title: Protease-catalyzed monoacylation of 2-O-alpha-D-Glucopyranosyl-L-ascorbic acid in pyridine.
abstract: 2-O-alpha-D-Glucopyranosyl-6-O-octanoyl-L-ascorbic acid was enzymatically synthesized from 2-O-alpha-D-glucopyranosyl-L-ascorbic acid (AA-2G) and vinyl octanoate with a protease from Bacillus subtilis in pyridine. Furthermore, with various linear saturated fatty acid vinylesters as acyl donors, AA-2G was also converted to their corresponding 6-O-acyl AA-2G in the same manner. The reactivities of transacylation decreased with increasing length of the acyl groups. Thus, short chain acyl groups were transferred to AA-2G by this protease more efficiently than were long chain acyl groups. This enzymatic method is recommended for the synthesis of 6-Acyl-AA-2G with short or medium length chain acyl groups.
authors.affiliation: Department of Immunochemistry, Faculty of Pharmaceutical Sciences, Okayama University, Japan.
authors.forename: A
authors.initials: A
authors.lastname: Tai
authors.forename: S
authors.initials: S
authors.lastname: Okazaki
authors.forename: N
authors.initials: N
authors.lastname: Tsubosaka
authors.forename: I
authors.initials: I
authors.lastname: Yamamoto
mesh_terms: D000215:Acylation; D000217:Acyltransferases / Q000378:metabolism; D001205:Ascorbic Acid / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000378:metabolism*; D001412:Bacillus subtilis / Q000201:enzymology; D002384:Catalysis; D010450:Endopeptidases / Q000378:metabolism*; D011725:Pyridines / Q000378:metabolism*
chemical_list: D011725:Pyridines; C065378:ascorbic acid 2-O-glucoside; D000217:Acyltransferases; D010450:Endopeptidases; C023666:pyridine; D001205:Ascorbic Acid