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Literature summary for 1.1.1.422 extracted from

  • Shanati, T.; Ansorge-Schumacher, M.B.
    Biodegradation of ephedrine isomers by Arthrobacter sp. strain TS-15 discovery of novel ephedrine and pseudoephedrine dehydrogenases (2020), Appl. Environ. Microbiol., 86, e02487-19 .
    View publication on PubMedView publication on EuropePMC
Search for more literature for 1.1.1.422

Application

Application Comment Organism
additional information both (R,S)-(-)-ephedrine and (S,S)-(+)-pseudoephedrine are constituents of various over-the-counter (OTC) drugs and are also used as decongestants and stimulants. Arthrobacter sp. TS-15 and its isolated ephedrine-oxidizing enzymes have potential for use in decontamination and synthetic applications Arthrobacter sp. TS-15

Cloned(Commentary)

Cloned (Comment) Organism
expression in Escherichia coli Arthrobacter sp. TS-15
recombinant expression of His-tagged enzyme in Escherichia coli strain T7 SHuffle(DE3) Arthrobacter sp. TS-15

KM Value [mM]

KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
0.26
-
 (+)-(1S,2S)-pseudoephedrine pH 7.8, 25°C Arthrobacter sp. TS-15
0.263
-
 (S,S)-(+)-pseudoephedrine pH 7.8, 25°C Arthrobacter sp. TS-15
0.33
-
 (S,R)-(+)-ephedrine pH 7.8, 25°C Arthrobacter sp. TS-15
3.4
-
 NAD+ pH 7.8, 25°C Arthrobacter sp. TS-15

Molecular Weight [Da]

Molecular Weight [Da] Molecular Weight Maximum [Da] Comment Organism
30000
-
-
 Arthrobacter sp. TS-15

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
(+)-(1S,2S)-pseudoephedrine + NAD+ Arthrobacter sp. TS-15
-
 (S)-2-(methylamino)-1-phenylpropan-1-one + NADH + H+
-
 ?
(S,R)-(+)-ephedrine + NAD+ Arthrobacter sp. TS-15
-
 (R)-2-methylimino-1-phenylpropan-1-ol + NADH + H+
-
 ?
(S,S)-(+)-pseudoephedrine + NAD+ Arthrobacter sp. TS-15
-
 (S)-2-(methylamino)-1-phenylpropan-1-one + NADH + H+
-
 ?
1-phenylpropan-1,2-dione + NAD+ Arthrobacter sp. TS-15
-
 phenylacetylcarbinol + NADH + H+
-
 ?
1-phenylpropan-1,2-dione + NAD+ Arthrobacter sp. TS-15 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 phenylacetylcarbinol + NADH + H+
-
 ?
additional information Arthrobacter sp. TS-15 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 ?
-
-

Organism

Organism UniProt Comment Textmining
Arthrobacter sp. TS-15 A0A545BBS8
-
-
Arthrobacter sp. TS-15 A0A545BBS8 DSM 32400, isolated from soil
-

Purification (Commentary)

Purification (Comment) Organism
-
 Arthrobacter sp. TS-15
recombinant His-tagged enzyme from Escherichia coli strain T7 SHuffle(DE3) by nickel affinity chromatography Arthrobacter sp. TS-15

Source Tissue

Source Tissue Comment Organism Textmining
additional information the Gram-positive soil bacterium Arthrobacter sp. strain TS-15 (DSM 32400) is capable of metabolizing all isomers of ephedrine as a sole source of carbon and energy. (S,S)-(+)-pseudoephedrine is consumed within the shortest time period (half-life of approx. 6.3 h) and is accompanied by the fastest culture growth (generation time of approximately 4.4 h) Arthrobacter sp. TS-15
-

Specific Activity [micromol/min/mg]

Specific Activity Minimum [µmol/min/mg] Specific Activity Maximum [µmol/min/mg] Comment Organism
4.7
-
 substrate: (+)-(1S,2S)-pseudoephedrine, pH 7.8, 25°C Arthrobacter sp. TS-15
4.7
-
 purified native enzyme, substrate (-)-ephedrine, pH 7.8, 25°C Arthrobacter sp. TS-15

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
(+)-(1S,2S)-pseudoephedrine + NAD+
-
 Arthrobacter sp. TS-15 (S)-2-(methylamino)-1-phenylpropan-1-one + NADH + H+
-
 ?
(+)-(1S,2S)-pseudoephedrine + NAD+ the enzyme is strictly stereospecific for the diastereomers (S,S)-(+)-pseudoephedrine and (S,R)-(+)-ephedrine Arthrobacter sp. TS-15 (S)-2-(methylamino)-1-phenylpropan-1-one + NADH + H+
-
 ?
(S,R)-(+)-ephedrine + NAD+ the enzyme is strictly stereospecific for the diastereomers (S,S)-(+)-pseudoephedrine and (S,R)-(+)-ephedrine Arthrobacter sp. TS-15 ? + NADH + H+
-
 ?
(S,R)-(+)-ephedrine + NAD+
-
 Arthrobacter sp. TS-15 (R)-2-methylimino-1-phenylpropan-1-ol + NADH + H+
-
 ?
(S,S)-(+)-pseudoephedrine + NAD+
-
 Arthrobacter sp. TS-15 (S)-2-(methylamino)-1-phenylpropan-1-one + NADH + H+
-
 ?
1-phenylpropan-1,2-dione + NAD+
-
 Arthrobacter sp. TS-15 phenylacetylcarbinol + NADH + H+
-
 ?
1-phenylpropan-1,2-dione + NAD+ 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 Arthrobacter sp. TS-15 phenylacetylcarbinol + NADH + H+
-
 ?
additional information no activity on (S,N)-(+)-(pseudo)ephedrine or (R,N)-(-)-(pseudo)ephedrine Arthrobacter sp. TS-15 ?
-
-
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 Arthrobacter sp. TS-15 ?
-
-
additional information pseudoephedrine dehydrogenase (PseDH) selectively converts (S,S)-(+)-pseudoephedrine and (S,R)-(+)-ephedrine to (S)- and (R)-methcathinone, respectively Arthrobacter sp. TS-15 ?
-
-

Synonyms

Synonyms Comment Organism
PseDH
-
 Arthrobacter sp. TS-15

Temperature Optimum [°C]

Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
25
-
 assay at Arthrobacter sp. TS-15

Turnover Number [1/s]

Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Comment Organism Structure
1.45
-
 (S,R)-(+)-ephedrine pH 7.8, 25°C Arthrobacter sp. TS-15
3.77
-
 (+)-(1S,2S)-pseudoephedrine pH 7.8, 25°C Arthrobacter sp. TS-15
3.77
-
 (S,S)-(+)-pseudoephedrine pH 7.8, 25°C Arthrobacter sp. TS-15
9.22
-
 NAD+ pH 7.8, 25°C Arthrobacter sp. TS-15

pH Optimum

pH Optimum Minimum pH Optimum Maximum Comment Organism
7.8
-
 assay at Arthrobacter sp. TS-15

Cofactor

Cofactor Comment Organism Structure
additional information no activity with NADP+ Arthrobacter sp. TS-15
NAD+
-
 Arthrobacter sp. TS-15
NAD+ the enzyme is strictly NAD+-dependent Arthrobacter sp. TS-15

Expression

Organism Comment Expression
Arthrobacter sp. TS-15 (S,S)-(+)-pseudoephedrine induces the enzyme up

General Information

General Information Comment Organism
evolution the enzyme belongs to the superfamily of short-chain dehydrogenases Arthrobacter sp. TS-15
metabolism the enzyme is involved in the ephedrine metabolism, overview Arthrobacter sp. TS-15
physiological function Arthrobacter sp. TS-15 is capable of metabolizing all isomers of ephedrine as a sole source of carbon and energy. Enantioselective oxidation of (-)-(R,N)-(pseudo)ephedrine and (+)-(S,N)-(pseudo)ephedrine catalyzed by PseDH and EDH, respectively, overview Arthrobacter sp. TS-15

kcat/KM [mM/s]

kcat/KM Value [1/mMs-1] kcat/KM Value Maximum [1/mMs-1] Substrate Comment Organism Structure
2.71
-
 NAD+ pH 7.8, 25°C Arthrobacter sp. TS-15
4.39
-
 (S,R)-(+)-ephedrine pH 7.8, 25°C Arthrobacter sp. TS-15
14.34
-
 (S,S)-(+)-pseudoephedrine pH 7.8, 25°C Arthrobacter sp. TS-15