Glycosamino Acids: New Building Blocks for Combinatorial Synthesis

In order to produce inexpensive, chemically diverse carbohydrate building blocks more amenable for use in combinatorial organic synthesis, amine and carboxylic acid functional groups were incorporated into several monosaccharides. A series of 12 new glycosamino acids was prepared from commercially available starting materials. Conventional peptide synthesis solution coupling techniques were used to ligate glycosamino acids, producing oligomeric “glycotides”. Finally, a library of glycotides was produced by coupling of a glycosamino acid mixture to a rigid template.