="/wiki/Avocado" title="Avocado">avocadoes</a><sup id="cite_ref-AvocadoHeptoses_3-0" class="reference"><a href="#cite_note-AvocadoHeptoses-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup></li> <li><small>L</small>-<i>glycero</i>-<small>D</small>-<i>manno</i>-heptose (an aldose), a late intermediate in lipid A biosynthesis.<sup id="cite_ref-4" class="reference"><a href="#cite_note-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup></li></ul> <div class="mw-heading mw-heading2"><h2 id="Structural_role">Structural role</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Heptose&action=edit&section=2" title="Edit section: Structural role"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The production of heptose is conserved across <a href="/wiki/Gram-negative_bacteria" title="Gram-negative bacteria">gram-negative bacteria</a>. In the form of L-glycero-D-mannose-heptose, heptose is a key component in the secondary membrane of gram-negative bacteria. Gram-negative bacteria, in addition to having a <a href="/wiki/Cell_wall" title="Cell wall">cell wall</a>, are also encapsulated by a membrane composed of <a href="/wiki/Lipopolysaccharide" title="Lipopolysaccharide">lipopolysaccharides</a>.<sup id="cite_ref-:0_5-0" class="reference"><a href="#cite_note-:0-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> These lipopolysaccharides comprise an <a href="/wiki/Endotoxin" class="mw-redirect" title="Endotoxin">endotoxin</a> that acts as an immune system <a href="/wiki/Agonist" title="Agonist">agonist</a> and elicits strong responses. This toxin, known as <a href="/wiki/Lipid_A" title="Lipid A">lipid A</a>, consists of a core of one to three heptose molecules.<sup id="cite_ref-:0_5-1" class="reference"><a href="#cite_note-:0-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> The 7-carbon heptose molecules are essential for stability in the lipopolysaccharide membrane, forming an interconnected network utilizing divalent cations.<sup id="cite_ref-:0_5-2" class="reference"><a href="#cite_note-:0-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Role_in_cell_signaling">Role in cell signaling</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Heptose&action=edit&section=3" title="Edit section: Role in cell signaling"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Heptose, in the form of heptose 1-7-bisphosphate, has been found to be one of the components responsible for the <a href="/wiki/Pathogen" title="Pathogen">pathogenic</a> nature of gram negative bacteria. In the bacterium biosynthesis pathway, heptose is <a href="/wiki/Phosphorylation" title="Phosphorylation">phosphorylated</a> to heptose 1-7-bisphosphate. In addition, like other sugars, heptose may exist in either the <a href="/wiki/Anomer" title="Anomer">alpha anomer</a> or the <a href="/wiki/Anomer" title="Anomer">beta anomer</a>. Before synthetic production of heptose-bisphosphate (HBP) for studies, cytosolic HBP was thought to influence <a href="/wiki/NF-%CE%BAB" title="NF-κB">NF-kB</a>, a <a href="/wiki/Transcription_factor" title="Transcription factor">transcription factor</a> in mammalian cells.<sup id="cite_ref-:0_5-3" class="reference"><a href="#cite_note-:0-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-:1_6-0" class="reference"><a href="#cite_note-:1-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> Along with producing the first synthetic version of HBP, it was shown that the beta form of the heptose acts as a <a href="/wiki/Pathogen-associated_molecular_pattern" title="Pathogen-associated molecular pattern">pathogen-associated molecular pattern</a> (PAMP) and activates the NF-kB signaling pathway.<sup id="cite_ref-:1_6-1" class="reference"><a href="#cite_note-:1-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> A PAMP is a specific structure, component, or molecule that triggers the immune response after recognition by <a href="/wiki/Pattern_recognition_receptor" title="Pattern recognition receptor">pattern recognition receptors</a> on mammalian cells.<sup id="cite_ref-:0_5-4" class="reference"><a href="#cite_note-:0-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p> <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=Heptose&action=edit&section=4" 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"><ol class="references"> <li id="cite_note-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-1">^</a></b></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output 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a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and 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Retrieved <span class="nowrap">2018-06-26</span></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+the+American+Society+for+Horticultural+Science&rft.atitle=Postulated+Physiological+Roles+of+the+Seven-carbon+Sugars%2C+Mannoheptulose%2C+and+Perseitol+in+Avocado&rft.volume=127&rft.issue=1&rft.pages=%3Cspan+class%3D%22nowrap%22%3E108-%3C%2Fspan%3E114&rft.date=2002-01-01&rft_id=info%3Adoi%2F10.21273%2FJASHS.127.1.108&rft.aulast=Liu&rft.aufirst=Xuan&rft.au=Sievert%2C+James&rft.au=Arpaia%2C+Mary+Lu&rft.au=Madore%2C+Monica+A.&rft_id=http%3A%2F%2Fjournal.ashspublications.org%2Fcontent%2F127%2F1%2F108.abstract&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHeptose" class="Z3988"></span></span> </li> <li id="cite_note-4"><span class="mw-cite-backlink"><b><a href="#cite_ref-4">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFTaylorBlakelyde_LeonWalker2008" class="citation journal cs1">Taylor, Patricia L.; Blakely, Kim M.; de Leon, Gladys P.; Walker, John R.; McArthur, Fiona; Evdokimova, Elena; Zhang, Kun; Valvano, Miguel A.; Wright, Gerard D.; Junop, Murray S. 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href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/27658039">27658039</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=PLOS+Pathogens&rft.atitle=Heptose+Sounds+the+Alarm%3A+Innate+Sensing+of+a+Bacterial+Sugar+Stimulates+Immunity&rft.volume=12&rft.issue=9&rft.pages=e1005807&rft.date=2016-09-22&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC5033458%23id-name%3DPMC&rft.issn=1553-7374&rft_id=info%3Apmid%2F27658039&rft_id=info%3Adoi%2F10.1371%2Fjournal.ppat.1005807&rft.aulast=Gaudet&rft.aufirst=Ryan+G.&rft.au=Gray-Owen%2C+Scott+D.&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC5033458&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHeptose" class="Z3988"></span></span> </li> <li id="cite_note-:1-6"><span class="mw-cite-backlink">^ <a href="#cite_ref-:1_6-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-:1_6-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFInukiAibaKawakamiAkiyama2017" class="citation journal cs1">Inuki, Shinsuke; Aiba, Toshihiko; Kawakami, Shota; Akiyama, Taishin; Inoue, Jun-ichiro; Fujimoto, Yukari (2017-06-16). <a rel="nofollow" class="external text" href="https://pubs.acs.org/doi/10.1021/acs.orglett.7b01158">"Chemical Synthesis of d - glycero - d - manno -Heptose 1,7-Bisphosphate and Evaluation of Its Ability to Modulate NF-κB Activation"</a>. <i>Organic Letters</i>. <b>19</b> (12): <span class="nowrap">3079–</span>3082. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Facs.orglett.7b01158">10.1021/acs.orglett.7b01158</a>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/1523-7060">1523-7060</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/28541700">28541700</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Organic+Letters&rft.atitle=Chemical+Synthesis+of+d+-+glycero+-+d+-+manno+-Heptose+1%2C7-Bisphosphate+and+Evaluation+of+Its+Ability+to+Modulate+NF-%CE%BAB+Activation&rft.volume=19&rft.issue=12&rft.pages=%3Cspan+class%3D%22nowrap%22%3E3079-%3C%2Fspan%3E3082&rft.date=2017-06-16&rft.issn=1523-7060&rft_id=info%3Apmid%2F28541700&rft_id=info%3Adoi%2F10.1021%2Facs.orglett.7b01158&rft.aulast=Inuki&rft.aufirst=Shinsuke&rft.au=Aiba%2C+Toshihiko&rft.au=Kawakami%2C+Shota&rft.au=Akiyama%2C+Taishin&rft.au=Inoue%2C+Jun-ichiro&rft.au=Fujimoto%2C+Yukari&rft_id=https%3A%2F%2Fpubs.acs.org%2Fdoi%2F10.1021%2Facs.orglett.7b01158&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHeptose" class="Z3988"></span></span> </li> </ol></div></div> <div class="navbox-styles"><style data-mw-deduplicate="TemplateStyles:r1129693374">.mw-parser-output .hlist dl,.mw-parser-output .hlist ol,.mw-parser-output .hlist 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.navbar{display:none!important}}</style><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Carbohydrates" title="Template:Carbohydrates"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Carbohydrates" title="Template talk:Carbohydrates"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Carbohydrates" title="Special:EditPage/Template:Carbohydrates"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Types_of_carbohydrates184" style="font-size:114%;margin:0 4em">Types of <a href="/wiki/Carbohydrate" title="Carbohydrate">carbohydrates</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%">General</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/Aldose" title="Aldose">Aldose</a></li> <li><a href="/wiki/Ketose" title="Ketose">Ketose</a></li> <li><a href="/wiki/Furanose" title="Furanose">Furanose</a></li> <li><a href="/wiki/Pyranose" title="Pyranose">Pyranose</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Geometry</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/Anomer" title="Anomer">Anomer</a></li> <li><a href="/wiki/Cyclohexane_conformation" title="Cyclohexane conformation">Cyclohexane conformation</a></li> <li><a href="/wiki/Epimer" title="Epimer">Epimer</a></li> <li><a href="/wiki/Mutarotation" title="Mutarotation">Mutarotation</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Monosaccharide" title="Monosaccharide">Monosaccharides</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Diose" title="Diose">Dioses</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>Aldodiose <ul><li><a href="/wiki/Glycolaldehyde" title="Glycolaldehyde">Glycolaldehyde</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Triose" title="Triose">Trioses</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>Aldotriose <ul><li><a href="/wiki/Glyceraldehyde" title="Glyceraldehyde">Glyceraldehyde</a></li></ul></li> <li>Ketotriose <ul><li><a href="/wiki/Dihydroxyacetone" title="Dihydroxyacetone">Dihydroxyacetone</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Tetrose" title="Tetrose">Tetroses</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>Aldotetroses <ul><li><a href="/wiki/Erythrose" title="Erythrose">Erythrose</a></li> <li><a href="/wiki/Threose" title="Threose">Threose</a></li></ul></li> <li>Ketotetrose <ul><li><a href="/wiki/Erythrulose" title="Erythrulose">Erythrulose</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Pentose" title="Pentose">Pentoses</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>Aldopentoses <ul><li><a href="/wiki/Arabinose" title="Arabinose">Arabinose</a></li> <li><a href="/wiki/Lyxose" title="Lyxose">Lyxose</a></li> <li><a href="/wiki/Ribose" title="Ribose">Ribose</a></li> <li><a href="/wiki/Xylose" title="Xylose">Xylose</a></li></ul></li> <li>Ketopentoses <ul><li><a href="/wiki/Ribulose" title="Ribulose">Ribulose</a></li> <li><a href="/wiki/Xylulose" title="Xylulose">Xylulose</a></li></ul></li> <li><a href="/wiki/Deoxy_sugar" title="Deoxy sugar">Deoxy sugars</a> <ul><li><a href="/wiki/Deoxyribose" title="Deoxyribose">Deoxyribose</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Hexose" title="Hexose">Hexoses</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/Aldohexose" class="mw-redirect" title="Aldohexose">Aldohexoses</a> <ul><li><a href="/wiki/Allose" title="Allose">Allose</a></li> <li><a href="/wiki/Altrose" title="Altrose">Altrose</a></li> <li><a href="/wiki/Galactose" title="Galactose">Galactose</a></li> <li><a href="/wiki/Glucose" title="Glucose">Glucose</a></li> <li><a href="/wiki/Gulose" title="Gulose">Gulose</a></li> <li><a href="/wiki/Idose" title="Idose">Idose</a></li> <li><a href="/wiki/Mannose" title="Mannose">Mannose</a></li> <li><a href="/wiki/Talose" title="Talose">Talose</a></li></ul></li> <li><a href="/wiki/Ketohexose" class="mw-redirect" title="Ketohexose">Ketohexoses</a> <ul><li><a href="/wiki/Fructose" title="Fructose">Fructose</a></li> <li><a href="/wiki/Psicose" title="Psicose">Psicose</a></li> <li><a href="/wiki/Sorbose" title="Sorbose">Sorbose</a></li> <li><a href="/wiki/Tagatose" title="Tagatose">Tagatose</a></li></ul></li> <li>Deoxy sugars <ul><li><a href="/wiki/Fucose" title="Fucose">Fucose</a></li> <li><a href="/wiki/Fuculose" title="Fuculose">Fuculose</a></li> <li><a href="/wiki/Rhamnose" title="Rhamnose">Rhamnose</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a class="mw-selflink selflink">Heptoses</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>Ketoheptoses <ul><li><a href="/wiki/Mannoheptulose" title="Mannoheptulose">Mannoheptulose</a></li> <li><a href="/wiki/Sedoheptulose" title="Sedoheptulose">Sedoheptulose</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Above 7</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/Octose" title="Octose">Octoses</a></li> <li><a href="/wiki/Nonose" title="Nonose">Nonoses</a> <ul><li><a href="/wiki/Neuraminic_acid" title="Neuraminic acid">Neuraminic acid</a></li></ul></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Multiple</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Disaccharide" title="Disaccharide">Disaccharides</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/Cellobiose" title="Cellobiose">Cellobiose</a></li> <li><a href="/wiki/Isomaltose" title="Isomaltose">Isomaltose</a></li> <li><a href="/wiki/Isomaltulose" title="Isomaltulose">Isomaltulose</a></li> <li><a href="/wiki/Lactose" title="Lactose">Lactose</a></li> <li><a href="/wiki/Lactulose" title="Lactulose">Lactulose</a></li> <li><a href="/wiki/Maltose" title="Maltose">Maltose</a></li> <li><a href="/wiki/Sucrose" title="Sucrose">Sucrose</a></li> <li><a href="/wiki/Trehalose" title="Trehalose">Trehalose</a></li> <li><a href="/wiki/Turanose" title="Turanose">Turanose</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Trisaccharide" title="Trisaccharide">Trisaccharides</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/Maltotriose" title="Maltotriose">Maltotriose</a></li> <li><a href="/wiki/Melezitose" title="Melezitose">Melezitose</a></li> <li><a href="/wiki/Raffinose" title="Raffinose">Raffinose</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Tetrasaccharide" title="Tetrasaccharide">Tetrasaccharides</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/Stachyose" title="Stachyose">Stachyose</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other<br /> <a href="/wiki/Oligosaccharide" title="Oligosaccharide">oligosaccharides</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/Acarbose" title="Acarbose">Acarbose</a></li> <li><a href="/wiki/Fructooligosaccharide" title="Fructooligosaccharide">Fructooligosaccharide</a> (FOS)</li> <li><a href="/wiki/Galactooligosaccharide" title="Galactooligosaccharide">Galactooligosaccharide</a> (GOS)</li> <li><a href="/wiki/Isomaltooligosaccharide" title="Isomaltooligosaccharide">Isomaltooligosaccharide</a> (IMO)</li> <li><a href="/wiki/Maltodextrin" title="Maltodextrin">Maltodextrin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Polysaccharide" title="Polysaccharide">Polysaccharides</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/Beta-glucan" title="Beta-glucan">Beta-glucan</a> <ul><li><a href="/wiki/Oat_beta-glucan" title="Oat beta-glucan">Oat beta-glucan</a></li> <li><a href="/wiki/Lentinan" title="Lentinan">Lentinan</a></li> <li><a href="/wiki/Schizophyllan" title="Schizophyllan">Sizofiran</a></li> <li><a href="/wiki/Zymosan" title="Zymosan">Zymosan</a></li> <li><a href="/wiki/Cellulose" title="Cellulose">Cellulose</a></li> <li><a href="/wiki/Chitin" title="Chitin">Chitin</a></li></ul></li> <li><a href="/wiki/Chitosan" title="Chitosan">Chitosan</a></li> <li><a href="/wiki/Dextrin" title="Dextrin">Dextrin</a> / <a href="/wiki/Dextran" title="Dextran">Dextran</a></li> <li><i><a href="/wiki/Fructose" title="Fructose">Fructose</a> / <a href="/wiki/Fructan" title="Fructan">Fructan</a></i> <ul><li><a href="/wiki/Inulin" title="Inulin">Inulin</a></li></ul></li> <li><i><a href="/wiki/Galactose" title="Galactose">Galactose</a> / <a href="/wiki/Galactose" title="Galactose">Galactan</a></i></li> <li><i><a href="/wiki/Glucose" title="Glucose">Glucose</a> / <a href="/wiki/Glucan" title="Glucan">Glucan</a></i> <ul><li><a href="/wiki/Glycogen" title="Glycogen">Glycogen</a></li></ul></li> <li><a href="/wiki/Hemicellulose" title="Hemicellulose">Hemicellulose</a></li> <li><a href="/wiki/Levan_polysaccharide" title="Levan polysaccharide">Levan beta 2→6</a></li> <li><a href="/wiki/Lignin" title="Lignin">Lignin</a></li> <li><a href="/wiki/Mannans" title="Mannans">Mannan</a></li> <li><a href="/wiki/Pectin" title="Pectin">Pectin</a></li> <li><a href="/wiki/Starch" title="Starch">Starch</a> <ul><li><a href="/wiki/Amylopectin" title="Amylopectin">Amylopectin</a></li> <li><a href="/wiki/Amylose" title="Amylose">Amylose</a></li></ul></li> <li><a href="/wiki/Xanthan_gum" title="Xanthan gum">Xanthan gum</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <ul><li><span class="noviewer" typeof="mw:File"><span title="Category"><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/16px-Symbol_category_class.svg.png" decoding="async" width="16" height="16" class="mw-file-element" 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