Glycosyl amino acids are constituents of glycopeptides and glycoproteins playing key
roles in biological processes. We have synthesized C-glucosyl aminooxy acid derivatives as novel glycosyl amino acid building blocks for
the generation of glycopeptide and glycoprotein mimics. These compounds can be readily
prepared from C-allyl glucosides, through dihydroxylation, selective tritylation, Mitsunobu reaction
with PhthNOH, detritylation, and oxidation. Both C-glucosyl l- and d-α-aminooxy esters have been successfully synthesized. With the ready availability
of C-allyl glycosides, the present methodology could be applied to the synthesis of other
C-glycosyl aminooxy acid derivatives.
Key words
aminooxy acids - glycopeptides - glycosyl aminooxy acids -
C-allyl glycosides - Mitsunobu reaction
