1.1.1.423: (1R,2S)-ephedrine 1-dehydrogenase
This is an abbreviated version!
For detailed information about (1R,2S)-ephedrine 1-dehydrogenase, go to the full flat file.
Reaction
Synonyms
EDH, ephedrine dehydrogenase
ECTree
1.1.1.423 (1R,2S)-ephedrine 1-dehydrogenaseAdvanced search results
results (
results (Substrates Products
Substrates Products on EC 1.1.1.423 - (1R,2S)-ephedrine 1-dehydrogenase
Please wait a moment until all data is loaded. This message will disappear when all data is loaded.
top
SUBSTRATE 
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
(4-chlorophenyl)-2-pyridinylmethanone + NAD+
(S)-(4-chlorophenyl)(pyridin-2-yl)methanol + NADH + H+
specifc activity: 1.74 U/mg. Product: 70% (S) enantiomeric excess
-
-
?
(4-chlorophenyl)-2-pyridinylmethanone + NADH + H+
(R)-(4-chlorophenyl)(pyridin-2-yl)methanol + NAD+
2.7% of the activity as compared to 1-phenyl-1,2-propanedione. The (R)-enantiomer is formed with 70% enantiomeric excess
-
-
?
(R,R)-(-)-pseudoephedrine + NAD+
? + NADH + H+
the enzyme exhibits a strict enantioselectivity for the oxidation of (-)-(1R,2S)-ephedrine and (R,R)-(-)-pseudoephedrine
-
-
?
1,2-indandione + NAD+
? + NADH + H+
specifc 50.05 U/mg
-
-
?
1,2-indanedione + NADH + H+
1-hydroxy-1,3-dihydro-2H-inden-2-one + NAD+
78.1% of the activity as compared to 1-phenyl-1,2-propanedione
-
-
?
1,2-naphthoquinone + NAD+
? + NADH + H+
specifc activity: 13.89 U/mg
-
-
?
1,2-naphthoquinone + NADH + H+
1-hydroxynaphthalen-2(1H)-one + NAD+
21.7% of the activity as compared to 1-phenyl-1,2-propanedione
-
-
?
1-phenyl-1,2-propanedione + NAD+
(R)-phenylacetylcarbinol + NADH + H+
specifc activity: 64.02 U/mg. Product: 99% (R) enantiomeric excess
-
-
?
1-phenyl-1,2-propanedione + NADH + H+
(R)-phenylacetylcarbinol + NAD+
substrate with highest activity. Full conversion and enantiomeric excess of more than 99%
-
-
?
1-phenyl-1,3-butanedione + NAD+
(4R)-4-hydroxy-4-phenylbutan-2-one + NADH + H+
specifc activity: 13.64 U/mg. Product: 98% (R) enantiomeric excess
-
-
?
1-phenyl-1,3-butanedione + NADH + H+
(4R)-4-hydroxy-4-phenylbutan-2-one + NAD+
21.3% of the activity as compared to 1-phenyl-1,2-propanedione. The (R)-enantiomer is formed with 98% enantiomeric excess
-
-
?
1-phenyl-1-propanone + NAD+
(1R)-1-phenylpropan-1-ol + NADH + H+
specifc activity: 1.55 U/mg. Product: 99% (R) enantiomeric excess
-
-
?
1-phenyl-1-propanone + NADH + H+
(1R)-1-phenylpropan-1-ol + NAD+
2.4% of the activity as compared to 1-phenyl-1,2-propanedione. The (R)-enantiomer is formed with 99% enantiomeric excess
-
-
?
2,2'-dichlorobenzil + NAD+
(2R)-1,2-bis(2-chlorophenyl)-2-hydroxyethan-1-one + NADH + H+
specifc activity: 27.91 U/mg. Product: 94% (R) enantiomeric excess
-
-
?
2,2'-dichlorobenzil + NADH + H+
(2R)-1,2-bis(2-chlorophenyl)-2-hydroxyethan-1-one + NAD+
43.6% of the activity as compared to 1-phenyl-1,2-propanedione. The (R)-enantiomer is formed with 4% enantiomeric excess
-
-
?
2,2'-furil + NAD+
(2R)-1,2-di(furan-2-yl)-2-hydroxyethan + NADH + H+
specifc activity: 19.95 U/mg. Product: 99% (R) enantiomeric excess
-
-
?
2,2'-furil + NADH + H+
(2R)-1,2-di(furan-2-yl)-2-hydroxyethan-1-one + NAD+
20% of the activity as compared to 1-phenyl-1,2-propanedione. The (R)-enantiomer is formed with 99% enantiomeric excess
-
-
?
2,2'-thenil + NAD+
(2R)-2-hydroxy-1,2-di(thiophen-2-yl)ethan-1-one + NADH + H+
specifc activity: 46.77 U/mg. Product: 99% (R) enantiomeric excess
-
-
?
2,2'-thenil + NADH + H+
(2R)-2-hydroxy-1,2-di(thiophen-2-yl)ethan-1-one + NAD+
46.8% of the activity as compared to 1-phenyl-1,2-propanedione. The (R)-enantiomer is formed with 99% enantiomeric excess
-
-
?
2-aminoacetophenone + NAD+
(1R)-2-amino-1-phenylethan-1-ol + NADH + H+
specifc activity: 25.79 U/mg. Product: 99% (R) enantiomeric excess
-
-
?
2-aminoacetophenone + NADH + H+
(1R)-2-amino-1-phenylethan-1-ol + NAD+
40.3% of the activity as compared to 1-phenyl-1,2-propanedione. The (R)-enantiomer is formed with 99% enantiomeric excess
-
-
?
2-bromo-1-(3-chlorophenyl)-1-propanone + NAD+
(R,S)-2-bromo-1-(3-chlorophenyl)propan-1-ol + NADH + H+
specifc activity: 5.1 U/mg
-
-
?
2-bromo-1-(3-chlorophenyl)-1-propanone + NADH + H+
2-bromo-1-(3-chlorophenyl)propan-1-ol + NAD+
7.9% of the activity as compared to 1-phenyl-1,2-propanedione
-
-
?
2-bromoacetophenone + NAD+
(1R)-2-bromo-1-phenylethan-1-ol + NADH + H+
specifc activity: 9.44 U/mg. Product: 85% (R) enantiomeric excess
-
-
?
2-bromoacetophenone + NADH + H+
(1R)-2-bromo-1-phenylethan-1-ol + NAD+
14.8% of the activity as compared to 1-phenyl-1,2-propanedione. The (R)-enantiomer is formed with 85% enantiomeric excess
-
-
?
2-chloro-1-phenyl-1-propane + NAD+
(R,S)-2-chloro-1-phenylpropan-1-ol + NADH + H+
specifc activity: 8.0 U/mg
-
-
?
2-chloro-1-phenyl-1-propanone + NADH + H+
2-chloro-1-phenyl-1-propan-1-ol + NAD+
12.5% of the activity as compared to 1-phenyl-1,2-propanedione
-
-
?
2-chloroacetophenone + NAD+
(1R)-2-chloro-1-phenylethan-1-ol + NADH + H+
specifc activity: 8.71 U/mg. Product: 98% (R) enantiomeric excess
-
-
?
2-chloroacetophenone + NADH + H+
(1R)-2-chloro-1-phenylethan-1-ol + NAD+
13.6% of the activity as compared to 1-phenyl-1,2-propanedione. The (R)-enantiomer is formed with 98% enantiomeric excess
-
-
?
2-thenoylacetonitrile + NAD+
(3R)-3-hydroxy-3-(thiophen-2-yl)propanenitril + NADH + H+
specifc activity: 6.87 U/mg. Product: 99% (R) enantiomeric excess
-
-
?
2-thenoylacetonitrile + NADH + H+
(2R)-hydroxy(thiophen-2-yl)acetonitrile + NAD+
6.87% of the activity as compared to 1-phenyl-1,2-propanedione. The (R)-enantiomer is formed with 99% enantiomeric excess
-
-
?
3-chloropropiophenone + NAD+
(1R)-3-chloro-1-phenylpropan-1-ol + NADH + H+
specifc activity: 4.45 U/mg. Product: 99% (R) enantiomeric excess
-
-
?
3-chloropropiophenone + NADH + H+
(1R)-3-chloro-1-phenylpropan-1-ol + NAD+
6.9% of the activity as compared to 1-phenyl-1,2-propanedione. The (R)-enantiomer is formed with 99% enantiomeric excess
-
-
?
4,4'-difluorobenzil + NAD+
(2R)-1,2-bis(4-fluorophenyl)-2-hydroxyethan-1-one + NADH + H+
specifc activity: 48.2 U/mg. Product: 99% (R) enantiomeric excess
-
-
?
4,4'-difluorobenzil + NADH + H+
(2R)-1,2-bis(4-fluorophenyl)-2-hydroxyethan-1-one + NAD+
75.3% of the activity as compared to 1-phenyl-1,2-propanedione. The (R)-enantiomer is formed with 99% enantiomeric excess
-
-
?
4,4'-dimethylbenzil + NAD+
(2R)-2-hydroxy-1,2-bis(4-methylphenyl)ethan-1-one + NADH + H+
specifc activity: 3.12 U/mg. Product: 99% (R) enantiomeric excess
-
-
?
4,4'-dimethylbenzil + NADH + H+
(2R)-1,2-bis(4-methylphenyl)-2-hydroxyethan-1-one + NAD+
4.8% of the activity as compared to 1-phenyl-1,2-propanedione. The (R)-enantiomer is formed with 99% enantiomeric excess
-
-
?
4-chlorobenzil + NAD+
? + NADH + H+
specifc activity: 6.5 U/mg. Product: 95% (R) enantiomeric excess
-
-
?
4-chlorobenzil + NADH + H+
? + NAD+
10.2% of the activity as compared to 1-phenyl-1,2-propanedione. The (R)-enantiomer is formed with 58% enantiomeric excess
-
-
?
benzil + NAD+
(2R)-2-hydroxy-1,2-diphenylethan-1-one + NADH + H+
specifc activity: 47.06 U/mg. Product: 99% enantiomeric (R) excess
-
-
?
benzil + NADH + H+
(2R)-2-hydroxy-1,2-diphenylethan-1-one + NAD+
73.5% of the activity as compared to 1-phenyl-1,2-propanedione. The (R)-enantiomer is formed with 99% enantiomeric excess
?
-
?
ethyl 2-chlorobenzoylacetate + NAD+
ethyl (R,S)-2-chloro-3-hydroxy-3-phenylpropanoate + NADH + H+
specifc activity: 35.21 U/mg
-
-
?
ethyl 2-chlorobenzoylacetate + NADH + H+
ethyl 2-chloro-3-hydroxy-3-phenylpropanoate + NAD+
54.9% of the activity as compared to 1-phenyl-1,2-propanedione
-
-
?
isatin + NAD+
? + NADH + H+
specifc activity: 7.84 U/mg. Product: 52% (R) enantiomeric excess
-
-
?
isatin + NADH + H+
(3R)-3-hydroxy-1,3-dihydro-2H-indol-2-one + NAD+
12.25% of the activity as compared to 1-phenyl-1,2-propanedione. The (R)-enantiomer is formed with 52% enantiomeric excess
-
-
?
methyl benzoylformate + NAD+
methyl (2R)-hydroxy(phenyl)acetate + NADH + H+
specifc activity: 46.56 U/mg. Product: 98% (R) enantiomeric excess
-
-
?
methyl benzoylformate + NADH + H+
methyl (2S)-hydroxy(phenyl)acetate + NAD+
72.7% of the activity as compared to 1-phenyl-1,2-propanedione. The (R)-enantiomer is formed with 98% enantiomeric excess
-
-
?
phenyl-2-pyridinylmethanone + NAD+
(R)-phenyl(pyridin-2-yl)methanol + NADH + H+
specifc activity: 2.81 U/mg. Product: 24% (R) enantiomeric excess
-
-
?
phenyl-2-pyridinylmethanone + NADH + H+
(R)-phenyl(pyridin-2-yl)methanol + NAD+
4.4% of the activity as compared to 1-phenyl-1,2-propanedione. The (R)-enantiomer is formed with 24% enantiomeric excess
-
-
?
phenylglyoxal + NAD+
(2R)-hydroxy(phenyl)acetaldehyde + NADH + H+
specifc activity: 12.1 U/mg. Product: 99% (R) enantiomeric excess
-
-
?
phenylglyoxal + NADH + H+
(2R)-hydroxy(phenyl)acetaldehyde + NAD+
18.9% of the activity as compared to 1-phenyl-1,2-propanedione. The (R)-enantiomer is formed with 99% enantiomeric excess
-
-
?
additional information
?
-
no activity on (S,N)-(+)-(pseudo)ephedrine or (R,N)-(-)-(pseudo)ephedrine
-
-
-
(-)-(1R,2S)-ephedrine + NAD+
(S)-2-methylamino-1-phenylpropan-1-one + NADH + H+
-
-
-
?
(-)-(1R,2S)-ephedrine + NAD+
(S)-2-methylamino-1-phenylpropan-1-one + NADH + H+
the enzyme acts on a broad range of different aryl-alkyl ketones, such as haloketones, ketoamines, diketones, and ketoesters. It accepts various types of aryl groups including phenyl-, pyridyl-, thienyl-, and furyl-rings, but the presence of an aromatic ring is essential for the activity. In addition, the presence of a functional group on the alkyl chain, such as an amine, a halogen, or a ketone, is also crucial. The enzyme exhibits a strict Prelog enantioselectivity. When acting on diketones, it catalyses the reduction of only the keto group closest to the ring, with no further reduction to the diol. (-)-(1R,2S)-ephedrine i.e. (1R,2S)-1-phenyl-1-hydroxy-2-methylaminopropane. (S)-2-methylamino-1-phenylpropan-1-one i.e. (S)-methcathinone
-
-
?
(-)-(1R,2S)-ephedrine + NAD+
(S)-2-methylamino-1-phenylpropan-1-one + NADH + H+
the enzyme exhibits a strict enantioselectivity for the oxidation of (-)-(1R,2S)-ephedrine and (R,R)-(-)-pseudoephedrine
-
-
?
