Synthesis of CJ-15,208, a novel κ-opioid receptor antagonist
A strategy to select linear precursor peptides favoring cyclization was developed and cyclization conditions were optimized. The tryptophan isomers of the cyclic tetrapeptide CJ-15,208, reported to be a kappa opioid receptor (KOR) antagonist [Saito, T.; Hirai, H.; Kim, Y. J.; Kojima, Y.; Matsunaga,...
Gespeichert in:
| Veröffentlicht in: | Tetrahedron letters 2010-09, Vol.51 (38), p.5020-5023 |
|---|---|
| Hauptverfasser: | , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 5023 |
|---|---|
| container_issue | 38 |
| container_start_page | 5020 |
| container_title | Tetrahedron letters |
| container_volume | 51 |
| creator | Ross, Nicolette C. Kulkarni, Santosh S. McLaughlin, Jay P. Aldrich, Jane V. |
| description | A strategy to select linear precursor peptides favoring cyclization was developed and cyclization conditions were optimized.
The tryptophan isomers of the cyclic tetrapeptide CJ-15,208, reported to be a kappa opioid receptor (KOR) antagonist [Saito, T.; Hirai, H.; Kim, Y. J.; Kojima, Y.; Matsunaga, Y.; Nishida, H.; Sakakibara, T.; Suga, O.; Sujaku, T.; Kojima, N.
J. Antibiot. (Tokyo)
2002,
55, 847–854.], were synthesized to determine the tryptophan stereochemistry in the natural product. A strategy was developed to select linear precursor peptides that favor cyclization using molecular modeling, and optimized cyclization conditions are reported. The optical rotation of the
l-Trp isomer is consistent with that of the natural product. Unexpectedly both isomers exhibit similar nanomolar affinity for KOR. |
| doi_str_mv | 10.1016/j.tetlet.2010.07.086 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_pubme</sourceid><recordid>TN_cdi_pubmedcentral_primary_oai_pubmedcentral_nih_gov_3411353</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><els_id>S0040403910012797</els_id><sourcerecordid>1835551807</sourcerecordid><originalsourceid>FETCH-LOGICAL-c463t-7d02488edef6673a9729b46759f0f5bb01de83a9f9e912a44d67dec57426c3843</originalsourceid><addsrcrecordid>eNp9kMlqHDEQhkVIsMfLG4TQxxzck1Jr7YMNZoizYMjB9llopGpbQ09rImkG_Gp5iDxTZMZxkkvqUlDL_1d9hLylMKdA5YfVvGAZscw7qCVQc9DyFZlRrVjLhKavyQyAQ8uB9YfkKOcV1JAaDshh12kpeqZm5PzmcSoPmENu4tAsvrZUnHWgzxrbTHGHY_PzRxs3IQbfJHS4KTE1dir2Pk4hlxPyZrBjxtPnfEzurj7eLj63198-fVlcXreOS1Za5aHjWqPHQUrFbK-6fsmlEv0Ag1gugXrUtTz02NPOcu6l8uiE4p10THN2TC72upvtco3e4VSSHc0mhbVNjybaYP7tTOHB3MedYZxSJlgVeP8skOL3LeZi1iE7HEc7YdxmQzUTQlANqo7y_ahLMeeEw4sNBfNE3qzMnrx5Im9AmUq-rr37-8SXpd-o__yAFdQuYDLZBZwc-lDJFuNj-L_DL5iVlmk</addsrcrecordid><sourcetype>Open Access Repository</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1835551807</pqid></control><display><type>article</type><title>Synthesis of CJ-15,208, a novel κ-opioid receptor antagonist</title><source>ScienceDirect Journals (5 years ago - present)</source><creator>Ross, Nicolette C. ; Kulkarni, Santosh S. ; McLaughlin, Jay P. ; Aldrich, Jane V.</creator><creatorcontrib>Ross, Nicolette C. ; Kulkarni, Santosh S. ; McLaughlin, Jay P. ; Aldrich, Jane V.</creatorcontrib><description>A strategy to select linear precursor peptides favoring cyclization was developed and cyclization conditions were optimized.
The tryptophan isomers of the cyclic tetrapeptide CJ-15,208, reported to be a kappa opioid receptor (KOR) antagonist [Saito, T.; Hirai, H.; Kim, Y. J.; Kojima, Y.; Matsunaga, Y.; Nishida, H.; Sakakibara, T.; Suga, O.; Sujaku, T.; Kojima, N.
J. Antibiot. (Tokyo)
2002,
55, 847–854.], were synthesized to determine the tryptophan stereochemistry in the natural product. A strategy was developed to select linear precursor peptides that favor cyclization using molecular modeling, and optimized cyclization conditions are reported. The optical rotation of the
l-Trp isomer is consistent with that of the natural product. Unexpectedly both isomers exhibit similar nanomolar affinity for KOR.</description><identifier>ISSN: 0040-4039</identifier><identifier>EISSN: 1873-3581</identifier><identifier>DOI: 10.1016/j.tetlet.2010.07.086</identifier><identifier>PMID: 22865937</identifier><language>eng</language><publisher>England: Elsevier Ltd</publisher><subject>Cyclic tetrapeptide ; Cyclization ; Molecular modeling</subject><ispartof>Tetrahedron letters, 2010-09, Vol.51 (38), p.5020-5023</ispartof><rights>2010 Elsevier Ltd</rights><rights>2010 Elsevier Ltd. All rights reserved. 2010</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c463t-7d02488edef6673a9729b46759f0f5bb01de83a9f9e912a44d67dec57426c3843</citedby><cites>FETCH-LOGICAL-c463t-7d02488edef6673a9729b46759f0f5bb01de83a9f9e912a44d67dec57426c3843</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.tetlet.2010.07.086$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>230,314,780,784,885,3541,27915,27916,45986</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/22865937$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Ross, Nicolette C.</creatorcontrib><creatorcontrib>Kulkarni, Santosh S.</creatorcontrib><creatorcontrib>McLaughlin, Jay P.</creatorcontrib><creatorcontrib>Aldrich, Jane V.</creatorcontrib><title>Synthesis of CJ-15,208, a novel κ-opioid receptor antagonist</title><title>Tetrahedron letters</title><addtitle>Tetrahedron Lett</addtitle><description>A strategy to select linear precursor peptides favoring cyclization was developed and cyclization conditions were optimized.
The tryptophan isomers of the cyclic tetrapeptide CJ-15,208, reported to be a kappa opioid receptor (KOR) antagonist [Saito, T.; Hirai, H.; Kim, Y. J.; Kojima, Y.; Matsunaga, Y.; Nishida, H.; Sakakibara, T.; Suga, O.; Sujaku, T.; Kojima, N.
J. Antibiot. (Tokyo)
2002,
55, 847–854.], were synthesized to determine the tryptophan stereochemistry in the natural product. A strategy was developed to select linear precursor peptides that favor cyclization using molecular modeling, and optimized cyclization conditions are reported. The optical rotation of the
l-Trp isomer is consistent with that of the natural product. Unexpectedly both isomers exhibit similar nanomolar affinity for KOR.</description><subject>Cyclic tetrapeptide</subject><subject>Cyclization</subject><subject>Molecular modeling</subject><issn>0040-4039</issn><issn>1873-3581</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2010</creationdate><recordtype>article</recordtype><recordid>eNp9kMlqHDEQhkVIsMfLG4TQxxzck1Jr7YMNZoizYMjB9llopGpbQ09rImkG_Gp5iDxTZMZxkkvqUlDL_1d9hLylMKdA5YfVvGAZscw7qCVQc9DyFZlRrVjLhKavyQyAQ8uB9YfkKOcV1JAaDshh12kpeqZm5PzmcSoPmENu4tAsvrZUnHWgzxrbTHGHY_PzRxs3IQbfJHS4KTE1dir2Pk4hlxPyZrBjxtPnfEzurj7eLj63198-fVlcXreOS1Za5aHjWqPHQUrFbK-6fsmlEv0Ag1gugXrUtTz02NPOcu6l8uiE4p10THN2TC72upvtco3e4VSSHc0mhbVNjybaYP7tTOHB3MedYZxSJlgVeP8skOL3LeZi1iE7HEc7YdxmQzUTQlANqo7y_ahLMeeEw4sNBfNE3qzMnrx5Im9AmUq-rr37-8SXpd-o__yAFdQuYDLZBZwc-lDJFuNj-L_DL5iVlmk</recordid><startdate>20100920</startdate><enddate>20100920</enddate><creator>Ross, Nicolette C.</creator><creator>Kulkarni, Santosh S.</creator><creator>McLaughlin, Jay P.</creator><creator>Aldrich, Jane V.</creator><general>Elsevier Ltd</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><scope>5PM</scope></search><sort><creationdate>20100920</creationdate><title>Synthesis of CJ-15,208, a novel κ-opioid receptor antagonist</title><author>Ross, Nicolette C. ; Kulkarni, Santosh S. ; McLaughlin, Jay P. ; Aldrich, Jane V.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c463t-7d02488edef6673a9729b46759f0f5bb01de83a9f9e912a44d67dec57426c3843</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2010</creationdate><topic>Cyclic tetrapeptide</topic><topic>Cyclization</topic><topic>Molecular modeling</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Ross, Nicolette C.</creatorcontrib><creatorcontrib>Kulkarni, Santosh S.</creatorcontrib><creatorcontrib>McLaughlin, Jay P.</creatorcontrib><creatorcontrib>Aldrich, Jane V.</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>Tetrahedron letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Ross, Nicolette C.</au><au>Kulkarni, Santosh S.</au><au>McLaughlin, Jay P.</au><au>Aldrich, Jane V.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of CJ-15,208, a novel κ-opioid receptor antagonist</atitle><jtitle>Tetrahedron letters</jtitle><addtitle>Tetrahedron Lett</addtitle><date>2010-09-20</date><risdate>2010</risdate><volume>51</volume><issue>38</issue><spage>5020</spage><epage>5023</epage><pages>5020-5023</pages><issn>0040-4039</issn><eissn>1873-3581</eissn><abstract>A strategy to select linear precursor peptides favoring cyclization was developed and cyclization conditions were optimized.
The tryptophan isomers of the cyclic tetrapeptide CJ-15,208, reported to be a kappa opioid receptor (KOR) antagonist [Saito, T.; Hirai, H.; Kim, Y. J.; Kojima, Y.; Matsunaga, Y.; Nishida, H.; Sakakibara, T.; Suga, O.; Sujaku, T.; Kojima, N.
J. Antibiot. (Tokyo)
2002,
55, 847–854.], were synthesized to determine the tryptophan stereochemistry in the natural product. A strategy was developed to select linear precursor peptides that favor cyclization using molecular modeling, and optimized cyclization conditions are reported. The optical rotation of the
l-Trp isomer is consistent with that of the natural product. Unexpectedly both isomers exhibit similar nanomolar affinity for KOR.</abstract><cop>England</cop><pub>Elsevier Ltd</pub><pmid>22865937</pmid><doi>10.1016/j.tetlet.2010.07.086</doi><tpages>4</tpages><oa>free_for_read</oa></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0040-4039 |
| ispartof | Tetrahedron letters, 2010-09, Vol.51 (38), p.5020-5023 |
| issn | 0040-4039 1873-3581 |
| language | eng |
| recordid | cdi_pubmedcentral_primary_oai_pubmedcentral_nih_gov_3411353 |
| source | ScienceDirect Journals (5 years ago - present) |
| subjects | Cyclic tetrapeptide Cyclization Molecular modeling |
| title | Synthesis of CJ-15,208, a novel κ-opioid receptor antagonist |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-15T02%3A42%3A37IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_pubme&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Synthesis%20of%20CJ-15,208,%20a%20novel%20%CE%BA-opioid%20receptor%20antagonist&rft.jtitle=Tetrahedron%20letters&rft.au=Ross,%20Nicolette%20C.&rft.date=2010-09-20&rft.volume=51&rft.issue=38&rft.spage=5020&rft.epage=5023&rft.pages=5020-5023&rft.issn=0040-4039&rft.eissn=1873-3581&rft_id=info:doi/10.1016/j.tetlet.2010.07.086&rft_dat=%3Cproquest_pubme%3E1835551807%3C/proquest_pubme%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=1835551807&rft_id=info:pmid/22865937&rft_els_id=S0040403910012797&rfr_iscdi=true |