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Literature summary for 1.1.1.1 extracted from

  • Zhu, D.; Hyatt, B.; Hua, L.
    Enzymatic hydrogen transfer reduction of alpha-chloro aromatic ketones catalyzed by a hyperthermophilic alcohol dehydrogenase (2009), J. Mol. Catal. B, 56, 272-276 .
No PubMed abstract available

Application

Application Comment Organism
pharmacology the alcohol dehydrogenase effectively catalyzes the reductions of various substituted alpha-chloroacetophenones to form the (R)-enantiomer of the corresponding chlorohydrins with excellent ennatiomeric purity. The co-factor NADH can be recycled by the D-glucose dehydrogenase and D-glucose regeneration system or via the simple hydrogen transfer mode using iso-propanol as the hydrogen donor. The applicability of the alcohol-dehydrogenase-catalyzed hydrogen transfer reduction in the synthesis of optically active chlorohydrins is demonstrated by carrying out several reductions on the preparative scale. Thus enzyme is a valuable biocatalyst for the preparation of chiral chlorohydrins of pharmaceutical interest Pyrococcus furiosus

Organism

Organism UniProt Comment Textmining
Pyrococcus furiosus AE010289.1
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Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
2-chloro-1-(2,4-dichlorophenyl)ethan-1-one + NADH + H+ production of with (1R)-2-chloro-1-(2,4-dichlorophenyl)ethan-1-ol 99% enantiomeric excess Pyrococcus furiosus (1R)-2-chloro-1-(2,4-dichlorophenyl)ethan-1-ol + NAD+
-
?
2-chloro-1-(2,4-difluorophenyl)ethan-1-one + NADH + H+ production of (1R)-2-chloro-1-(2,4-fluorophenyl)ethan-1-ol with 99% enantiomeric excess Pyrococcus furiosus (1R)-2-chloro-1-(2,4-fluorophenyl)ethan-1-ol + NAD+
-
?
2-chloro-1-(4-fluorophenyl)ethan-1-one + NADH + H+ production of (1R)-2-chloro-1-(4-fluorophenyl)ethan-1-ol with 98% enantiomeric excess Pyrococcus furiosus (1R)-2-chloro-1-(4-fluorophenyl)ethan-1-ol + NAD+
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?
N-[4-(chloroacetyl)-2-nitrophenyl]acetamide + NADH + H+ production of N-[4-[(1R)-2-chloro-1-hydroxyethyl]-2-nitrophenyl]acetamide with 98% enantiomeric excess Pyrococcus furiosus N-[4-[(1R)-2-chloro-1-hydroxyethyl]-2-nitrophenyl]acetamide + NAD+
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?

Synonyms

Synonyms Comment Organism
PFADH
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Pyrococcus furiosus

Temperature Optimum [°C]

Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
37
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assay at Pyrococcus furiosus

pH Optimum

pH Optimum Minimum pH Optimum Maximum Comment Organism
7
-
assay Pyrococcus furiosus

Cofactor

Cofactor Comment Organism Structure
NADH the cofactor NADH can be recycled with D-glucose dehydrogenase/D-glucose system or in a coupled substrate approach using isopropanol as the hydrogen donor Pyrococcus furiosus