Enzymatic synthesis of a novel trehalose derivative, 3,3 '-diketotrehalose, and its potential application as the trehalase enzyme inhibitor

We reported the preparation of a novel trehalose derivative based on enzyma tic oxidation of trehalose by water-soluble glucose-3-dehydrogenase (G3DH) from marine bacterium Halolomonas sp. alpha -15 cells. The product of G3DH enzymatic conversion was 3,3'-diketotrehalose (3,3'dkT), a novel trehalose derivative of which both third hydroxy groups of glucopyranosides mere oxid ized, 3,3'dkT was revealed to show an inhibitory effect toward pig-kidney a nd Bombyx mori trehalases. The IC50 values of 3,3'dkT mere 0.8 and 2.5 mM a nd K-i values mere 0.2 and 0.6 mM for pig-kidney and for B. mori trehalases , respectively. In addition, 3,3'dkT did not show any inhibitory effect on both maltase and mannosidase activities. Therefore, 3,3'dkT was a specific inhibitor of trehalases. (C) 2001 Federation of European Biochemical Societ ies. Published by Elsevier Science B.V. All rights reserved.