1.5.1.18: ephedrine dehydrogenase
This is an abbreviated version!
For detailed information about ephedrine dehydrogenase, go to the full flat file.
Reaction
Synonyms
EDH
ECTree
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Substrates Products
Substrates Products on EC 1.5.1.18 - ephedrine dehydrogenase
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REACTION DIAGRAM
(-)-ephedrine + NAD+
(R)-2-methylimino-1-phenylpropan-1-ol + NADH + H+
-
-
-
?
1-phenylpropan-1,2-dione + NADH + H+
(R)-phenylacetylcarbinol + NAD+
high activity
-
-
r
ethyl 2-chlorobenzyolacetate + NADH + H+
?
low activity
-
-
r
2-imino-1-hydroxy-1-phenylpropane + NADH
-
higher rate than (-)-ephedrine
-
-
?
(+)-norephedrine + NAD+
2-imino-1-hydroxy-1-phenylpropane + NADH
-
norephedrine is identical with threo-2-amino-1-hydroxy-1-phenylpropane
-
-
?
2-methylimino-1-phenylpropan-1-ol + NADH
-
higher rate than (-)-ephedrine
-
-
?
(+)-pseudoephedrine + NAD+
2-methylimino-1-phenylpropan-1-ol + NADH
-
pseudoephedrine is identical with DL-threo-2-(methylamino)-1-phenylpropan-1-ol
-
-
?
(R)-2-methylimino-1-phenylpropan-1-ol + NADH
-
(-)-ephedrine is identical with 2-methylamino-1-phenyl-1-propanal
phenylacetylcarbinol is identical with 1-hydroxy-1-phenylpropan-2-one, three products: NADH, methylamine and phenylacetylcarbinol or its tautomeric form methylbenzoylcarbinol, ratio of NADH to methylamine is 1:1.1, enzyme attacks (-)-ephedrine at CH-NHCH3, yielding 2-methylimino-1-phenylpropanol, which is immediately hydrolyzed forming methylamine and phenylacetylcarbinol
?
(-)-ephedrine + NAD+
(R)-2-methylimino-1-phenylpropan-1-ol + NADH
-
first step in the catabolism of (-)-ephedrine
-
?
(-)-ephedrine + NAD+
(R)-2-methylimino-1-phenylpropan-1-ol + NADH
-
plays role in the metabolism of quite a number of different aromatic and aliphatic amino alcohols
-
?
4-[(1R,2E)-1-hydroxy-2-(methylimino)ethyl]phenol + NADH
-
higher rate than (-)-ephedrine
-
-
?
(-)-sympatol + NAD+
4-[(1R,2E)-1-hydroxy-2-(methylimino)ethyl]phenol + NADH
-
sympatol is identical with p-hydroxy-alpha-[(methylamino)methyl]benzyl tartrate
-
-
?
(R)-2-methylimino-1-phenylpropan-1-ol + NADH + H+
-
-
-
?
(R,R)-(-)-pseudoephedrine + NAD+
(R)-2-methylimino-1-phenylpropan-1-ol + NADH + H+
-
-
-
r
(R)-2-methylimino-1-phenylpropan-1-ol + NADH + H+
-
-
-
?
(R,S)-(-)-ephedrine + NAD+
(R)-2-methylimino-1-phenylpropan-1-ol + NADH + H+
-
-
-
r
phenylacetylcarbinol + NADH + H+
-
-
-
?
1-phenylpropan-1,2-dione + NAD+
phenylacetylcarbinol + NADH + H+
EDH overcomes the stability of the conjugated molecule PPD by reducing it to alpha-hydroxyketone (R)- and (S)-PAC, respectively. Phenylacetylcarbinol (PAC) cannot be oxidized by these dehydrogenases and possibly undergoes a cleavage reaction to yield benzaldehyde and acetaldehyde
-
-
?
p-hydroxy-alpha-[(1-methylimino)ethyl]benzyl alcohol + NADH
-
higher rate than (-)-ephedrine
-
-
?
suprifene + NAD+
p-hydroxy-alpha-[(1-methylimino)ethyl]benzyl alcohol + NADH
-
suprifene is identical with p-hydroxyephedrine
-
-
?
?
-
-
wide range of ethanolamines as substrates, overview
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-
?
additional information
?
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ephedrine dehydrogenase (EDH) exhibits strict selectivity for the oxidation of the diastereomers (R,S)-(-)-ephedrine and (R,R)-(-)-pseudoephedrine. Conversion of all ephedrine isomers required the addition of NAD+ as an oxidant. Without a surplus oxidant or in the presence of NADP+, cell lysates do not significantly convert ephedrine
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-
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additional information
?
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enzyme EDH exhibits a strict enantioselectivity for the oxidation of (R,S)-(-)-ephedrine and (R,R)-(-)-pseudoephedrine
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-
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additional information
?
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enzyme EDH is specific for the enantioselective oxidation of (-)-(R) N-(pseudo)ephedrine. Prelog-specific EDH catalyzes the regio- and enantiospecific reduction of 1-phenyl-1,2-propanedione to (R)-phenylacetylcarbinol with full conversion and enantiomeric excess of over 99%. In addition, the enzyme performs the reduction of a wide range of aryl-aliphatic carbonyl compounds, including ketoamines, ketoesters, and haloketones, to the corresponding enantiopure alcohols. The enzyme performs the reduction of aromatic ketones with a strict regioselectivity for the first carbonyl function on the alpha-position close to the aromatic ring. Substrate specificity and stereochemistry, overview. No activity with acetophenone, poor activity with 4,4-dimethylbenzil, 2-thenoylacetonitrile, 4-(chlorophenyl)-2-pyridinylmethanone, phenyl-2-pyridinylmethanone, 2-chloroacetophenone, 3-chloropropiophenone, 1-phenyl-1-propanone, 4-chlorobenzil, 2-chloro-1-phenyl-1-propanone, 2-bromo-1-(3-chlorophenyl)-1-propanone, and isatin
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