Synthesis of neoglycopeptides by chemoselective reaction of carbohydrates with peptides containing a novel N′-methyl-aminooxy amino acid

A novel N′-methyl-aminooxy amino acid has been designed, synthesized, and successfully incorporated into peptides using standard solid-phase peptide synthesis procedures. Reaction of these peptides with native reducing sugars yields neoglycopeptides via a chemoselective reaction with the aminooxy side chains. The key feature of the new amino acid is that it maintains attached sugars in their cyclic conformations and close to the peptide backbone.