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Article: Encouraging progress in the ω-aspartylation of complex oligosaccharides as a general route to β-N-linked glycopolypeptides

TitleEncouraging progress in the ω-aspartylation of complex oligosaccharides as a general route to β-N-linked glycopolypeptides
Authors
Wang, PLi, XZhu, JChen, JYuan, YWu, XDanishefsky, SJ
Issue Date2011
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, 2011, v. 133 n. 5, p. 1597-1602 How to Cite?
DOI: http://dx.doi.org/10.1021/ja110115a
AbstractDescribed herein is a method for the joining of complex peptides to complex oligosaccharides via an N-linkage. The ω-aspartylation is conducted by coupling fully deprotected glycosylamine with a peptide containing a unique thioacid at the ω-aspartate carboxyl. In the presence of HOBT, under conditions that, in principle, allow for oxidation, complex components are combined in encouraging yields to produce structurally and stereochemically defined N-linked glycopolypeptides wherein the carbohydrate domain can be quite complex. Various mechanisms for oxidative coupling are proposed. © 2011 American Chemical Society.
Persistent Identifierhttp://hdl.handle.net/10722/168506
ISSN
0002-7863
2021 Impact Factor: 16.383
2020 SCImago Journal Rankings: 7.115
ISI Accession Number ID
WOS:000287228500075
References
References in Scopus

 

DC FieldValueLanguage
dc.contributor.authorWang, Pen_US
dc.contributor.authorLi, Xen_US
dc.contributor.authorZhu, Jen_US
dc.contributor.authorChen, Jen_US
dc.contributor.authorYuan, Yen_US
dc.contributor.authorWu, Xen_US
dc.contributor.authorDanishefsky, SJen_US
dc.date.accessioned2012-10-08T03:19:47Z-
dc.date.available2012-10-08T03:19:47Z-
dc.date.issued2011en_US
dc.identifier.citationJournal Of The American Chemical Society, 2011, v. 133 n. 5, p. 1597-1602en_US
dc.identifier.issn0002-7863en_US
dc.identifier.urihttp://hdl.handle.net/10722/168506-
dc.description.abstractDescribed herein is a method for the joining of complex peptides to complex oligosaccharides via an N-linkage. The ω-aspartylation is conducted by coupling fully deprotected glycosylamine with a peptide containing a unique thioacid at the ω-aspartate carboxyl. In the presence of HOBT, under conditions that, in principle, allow for oxidation, complex components are combined in encouraging yields to produce structurally and stereochemically defined N-linked glycopolypeptides wherein the carbohydrate domain can be quite complex. Various mechanisms for oxidative coupling are proposed. © 2011 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.meshAmines - Chemistryen_US
dc.subject.meshAmino Acid Sequenceen_US
dc.subject.meshAspartic Acid - Chemistryen_US
dc.subject.meshGlycopeptides - Chemical Synthesis - Chemistryen_US
dc.subject.meshNitrogen - Chemistryen_US
dc.subject.meshOligosaccharides - Chemistryen_US
dc.titleEncouraging progress in the ω-aspartylation of complex oligosaccharides as a general route to β-N-linked glycopolypeptidesen_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/ja110115aen_US
dc.identifier.pmid21207981-
dc.identifier.scopuseid_2-s2.0-79551711838en_US
dc.relation.referenceshttp://www.scopus.com/mlt/select.url?eid=2-s2.0-79551711838&selection=ref&src=s&origin=recordpageen_US
dc.identifier.volume133en_US
dc.identifier.issue5en_US
dc.identifier.spage1597en_US
dc.identifier.epage1602en_US
dc.identifier.isiWOS:000287228500075-
dc.publisher.placeUnited Statesen_US
dc.identifier.scopusauthoridWang, P=35220801200en_US
dc.identifier.scopusauthoridLi, X=24168958800en_US
dc.identifier.scopusauthoridZhu, J=8583321500en_US
dc.identifier.scopusauthoridChen, J=35775129200en_US
dc.identifier.scopusauthoridYuan, Y=35180688100en_US
dc.identifier.scopusauthoridWu, X=26650236700en_US
dc.identifier.scopusauthoridDanishefsky, SJ=7202925243en_US
dc.identifier.issnl0002-7863-

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