Lipase-mediated synthesis of water-soluble plant stanol derivatives in tert-butanol

Abstract

The effects of solvents with different log P values, and of lipases on the synthesis of water-soluble plant stanol derivatives were investigated. Results showed that conversion in solvents with log P<0.37 was mainly controlled by the hydrophobicity of the solvent and subsequent complete or partial deactivation of the enzyme. The solubility of substrate was the leading factor for the conversion in solvents with log P>0.37. Lipozyme RM IM and tert-butanol was the most suitable biocatalyst and solvent, respectively. The highest yield (>51%) of plant stanyl sorbitol succinate was obtained under the selected conditions: 50 μmol/mL plant stanyl hemisuccinate, 1:3 molar ratio of plant stanyl hemisuccinate to d-sorbitol, 80 mg/mL 3 Å molecular sieves and 100mg/mL Lipozyme RM IM in tert-butanol, 150 r/min and 55 °C. Fourier transform infrared spectroscopy, mass spectroscopy and nuclear magnetic resonance spectroscopy were adopted to determine the structure of product, suggesting that water-soluble plant stanol derivatives were successfully synthesized.