Synthesis and conformational analysis of neoglycoconjugates derived from O- and S-glucose
[Display omitted] • The synthesis and the conformational analysis of four novel neoglycopeptides derived from glucose are described. • These neoglycopeptides incorporate both S- and O-glycosidic linkages. • The sugar and peptide moieties are linked by a four-atom carbon spacer. • The linker allows t...
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Published in | Carbohydrate research Vol. 373; pp. 1 - 8 |
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Main Authors | , , , , , |
Format | Journal Article |
Language | English |
Published |
OXFORD
Elsevier Ltd
24.05.2013
Elsevier |
Subjects | |
Online Access | Get full text |
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Summary: | [Display omitted]
• The synthesis and the conformational analysis of four novel neoglycopeptides derived from glucose are described. • These neoglycopeptides incorporate both S- and O-glycosidic linkages. • The sugar and peptide moieties are linked by a four-atom carbon spacer. • The linker allows the carbohydrate to explore a wide-ranging conformational space.
Using olefin metathesis as a key step, four neoglycoconjugates incorporating α-O-glucose, α-S-glucose or β-S-glucose as a carbohydrate unit and l-serine or l-cysteine as an amino acid moiety have been synthesized. The four-atom carbon spacer allows the carbohydrate to explore a wide-ranging conformational space, which may have important implications for the molecular recognition of these molecules. |
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Bibliography: | ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 |
ISSN: | 0008-6215 1873-426X |
DOI: | 10.1016/j.carres.2013.02.013 |