9.05 Technology-Enabled Synthesis of Carbohydrates

Automated solid-phase oligosaccharide synthesis has revolutionized the emerging field of glycomics. The automation process, in which selectively functionalized monosaccharide building blocks are added sequentially to a growing oligosaccharide chain connected via an inert linker to a solid support, has been used to prepare a number of biologically relevant oligosaccharide-based constructs in record time and on scales that would have been impossible using standard solution-phase synthetic techniques. This review highlights recent developments in automated solid-phase oligosaccharide synthesis including engineering advancements that have led to the design of a fully automated platform, new and improved linker strategies that have broadened the scope of the chemical reactions that can be used in automation, and recent developments in the synthesis of functionalized monosaccharide building blocks. The automated solid-phase synthesis of biologically relevant carbohydrate constructs including bacterial and viral antigens, cancer antigens, vaccine candidates, and N-linked core oligosaccharides is also presented.