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Application of n-pentenyl glycosides in the regio- and stereo-controlled synthesis of α-linked N-glycopeptides

✍ Scribed by Andrew J. Ratcliffe; Peter Konradsson; Bert Fraser Reid

Publisher
Elsevier Science
Year
1992
Tongue
English
Weight
955 KB
Volume
216
Category
Article
ISSN
0008-6215

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✦ Synopsis

The N-glycopeptides alpha-Glc-(1----Asn and alpha-Glc-(1----6)-beta-Glc- (1----6)-alpha-Glc-(1----Asn have been synthesized efficiently from pent-4-enyl D-glucopyranoside derivatives. The methodology illustrates (a) a novel route for formation of the N-alpha-D-glucosyl-asparagine link, and (b) stereo-controlled construction of the glycan backbone alpha-Glc-(1----6)-beta-Glc-(1----6)-Glc in which the reactivity of each pentenyl glycosyl donor is controlled by an appropriate promoter. This strategy minimizes the number of changes of protecting groups that is required.

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