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Journal of Bioscience and Bioengineering, Vol.113, No.4, 545-548, 2012
Intramolecular acyl migration and enzymatic hydrolysis of 2-O-alpha-D-glucopyranosyl-6-O-(2-pentylheptanoyl)-L-ascorbic acid
2-O-alpha-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-alpha-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 12 h, 6-bDode-AA-2G, which hardly underwent acyl migration to give 5-bDode-AA-2G, was predominantly hydrolyzed with alpha-glucosidase and then with esterase to ascorbic acid. (C) 2011, The Society for Biotechnology, Japan. All rights reserved.
Keywords:Acyl migration;6-bDode-AA-2G;Lipophilic ascorbic acid derivative;Stable ascorbic acid derivative;Enzymatic hydrolysis