Preparation of 3-amino-3-deoxy derivatives of trehalose and sucrose and their activities

Abstract

The 3-keto derivatives of trehalose and sucrose respectively were prepared by a one-step enzymatic route using D-glucoside 3-dehydrogenase from Flavobacterium saccharophilum. Reductive amination of 3-ketotrehalose with ammonium acetate and sodium cyanoborohydride gave three compounds, 3-amino-3-deoxy-α-D-allopyranosyl α-D-glucopyranoside, 3-amino-3-deoxy-α-D-glucopyranosyl α-D-glucopyranoside 3-trehalosamine) and 3-amino-3-deoxy-α-D-mannopyranosyl α-D-glucopyranoside. From the reductive amination of 3-ketosucrose, 3-amino-3-deoxy-α-D-allopyranosyl β-D-fructofuranoside and 3-amino-3-deoxy-α-D-glucopyranosyl β-D-fructofuranoside were obtained. The antibiotic and glycohydrolase inhibitory activities of these 3-amino-3-deoxy derivatives were determined. © 1989, JAPAN ANTIBIOTICS RESEARCH ASSOCIATION. All rights reserved.