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Article: The total synthesis of moenomycin A

TitleThe total synthesis of moenomycin A
Authors
Issue Date2006
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, 2006, v. 128 n. 47, p. 15084-15085 How to Cite?
AbstractMoenomycin A is the only known natural antibiotic that inhibits bacterial cell wall synthesis by binding to the transglycosylases that catalyze formation of the carbohydrate chains of peptidoglycan. We report here the total synthesis of moenomycin A using the sulfoxide glycosylation method. A newly discovered byproduct of sulfoxide reactions was isolated that resulted in substantial loss of the glycosyl acceptor. A general method to suppress this byproduct was introduced, which enabled the glycosylations to proceed efficiently. The inverse addition protocol for sulfoxide glycosylations also proved essential in constructing some of the glycosidic linkages. The synthetic route is flexible and will allow for derivatives to be constructed to further analyze moenomycin A's mechanism of action. Copyright © 2006 American Chemical Society.
Persistent Identifierhttp://hdl.handle.net/10722/168078
ISSN
2015 Impact Factor: 13.038
2015 SCImago Journal Rankings: 7.123
ISI Accession Number ID
References

 

DC FieldValueLanguage
dc.contributor.authorTaylor, JGen_US
dc.contributor.authorLi, Xen_US
dc.contributor.authorOberthür, Men_US
dc.contributor.authorZhu, Wen_US
dc.contributor.authorKahne, DEen_US
dc.date.accessioned2012-10-08T03:14:51Z-
dc.date.available2012-10-08T03:14:51Z-
dc.date.issued2006en_US
dc.identifier.citationJournal Of The American Chemical Society, 2006, v. 128 n. 47, p. 15084-15085en_US
dc.identifier.issn0002-7863en_US
dc.identifier.urihttp://hdl.handle.net/10722/168078-
dc.description.abstractMoenomycin A is the only known natural antibiotic that inhibits bacterial cell wall synthesis by binding to the transglycosylases that catalyze formation of the carbohydrate chains of peptidoglycan. We report here the total synthesis of moenomycin A using the sulfoxide glycosylation method. A newly discovered byproduct of sulfoxide reactions was isolated that resulted in substantial loss of the glycosyl acceptor. A general method to suppress this byproduct was introduced, which enabled the glycosylations to proceed efficiently. The inverse addition protocol for sulfoxide glycosylations also proved essential in constructing some of the glycosidic linkages. The synthetic route is flexible and will allow for derivatives to be constructed to further analyze moenomycin A's mechanism of action. Copyright © 2006 American Chemical Society.en_US
dc.languageengen_US
dc.publisherAmerican Chemical Society. The Journal's web site is located at http://pubs.acs.org/journals/jacsat/index.htmlen_US
dc.relation.ispartofJournal of the American Chemical Societyen_US
dc.subject.meshAnti-Bacterial Agents - Chemical Synthesisen_US
dc.subject.meshBambermycins - Chemical Synthesisen_US
dc.subject.meshCarbohydrate Sequenceen_US
dc.subject.meshGlycosylationen_US
dc.subject.meshMolecular Sequence Dataen_US
dc.titleThe total synthesis of moenomycin Aen_US
dc.typeArticleen_US
dc.identifier.emailLi, X:xuechenl@hku.hken_US
dc.identifier.authorityLi, X=rp00742en_US
dc.description.naturelink_to_subscribed_fulltexten_US
dc.identifier.doi10.1021/ja065907xen_US
dc.identifier.pmid17117848-
dc.identifier.scopuseid_2-s2.0-33845193905en_US
dc.relation.referenceshttp://www.scopus.com/mlt/select.url?eid=2-s2.0-33845193905&selection=ref&src=s&origin=recordpageen_US
dc.identifier.volume128en_US
dc.identifier.issue47en_US
dc.identifier.spage15084en_US
dc.identifier.epage15085en_US
dc.identifier.isiWOS:000242216100025-
dc.publisher.placeUnited Statesen_US
dc.identifier.scopusauthoridTaylor, JG=7405408594en_US
dc.identifier.scopusauthoridLi, X=24168958800en_US
dc.identifier.scopusauthoridOberthür, M=6602337316en_US
dc.identifier.scopusauthoridZhu, W=15123327400en_US
dc.identifier.scopusauthoridKahne, DE=7004815939en_US

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