chapter  6
6 Pages

Synthesis of Glycosyl Vinyl Sulfones for Bioconjugation

The covalent coupling of two biomolecules to each other (bioconjugation) or to a solid support (immobilization) is one of the cornerstones of omic sciences.1 Among numerous chemical strategies to attain this goal, the versatile Michael-type addition of amine and thiol groups to vinyl sulfones is an attractive methodology.2 The latter are excellent Michael acceptors because of the electron-poor nature of their double bond, owed to the sulfone’s electron-withdrawing capability that makes them good electrophiles.3,4 All the conjugate additions with vinyl sulfones share a similar reaction pattern, namely, the addition to the β-position of the sulfone. Accordingly, these reactions are well-established methods for creating β-heterosubstituted

Experimental Methods .............................................................................................40 General Methods .................................................................................................40