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Article: Total Synthesis and Structural Establishment/Revision of the Antibiotics A54145

TitleTotal Synthesis and Structural Establishment/Revision of the Antibiotics A54145
Authors
Issue Date2019
PublisherAmerican Chemical Society. The Journal's web site is located at http://pubs.acs.org/journals/orlef7/index.html
Citation
Organic Letters, 2019, v. 21 n. 14, p. 5639-5644 How to Cite?
AbstractA54145 is a family of antibacterial cyclic lipodepsipeptides structurally resembling daptomycin. Since its discovery in 1990, only the ambiguous structure of the methoxy-aspartic acid (MeO-Asp) and the hydroxy-asparagine (HO-Asn) have been reported. We have developed efficient routes to obtain the fully protected L-MeO-Asp and L-HO-Asn building blocks compatible with Fmoc-SPPS, and a total synthesis of A54145 that enabled us to establish its structure, consisting of L-3S-HO-Asn and L-3R-MeO-Asp, revising the wrongly proposed structure of L-3S-MeO-Asp.
Persistent Identifierhttp://hdl.handle.net/10722/272839
ISSN
2017 Impact Factor: 6.492
2015 SCImago Journal Rankings: 3.187

 

DC FieldValueLanguage
dc.contributor.authorChen, D-
dc.contributor.authorChow, HY-
dc.contributor.authorPo, KHL-
dc.contributor.authorMa, W-
dc.contributor.authorLeung, LY-
dc.contributor.authorSun, Z-
dc.contributor.authorLiu, M-
dc.contributor.authorLi, X-
dc.date.accessioned2019-08-06T09:17:32Z-
dc.date.available2019-08-06T09:17:32Z-
dc.date.issued2019-
dc.identifier.citationOrganic Letters, 2019, v. 21 n. 14, p. 5639-5644-
dc.identifier.issn1523-7060-
dc.identifier.urihttp://hdl.handle.net/10722/272839-
dc.description.abstractA54145 is a family of antibacterial cyclic lipodepsipeptides structurally resembling daptomycin. Since its discovery in 1990, only the ambiguous structure of the methoxy-aspartic acid (MeO-Asp) and the hydroxy-asparagine (HO-Asn) have been reported. We have developed efficient routes to obtain the fully protected L-MeO-Asp and L-HO-Asn building blocks compatible with Fmoc-SPPS, and a total synthesis of A54145 that enabled us to establish its structure, consisting of L-3S-HO-Asn and L-3R-MeO-Asp, revising the wrongly proposed structure of L-3S-MeO-Asp.-
dc.languageeng-
dc.publisherAmerican Chemical Society. The Journal's web site is located at http://pubs.acs.org/journals/orlef7/index.html-
dc.relation.ispartofOrganic Letters-
dc.rightsThis document is the Accepted Manuscript version of a Published Work that appeared in final form in [JournalTitle], copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see [insert ACS Articles on Request author-directed link to Published Work, see http://pubs.acs.org/page/policy/articlesonrequest/index.html].-
dc.titleTotal Synthesis and Structural Establishment/Revision of the Antibiotics A54145-
dc.typeArticle-
dc.identifier.emailChen, D: delinc@hku.hk-
dc.identifier.emailLi, X: xuechenl@hku.hk-
dc.identifier.authorityLi, X=rp00742-
dc.description.naturelink_to_subscribed_fulltext-
dc.identifier.doi10.1021/acs.orglett.9b01972-
dc.identifier.pmid31265311-
dc.identifier.scopuseid_2-s2.0-85069847781-
dc.identifier.hkuros300314-
dc.identifier.volume21-
dc.identifier.issue14-
dc.identifier.spage5639-
dc.identifier.epage5644-
dc.publisher.placeUnited States-

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