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Literature summary for 1.1.1.B3 extracted from

  • Dudzik, A.; Snoch, W.; Borowiecki, P.; Opalinska-Piskorz, J.; Witko, M.; Heider, J.; Szaleniec, M.
    Asymmetric reduction of ketones and beta-keto esters by (S)-1-phenylethanol dehydrogenase from denitrifying bacterium Aromatoleum aromaticum (2015), Appl. Microbiol. Biotechnol., 99, 5055-5069 .
    View publication on PubMedView publication on EuropePMC
Search for more literature for 1.1.1.B3

KM Value [mM]

KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
additional information
-
 additional information kinetics Aromatoleum aromaticum

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
(S)-1-phenylethanol + NAD+ Aromatoleum aromaticum
-
 acetophenone + NADH + H+
-
 r
(S)-1-phenylethanol + NAD+ Aromatoleum aromaticum EbN1
-
 acetophenone + NADH + H+
-
 r

Organism

Organism UniProt Comment Textmining
Aromatoleum aromaticum
-
-
-
Aromatoleum aromaticum EbN1
-
-
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
(R)-3-phenyl-1-indanol + NADH + H+ 100% (S)-enantiospecific product Aromatoleum aromaticum (R)-3-phenyl-1-indanol + NAD+
-
 r
(S)-1-phenylethanol + NAD+
-
 Aromatoleum aromaticum acetophenone + NADH + H+
-
 r
(S)-1-phenylethanol + NAD+ the enzyme catalyzes the stereospecific oxidation of (S)-1-phenylethanol to acetophenone during anaerobic ethylbenzene mineralization, but also the reverse reaction, i.e. NADH-dependent enantioselective reduction of acetophenone to (S)-1-phenylethanol, high enantioselectivity of the reaction Aromatoleum aromaticum acetophenone + NADH + H+
-
 r
(S)-1-phenylethanol + NAD+
-
 Aromatoleum aromaticum EbN1 acetophenone + NADH + H+
-
 r
(S)-1-phenylethanol + NAD+ the enzyme catalyzes the stereospecific oxidation of (S)-1-phenylethanol to acetophenone during anaerobic ethylbenzene mineralization, but also the reverse reaction, i.e. NADH-dependent enantioselective reduction of acetophenone to (S)-1-phenylethanol, high enantioselectivity of the reaction Aromatoleum aromaticum EbN1 acetophenone + NADH + H+
-
 r
(S)-1-[4-(1-hydroxyethyl)phenyl]-methylketone + NADH + H+ 100% (S)-enantiospecific product Aromatoleum aromaticum (S)-1-(4-(1-hydroxy-ethyl)-phenyl)-ethanol + NAD+
-
 r
(S)-3-phenyl-1-indanone + NADH + H+ 100% (S)-enantiospecific product Aromatoleum aromaticum (S)-3-phenyl-1-indanol + NAD+
-
 r
1-(furan-2-yl)methylketone + NADH + H+ 100% (S)-enantiospecific product Aromatoleum aromaticum (S)-1-(furan-2-yl)ethanol + NAD+
-
 r
1-indanone + NADH + H+ 100% (S)-enantiospecific product Aromatoleum aromaticum (S)-1-indanol + NAD+
-
 r
1-indanone + NADH + H+ 100% (S)-enantiospecific product Aromatoleum aromaticum EbN1 (S)-1-indanol + NAD+
-
 r
1-tetralone + NADH + H+ 100% (S)-enantiospecific product Aromatoleum aromaticum (S)-1,2,3,4-tetrahydronaphthalen-1-ol + NAD+
-
 r
2'-fluoroacetophenone + NADH + H+ 100% (S)-enantiospecific product Aromatoleum aromaticum (S)-1-(2-fluorophenyl)ethanol + NAD+
-
 r
2'-hydroxyacetophenone + NADH + H+ 100% (S)-enantiospecific product Aromatoleum aromaticum (S)-2-(1-hydroxyethyl)phenol + NAD+
-
 r
2,2,2-trifluoroacetophenone + NADH + H+ 100% (S)-enantiospecific product Aromatoleum aromaticum (S)-1-phenyl-2,2,2-trifluoroethan-1-ol + NAD+
-
 r
2,2-dichloroacetophenone + NADH + H+ 100% (S)-enantiospecific product Aromatoleum aromaticum (S)-2,2-dichloro-1-phenylethanol + NAD+
-
 r
2,2-difluoroacetophenone + NADH + H+ 100% (S)-enantiospecific product Aromatoleum aromaticum (S)-2,2-difluoro-1-phenylethan-1-ol + NAD+
-
 r
2,4'-dichloroacetophenone + NADH + H+ 100% (S)-enantiospecific product Aromatoleum aromaticum (S)-2-chloro-1-(4-chloro-phenyl)-ethanol + NAD+
-
 r
2-acetylpyridine + NADH + H+ 100% (S)-enantiospecific product Aromatoleum aromaticum (S)-1-(pyridin-2-yl)ethanol + NAD+
-
 r
2-acetylthiophene + NADH + H+ 100% (S)-enantiospecific product Aromatoleum aromaticum (S)-1-(thiophen-2-yl)ethanol + NAD+
-
 r
2-chloroacetophenone + NADH + H+ 100% (R)-enantiospecific product Aromatoleum aromaticum (R)-2-chloro-1-phenylethanol + NAD+
-
 r
2-cyanoacetophenone + NADH + H+ 100% (S)-enantiospecific product Aromatoleum aromaticum (S)-3-hydroxy-3-phenylpropanenitrile + NAD+
-
 r
2-fluoroacetophenone + NADH + H+ 100% (S)-enantiospecific product Aromatoleum aromaticum (S)-2-fluoro-1-phenylethan-1-ol + NAD+
-
 r
3'-aminoacetophenone + NADH + H+ 100% (S)-enantiospecific product Aromatoleum aromaticum (S)-1-(3-aminophenyl)ethanol + NAD+
-
 r
3'-bromoacetophenone + NADH + H+ 100% (S)-enantiospecific product Aromatoleum aromaticum (S)-1-(3-bromophenyl)ethanol + NAD+
-
 r
3'-chloroacetophenone + NADH + H+ 100% (S)-enantiospecific product Aromatoleum aromaticum (S)-1-(3-chlorophenyl)ethanol + NAD+
-
 r
3'-fluoroacetophenone + NADH + H+ 100% (S)-enantiospecific product Aromatoleum aromaticum (S)-1-(3-fluorophenyl)ethanol + NAD+
-
 r
3'-hydroxyacetophenone + NADH + H+ 100% (S)-enantiospecific product Aromatoleum aromaticum (S)-3-[(1)-1-hydroxyethyl]phenol + NAD+
-
 r
3'-methoxyacetophenone + NADH + H+ 100% (S)-enantiospecific product Aromatoleum aromaticum (S)-1-(3-methoxyphenyl)ethanol + NAD+
-
 r
3'-methylacetophenone + NADH + H+ 100% (S)-enantiospecific product Aromatoleum aromaticum (S)-1-(3-methylphenyl)ethanol + NAD+
-
 r
3-(3-bromo-phenyl)-3-oxo-propionic acid methyl ester + NADH + H+ 100% (S)-enantiospecific product Aromatoleum aromaticum (S)-methyl 3-(3-bromophenyl)-3-hydroxypropanoate + NAD+
-
 r
3-(3-chloro-phenyl)-3-oxo-propionic acid methyl ester + NADH + H+ 100% (S)-enantiospecific product Aromatoleum aromaticum (S)-methyl 3-(3-chlorophenyl)-3-hydroxypropanoate + NAD+
-
 r
3-(3-fluoro-phenyl)-3-oxo-propionic acid methyl ester + NADH + H+ 100% (S)-enantiospecific product Aromatoleum aromaticum (S)-methyl 3-(3-fluorophenyl)-3-hydroxypropanoate + NAD+
-
 r
3-(3-methoxyphenyl)-3-oxo-propionic acid methylester + NADH + H+ 100% (S)-enantiospecific product Aromatoleum aromaticum (S)-methyl 3-hydroxy-3-(3-methoxyphenyl)propanoate + NAD+
-
 r
3-(4-methoxy-phenyl)-3-oxo-propionic acid methyl ester + NADH + H+ 100% (S)-enantiospecific product Aromatoleum aromaticum (S)-methyl 3-hydroxy-3-(4-methoxyphenyl)propanoate + NAD+
-
 r
3-acetylpyridine + NADH + H+ 100% (S)-enantiospecific product Aromatoleum aromaticum (S)-1-(pyridin-3-yl)ethanol + NAD+
-
 r
3-coumaranone + NADH + H+ 100% (S)-enantiospecific product Aromatoleum aromaticum (S)-2,3-dihydro-1-benzofuran-3-ol + NAD+
-
 r
4'-acetyl acetophenone + NADH + H+ 100% (S)-enantiospecific product Aromatoleum aromaticum (S)-1-(4-(1-hydroxy-ethyl)-phenyl)-ethanol + NAD+
-
 r
4'-acetylbiphenyl + NADH + H+ 100% (S)-enantiospecific product Aromatoleum aromaticum (S)-1-(biphenyl-4-yl)ethanol + NAD+
-
 r
4'-acetylphenyl methanesulfonate + NADH + H+ 100% (S)-enantiospecific product Aromatoleum aromaticum (S)-4-(1-hydroxyethyl)phenyl methanesulfonate + NAD+
-
 r
4'-aminoacetophenone + NADH + H+ 50% (S)-enantiospecific product Aromatoleum aromaticum (S)-1-(4-aminophenyl)ethanol + NAD+
-
 r
4'-bromoacetophenone + NADH + H+ 100% (S)-enantiospecific product Aromatoleum aromaticum (S)-1-(4-bromophenyl)ethanol + NAD+
-
 r
4'-chloroacetophenone + NADH + H+ 100% (S)-enantiospecific product Aromatoleum aromaticum (S)-1-(4-chlorophenyl)ethanol + NAD+
-
 r
4'-ethylacetophenone + NADH + H+ 100% (S)-enantiospecific product Aromatoleum aromaticum (S)-1-(4-ethylphenyl)ethanol + NAD+
-
 r
4'-fluoroacetophenone + NADH + H+ 100% (S)-enantiospecific product Aromatoleum aromaticum (S)-1-(4-fluorophenyl)ethanol + NAD+
-
 r
4'-hydroxyacetophenone + NADH + H+ 90% (S)-enantiospecific product Aromatoleum aromaticum (S)-4-(1-hydroxyethyl)phenol + NAD+
-
 r
4'-methoxyacetophenone + NADH + H+ 100% (S)-enantiospecific product Aromatoleum aromaticum (S)-1-(4-methoxyphenyl)ethanol + NAD+
-
 r
4'-nitroacetophenone + NADH + H+ 100% (S)-enantiospecific product Aromatoleum aromaticum (S)-1-(4-nitrophenyl)ethanol + NAD+
-
 r
4-acetylbenzonitrile + NADH + H+ 100% (S)-enantiospecific product Aromatoleum aromaticum (S)-4-(1-hydroxyethyl)benzonitrile + NAD+
-
 r
4-acetylpyridine + NADH + H+ 100% (S)-enantiospecific product Aromatoleum aromaticum (S)-1-(pyridin-4-yl)ethanol + NAD+
-
 r
6-hydroxy-1-indanone + NADH + H+ 100% (S)-enantiospecific product Aromatoleum aromaticum (S)-2,3-dihydro-1H-indene-1,6-diol + NAD+
-
 r
acetophenone + NADH + H+ 100% (S)-enantiospecific product Aromatoleum aromaticum (S)-1-phenylethanol + NAD+
-
 r
acetophenone + NADH + H+ 100% (S)-enantiospecific product Aromatoleum aromaticum EbN1 (S)-1-phenylethanol + NAD+
-
 r
methyl (4-chlorobenzoyl)acetate + NADH + H+ 100% (S)-enantiospecific product Aromatoleum aromaticum (S)-methyl 3-(4-chlorophenyl)-3-hydroxypropanoate + NAD+
-
 r
methyl 3-(4-ethylphenyl)-3-oxopropanoate + NADH + H+ 100% (S)-enantiospecific product Aromatoleum aromaticum (S)-methyl 3-(4-ethylphenyl)-3-hydroxypropanoate + NAD+
-
 r
methyl 3-(4-methylphenyl)-3-oxopropanoate + NADH + H+ 100% (S)-enantiospecific product Aromatoleum aromaticum (S)-methyl 3-hydroxy-3-(4-methylphenyl)propanoate + NAD+
-
 r
methyl 3-oxo-3-phenylpropanoate + NADH + H+ 100% (S)-enantiospecific product Aromatoleum aromaticum (S)-methyl 3-hydroxy-3-phenylpropanoate + NAD+
-
 r
methyl 4-bromobenzoylacetate + NADH + H+ 100% (S)-enantiospecific product Aromatoleum aromaticum (S)-methyl 3-(4-bromophenyl)-3-hydroxypropanoate + NAD+
-
 r
methyl 4-fluorobenzoylacetate + NADH + H+ 100% (S)-enantiospecific product Aromatoleum aromaticum (S)-methyl 3-(4-fluorophenyl)-3-hydroxypropanoate + NAD+
-
 r
additional information application of PEDH for asymmetric reduction of 42 prochiral ketones and 11 beta-keto esters to enantiopure secondary alcohols, high enantioselectivity of the reaction, substrate binding mechanism analysis by molecular docking, modeling of enzyme-substrate complexes, overview Aromatoleum aromaticum ?
-
 ?
additional information application of PEDH for asymmetric reduction of 42 prochiral ketones and 11 beta-keto esters to enantiopure secondary alcohols, high enantioselectivity of the reaction, substrate binding mechanism analysis by molecular docking, modeling of enzyme-substrate complexes, overview Aromatoleum aromaticum EbN1 ?
-
 ?
propiophenone + NADH + H+ 100% (S)-enantiospecific product Aromatoleum aromaticum (S)-1-phenylpropan-1-ol + NAD+
-
 r

Temperature Optimum [°C]

Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
30
-
-
 Aromatoleum aromaticum

pH Optimum

pH Optimum Minimum pH Optimum Maximum Comment Organism
5.5
-
 ketone reduction Aromatoleum aromaticum
5.8
-
 alcohol oxidation Aromatoleum aromaticum

Cofactor

Cofactor Comment Organism Structure
NAD+
-
 Aromatoleum aromaticum
NADH
-
 Aromatoleum aromaticum

General Information

General Information Comment Organism
evolution the enzyme belongs to the short-chain dehydrogenase/reductase family Aromatoleum aromaticum
metabolism strain EbN1 produces (S)-1-phenylethanol via a direct anaerobic oxidation of ethylbenzene by the molybdenum enzyme ethylbenzene dehydrogenase. In the second step of the pathway, PEDH catalyzes the stereospecific conversion of (S)-1-phenylethanol to acetophenone and is also capable to catalyze the industrially important reverse reaction, namely, NADH-dependent enantioselective reduction of acetophenone to (S)-1-phenylethanol Aromatoleum aromaticum