Non-reductive coupling of branched amino fatty acid esters with mono and disaccharides: synthesis of a new class of alkyl glycosylamines.

Abstract

A new class of alkyl glycosylamines, using methyl 9- (1) or methyl 12-aminooctadecanoate (2) and carbohydrates (glucose (3a), galactose (3b), lactose (3c), and maltose (3d)), has been synthesized. In order to accomplish the binding of the amino fatty acid esters 1-2 with carbohydrates 3a-d the method described by Helferich, which is using peracetylated carbohydrate bromides, was employed. The yields ranged between 26 and 55%. The chemical structures were identified using 'H and 13 C NMR-spectroscopy including 2D techniques and FT-IR. The critical micelle concentrations and the surface tension profiles of these N-Alkyl-D-glycosides in water were determined.