A high affinity, mu-opioid receptor-selective enkephalin analogue lacking an N-terminal tyrosine
We report a high affinity, μ opioid receptor selective enkephalin analogue in which the N-terminal tyrosine residue thought to be required for such high affinity is replaced by phenylalanine. The high affinity can be traced to a shift of the ligand's N-terminal residue within the μ receptor bin...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry letters 1998-10, Vol.8 (19), p.2681-2684 |
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| container_end_page | 2684 |
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| container_issue | 19 |
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| container_title | Bioorganic & medicinal chemistry letters |
| container_volume | 8 |
| creator | Mosberg, Henry I. Ho, Jeffrey C. Sobczyk-Kojiro, Katarzyna |
| description | We report a high affinity, μ opioid receptor selective enkephalin analogue in which the N-terminal tyrosine residue thought to be required for such high affinity is replaced by phenylalanine. The high affinity can be traced to a shift of the ligand's N-terminal residue within the μ receptor binding pocket, which diminishes the importance of the usual hydrogen bond between the tyrosine phenolic moiety and the receptor.
The synthesis of the potent μ opioid receptor agonist JH-54 is described. |
| doi_str_mv | 10.1016/S0960-894X(98)00476-4 |
| format | Article |
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The synthesis of the potent μ opioid receptor agonist JH-54 is described.</description><identifier>ISSN: 0960-894X</identifier><identifier>EISSN: 1464-3405</identifier><identifier>DOI: 10.1016/S0960-894X(98)00476-4</identifier><identifier>PMID: 9873602</identifier><language>eng</language><publisher>Oxford: Elsevier Ltd</publisher><subject>Biological and medical sciences ; Enkephalins - chemical synthesis ; Enkephalins - metabolism ; Enkephalins - pharmacology ; Kinetics ; Medical sciences ; Neuropharmacology ; Neurotransmitters. Neurotransmission. Receptors ; Peptidergic system (neuropeptide, opioid peptide, opiates...). Adenosinergic and purinergic systems ; Peptides, Cyclic - chemistry ; Peptides, Cyclic - metabolism ; Peptides, Cyclic - pharmacology ; Pharmacology. Drug treatments ; Receptors, Opioid, mu - drug effects ; Receptors, Opioid, mu - metabolism ; Structure-Activity Relationship ; Tyrosine - chemistry</subject><ispartof>Bioorganic & medicinal chemistry letters, 1998-10, Vol.8 (19), p.2681-2684</ispartof><rights>1998</rights><rights>1998 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c389t-2c2508500ac1ba362366b03dae8ec662547ad4349b33ed613b393d79b60c78ad3</citedby><cites>FETCH-LOGICAL-c389t-2c2508500ac1ba362366b03dae8ec662547ad4349b33ed613b393d79b60c78ad3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/S0960-894X(98)00476-4$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3536,27903,27904,45974</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=2423189$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/9873602$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Mosberg, Henry I.</creatorcontrib><creatorcontrib>Ho, Jeffrey C.</creatorcontrib><creatorcontrib>Sobczyk-Kojiro, Katarzyna</creatorcontrib><title>A high affinity, mu-opioid receptor-selective enkephalin analogue lacking an N-terminal tyrosine</title><title>Bioorganic & medicinal chemistry letters</title><addtitle>Bioorg Med Chem Lett</addtitle><description>We report a high affinity, μ opioid receptor selective enkephalin analogue in which the N-terminal tyrosine residue thought to be required for such high affinity is replaced by phenylalanine. The high affinity can be traced to a shift of the ligand's N-terminal residue within the μ receptor binding pocket, which diminishes the importance of the usual hydrogen bond between the tyrosine phenolic moiety and the receptor.
The synthesis of the potent μ opioid receptor agonist JH-54 is described.</description><subject>Biological and medical sciences</subject><subject>Enkephalins - chemical synthesis</subject><subject>Enkephalins - metabolism</subject><subject>Enkephalins - pharmacology</subject><subject>Kinetics</subject><subject>Medical sciences</subject><subject>Neuropharmacology</subject><subject>Neurotransmitters. Neurotransmission. Receptors</subject><subject>Peptidergic system (neuropeptide, opioid peptide, opiates...). Adenosinergic and purinergic systems</subject><subject>Peptides, Cyclic - chemistry</subject><subject>Peptides, Cyclic - metabolism</subject><subject>Peptides, Cyclic - pharmacology</subject><subject>Pharmacology. Drug treatments</subject><subject>Receptors, Opioid, mu - drug effects</subject><subject>Receptors, Opioid, mu - metabolism</subject><subject>Structure-Activity Relationship</subject><subject>Tyrosine - chemistry</subject><issn>0960-894X</issn><issn>1464-3405</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1998</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkF1LHDEUhoNUdLX-BCEXpbTQaDLJZJKrIlJbQfTCFnoXM8mZ3dSZzJjMCPvvnXWXve3VgfM-54MHoXNGLxhl8vKRakmJ0uLvF62-UioqScQBWjAhBeGClh_QYo8co5Oc_1HKBBXiCB1pVXFJiwV6usKrsFxh2zQhhnH9DXcT6YfQB48TOBjGPpEMLbgxvAKG-AzDyrYhYhtt2y8nwK11zyEu5wa-JyOkLswJHtepzyHCR3TY2DbD2a6eoj83P35f_yJ3Dz9vr6_uiONKj6RwRUlVSal1rLZcFlzKmnJvQYGTsihFZb3gQtecg5eM11xzX-laUlcp6_kp-rzdO6T-ZYI8mi5kB21rI_RTNlIzJqtKzGC5Bd38YE7QmCGFzqa1YdRszJp3s2ajzWhl3s2azdz57sBUd-D3UzuVc_5pl9vsbNskG13Ie6wQBWdKz9j3LQazjNcAyWQXIDrwYfY9Gt-H_zzyBg17lfI</recordid><startdate>19981006</startdate><enddate>19981006</enddate><creator>Mosberg, Henry I.</creator><creator>Ho, Jeffrey C.</creator><creator>Sobczyk-Kojiro, Katarzyna</creator><general>Elsevier Ltd</general><general>Elsevier</general><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>19981006</creationdate><title>A high affinity, mu-opioid receptor-selective enkephalin analogue lacking an N-terminal tyrosine</title><author>Mosberg, Henry I. ; Ho, Jeffrey C. ; Sobczyk-Kojiro, Katarzyna</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c389t-2c2508500ac1ba362366b03dae8ec662547ad4349b33ed613b393d79b60c78ad3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1998</creationdate><topic>Biological and medical sciences</topic><topic>Enkephalins - chemical synthesis</topic><topic>Enkephalins - metabolism</topic><topic>Enkephalins - pharmacology</topic><topic>Kinetics</topic><topic>Medical sciences</topic><topic>Neuropharmacology</topic><topic>Neurotransmitters. Neurotransmission. Receptors</topic><topic>Peptidergic system (neuropeptide, opioid peptide, opiates...). Adenosinergic and purinergic systems</topic><topic>Peptides, Cyclic - chemistry</topic><topic>Peptides, Cyclic - metabolism</topic><topic>Peptides, Cyclic - pharmacology</topic><topic>Pharmacology. Drug treatments</topic><topic>Receptors, Opioid, mu - drug effects</topic><topic>Receptors, Opioid, mu - metabolism</topic><topic>Structure-Activity Relationship</topic><topic>Tyrosine - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Mosberg, Henry I.</creatorcontrib><creatorcontrib>Ho, Jeffrey C.</creatorcontrib><creatorcontrib>Sobczyk-Kojiro, Katarzyna</creatorcontrib><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Bioorganic & medicinal chemistry letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Mosberg, Henry I.</au><au>Ho, Jeffrey C.</au><au>Sobczyk-Kojiro, Katarzyna</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A high affinity, mu-opioid receptor-selective enkephalin analogue lacking an N-terminal tyrosine</atitle><jtitle>Bioorganic & medicinal chemistry letters</jtitle><addtitle>Bioorg Med Chem Lett</addtitle><date>1998-10-06</date><risdate>1998</risdate><volume>8</volume><issue>19</issue><spage>2681</spage><epage>2684</epage><pages>2681-2684</pages><issn>0960-894X</issn><eissn>1464-3405</eissn><abstract>We report a high affinity, μ opioid receptor selective enkephalin analogue in which the N-terminal tyrosine residue thought to be required for such high affinity is replaced by phenylalanine. The high affinity can be traced to a shift of the ligand's N-terminal residue within the μ receptor binding pocket, which diminishes the importance of the usual hydrogen bond between the tyrosine phenolic moiety and the receptor.
The synthesis of the potent μ opioid receptor agonist JH-54 is described.</abstract><cop>Oxford</cop><pub>Elsevier Ltd</pub><pmid>9873602</pmid><doi>10.1016/S0960-894X(98)00476-4</doi><tpages>4</tpages></addata></record> |
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| ispartof | Bioorganic & medicinal chemistry letters, 1998-10, Vol.8 (19), p.2681-2684 |
| issn | 0960-894X 1464-3405 |
| language | eng |
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| source | MEDLINE; Elsevier ScienceDirect Journals |
| subjects | Biological and medical sciences Enkephalins - chemical synthesis Enkephalins - metabolism Enkephalins - pharmacology Kinetics Medical sciences Neuropharmacology Neurotransmitters. Neurotransmission. Receptors Peptidergic system (neuropeptide, opioid peptide, opiates...). Adenosinergic and purinergic systems Peptides, Cyclic - chemistry Peptides, Cyclic - metabolism Peptides, Cyclic - pharmacology Pharmacology. Drug treatments Receptors, Opioid, mu - drug effects Receptors, Opioid, mu - metabolism Structure-Activity Relationship Tyrosine - chemistry |
| title | A high affinity, mu-opioid receptor-selective enkephalin analogue lacking an N-terminal tyrosine |
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