THE CARBOHYDRATE–PROTEIN LINKAGE IN GLYCOPROTEINS: PART I. THE SYNTHESES OF SOME MODEL SUBSTITUTED AMIDES AND AN L-SERYL-D-GLUCOSAMINIDE

Abstract

The syntheses of N-L-seryl-D-glucosamine, N-glycyl-D-glucosamine, N-L-glutamyl-D-glucosamine, and 1-O-β-L-seryl-N-acetyl-D-glucosaminide are described. These D-glucosamine derivatives may result from the fragmentation of some glycoproteins. The chemical properties of these compounds indicate that N-peptides are relatively stable in acid solution but unstable in neutral and alkaline solution. The seryl glucosaminide is relatively stable in alkaline solution but is hydrolyzed by acid.