Solvent effect on enzyme-catalyzed synthesis of β- d-glucosides using the reverse hydrolysis method: Application to the preparative-scale synthesis of 2-hydroxybenzyl and octyl β- d-glucopyranosides

• Published in: Enzyme and microbial technology Vol. 20; no. 8; pp. 597 - 603
• Main Authors: Vic, Gabin, Thomas, Daniel, Crout, David H.G.
• Format: Journal Article
• Language: English
• Published: Amsterdam Elsevier Inc 01-06-1997; Elsevier Science
• Subjects: alkyl-β- d-glucoside; almond-β- d-glucosidase; Bioconversions. Hemisynthesis; Biological and medical sciences; Biotechnology; biotransformation; Fundamental and applied biological sciences. Psychology; Methods. Procedures. Technologies; organic medium; Reverse hydrolysis; almond-β- d-glucosidase; Reverse hydrolysis; biotransformation; alkyl-β- d-glucoside; organic medium; Solvent effect; Enzymatic synthesis; Stability; Aldose; Enzyme; Prunus dulcis; Rosaceae; Reverse reaction; Hydrolysis; Organic solvent; β-Glucosidase; Dicotyledones; Glycosidases; Biotransformation; Angiospermae; Phenols; Hydrolases; Spermatophyta; Glycoside; O-Glycosidases
• ISSN: 0141-0229; 1879-0909
• DOI: 10.1016/S0141-0229(96)00201-3

Almond β-
d-glucosidase was used to catalyze alkyl-β-
d-glucoside synthesis by reacting glucose and the alcohol in organic media. The influence of five different solvents and the thermodynamic water activity on the reaction have been studied. The best yields were obtained in 80 or 90% (v/v) tert-butanol, acetone, or acetonitrile where the enzyme is very stable. In this enzymatic synthesis under thermodynamic control, the yield increases as the water activity of the reaction medium decreases. Enzymatic preparative-scale syntheses were performed in a
tert-butanol-water mixture which was found to be the most appropriate medium. 2-Hydroxybenzyl β-
d-glucopyranoside was obtained in 17% yield using a 90:10 (v/v)
tert-butanol-water mixture. Octyl-β-glucopyranoside was obtained in 8% yield using a 60:30:10 (v/v)
tert-butanol-octanol-water mixture.