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Synthesis of CJ-15,208, a novel κ-opioid receptor antagonist

dc.contributor.authorRoss, Nicolette C.
dc.contributor.authorKulkarni, Santosh S.
dc.contributor.authorMcLaughlin, Jay P.
dc.contributor.authorAldrich, Jane V.
dc.date.accessioned2017-04-19T20:37:01Z
dc.date.available2017-04-19T20:37:01Z
dc.date.issued2010-09-20
dc.identifier.citationRoss, Nicolette C. et al. “Synthesis of CJ-15,208, a Novel Κ-Opioid Receptor Antagonist.” Tetrahedron letters 51.38 (2010): 5020–5023.en_US
dc.identifier.urihttp://hdl.handle.net/1808/23743
dc.description.abstractThe 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.en_US
dc.publisherElsevieren_US
dc.rightsThis is an open access article under the terms of the Creative Commons Attribution-NonCommercial-NoDerivs License 3.0 (CC BY-NC-ND 3.0 US), which permits use and distribution in any medium, provided the original work is properly cited, the use is non-commercial and no modifications or adaptations are made.en_US
dc.rights.urihttp://creativecommons.org/licenses/by-nc-nd/3.0/
dc.subjectCyclic tetrapeptideen_US
dc.subjectCyclizationen_US
dc.subjectMolecular modelingen_US
dc.titleSynthesis of CJ-15,208, a novel κ-opioid receptor antagonisten_US
dc.typeArticleen_US
kusw.kuauthorAldrich, Jane V.
kusw.kudepartmentPharmaceutical Chemistryen_US
dc.identifier.doi10.1016/j.tetlet.2010.07.086en_US
kusw.oaversionScholarly/refereed, author accepted manuscripten_US
kusw.oapolicyThis item meets KU Open Access policy criteria.en_US
dc.rights.accessrightsopenAccess


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This is an open access article under the terms of the Creative Commons Attribution-NonCommercial-NoDerivs License 3.0 (CC BY-NC-ND 3.0 US), which permits use and distribution in any medium, provided the original work is properly cited, the use is non-commercial and no modifications or adaptations are made.
Except where otherwise noted, this item's license is described as: This is an open access article under the terms of the Creative Commons Attribution-NonCommercial-NoDerivs License 3.0 (CC BY-NC-ND 3.0 US), which permits use and distribution in any medium, provided the original work is properly cited, the use is non-commercial and no modifications or adaptations are made.