Bioorganic & Medicinal Chemistry Letters 2005-06-02

Redox-responsive and calcium-dependent switching of glycosyldisulfide interactions with Concanavalin A.

Zhichao Pei, Teodor Aastrup, Henrik Anderson, Olof Ramström

Index: Bioorg. Med. Chem. Lett. 15 , 2707-10, (2005)

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Abstract

Glycosyldisulfides can interact efficiently with carbohydrate-binding entities. This has been shown for a range of thiosaccharide dimers when tested for their effects against the lectin Concanavalin A using a modified quartz crystal microbalance-technique. Contrary to the thiosaccharide monomers, showing no significant binding up to 10 mM, several of the dimers showed IC(50)-values in the low millimolar range. Three of the glycosyldisulfides tested also displayed very high positive apparent cooperativity effects that were found to be both calcium-dependent and redox-responsive.