Asymmetric reduction of ketopantolactone using a strictly (R)-stereoselective carbonyl reductase through efficient NADPH regeneration and the substrate constant-feeding strategy

Biotechnol Lett. 2017 Nov;39(11):1741-1746. doi: 10.1007/s10529-017-2415-1. Epub 2017 Aug 21.

Abstract

Objectives: To characterize a recombinant carbonyl reductase from Saccharomyces cerevisiae (SceCPR1) and explore its use in asymmetric synthesis of (R)-pantolactone [(R)-PL].

Results: The NADPH-dependent SceCPR1 exhibited strict (R)-enantioselectivity and high activity in the asymmetric reduction of ketopantolactone (KPL) to (R)-PL. Escherichia coli, coexpressing SceCPR1 and glucose dehydrogenase from Exiguobacterium sibiricum (EsGDH), was constructed to fulfill efficient NADPH regeneration. During the whole-cell catalyzed asymmetric reduction of KPL, the spontaneous hydrolysis of KPL significantly affected the yield of (R)-PL, which was effectively alleviated by the employment of the substrate constant-feeding strategy. The established whole-cell bioreduction for 6 h afforded 458 mM (R)-PL with the enantiomeric excess value of >99.9% and the yield of 91.6%.

Conclusions: Escherichia coli coexpressing SceCPR1 and EsGDH efficiently catalyzed the asymmetric synthesis of (R)-PL through the substrate constant-feeding strategy.

Keywords: (R)-Pantolactone; Asymmetric reduction; Carbonyl reductase; Coenzyme regeneration; Ketopantolactone; Saccharomyces cerevisiae; Spontaneous hydrolysis.

MeSH terms

  • 4-Butyrolactone / analogs & derivatives*
  • 4-Butyrolactone / metabolism
  • Alcohol Oxidoreductases / metabolism
  • Cloning, Molecular
  • Cyclophilin A / genetics
  • Cyclophilin A / metabolism*
  • Escherichia coli / genetics
  • Escherichia coli / growth & development
  • Glucose 1-Dehydrogenase / genetics
  • Glucose 1-Dehydrogenase / metabolism
  • NADP / metabolism*
  • Oxidation-Reduction
  • Saccharomyces cerevisiae / enzymology*
  • Saccharomyces cerevisiae Proteins / genetics
  • Saccharomyces cerevisiae Proteins / metabolism*
  • Stereoisomerism
  • Substrate Specificity

Substances

  • Saccharomyces cerevisiae Proteins
  • keto-pantoyllactone
  • NADP
  • pantolactone
  • Alcohol Oxidoreductases
  • Glucose 1-Dehydrogenase
  • CPR1 protein, S cerevisiae
  • Cyclophilin A
  • 4-Butyrolactone