KEGG   ENZYME: 1.1.1.422
Entry
EC 1.1.1.422                Enzyme                                 

Name
pseudoephedrine dehydrogenase;
PseDH
Class
Oxidoreductases;
Acting on the CH-OH group of donors;
With NAD+ or NADP+ as acceptor
Sysname
(+)-(1S,2S)-pseudoephedrine:NAD+ 1-oxidoreductase
Reaction(IUBMB)
(+)-(1S,2S)-pseudoephedrine + NAD+ = (S)-2-(methylamino)-1-phenylpropan-1-one + NADH + H+ [RN:R12522]
Reaction(KEGG)
R12522
Substrate
(+)-(1S,2S)-pseudoephedrine [CPD:C02765];
NAD+ [CPD:C00003]
Product
(S)-2-(methylamino)-1-phenylpropan-1-one [CPD:C22263];
NADH [CPD:C00004];
H+ [CPD:C00080]
Comment
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 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. cf. EC 1.1.1.423, ephedrine dehydrogenase.
History
EC 1.1.1.422 created 2020
Reference
1
  Authors
Shanati, T., Lockie, C., Beloti, L., Grogan, G. and Ansorge-Schumacher, M.B.
  Title
Two enantiocomplementary ephedrine dehydrogenases from Arthrobacter sp. TS-15 with broad substrate specificity.
  Journal
ACS Catal 9:6202-6211 (2019)
Reference
2
  Authors
Shanati, T., Ansorge-Schumacher, M.
  Title
Enzymes and methods for the stereoselective reduction of carbonyl compounds, oxidation and stereoselective reductive amination - for the enantioselective preparation of alcohol amine compounds.
  Journal
(2019)
Reference
3  [PMID:31900306]
  Authors
Shanati T, Ansorge-Schumacher MB
  Title
Biodegradation of Ephedrine Isomers by Arthrobacter sp. Strain TS-15: Discovery of Novel Ephedrine and Pseudoephedrine Dehydrogenases.
  Journal
Appl Environ Microbiol 86 (2020)
DOI:10.1128/AEM.02487-19
Other DBs
ExplorEnz - The Enzyme Database: 1.1.1.422
IUBMB Enzyme Nomenclature: 1.1.1.422
ExPASy - ENZYME nomenclature database: 1.1.1.422
BRENDA, the Enzyme Database: 1.1.1.422

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