Synthesis of (2R)- and (2S)-aminooxy analogues of β-O-glucosylserine andN-oxyamide linked glycoconjugates

Abstract

Glycosyl amino acids are constituents of glycopeptides and glycoproteins playing important roles in various cellular activities and pathogenic processes. We have stereoselectively synthesized both (2R)- and (2S)-aminooxy analogues of β-O-glucosylserine from sn-(3-β-O-glucosyl)glycerol through selective protection, Mitsunobu reaction, oxidation and Lattrell-Dax epimerization reactions. N-oxyamide linked glycopetides and glycolipids have been prepared from the β-O-glucosyl aminooxy acid derivatives. 1H NMR and IR studies suggest the formation of an α N−O turn structure in the glycopeptide 19.