Highly efficient synthesis of arbutin esters catalyzed by whole cells of Candida parapsilosis.

Abstract

Acylation modification of phenol glycosides is currently of great interest due to the improved bioavailability and multiple functions. In this work, mono- or diesters of arbutin, an important phenol glycoside derivative, can be controllably synthesized by using whole-cell biocatalytic systems. Among fourteen microbial strains selected, Candida parapsilosis cells showed the best catalytic activity and high organic solvent tolerance. Compared with the best pure solvent tetrahydrofuran, the use of a binary solvent pyridine-isooctane gave a slightly lower conversion (98.3% vs. 97.2%) and selectivity (85.3% vs. 80.5%) and much higher substrate solubility (37.1 vs. 214.0 mg mL−1), in a 24 h bioconversion of arbutin with a VP-arbutin molar ratio of 15 and whole cell dosage of 30 mg mL−1. The production of various arbutin esters with different fatty acid chain lengths can be realized by using this whole-cell strategy, with the substrate conversion and 6′-regioselectivity of 54.1–98.3% and 83.2–99.0%, respectively.