Efficient production of l-menthyl α-glucopyranoside from l-menthol via whole-cell biotransformation using recombinant Escherichia coli

Biotechnol Lett. 2021 Sep;43(9):1757-1764. doi: 10.1007/s10529-021-03100-6. Epub 2021 May 26.

Abstract

l-Menthyl α-D-glucopyranoside (α-MenG) is a glycoside derivative of l-menthol with improved water-solubility and new flavor property as a food additive. α-MenG can be synthesized through biotransformation, but its scale-up production was rarely reported. In this study, the properties of an α-glucosidase from Xanthomonas campestris pv. campestris 8004 (Agl-2) in catalyzing the glucosylation of menthol was investigated. Agl-2 can almost completely glycosylate l-menthol (> 99%) when using 1.2 M maltose as glycosyl donor. Accumulated glucose resulted from maltose hydrolysis and transglycosylation caused the inhibition of the glucosylation rate (40% reduction of the glucosylation rate in the presence of 1.2 M glucose) which can be avoided through whole-cell catalysis with recombinant E. coli. Interestingly, in spite of the poor solubility of menthol, the productivity of α-MenG reached 24.7 g/(L·h) in a 2 L catalyzing system, indicating industrialization of the reported approach.

Keywords: Glucosylation; Xanthomonas campestris; l-menthyl α-D-glucopyranoside; α-glucosidase.

MeSH terms

  • Bacterial Proteins / genetics
  • Bacterial Proteins / metabolism
  • Biocatalysis
  • Biotransformation
  • Escherichia coli / genetics
  • Escherichia coli / growth & development*
  • Glucosides / chemistry*
  • Glycosylation
  • Hydrolysis
  • Maltose / chemistry
  • Menthol / chemistry*
  • Protein Engineering
  • Xanthomonas campestris / enzymology*
  • Xanthomonas campestris / genetics
  • alpha-Glucosidases / genetics
  • alpha-Glucosidases / metabolism*

Substances

  • Bacterial Proteins
  • Glucosides
  • Menthol
  • Maltose
  • alpha-Glucosidases