Studies of carbohydrate-carbohydrate-interactions by atomic force microscopy employing functionalized 4-acetylthio-butyl glucopyranosides

Abstract

By Fischer glycosylation both anomers of 4-chlorobutyl gluco-as well as galactopyranosides were obtained and transformed into the corresponding 4-acetylthio-butyl glycopyranosides. Dependent on the precursors two straightforward routes were followed to obtain the appropriate 3-O-sulfated derivatives. Unsubstituted and sulfated glucopyranosides were attached to gold surfaces a gold tips. Their interactions were studied using atomic force microscopy for simulations of intercellular glycoside-based interactions and discussed in-depth.

Keywords: 3-O-Sulfates; 4−Acetylthio-butyl gluco- and galactopyranosides; Atomic force microscopy (AFM); Fischer glycosylation; Force sensor experiments; Saccharide-saccharide interdependence; Simulation of intercellular interaction.