Protease-catalyzed monoacylation of 2-O-α-D-glucopyranosyl-L-ascorbic acid in three solvent systems.
6-O-dodecanoyl-2-O-α-D-glucopyranosyl-L-ascorbic acid (6-sDode-AA-2G) was synthesized from 2-O-α-D-glucopyranosyl-L-ascorbic acid and vinyl laurate with a protease from Bacillus subtilis in 30% dimethylformamide (DMF)/dioxane with a low water content. The addition of 3% (v/v) water to DMF/dioxane dramatically enhanced the 6-sDode-AA-2G synthesis. The optimum reaction conditions enabled 6-sDode-AA-2G to be synthesized in a yield of 38.1%.
Tai
Akihiro
A
Faculty of Life and Environmental Sciences, Prefectural University of Hiroshima. atai@pu-hiroshima.ac.jp
Iwaoka
Yuji
Y
Mori
Tasuku
T
Ito
Hideyuki
H
D000215:Acylation; D001205:Ascorbic Acid / Q000031:analogs & derivatives* / Q000737:chemistry; D001412:Bacillus subtilis / Q000201:enzymology; D002384:Catalysis; D004126:Dimethylformamide; D004146:Dioxanes; D010450:Endopeptidases / Q000737:chemistry / Q000378:metabolism*; D007218:Industrial Microbiology / Q000379:methods; D012997:Solvents; D014867:Water
D004146:Dioxanes; D012997:Solvents; D014867:Water; C065378:ascorbic acid 2-O-glucoside; D004126:Dimethylformamide; D010450:Endopeptidases; C025223:1,4-dioxane; D001205:Ascorbic Acid