Monoacylation of 2-O-alpha-D-glucopyranosyl-L-ascorbic acid by protease in N,N-dimethylformamide with low water content.
2-O-alpha-D-Glucopyranosyl-L-ascorbic acid (AA-2G) laurate was synthesized from AA-2G and vinyl laurate with a protease from Bacillus subtilis in N,N-dimethylformamide (DMF) with low water content. Addition of water to DMF dramatically enhanced monoacyl AA-2G synthesis. Maximum synthetic activity was observed when 3% (v/v) water was added to the reaction medium. Under the optimal reaction conditions, 5-O-dodecanoyl-2-O-alpha-D-glucopyranosyl-L-ascorbic acid, 2-O-(6'-O-dodecanoyl-alpha-D-glucopyranosyl)-L-ascorbic acid, and 6-O-dodecanoyl-2-O-alpha-D-glucopyranosyl-L-ascorbic acid were synthesized in yields of 5.5%, 3.2%, and 20.4%, respectively.
Tai
Akihiro
A
Faculty of Life and Environmental Sciences, Prefectural University of Hiroshima, Shobara, Hiroshima 727-0023, Japan. atai@pu-hiroshima.ac.jp
Mori
Tasuku
T
Kimura
Yuka
Y
Ito
Hideyuki
H
D000215:Acylation; D001205:Ascorbic Acid / Q000031:analogs & derivatives* / Q000737:chemistry / Q000378:metabolism; D055162:Biocatalysis; D002240:Carbohydrate Sequence; D004126:Dimethylformamide; D005559:Formamides; D008968:Molecular Conformation; D010447:Peptide Hydrolases / Q000378:metabolism*; D013237:Stereoisomerism; D014867:Water / Q000032:analysis*
D005559:Formamides; D014867:Water; C065378:ascorbic acid 2-O-glucoside; D004126:Dimethylformamide; D010447:Peptide Hydrolases; D001205:Ascorbic Acid