Green synthesis of chiral aromatic alcohols with Lactobacillus kefiri P2 as a novel biocatalyst

Yasemin Baydaş, Enes Dertli, Engin Şahin*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

22 Citations (Scopus)

Abstract

Biocatalytic reduction is a very important field of research in synthetic organic chemistry. Herein, three different Lactic Acid Bacteria (LAB) strains were evaluated for their bioreduction potential using acetophenone as a model substrate. Among these strains, Lactobacillus kefiri P2 strain was determined as the best asymmetric reduction biocatalyst. Reaction optimization parameters such as reaction time, temperature, agitation speed and pH were systematically optimized using Lactobacillus kefiri P2 strain and model substrate acetophenone. Under these optimized reaction conditions, secondary chiral alcohols were obtained by bioreduction of various prochiral ketones with results up to 99% enantiomeric excess. In addition, the steric and electronic effects of substituents on enantioselectivity and conversion were evaluated. It has been shown that Lactobacillus kefiri P2 biocatalyst was an effective catalyst for asymmetric reduction. This method provides an environmentally friendly method for the synthesis of optically pure alcohols and an alternative approach to chemical catalysts.

Original languageEnglish
Pages (from-to)1035-1045
Number of pages11
JournalSynthetic Communications
Volume50
Issue number7
DOIs
Publication statusPublished - 2 Apr 2020
Externally publishedYes

Bibliographical note

Publisher Copyright:
© 2020, © 2020 Taylor & Francis Group, LLC.

Keywords

  • aromatic ketones
  • Asymmetric synthesis
  • bioreduction
  • Lactobacillus kefiri
  • whole cell

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