Hydrogen-driven cofactor regeneration for stereoselective whole-cell C=C bond reduction in Cupriavidus necator

Research output: Contribution to journalArticleResearchpeer-review

Abstract

The coupling of recombinantly expressed oxidoreductases to endogenous hydrogenases for cofactor‐recycling permits the omission of organic cosubstrates as sacrificial electron donors in whole‐cell biotransformations. This increases atom efficiency and simplifies the reaction. We have expressed a recombinant ene‐reductase in the hydrogen‐oxidizing proteobacterium Cupriavidus necator H16. In hydrogen‐driven biotransformations, whole cells catalyzed asymmetric C=C bond reduction of unsaturated cyclic ketones with stereoselectivities up to >99% ee. The use of hydrogen as a substrate for growth and cofactor regeneration is particularly attractive as it represents a strategy for improving atom efficiency and reducing side product formation associated with the recycling of organic cofactors.
LanguageEnglish
Pages2361-2365
Number of pages5
JournalChemSusChem
Volume12
Issue number11
Early online date19 Mar 2019
DOIs
StatusPublished - 19 Mar 2019

Fingerprint

Hydrogen
regeneration
biotransformation
hydrogen
Recycling
Oxidoreductases
recycling
Hydrogenase
Stereoselectivity
Atoms
ketone
Ketones
substrate
electron
Electrons
Substrates
Biotransformation
Proteobacteria
asoxime chloride
product

Keywords

  • Hydrogenation
  • Biotransformations
  • Biocatalysis
  • Assymetric synthesis
  • Reduction
  • biotransformation
  • asymmetric synthesis
  • reduction
  • hydrogenation
  • biocatalysis

ASJC Scopus subject areas

  • Energy(all)
  • Chemical Engineering(all)
  • Materials Science(all)
  • Environmental Chemistry

Fields of Expertise

  • Human- & Biotechnology

Cite this

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title = "Hydrogen-driven cofactor regeneration for stereoselective whole-cell C=C bond reduction in Cupriavidus necator",
abstract = "The coupling of recombinantly expressed oxidoreductases to endogenous hydrogenases for cofactor‐recycling permits the omission of organic cosubstrates as sacrificial electron donors in whole‐cell biotransformations. This increases atom efficiency and simplifies the reaction. We have expressed a recombinant ene‐reductase in the hydrogen‐oxidizing proteobacterium Cupriavidus necator H16. In hydrogen‐driven biotransformations, whole cells catalyzed asymmetric C=C bond reduction of unsaturated cyclic ketones with stereoselectivities up to >99{\%} ee. The use of hydrogen as a substrate for growth and cofactor regeneration is particularly attractive as it represents a strategy for improving atom efficiency and reducing side product formation associated with the recycling of organic cofactors.",
keywords = "Hydrogenation, Biotransformations, Biocatalysis, Assymetric synthesis, Reduction, biotransformation, asymmetric synthesis, reduction, hydrogenation, biocatalysis",
author = "{Assil Companioni}, Leen and Sandy Schmidt and Petra Heidinger and Helmut Schwab and Robert Kourist",
year = "2019",
month = "3",
day = "19",
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language = "English",
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journal = "ChemSusChem",
issn = "1864-5631",
publisher = "Wiley-VCH",
number = "11",

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T1 - Hydrogen-driven cofactor regeneration for stereoselective whole-cell C=C bond reduction in Cupriavidus necator

AU - Assil Companioni, Leen

AU - Schmidt, Sandy

AU - Heidinger, Petra

AU - Schwab, Helmut

AU - Kourist, Robert

PY - 2019/3/19

Y1 - 2019/3/19

N2 - The coupling of recombinantly expressed oxidoreductases to endogenous hydrogenases for cofactor‐recycling permits the omission of organic cosubstrates as sacrificial electron donors in whole‐cell biotransformations. This increases atom efficiency and simplifies the reaction. We have expressed a recombinant ene‐reductase in the hydrogen‐oxidizing proteobacterium Cupriavidus necator H16. In hydrogen‐driven biotransformations, whole cells catalyzed asymmetric C=C bond reduction of unsaturated cyclic ketones with stereoselectivities up to >99% ee. The use of hydrogen as a substrate for growth and cofactor regeneration is particularly attractive as it represents a strategy for improving atom efficiency and reducing side product formation associated with the recycling of organic cofactors.

AB - The coupling of recombinantly expressed oxidoreductases to endogenous hydrogenases for cofactor‐recycling permits the omission of organic cosubstrates as sacrificial electron donors in whole‐cell biotransformations. This increases atom efficiency and simplifies the reaction. We have expressed a recombinant ene‐reductase in the hydrogen‐oxidizing proteobacterium Cupriavidus necator H16. In hydrogen‐driven biotransformations, whole cells catalyzed asymmetric C=C bond reduction of unsaturated cyclic ketones with stereoselectivities up to >99% ee. The use of hydrogen as a substrate for growth and cofactor regeneration is particularly attractive as it represents a strategy for improving atom efficiency and reducing side product formation associated with the recycling of organic cofactors.

KW - Hydrogenation

KW - Biotransformations

KW - Biocatalysis

KW - Assymetric synthesis

KW - Reduction

KW - biotransformation

KW - asymmetric synthesis

KW - reduction

KW - hydrogenation

KW - biocatalysis

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U2 - 10.1002/cssc.201900327

DO - 10.1002/cssc.201900327

M3 - Article

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EP - 2365

JO - ChemSusChem

T2 - ChemSusChem

JF - ChemSusChem

SN - 1864-5631

IS - 11

ER -