KEGG ENZYME: 1.1.1.422

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;
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

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

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

patent (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:e02487-19 (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

All links

Chemical substance (5)   
   KEGG COMPOUND (5)   
Chemical reaction (2)   
   KEGG REACTION (1)   
   KEGG RCLASS (1)   
All databases (7)   

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