Intramolecular acyl migration and enzymatic hydrolysis of 2-O-α-D-glucopyranosyl-6-O-(2-pentylheptanoyl)-L-ascorbic acid

Abstract

2-O-α-D-Glucopyranosyl-6-O-(2-pentylheptanoyl)-L-ascorbic acid (6-bDode-AA-2G) underwent an intramolecular acyl migration to yield approximately 12% of 2-O-α-D-glucopyranosyl-5-O-(2-pentylheptanoyl)-L-ascorbic acid (5-bDode-AA-2G) in neutral solutions for 3 days. In small intestine homogenate from guinea pigs for 12h, 6-bDode-AA-2G, which hardly underwent acyl migration to give 5-bDode-AA-2G, was predominantly hydrolyzed with α-glucosidase and then with esterase to ascorbic acid.