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
1.5.1.18 ephedrine dehydrogenaseAdvanced search results
results (
results (Substrates Products
Substrates Products on EC 1.5.1.18 - ephedrine 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
(-)-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
(+)-norephedrine + NAD+
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
-
-
?
(+)-pseudoephedrine + NAD+
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
-
-
?
(-)-ephedrine + NAD+
(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
-
?
(-)-sympatol + NAD+
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,R)-(-)-pseudoephedrine + NAD+
(R)-2-methylimino-1-phenylpropan-1-ol + NADH + H+
-
-
-
?
(R,R)-(-)-pseudoephedrine + NAD+
(R)-2-methylimino-1-phenylpropan-1-ol + NADH + H+
-
-
-
r
(R,S)-(-)-ephedrine + NAD+
(R)-2-methylimino-1-phenylpropan-1-ol + NADH + H+
-
-
-
?
(R,S)-(-)-ephedrine + NAD+
(R)-2-methylimino-1-phenylpropan-1-ol + NADH + H+
-
-
-
r
1-phenylpropan-1,2-dione + NAD+
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
-
-
?
suprifene + NAD+
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
-
-
?
additional information
?
-
-
wide range of ethanolamines as substrates, overview
-
-
?
additional information
?
-
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
-
-
-
additional information
?
-
enzyme EDH exhibits a strict enantioselectivity for the oxidation of (R,S)-(-)-ephedrine and (R,R)-(-)-pseudoephedrine
-
-
-
additional information
?
-
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
-
-
-
