How to Turn Yeast Cells into a Sustainable and Switchable Biocatalyst? On-Demand Catalysis of Ketone Bioreduction or Acyloin Condensation

László Nagy-Györ, Mihai Lǎcǎtuş, Diána Balogh-Weiser, Pál Csuka, Viktória Bódai, Balázs Erdélyi, Zsófia Molnár, Gábor Hornyánszky, Csaba Paizs, László Poppe

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1 Citation (Scopus)

Abstract

In this study, yeast strains were screened and immobilized in a form preserving the multifaceted biocatalytic activity. Immobilization of the silica-supported whole cells of various yeasts, such as Lodderomyces elongisporus, Pichia carsonii, Candida norvegica, and Debaryomyces fabryi, by sol-gel entrapment resulted in easy-to-handle biocatalysts that mediated efficiently different types of synthetic reactions. In the present study, the enantiotope selective reduction of prochiral ketones 1a-d and the acyloin condensation of benzaldehyde 3 were studied, representing two remarkably diverse types of biotransformation. The yeast cell biocatalysts - in the presence of fresh or recovered NADH cofactor - could be applied for continuous-flow bioreduction of ketones 1a-d with moderate to good yields (20 to 92%) and excellent enantiomeric purity (>99%). Immobilized L. elongisporus and P. carsonii cells could also mediate acyloin condensation of benzaldehyde 3 in batch as well as in continuous-flow mode. The switchable biocatalytic activity of the immobilized yeast cells was demonstrated by consecutive biotransformations under continuous-flow conditions involving reduction of phenylacetone 1a to (S)-phenylpropane-2-ol [(S)-2a] first, followed by conversion of benzaldehyde 3 to (R)-1-hydroxy-1-phenylpropan-2-one [(R)-4] and reduction of 1a to (S)-2a again by using the same packed-bed bioreactor.

Original languageEnglish
Pages (from-to)19375-19383
Number of pages9
JournalACS Sustainable Chemistry and Engineering
Volume7
Issue number24
DOIs
Publication statusPublished - Dec 16 2019

Keywords

  • Acyloin condensation
  • Continuous flow
  • Ketone reduction
  • Multipurpose biocatalyst
  • Sol-gel entrapment
  • Whole-cell immobilization
  • Yeast

ASJC Scopus subject areas

  • Chemistry(all)
  • Environmental Chemistry
  • Chemical Engineering(all)
  • Renewable Energy, Sustainability and the Environment

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  • Cite this

    Nagy-Györ, L., Lǎcǎtuş, M., Balogh-Weiser, D., Csuka, P., Bódai, V., Erdélyi, B., Molnár, Z., Hornyánszky, G., Paizs, C., & Poppe, L. (2019). How to Turn Yeast Cells into a Sustainable and Switchable Biocatalyst? On-Demand Catalysis of Ketone Bioreduction or Acyloin Condensation. ACS Sustainable Chemistry and Engineering, 7(24), 19375-19383. https://doi.org/10.1021/acssuschemeng.9b03367