Synthesis of alkyl fucosides through β-glucosidase-catalyzed condensation of fucose and 1-alcohols

Abstract

β-Glucosidase from almond catalyzed condensations of fucose and 1-alcohols with carbon numbers of 6 to 8 produce the corresponding 1-alkyl β-d-fucosides. The enzyme also catalyzed the condensation of galactose and 1-hexanol. The conversion for the synthesis of hexyl fucoside was higher than those for the syntheses of hexyl glucoside and galactoside. The effect of initial saccharide concentrations on the conversions to alkyl glycosides was examined. The conversions at day 8 were almost the same at the low initial concentrations of the saccharides. However, the conversion significantly decreased as the concentrations increased. The surfactant properties of the prepared alkyl glycosides were measured. The critical micelle concentrations of the alkyl fucosides were lower than those of the glucosides and galactosides with the same alkyl chains.