Synthesis of Oligosaccharide Libraries by Random Glycosylation

The biological importance and activity of glycostructures in cellular interactions is focus of numerous investigations to date. Aim is to probe the activity of diverse natural- and non-natural glycoconjugates in order to identify and correlate structure-activity relationships. The complexity of glycostructures and their synthetic realization has been a major obstacle, since synthetic methodologies are used on a case by case basis; hence access to a variety of complex glycostructures has been limited. Combinatorial chemistry is a powerful tool for the study of structure-function relationship of e.g. proteins and nucleic acids and small molecules, but has been little regarded within the recent decade in the field of carbohydrate chemistry. This paper focuses on combinatorial glycosylation strategy attempts from partially protected glycosyl acceptors, to the development of solution phase glyco-combinatorial chemistry using entirely unprotected non-reducing acceptors to generate random libraries of regioisomeric oligosaccharides.