Solid phase synthesis of oligosaccharides

Abstract

Oligosaccharides are involved in many fundamental biological processes. However, relatively little is known about the precise molecular mechanism of action of these macromolecules, because the complexity of these structures impeded their synthesis by chemical methods analogous to those employed to create oligonucleotides and peptides. Herein, we describe recently developed techniques for solid-supported oligosaccharide synthesis. Several key aspects of solid phase synthesis are highlighted and examined, including the choice of resin and the challenge of real-time reaction monitoring. Recent examples of manual and automated solid-supported syntheses of complex oligosaccharides are given and the automated solid phase synthesis of the tumor-associated carbohydrate antigen Globo-H is highlighted.