Vinyl Sulfone Functionalization: A tool for the Study of the Lectin–Carbohydrate Interactions

What is it about?

We described a new approach to create saccharide-based systems. Representative monosaccharides and disaccharides were derivatized at their anomeric carbon with a vinyl sulfone group spanned by an ethylthio linker and covalent linkage in mild conditions via Michael-type additions with the amine and thiol groups from functionalized supports and those naturally present in biomolecules. The introduction of the ethylthio linker between the biorecognizable element (i.e., saccharide) and the reactive group (i.e., vinyl sulfone) was found to preserve the functionality of the former.

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Why is it important?

The capability of the vinyl sulfone saccharides for the study of lectin–carbohydrate interactions was demonstrated by (i) immobilizing them on both amine-functionalized supports (glass slides and microwell plates) and polylysine-coated glass slides to create sugar arrays that selectively bind lectins (ii) coupling to model proteins to yield neoglycoproteins that are recognized by lectins and (iii) using vinyl sulfone saccharides as tags to allow the detection of the labeled biomolecule by HRP-lectins.