| Synthesis of a galacto-configured C-ketoside-based gamma-sugar-amino acid and its use in peptide coupling reactions. | |
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MedLine Citation:
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PMID: 16616901 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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Gamma-sugar-amino acid analogues in the form of C-ketosides can be prepared in 5-6 steps starting from D-galactono-1,5-lactone. The key step in the synthesis is the trimethylsilyl trifluoromethanesulfonate (TMSOTf) promoted C-glycosylation of 2-deoxy-3-ulopyranosonates with trimethylsilyl cyanide. Hydrogenation of the resulting beta-cyano esters provides C-ketoside-based gamma-sugar-amino acids that serve as building blocks for the synthesis of unnatural neoglycopeptides. |
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Authors:
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Frank Schweizer; Ole Hindsgaul |
Publication Detail:
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Type: Journal Article; Research Support, Non-U.S. Gov't Date: 2006-04-17 |
Journal Detail:
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Title: Carbohydrate research Volume: 341 ISSN: 0008-6215 ISO Abbreviation: Carbohydr. Res. Publication Date: 2006 Jul |
Date Detail:
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Created Date: 2006-06-05 Completed Date: 2006-08-28 Revised Date: 2006-11-15 |
Medline Journal Info:
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Nlm Unique ID: 0043535 Medline TA: Carbohydr Res Country: Netherlands |
Other Details:
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Languages: eng Pagination: 1730-6 Citation Subset: IM |
Affiliation:
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Department of Chemistry, University of Manitoba, Winnipeg, Manitoba, Canada R3T 2N2. schweize@cc.umanitoba.ca |
Export Citation:
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| MeSH Terms | |
Descriptor/Qualifier:
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Amino Acids
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chemistry Glycopeptides / chemical synthesis* Peptides / chemical synthesis* Sugar Acids / chemistry |
| Chemical | |
Reg. No./Substance:
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0/Amino Acids; 0/Glycopeptides; 0/Peptides; 0/Sugar Acids |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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