Biotransformation using halotolerant yeast in seawater: a sustainable strategy to produce R-(-)-phenylacetylcarbinol

Appl Microbiol Biotechnol. 2018 Jun;102(11):4717-4727. doi: 10.1007/s00253-018-8945-1. Epub 2018 Apr 7.

Abstract

Acyloin condensation between benzaldehyde and decarboxylated pyruvate results in the production of R-(-)-phenylacetylcarbinol, a chiral precursor of the drug ephedrine. Huge research efforts have been made to improve the conditions of this reaction and to avoid the generation of by-products. Recently, we reported the advantages of using whole cells of the yeast Debaryomyces etchellsii as biocatalysts for this purpose. In this work, a new strategy, which fulfills green chemistry principles, is proposed and is based on using seawater as a gentle solvent. We demonstrate that, under these conditions, several improvements can be made compared to employing freshwater: (1) the conversion of the starting material in (R)-PAC is higher and with a minimum production of by-products; (2) it is possible to increase at least twofold the benzaldehyde load in the reaction medium; (3) cells can maintain their activity after several recycling rounds, which makes (R)-PAC production an easy and economical process.

Keywords: Biocatalysis; Debaryomyces; Green chemistry; Phenylacetylcarbinol; Seawater.

MeSH terms

  • Acetone / analogs & derivatives*
  • Acetone / chemistry
  • Acetone / metabolism
  • Ascomycota / metabolism*
  • Biotransformation
  • Prodrugs / chemistry
  • Prodrugs / metabolism*
  • Seawater / chemistry
  • Technology, Pharmaceutical / methods*

Substances

  • Prodrugs
  • Acetone
  • 1-hydroxy-1-phenyl-2-propanone