Application of n-pentenyl glycosides in the regio- and stereo-controlled synthesis of alpha-linked N-glycopeptides.
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.
Ratcliffe
A J
AJ
Department of Chemistry, Paul M. Gross Chemical Laboratory, Duke University, Durham, North Carolina 27706.
Konradsson
P
P
Reid
B F
BF
D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D006020:Glycopeptides / Q000138:chemical synthesis* / Q000737:chemistry; D006027:Glycosides / Q000737:chemistry; D008969:Molecular Sequence Data
D006020:Glycopeptides; D006027:Glycosides