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Information on EC 1.1.1.423 - (1R,2S)-ephedrine 1-dehydrogenase
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1.1.1.423 (1R,2S)-ephedrine 1-dehydrogenaseIUBMB Comments
The enzyme, characterized from the bacterium Arthrobacter sp. TS-15, acts on a broad range of different aryl-alkyl ketones, such as haloketones, ketoamines, diketones, and ketoesters. It exhibits a strict enantioselectivity and 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. When acting on diketones, it catalyses the reduction of only the keto group closest to the ring, with no further reduction to the diol. cf. EC 1.1.1.422, pseudoephedrine dehydrogenase and EC 1.5.1.18, ephedrine dehydrogenase.
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The expected taxonomic range for this enzyme is: Arthrobacter sp. TS-15
Reaction Schemes
+
=
(S)-2-(methylamino)-1-phenylpropan-1-one
+
+
Synonyms
EDH, ephedrine dehydrogenase, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
EDH
ephedrine dehydrogenase
-
-
-
-
EDH
-
-
ambiguous
-
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
(-)-(1R,2S)-ephedrine + NAD+ = (S)-2-(methylamino)-1-phenylpropan-1-one + NADH + H+
-
-
-
-
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SYSTEMATIC NAME
IUBMB Comments
()-(1R,2S)-ephedrine:NAD+ 1-oxidoreductase
The enzyme, characterized from the bacterium Arthrobacter sp. TS-15, acts on a broad range of different aryl-alkyl ketones, such as haloketones, ketoamines, diketones, and ketoesters. It exhibits a strict enantioselectivity and 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. When acting on diketones, it catalyses the reduction of only the keto group closest to the ring, with no further reduction to the diol. cf. EC 1.1.1.422, pseudoephedrine dehydrogenase and EC 1.5.1.18, ephedrine dehydrogenase.
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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
-
-
?
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NATURAL SUBSTRATE
NATURAL 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
(-)-(1R,2S)-ephedrine + NAD+
(S)-2-methylamino-1-phenylpropan-1-one + NADH + H+
-
-
-
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
NADH
no apparent activity with NADP(H)+ and full catalytic activity with NAD(H). The preference for NADH makes the utilization of the enzyme an attractive for industrial applications, since NADH is more stable and less expensive than NADPH under operational reaction conditions
NAD+
no apparent activity with NADP(H)+ and full catalytic activity with NAD(H). The preference for NADH makes the utilization of the enzyme an attractive for industrial applications, since NADH is more stable and less expensive than NADPH under operational reaction conditions
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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TEMPERATURE RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
55 - 75
55°C: about 40% of maximal activity, 75°C: about 75% of maximal activity
65 - 75
65°C: about 55% of maximal activity, 75°C: about 75% of maximal activity
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable).
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable). Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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SUBUNIT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
dimer
4 * 27000, SDS-PAGE, the smallest oligomeric state seems to be a dimer, the predominant oligomeric state is the tetramer
tetramer
tetramer
4 * 27000, SDS-PAGE, the smallest oligomeric state seems to be a dimer, the predominant oligomeric state is the tetramer
tetramer
4 * 27000, the enzyme tends to form higher oligomeric states, up to a hexadecamer, SDS-PAGE
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pH STABILITY
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
7.5 - 8.5
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TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
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CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
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APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
industry
the wide substrate spectrum of these dehydrogenases, combined with their regio- and enantioselectivity, suggests a high potential for the industrial production of valuable chiral compounds
synthesis
synthesis
the wide substrate spectrum of these dehydrogenases, combined with their regio- and enantioselectivity, suggests a high potential for the industrial production of valuable chiral compounds
synthesis
the enzyme catalyzes the oxidation of an isomer of ephedrine and the regio- and enantioselective reduction of sterically demanding substrate 1-phenyl-1,2-propanedione to give (R)-phenylacetylcarbinol
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REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Shanati, T.; Lockie, C.; Beloti, L.; Grogan, G.; Ansorge-Schumacher, M.B.
Two enantiocomplementary ephedrine dehydrogenases from Arthrobacter sp. TS-15 with broad substrate specificity
ACS Catal.
9
6202-6211
2019
Arthrobacter sp. TS-15 (A0A545BBR2)
-
brenda
Shanati, T.; Ansorge-Schumacher, M.B.
Biodegradation of ephedrine isomers by Arthrobacter sp. strain TS-15 discovery of novel ephedrine and pseudoephedrine dehydrogenases
Appl. Environ. Microbiol.
86
e02487-19
2020
Arthrobacter sp. TS-15 (A0A545BBR2)
brenda
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Release 2023.1 (January 2023)
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