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Article: Concise synthesis of the calicheamicin oligosaccharide using the sulfoxide glycosylation method

TitleConcise synthesis of the calicheamicin oligosaccharide using the sulfoxide glycosylation method
Authors
Issue Date1994
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, 1994, v. 116 n. 5, p. 1766-1775 How to Cite?
AbstractA short synthesis of the calicheamicin oligosaccharide is reported. All the glycosidic linkages have been constructed using the sulfoxide glycosylation reaction, demonstrating the efficacy of the method. A general method to introduce N-O glycosidic linkages in oligosaccharides has been developed and employed to construct the N-O bond that connects rings A and B. In the final step of the synthesis, the two halves of the calicheamicin oligosaccharide are coupled in a completely deprotected form. This convergent synthesis permits the rapid construction of derivatives of the calicheamicin oligosaccharide to test the importance of particular structural features in DNA binding.
Persistent Identifierhttp://hdl.handle.net/10722/167514
ISSN
2015 Impact Factor: 13.038
2015 SCImago Journal Rankings: 7.123
ISI Accession Number ID

 

DC FieldValueLanguage
dc.contributor.authorKim, SHen_US
dc.contributor.authorAugeri, Den_US
dc.contributor.authorYang, Den_US
dc.contributor.authorKahne, Den_US
dc.date.accessioned2012-10-08T03:07:56Z-
dc.date.available2012-10-08T03:07:56Z-
dc.date.issued1994en_US
dc.identifier.citationJournal Of The American Chemical Society, 1994, v. 116 n. 5, p. 1766-1775en_US
dc.identifier.issn0002-7863en_US
dc.identifier.urihttp://hdl.handle.net/10722/167514-
dc.description.abstractA short synthesis of the calicheamicin oligosaccharide is reported. All the glycosidic linkages have been constructed using the sulfoxide glycosylation reaction, demonstrating the efficacy of the method. A general method to introduce N-O glycosidic linkages in oligosaccharides has been developed and employed to construct the N-O bond that connects rings A and B. In the final step of the synthesis, the two halves of the calicheamicin oligosaccharide are coupled in a completely deprotected form. This convergent synthesis permits the rapid construction of derivatives of the calicheamicin oligosaccharide to test the importance of particular structural features in DNA binding.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.titleConcise synthesis of the calicheamicin oligosaccharide using the sulfoxide glycosylation methoden_US
dc.typeArticleen_US
dc.identifier.emailYang, D:yangdan@hku.hken_US
dc.identifier.authorityYang, D=rp00825en_US
dc.description.naturelink_to_subscribed_fulltexten_US
dc.identifier.doi10.1021/ja00084a018en_US
dc.identifier.scopuseid_2-s2.0-0027940051en_US
dc.identifier.volume116en_US
dc.identifier.issue5en_US
dc.identifier.spage1766en_US
dc.identifier.epage1775en_US
dc.identifier.isiWOS:A1994NB16900018-
dc.publisher.placeUnited Statesen_US
dc.identifier.scopusauthoridKim, SH=8207117000en_US
dc.identifier.scopusauthoridAugeri, D=6602800131en_US
dc.identifier.scopusauthoridYang, D=7404800756en_US
dc.identifier.scopusauthoridKahne, D=7004815939en_US

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