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- Publisher Website: 10.1021/ja00084a018
- Scopus: eid_2-s2.0-0027940051
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Article: Concise synthesis of the calicheamicin oligosaccharide using the sulfoxide glycosylation method
Title | Concise synthesis of the calicheamicin oligosaccharide using the sulfoxide glycosylation method |
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Authors | |
Issue Date | 1994 |
Publisher | American 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? |
Abstract | A 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 Identifier | http://hdl.handle.net/10722/167514 |
ISSN | 2023 Impact Factor: 14.4 2023 SCImago Journal Rankings: 5.489 |
ISI Accession Number ID |
DC Field | Value | Language |
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dc.contributor.author | Kim, SH | en_US |
dc.contributor.author | Augeri, D | en_US |
dc.contributor.author | Yang, D | en_US |
dc.contributor.author | Kahne, D | en_US |
dc.date.accessioned | 2012-10-08T03:07:56Z | - |
dc.date.available | 2012-10-08T03:07:56Z | - |
dc.date.issued | 1994 | en_US |
dc.identifier.citation | Journal Of The American Chemical Society, 1994, v. 116 n. 5, p. 1766-1775 | en_US |
dc.identifier.issn | 0002-7863 | en_US |
dc.identifier.uri | http://hdl.handle.net/10722/167514 | - |
dc.description.abstract | A 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.language | eng | en_US |
dc.publisher | American Chemical Society. The Journal's web site is located at http://pubs.acs.org/journals/jacsat/index.html | en_US |
dc.relation.ispartof | Journal of the American Chemical Society | en_US |
dc.title | Concise synthesis of the calicheamicin oligosaccharide using the sulfoxide glycosylation method | en_US |
dc.type | Article | en_US |
dc.identifier.email | Yang, D:yangdan@hku.hk | en_US |
dc.identifier.authority | Yang, D=rp00825 | en_US |
dc.description.nature | link_to_subscribed_fulltext | en_US |
dc.identifier.doi | 10.1021/ja00084a018 | en_US |
dc.identifier.scopus | eid_2-s2.0-0027940051 | en_US |
dc.identifier.volume | 116 | en_US |
dc.identifier.issue | 5 | en_US |
dc.identifier.spage | 1766 | en_US |
dc.identifier.epage | 1775 | en_US |
dc.identifier.isi | WOS:A1994NB16900018 | - |
dc.publisher.place | United States | en_US |
dc.identifier.scopusauthorid | Kim, SH=8207117000 | en_US |
dc.identifier.scopusauthorid | Augeri, D=6602800131 | en_US |
dc.identifier.scopusauthorid | Yang, D=7404800756 | en_US |
dc.identifier.scopusauthorid | Kahne, D=7004815939 | en_US |
dc.identifier.issnl | 0002-7863 | - |