Versatile Functionalization of Carbohydrate Hydroxyl Groups through Their O-Cyanomethyl Ethers

O-Cyanomethyl ethers of carbohydrates are shown to be versatile intermediates for the preparation of sugar amines, carboxylic acids, amides, and amidine salts. This methodology for the functionalization of carbohydrates can thus provide a new array of analogs for the study of carbohydrate binding proteins. In addition, the resulting O-aminoethyl and O-carboxymethyl carbohydrates can be coupled to amino acids under standard conditions used in solid-phase peptide synthesis, providing a method for the construction of glycopeptides in which the carbohydrate moiety can be linked through any of its hydroxyl groups to the C- or the N-terminus of a given peptide.