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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
Kim, SHAugeri, DYang, DKahne, D
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?
DOI: http://dx.doi.org/10.1021/ja00084a018
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
0002-7863
2021 Impact Factor: 16.383
2020 SCImago Journal Rankings: 7.115
ISI Accession Number ID
WOS:A1994NB16900018

 

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
dc.identifier.issnl0002-7863-

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