Sulfolobus solfataricus beta-glycosidase-catalysed synthesis of sugar-alcohol conjugates in the presence of organic solvents

The thermostable beta-D-glycosidase from the archaeon Sulfolobus solfataric us was used for the glucosylation of secondary alcohols at high organic sol vent concentrations. Alkyl glucoside products were analysed by one- and two -dimensional NMR. Using a range of racemic secondary alcohols and various h ydrophilic organic solvents, small but significant substrate- and solvent-d ependent changes in the RIS ratios of alkyl glucoside products were detecte d. The anomeric specificity of the enzyme was apparently affected by butan- 2-one. A possible mechanistic model for solvent-induced changes at the acti ve site is presented.