Solid-phase oligosaccharide chemistry and its application to library synthesis.

Publisher Summary Combinatorial peptide and oligonucleotide chemistry enables large libraries of diverse sequences to be readily generated in a short time frame. This chapter discusses some recent developments in solid-phase carbohydrate chemistry and presents the methods to develop structurally diverse oligosaccharide libraries. A combinatorial solid-phase oligosaccharide synthesis (CSPOS) provides the ability to generate arrays of compounds instead of single molecules by linear syntheses and provides the chemist with an opportunity to fully exploit different aspects of diversity, whether it is structural, functional, or otherwise. This is particularly relevant when considering monosaccharides and carbohydrates due to the high functional density and stereoisomeric forms are found with these molecules. CSPOS platform is an ideal approach for the production of carbohydrate structures to enable the investigation of the biological roles of carbohydrates and to further drug discovery. One of the major problems to overcome, in order to fully develop an efficient CSPOS system, is the requirement to generate suitably protected building blocks for each monomer type as well as for each linkage position per monomer type, orthogonal protected to each other.