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Facile Stereoselective Reduction of Prochiral Ketones by using an F 420-dependent alcohol dehydrogenase
- Source :
- Chembiochem, ChemBioChem, 22(1):cbic.202000651, 156-159. WILEY-V C H VERLAG GMBH
- Publication Year :
- 2021
-
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.<br />An alternative to NADH dependence: An F420‐dependent alcohol dehydrogenase can be used to asymmetrically reduce prochiral ketones. Conveniently, using a cheap sacrificial cosubstrate (isopropanol), the same enzyme can regenerate the deazaflavin cofactor.
- Subjects :
- Ketone
reduction
prochiral ketones
010402 general chemistry
01 natural sciences
Biochemistry
Cofactor
chemistry.chemical_compound
enantioselectivity
Molecular Biology
Alcohol dehydrogenase
chemistry.chemical_classification
biology
Nicotinamide
Molecular Structure
010405 organic chemistry
Communication
Organic Chemistry
Enantioselective synthesis
Alcohol Dehydrogenase
Stereoisomerism
Ketones
Combinatorial chemistry
Communications
0104 chemical sciences
Enantiopure drug
chemistry
deazaflavin
Biocatalysis
Alcohols
biology.protein
Molecular Medicine
Stereoselectivity
Methanomicrobiaceae
Oxidation-Reduction
Subjects
Details
- Language :
- English
- ISSN :
- 14394227
- Volume :
- 22
- Issue :
- 1
- Database :
- OpenAIRE
- Journal :
- ChemBioChem
- Accession number :
- edsair.doi.dedup.....f9039f1b3d8ff0a5724560ccfe645f74