Enzymatic Synthesis of Glucoside Derivatives of Validamine and Valienamine.

Abstract

alpha- And beta-glucoside derivatives of validamine and valienamine were prepared by enzymatic transglucosidation using alpha- and beta-glucosidase of Rhodotorula lactosa. The structures of these derivatives have been elucidated by 13C- and 1H-nuclear magnetic resonance spectral analysis. Thus, 7-alpha-glucoside, 7-alpha-isomaltoside, and 4-alpha-glucoside of validamine and 7-alpha-glucoside, 7-alpha-isomaltoside, 4-alpha-glucoside, and 4-alpha-isomaltoside of valienamine were obtained from maltose and validamine or valienamine using alpha-glucosidase. 7-beta-glucoside, 2-beta-glucoside, and 4-beta-glucoside of validamine or valienamine were obtained from cellobiose and validamine or valienamine using beta-glucosidase. These derivatives were tested for alpha-glucosidase inhibitory activity on rat small intestinal glycosidases.