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Article: Total Synthesis of Daptomycin by Cyclization via a Chemoselective Serine Ligation

TitleTotal Synthesis of Daptomycin by Cyclization via a Chemoselective Serine Ligation
Authors
Issue Date2013
PublisherAmerican Chemical Society. The Journal's web site is located at http://pubs.acs.org/journals/jacsat/index.html
Citation
Journal of the American Chemical Society, 2013, v. 135 n. 16, p. 6272-6279 How to Cite?
AbstractA total synthesis of daptomycin, the first natural product antibiotic launched in a generation, was achieved. This convergent synthesis relies on an efficient macrocyclization via a serine ligation to assemble the 31-membered cyclic depsipeptide. The difficult esterification by the nonproteinogenic amino acid kynurenine was accomplished via the esterification of a threonine residue by a suitably protected Trp ester, followed by ozonolysis. This synthesis provides a foundation and framework to prepare varied analogues of daptomycin to establish its structure–activity profile.
Persistent Identifierhttp://hdl.handle.net/10722/185680
ISSN
2023 Impact Factor: 14.4
2023 SCImago Journal Rankings: 5.489
ISI Accession Number ID

 

DC FieldValueLanguage
dc.contributor.authorLam, HY-
dc.contributor.authorZhang, Y-
dc.contributor.authorLiu, H-
dc.contributor.authorXu, J-
dc.contributor.authorWong, CTT-
dc.contributor.authorXu, C-
dc.contributor.authorLi, X-
dc.date.accessioned2013-08-20T11:37:23Z-
dc.date.available2013-08-20T11:37:23Z-
dc.date.issued2013-
dc.identifier.citationJournal of the American Chemical Society, 2013, v. 135 n. 16, p. 6272-6279-
dc.identifier.issn0002-7863-
dc.identifier.urihttp://hdl.handle.net/10722/185680-
dc.description.abstractA total synthesis of daptomycin, the first natural product antibiotic launched in a generation, was achieved. This convergent synthesis relies on an efficient macrocyclization via a serine ligation to assemble the 31-membered cyclic depsipeptide. The difficult esterification by the nonproteinogenic amino acid kynurenine was accomplished via the esterification of a threonine residue by a suitably protected Trp ester, followed by ozonolysis. This synthesis provides a foundation and framework to prepare varied analogues of daptomycin to establish its structure–activity profile.-
dc.languageeng-
dc.publisherAmerican Chemical Society. The Journal's web site is located at http://pubs.acs.org/journals/jacsat/index.html-
dc.relation.ispartofJournal of the American Chemical Society-
dc.titleTotal Synthesis of Daptomycin by Cyclization via a Chemoselective Serine Ligation-
dc.typeArticle-
dc.identifier.emailZhang, Y: yimzhang@hku.hk-
dc.identifier.emailLiu, H: liuhan@hku.hk-
dc.identifier.emailWong, CTT: cttwong@hku.hk-
dc.identifier.emailLi, X: xuechenl@hku.hk-
dc.identifier.authorityLiu, H=rp02748-
dc.identifier.authorityLi, X=rp00742-
dc.description.naturelink_to_subscribed_fulltext-
dc.identifier.doi10.1021/ja4012468-
dc.identifier.pmid23560543-
dc.identifier.scopuseid_2-s2.0-84876726616-
dc.identifier.hkuros219112-
dc.identifier.volume135-
dc.identifier.issue16-
dc.identifier.spage6272-
dc.identifier.epage6279-
dc.identifier.isiWOS:000318204800053-
dc.publisher.placeUnited States-
dc.identifier.issnl0002-7863-

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