Synthesis of lauroyl saccharides through lipase-catalyzed condensation in microaqueous water-miscible solvents

Lauroyl saccharides were synthesized at 50°C through condensation in acetonitrile, acetone and tert-butanol with various water contents using the immobilized lipase Novozym®435. Saccharides used were glucose, galactose, mannose and fructose. The equilibrium yields of the monoesters in acetonitrile were significantly different among the saccharides tested. The apparent equilibrium constants based on the concentrations of substrates and products in acetonitrile could be correlated to the dynamic hydration numbers of the saccharides, indicating that the water activity played an important role during the condensation in the microaqueous water-miscible solvent. However, a significant correlation between the equilibrium constant for lauroyl fructose formation and parameters characterizing the solvent property could not be found.