Versatile functionalization of carbohydrate hydroxyl groups through their O-cyanomethyl ethers

The O-cyanomethyl ethers of carbohydrates act as intermediates for the production of sugar amines, carboxylic acids, amides and amidine salts. The technique of carbohydrate functionalization leads to a family of analogs for the study of carbohydrate binding proteins. The addition of amino acids to O-aminoethyl and O-carboxymethyl carbohydrates produces glycopeptides. The reaction enables linkage of the carbohydrate moiety through a hydroxyl group to the C- or the N-terminus of a peptide.