Efficient Regioselective Synthesis of the Crotonyl Polydatin Prodrug by Thermomyces lanuginosus Lipase: a Kinetics Study in Eco-friendly 2-Methyltetrahydrofuran

Appl Biochem Biotechnol. 2016 Jul;179(6):1011-22. doi: 10.1007/s12010-016-2047-2. Epub 2016 Apr 28.

Abstract

Bio-based solvents have recently been discussed as sustainable green and promising alternatives to conventional organic media for enzymatic processes. In this paper, highly regioselective synthesis of the 6″-O-crotonyl-polydatin catalyzed by Thermomyces lanuginosus lipase (TLL) in biomass-derived 2-methyltetrahydrofuran (2-MeTHF) was successfully performed for the first time. The results indicated that TLL lipase displayed significantly improved catalytic performance in 2-MeTHF than in other traditional solvents. Under the optimal conditions, the initial reaction rate, 6″-regioselectivity, and maximum substrate conversion were as high as 12.38 mM h(-1), 100 %, and 100 %, respectively. Moreover, further investigations on the operational stability, kinetic parameters like V max, K m, V max/K m, and E a revealed that 2-MeTHF exhibited excellent biocompatibility and rendered the greener process of the enzymatic acylation.

Keywords: 2-Methyltetrahydrofuran; 6″-O-Crotonyl-polydatin; Enzymatic acylation; Polydatin; Thermomyces lanuginosus lipase.

MeSH terms

  • Acylation
  • Catalysis
  • Eurotiales / enzymology*
  • Furans / chemistry*
  • Glucosides / biosynthesis*
  • Glucosides / chemistry
  • Kinetics
  • Lipase / biosynthesis*
  • Lipase / chemistry
  • Prodrugs / chemistry
  • Solvents / chemistry
  • Stereoisomerism
  • Stilbenes / chemistry
  • Substrate Specificity

Substances

  • Furans
  • Glucosides
  • Prodrugs
  • Solvents
  • Stilbenes
  • Lipase
  • 2-methyltetrahydrofuran
  • polydatin