Bioconjugation Reactions in Living Cells: Development, Advances, and Applications of Glycan-Specific Technologies

Bioorthogonal ligation reactions, in which synthetic organic chemistry can be accomplished in a physiological milieu including in living cells and animals, have flourished over the past two decades or so with the development of a profusion of coupling partners. This chapter gives an overview of bioorthogonal ligations including the best known example of this approach-the azide-alkyne "click" reaction-but also covers lesser known, more specialized, and recently emerging chemical advances in this field. Although a bioorthogonal ligation approach is proving broadly useful to address many biological and biomedical problems, its use in glycobiology is particularly significant. Accordingly this chapter focuses on examples where this approach is already being used to, or has the potential to, label cell surface glycans for a variety of research (e.g., in vitro and in vivo visualization of glycans) and medical applications (e.g., diagnosis and treatment of cancer and use in tissue engineering and regenerative medicine).