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<caption>SYM-2081 </caption> <tbody><tr> <td colspan="2" style="text-align:center; padding:2px;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:SYM2081.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6e/SYM2081.svg/200px-SYM2081.svg.png" decoding="async" width="200" height="101" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6e/SYM2081.svg/300px-SYM2081.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6e/SYM2081.svg/400px-SYM2081.svg.png 2x" data-file-width="512" data-file-height="259" /></a><figcaption></figcaption></figure> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Names </th></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/Chemical_nomenclature" title="Chemical nomenclature">IUPAC name</a> <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;">(2<i>S</i>,4<i>R</i>)-2-Amino-4-methylpentanedioic acid</div> </td></tr> <tr> <td colspan="2" style="text-align:left;">Other names <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;">(2<i>S</i>,4<i>R</i>)-4-Methylglutamic acid</div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Identifiers </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CAS_Registry_Number" title="CAS Registry Number">CAS Number</a></div> </td> <td><style data-mw-deduplicate="TemplateStyles:r1126788409">.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}</style><div class="plainlist"><ul><li><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=31137-74-3">31137-74-3</a></span></li><li><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=77842-39-8">77842-39-8</a></span></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">3D model (<a href="/wiki/JSmol" class="mw-redirect" title="JSmol">JSmol</a>)</div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=C%5BC%40H%5D%28C%5BC%40%40H%5D%28C%28%3DO%29O%29N%29C%28%3DO%29O">Interactive image</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChEBI" title="ChEBI">ChEBI</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chebi/searchId.do?chebiId=228160">CHEBI:228160</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChEMBL" title="ChEMBL">ChEMBL</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chembl/explore/compound/ChEMBL288166">ChEMBL288166</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChemSpider" title="ChemSpider">ChemSpider</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="www.chemspider.com"><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.86558.html">86558</a></span></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/IUPHAR/BPS" class="mw-redirect" title="IUPHAR/BPS">IUPHAR/BPS</a></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="www.guidetopharmacology.org"><a rel="nofollow" class="external text" href="http://www.guidetopharmacology.org/GRAC/LigandDisplayForward?tab=summary&ligandId=10821708">10821708</a></span></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/PubChem" title="PubChem">PubChem</a> <abbr title="Compound ID">CID</abbr></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="pubchem.ncbi.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/95883">95883</a></span></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CompTox_Chemicals_Dashboard" title="CompTox Chemicals Dashboard">CompTox Dashboard</a> <span style="font-weight:normal">(<abbr title="U.S. Environmental Protection Agency">EPA</abbr>)</span></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="comptox.epa.gov"><a rel="nofollow" class="external text" href="https://comptox.epa.gov/dashboard/chemical/details/DTXSID901300044">DTXSID901300044</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q12072315#P3117" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span></span></li></ul></div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal;"><div><a href="/wiki/International_Chemical_Identifier" title="International Chemical Identifier">InChI</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1S/C6H11NO4/c1-3(5(8)9)2-4(7)6(10)11/h3-4H,2,7H2,1H3,(H,8,9)(H,10,11)/t3-,4+/m1/s1</div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: KRKRAOXTGDJWNI-DMTCNVIQSA-N</div></div></li></ul> </div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal;"><div><a href="/wiki/Simplified_molecular-input_line-entry_system" class="mw-redirect" title="Simplified molecular-input line-entry system">SMILES</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.6em; word-wrap:break-word; text-indent:-1.5em; text-align:left; font-size:97%; line-height:120%;">C[C@H](C[C@@H](C(=O)O)N)C(=O)O</div></li></ul> </div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Properties </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Chemical_formula" title="Chemical formula">Chemical formula</a></div> </td> <td><span title="Carbon">C</span><sub>6</sub><span title="Hydrogen">H</span><sub>11</sub><span title="Nitrogen">N</span><span title="Oxygen">O</span><sub>4</sub> </td></tr> <tr> <td><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a> </td> <td><span class="nowrap"><span data-sort-value="7002161157000000000♠"></span>161.157</span> g·mol<sup>−1</sup>   </td></tr> <tr> <td>Appearance </td> <td>White solid </td></tr> <tr> <td colspan="2" style="text-align:left; background:#f8eaba; color:inherit; border:1px solid #a2a9b1;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Except where otherwise noted, data are given for materials in their <a href="/wiki/Standard_state" title="Standard state">standard state</a> (at 25 °C [77 °F], 100 kPa).</div> <div style="margin-top: 0.3em;"></div> <div style="margin-top: 0.3em; text-align: center;"><a href="/wiki/Wikipedia:Chemical_infobox#References" title="Wikipedia:Chemical infobox">Infobox references</a></div> </td></tr> </tbody></table><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Chemical compound</div> <p><b>SYM-2081</b> is a highly selective <a href="/wiki/Agonist" title="Agonist">agonist</a> for the <a href="/wiki/Kainate_receptor" title="Kainate receptor">kainate receptor</a>. This potent agonist has nearly 3,000 fold- and 200-fold selectivity for <a href="/wiki/Kainate_receptor" title="Kainate receptor">kainate receptors</a> over <a href="/wiki/AMPA_receptor" title="AMPA receptor">AMPA</a> and <a href="/wiki/NMDA_receptor" title="NMDA receptor">NMDA receptors</a>, respectively.<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> Given its potency and selectivity, it is a useful ligand for studying the role of <a href="/wiki/Kainate_receptors" class="mw-redirect" title="Kainate receptors">kainate receptors</a> in the <a href="/wiki/Central_nervous_system" title="Central nervous system">central nervous system</a>.<sup id="cite_ref-:0_2-0" class="reference"><a href="#cite_note-:0-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Synthesis">Synthesis</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=SYM-2081&action=edit&section=1" title="Edit section: Synthesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>SYM-2081 can be prepared through diastereomeric mixture via enzymatic synthesis, but the yield of this reaction is small.<sup id="cite_ref-:1_3-0" class="reference"><a href="#cite_note-:1-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> SYM-2081 can be produced at a multi-gram scale by starting with (<i>S</i>)-1-<i>t</i>-butoxycarbonyl-5-<i>t</i>-butyldiphenylsilyoxymethylpyrrolidine-2-one and treating it with one equivalent of <a href="/wiki/Lithium_bis(trimethylsilyl)amide" title="Lithium bis(trimethylsilyl)amide">lithium bis(trimethylsilyl)amide</a> in <a href="/wiki/Tetrahydrofuran" title="Tetrahydrofuran">tetrahydrofuran</a> (THF) at -78 °C.<sup id="cite_ref-:1_3-1" class="reference"><a href="#cite_note-:1-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> The resulting product was mixed with excess <a href="/wiki/Iodomethane" title="Iodomethane">iodomethane</a> which yielded 4-methylated products and some unreacted starting material.<sup id="cite_ref-:1_3-2" class="reference"><a href="#cite_note-:1-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> The trans product was purified through <a href="/wiki/Column_chromatography" title="Column chromatography">column chromatography</a>.<sup id="cite_ref-:1_3-3" class="reference"><a href="#cite_note-:1-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> Next, the product was crystallized by hexanes.<sup id="cite_ref-:1_3-4" class="reference"><a href="#cite_note-:1-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Tetra-n-butylammonium_fluoride" title="Tetra-n-butylammonium fluoride">Tetrabutylammonium fluoride</a> was used for its primary alcohol to selectively remove the <a href="/wiki/Tert-Butyldiphenylsilyl" title="Tert-Butyldiphenylsilyl"><i>tert</i>-butyldiphenylsilyl</a> (TBDPS) protecting group.<sup id="cite_ref-:1_3-5" class="reference"><a href="#cite_note-:1-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> The Sharpless procedure was used to <a href="/wiki/Redox" title="Redox">oxidize</a> the alcohol.<sup id="cite_ref-:1_3-6" class="reference"><a href="#cite_note-:1-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> This intermediate was hydrolyzed with <a href="/wiki/Lithium_hydroxide" title="Lithium hydroxide">lithium hydroxide</a> in <a href="/wiki/Aqueous_solution" title="Aqueous solution">aqueous</a> THF.<sup id="cite_ref-:1_3-7" class="reference"><a href="#cite_note-:1-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> Finally, the compound was treated with <a href="/wiki/Trifluoroacetic_acid" title="Trifluoroacetic acid">trifluoroacetic acid</a> (TFA) in <a href="/wiki/Dichloromethane" title="Dichloromethane">dichloromethane</a> to produce (2<i>S</i>,4<i>R</i>)-4-methylglutamic acid.<sup id="cite_ref-:1_3-8" class="reference"><a href="#cite_note-:1-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Research">Research</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=SYM-2081&action=edit&section=2" title="Edit section: Research"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Some research has indicated that having the methyl group in SYM-2081 is essential for its potency.<sup id="cite_ref-:0_2-1" class="reference"><a href="#cite_note-:0-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> SYM-2081 was 20 times more potent than its (2<i>R</i>,4<i>R</i>) isomer and 1000 times more potent than its (2<i>S</i>,4<i>S</i>) isomer.<sup id="cite_ref-:0_2-2" class="reference"><a href="#cite_note-:0-2"><span class="cite-bracket">[</span>2<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=SYM-2081&action=edit&section=3" 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 cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free 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 (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://www.rndsystems.com/products/sym-2081_0903">"SYM 2081"</a>. <i>R&D Systems</i>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=R%26D+Systems&rft.atitle=SYM+2081&rft_id=https%3A%2F%2Fwww.rndsystems.com%2Fproducts%2Fsym-2081_0903&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASYM-2081" class="Z3988"></span></span> </li> <li id="cite_note-:0-2"><span class="mw-cite-backlink">^ <a href="#cite_ref-:0_2-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-:0_2-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-:0_2-2"><sup><i><b>c</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFDonevanBegGuntherTwyman1998" class="citation journal cs1">Donevan, S. D.; Beg, A.; Gunther, J. M.; Twyman, R. E. (May 1998). <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/9580595">"The methylglutamate, SYM 2081, is a potent and highly selective agonist at kainate receptors"</a>. <i>The Journal of Pharmacology and Experimental Therapeutics</i>. <b>285</b> (2): <span class="nowrap">539–</span>545. <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/0022-3565">0022-3565</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/9580595">9580595</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+Journal+of+Pharmacology+and+Experimental+Therapeutics&rft.atitle=The+methylglutamate%2C+SYM+2081%2C+is+a+potent+and+highly+selective+agonist+at+kainate+receptors&rft.volume=285&rft.issue=2&rft.pages=%3Cspan+class%3D%22nowrap%22%3E539-%3C%2Fspan%3E545&rft.date=1998-05&rft_id=info%3Apmid%2F9580595&rft.issn=0022-3565&rft.aulast=Donevan&rft.aufirst=S.+D.&rft.au=Beg%2C+A.&rft.au=Gunther%2C+J.+M.&rft.au=Twyman%2C+R.+E.&rft_id=https%3A%2F%2Fpubmed.ncbi.nlm.nih.gov%2F9580595&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASYM-2081" class="Z3988"></span></span> </li> <li id="cite_note-:1-3"><span class="mw-cite-backlink">^ <a href="#cite_ref-:1_3-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-:1_3-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-:1_3-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-:1_3-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-:1_3-4"><sup><i><b>e</b></i></sup></a> <a href="#cite_ref-:1_3-5"><sup><i><b>f</b></i></sup></a> <a href="#cite_ref-:1_3-6"><sup><i><b>g</b></i></sup></a> <a href="#cite_ref-:1_3-7"><sup><i><b>h</b></i></sup></a> <a href="#cite_ref-:1_3-8"><sup><i><b>i</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFZi-Qiang_GuXiao-Fa_LinHesson1995" class="citation journal cs1">Zi-Qiang Gu; Xiao-Fa Lin; Hesson, David P. (1995). <a rel="nofollow" class="external text" href="https://doi.org/10.1016/0960-894X(95)00335-Q">"Diastereoselective synthesis of (2S,4R)-4-Methylglutamic acid (sym 2081): A high affinity and selective ligand at the kainate subtype of glutamate receptors"</a>. <i>Bioorganic & Medicinal Chemistry Letters</i>. <b>5</b> (17): <span class="nowrap">1973–</span>1976. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2F0960-894x%2895%2900335-q">10.1016/0960-894x(95)00335-q</a><span class="reference-accessdate">. Retrieved <span class="nowrap">2021-12-10</span></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Bioorganic+%26+Medicinal+Chemistry+Letters&rft.atitle=Diastereoselective+synthesis+of+%282S%2C4R%29-4-Methylglutamic+acid+%28sym+2081%29%3A+A+high+affinity+and+selective+ligand+at+the+kainate+subtype+of+glutamate+receptors&rft.volume=5&rft.issue=17&rft.pages=%3Cspan+class%3D%22nowrap%22%3E1973-%3C%2Fspan%3E1976&rft.date=1995&rft_id=info%3Adoi%2F10.1016%2F0960-894x%2895%2900335-q&rft.au=Zi-Qiang+Gu&rft.au=Xiao-Fa+Lin&rft.au=Hesson%2C+David+P.&rft_id=https%3A%2F%2Fdoi.org%2F10.1016%2F0960-894X%2895%2900335-Q&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASYM-2081" class="Z3988"></span></span> </li> </ol></div></div>    </div><noscript><img src="https://login.wikimedia.org/wiki/Special:CentralAutoLogin/start?useformat=desktop&type=1x1&usesul3=0" alt="" width="1" height="1" style="border: none; position: absolute;"></noscript> <div class="printfooter" data-nosnippet="">Retrieved from "<a dir="ltr" href="https://en.wikipedia.org/w/index.php?title=SYM-2081&oldid=1183322290">https://en.wikipedia.org/w/index.php?title=SYM-2081&oldid=1183322290</a>"</div></div> <div id="catlinks" class="catlinks" data-mw="interface"><div id="mw-normal-catlinks" class="mw-normal-catlinks"><a href="/wiki/Help:Category" title="Help:Category">Categories</a>: <ul><li><a href="/wiki/Category:Amino_acid_derivatives" title="Category:Amino acid derivatives">Amino acid derivatives</a></li><li><a href="/wiki/Category:Dicarboxylic_acids" title="Category:Dicarboxylic acids">Dicarboxylic acids</a></li></ul></div><div id="mw-hidden-catlinks" class="mw-hidden-catlinks mw-hidden-cats-hidden">Hidden categories: <ul><li><a href="/wiki/Category:Chemical_articles_with_multiple_compound_IDs" title="Category:Chemical articles with multiple compound IDs">Chemical articles with multiple compound IDs</a></li><li><a href="/wiki/Category:Multiple_chemicals_in_an_infobox_that_need_indexing" title="Category:Multiple chemicals in an infobox that need indexing">Multiple chemicals in an infobox that need indexing</a></li><li><a href="/wiki/Category:Chemical_articles_with_multiple_CAS_registry_numbers" title="Category:Chemical articles with multiple CAS registry numbers">Chemical articles with multiple CAS registry numbers</a></li><li><a href="/wiki/Category:Articles_without_InChI_source" title="Category:Articles without InChI source">Articles without InChI source</a></li><li><a href="/wiki/Category:Articles_without_KEGG_source" title="Category:Articles without KEGG source">Articles without KEGG source</a></li><li><a href="/wiki/Category:Articles_without_UNII_source" title="Category:Articles without UNII source">Articles without UNII source</a></li><li><a href="/wiki/Category:Articles_containing_unverified_chemical_infoboxes" title="Category:Articles containing unverified chemical infoboxes">Articles containing unverified chemical infoboxes</a></li><li><a href="/wiki/Category:Chembox_image_size_set" title="Category:Chembox image size set">Chembox image size set</a></li><li><a href="/wiki/Category:Articles_with_short_description" title="Category:Articles with short description">Articles with short description</a></li><li><a href="/wiki/Category:Short_description_matches_Wikidata" title="Category:Short description matches Wikidata">Short description matches Wikidata</a></li></ul></div></div> </div> </main> </div> <div class="mw-footer-container"> <footer id="footer" class="mw-footer" > <ul id="footer-info"> <li id="footer-info-lastmod"> This page was last edited on 3 November 2023, at 16:03<span class="anonymous-show"> (UTC)</span>.</li> <li id="footer-info-copyright">Text is available under the <a href="/wiki/Wikipedia:Text_of_the_Creative_Commons_Attribution-ShareAlike_4.0_International_License" title="Wikipedia:Text of the Creative Commons Attribution-ShareAlike 4.0 International License">Creative Commons Attribution-ShareAlike 4.0 License</a>; additional terms may apply. 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