Facile Stereoselective Reduction of Prochiral Ketones by using an F 420-dependent alcohol dehydrogenase

Caterina Martin, Gwen Tjallinks, Milos Trajkovic, Marco Fraaije*

*Corresponding author for this work

Research output: Contribution to journalArticleAcademicpeer-review

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Abstract

Effective procedures for the synthesis of optically pure alcohols are highly valuable. A commonly employed method involves the biocatalytic reduction of prochiral ketones. This is typically achieved by using nicotinamide cofactor-dependent reductases. In this work, we demonstrate that a rather unexplored class of enzymes can also be used for this. We used an F420-dependent alcohol dehydrogenase (ADF) from Methanoculleus thermophilicus that was found to reduce various ketones to enantiopure alcohols. The respective (S) alcohols were obtained in excellent enantiopurity (>99 % ee). Furthermore, we discovered that the deazaflavoenzyme can be used as a self-sufficient system by merely using a sacrificial cosubstrate (isopropanol) and a catalytic amount of cofactor F420 or the unnatural cofactor FOP to achieve full conversion. This study reveals that deazaflavoenzymes complement the biocatalytic toolbox for enantioselective ketone reductions.

Original languageEnglish
Article numbercbic.202000651
Pages (from-to)156-159
Number of pages4
JournalChemBioChem
Volume22
Issue number1
Early online date16-Sep-2020
DOIs
Publication statusPublished - 5-Jan-2021

Keywords

  • Biocatalysis
  • deazaflavin
  • enantioselectivity
  • prochiral ketones
  • reduction

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