1.1.1.422: pseudoephedrine dehydrogenase
This is an abbreviated version!
For detailed information about pseudoephedrine dehydrogenase, go to the full flat file.
Reaction
Synonyms
PseDH
ECTree
1.1.1.422 pseudoephedrine dehydrogenaseAdvanced search results
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results (Substrates Products
Substrates Products on EC 1.1.1.422 - pseudoephedrine 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
(+)-(1S,2S)-pseudoephedrine + NAD+
(S)-2-methylamino-1-phenylpropan-1-one + NADH + H+
-
-
-
?
(1S,2S)-(+)-pseudoephedrine + NAD+
(S)-2-(methylamino)-1-phenylpropan-1-one + NADH + H+
-
-
-
?
(4-chlorophenyl)-2-pyridinylmethanone + NAD+
(R)-(4-chlorophenyl)(pyridin-2-yl) methanol + NADH + H+
specifc activity: 0.2 U/mg. Product: 60% (R) enantiomeric excess
-
-
?
(S,R)-(+)-ephedrine + NAD+
(R)-2-methylimino-1-phenylpropan-1-ol + NADH + H+
-
-
-
?
(S,R)-(+)-ephedrine + NAD+
? + NADH + H+
the enzyme is strictly stereospecific for the diastereomers (S,S)-(+)-pseudoephedrine and (S,R)-(+)-ephedrine
-
-
?
(S,S)-(+)-pseudoephedrine + NAD+
(S)-2-(methylamino)-1-phenylpropan-1-one + NADH + H+
-
-
-
?
1,2-indandione + NAD+
? + NADH + H+
specifc activity: 9.52 U/mg
-
-
?
1,2-indanedione + NADH + H+
? + NAD+
5.9% of the activity as compared to methyl benzoylformate
-
-
?
1,2-naphthoquinone + NAD+
? + NADH + H+
specifc activity: 21.96 U/mg
-
-
?
1,2-naphthoquinone + NADH + H+
? + NAD+
13.7% of the activity as compared to methyl benzoylformate
-
-
?
1-phenyl-1,2-propanedione + NAD+
(S)-phenylacetylcarbinol + NADH + H+
specifc activity: 55.47 U/mg. Product: 99% (S) enantiomeric excess
-
-
?
1-phenyl-1,2-propanedione + NADH + H+
(S)-phenylacetylcarbinol + NAD+
34.6% of the activity as compared to methyl benzoylformate. (S)-Phenylacetylcarbinol is formed with more than 99% yield and more than 99% enantiomeric excess
-
-
?
1-phenylpropan-1,2-dione + NADH + H+
(S)-phenylacetylcarbinol + NAD+
-
-
-
r
2,2'-dichlorobenzil + NAD+
(2S)-1,2--bis(2-chlorophenyl)-2-hydroxyethan-1-one + NADH + H+
specifc activity: 10.08 U/mg. Product: 97% (S) enantiomeric excess
-
-
?
2,2'-dichlorobenzil + NADH + H+
? + NAD+
6.2% of the activity as compared to methyl benzoylformate
-
-
?
2,2'-furil + NAD+
(2S)-1,2-di(furan-2-yl)-2-hydroxyethan-1-one + NADH + H+
specifc activity: 0.66 U/mg. Product: 99% (S) enantiomeric excess
-
-
?
2,2'-thenil + NAD+
(2S)-2-hydroxy-1,2-di(thiophen-2-yl)ethan-1-one + NADH + H+
specifc activity: 0.58 U/mg. Product: 99% (S) enantiomeric excess
-
-
?
2-aminoacetophenone + NAD+
(1S)-2-amino-1-phenylethan-1-ol + NADH + H+
specifc activity: 9.49 U/mg. Product: 99% (S) enantiomeric excess
-
-
?
2-aminoacetophenone + NADH + H+
? + NAD+
5.9% of the activity as compared to methyl benzoylformate. The (S)-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: 12.58 U/mg
-
-
?
2-bromo-1-(3-chlorophenyl)-1-propanone + NADH + H+
?
-
-
-
r
2-bromo-1-(3-chlorophenyl)-1-propanone + NADH + H+
? + NAD+
7.8% of the activity as compared to methyl benzoylformate
-
-
?
2-bromoacetophenone + NAD+
(1S)-2-bromo-1-phenylethan-1-ol + NADH + H+
specifc activity: 3.75 U/mg. Product: 37% (S) enantiomeric excess
-
-
?
2-bromoacetophenone + NADH + H+
? + NAD+
2.3% of the activity as compared to methyl benzoylformate. The (S)-enantiomer is formed with 37% enantiomeric excess
-
-
?
2-chloro-1-phenyl-1-propane + NAD+
(R,S)-2-chloro-1-phenylpropan-1-ol + NADH + H+
specifc activity: 5.41 U/mg
-
-
?
2-chloro-1-phenyl-1-propanone + NADH + H+
? + NAD+
3.3% of the activity as compared to methyl benzoylformate
-
-
?
4,4'-difluorobenzil + NAD+
(2S)-1,2-bis(4fluorophenyl)-2-hydroxyethan-1-one + NADH + H+
specifc activity: 1.5 U/mg. Product: 99% (S) enantiomeric excess
-
-
?
4,4'-dimethylbenzil + NAD+
(2S)-2-hydroxy-1,2-bis(4-methylphenyl)ethan-1-one + NADH + H+
specifc activity: 2.93 U/mg. Product: 99% (S) enantiomeric excess
-
-
?
4-chlorobenzil + NAD+
? + NADH + H+
specifc activity: 5.26 U/mg
-
-
?
4-chlorobenzil + NADH + H+
? + NAD+
3.2% of the activity as compared to methyl benzoylformate
-
-
?
benzil + NAD+
(2S)-2-hydroxy-1,2-diphenylethan-1-one + NADH + H+
specifc activity: 2.4 U/mg. Product: 99% (S) enantiomeric excess
-
-
?
benzil + NADH + H+
? + NAD+
1.4% of the activity as compared to methyl benzoylformate
-
-
?
ethyl 2-chlorobenzoylacetate + NAD+
ethyl (R,S)-2-chloro-3-hydroxy-3-phenylpropanoate + NADH + H+
specifc activity: 16.13 U/mg
-
-
?
ethyl 2-chlorobenzoylacetate + NADH + H+
?
low activity
-
-
r
ethyl 2-chlorobenzoylacetate + NADH + H+
? + NAD+
10% of the activity as compared to methyl benzoylformate
-
-
?
isatin + NAD+
? + NADH + H+
specifc activity: 66.99 U/mg. Product: 89% (S) enantiomeric excess
-
-
?
isatin + NADH + H+
? + NAD+
41.8% of the activity as compared to methyl benzoylformate. The (S)-enantiomer is formed with 89% enantiomeric excess
-
-
?
methyl benzoylformate + NAD+
methyl (2S)-hydroxy(phenyl)acetate + NADH + H+
specifc activity: 160.12 U/mg. Product: 99% (S) enantiomeric excess
-
-
?
methyl benzoylformate + NADH + H+
? + NAD+
substrate with highest activity. The (S)-enantiomer is formed with 99% enantiomeric excess
-
-
?
phenyl-2-pyridinylmethanone + NAD+
(S)-phenyl(pyridin-1-yl)methynol + NADH + H+
specifc activity: 0.04 U/mg. Product: 5% (S) enantiomeric excess
-
-
?
phenylglyoxal + NAD+
(R,S)-hydroxy(phenyl)acetaldehyde + NADH + H+
specifc activity: 5.51 U/mg
-
-
?
phenylglyoxal + NADH + H+
? + NAD+
3.4% of the activity as compared to methyl benzoylformate
-
-
?
(+)-(1S,2S)-pseudoephedrine + NAD+
(S)-2-(methylamino)-1-phenylpropan-1-one + NADH + H+
-
-
-
?
(+)-(1S,2S)-pseudoephedrine + 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 anti-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. (+)-(1S,2S)-pseudoephedrine i.e. (1S,2S)-2-(methylamino)-1-phenylpropan-1-ol. (S)-2-(methylamino)-1-phenylpropan-1-one i.e. (S)-methcathinone
-
-
?
(+)-(1S,2S)-pseudoephedrine + NAD+
(S)-2-(methylamino)-1-phenylpropan-1-one + NADH + H+
the enzyme is strictly stereospecific for the diastereomers (S,S)-(+)-pseudoephedrine and (S,R)-(+)-ephedrine
-
-
?
1-phenylpropan-1,2-dione + NAD+
phenylacetylcarbinol + NADH + H+
-
-
-
?
1-phenylpropan-1,2-dione + NAD+
phenylacetylcarbinol + NADH + H+
PseDH overcomes the stability of the conjugated molecule PPD by reducing it to alpha-hydroxyketone (S)-PAC. Phenylacetylcarbinol (PAC) cannot be oxidized by these dehydrogenases and possibly undergoes a cleavage reaction to yield benzaldehyde and acetaldehyde
-
-
?
additional information
?
-
no activity with: acetophenone,2-thenoylacetonitrile, 2-chloroacetophenone, 3-chloropropiophenone, 1-phensyl-1,3-butanedione, 1-phenyl-1-propanone
-
-
?
additional information
?
-
no activity on (S,N)-(+)-(pseudo)ephedrine or (R,N)-(-)-(pseudo)ephedrine
-
-
-
additional information
?
-
PseDH is strictly stereospecific for the other diastereomers, (S,S)-(+)-pseudoephedrine and (S,R)-(+)-ephedrine. 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 (pseudo)ephedrine
-
-
-
additional information
?
-
enzyme PseDH is specific for the enantioselective oxidation of (S,S)-(+)-pseudoephedrine and (S,R)-(+)-ephedrine. Anti-prelog stereospecific PseDH 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 2-thenoylacetonitrile, 2-chloroacetophenone, 3-chloropropiophenone, 1-phenyl-1-propanone, acetophenone, and 1-phenyl-1,3-butanedione. Poor activity with 4,4'-dimethylbenzil, 4-(chlorophenyl)-2-pyridinylmethanone, phenyl-2-pyridinylmethanone, 4-chlorobenzil, 2-chloro-1-phenyl-1-propanone, phenylglyoxal, 2-bromoacetophenone, benzil, 2,2'-thenil, 2,2'-furil, and 4,4'-difluorobenzil
-
-
-
additional information
?
-
pseudoephedrine dehydrogenase (PseDH) selectively converts (S,S)-(+)-pseudoephedrine and (S,R)-(+)-ephedrine to (S)- and (R)-methcathinone, respectively
-
-
-
