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Literature summary for 1.5.1.18 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 1.5.1.18

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

Inhibitors

Inhibitors Comment Organism Structure
(R,R)-(-)-pseudoephedrine substrate inhibition Arthrobacter sp. TS-15
(R,S)-(-)-ephedrine substrate inhibition Arthrobacter sp. TS-15

KM Value [mM]

KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
0.036
-
 (R,S)-(-)-ephedrine pH 7.8, 25°C Arthrobacter sp. TS-15
0.094
-
 (R,R)-(-)-pseudoephedrine pH 7.8, 25°C Arthrobacter sp. TS-15

Natural Substrates/ Products (Substrates)

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

Organism

Organism UniProt Comment Textmining
Arthrobacter sp. TS-15 A0A545BBR2 DSM 32400, isolated from soil
-

Purification (Commentary)

Purification (Comment) Organism
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. No growth on ephedrine as the sole source of nitrogen occurs because Arthrobacter sp. TS-15 cannot metabolize the nitrogen in ephedrine 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
-
 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.
(-)-ephedrine + NAD+
-
 Arthrobacter sp. TS-15 (R)-2-methylimino-1-phenylpropan-1-ol + NADH + H+
-
 ?
(R,R)-(-)-pseudoephedrine + NAD+
-
 Arthrobacter sp. TS-15 (R)-2-methylimino-1-phenylpropan-1-ol + NADH + H+
-
 ?
(R,S)-(-)-ephedrine + NAD+
-
 Arthrobacter sp. TS-15 (R)-2-methylimino-1-phenylpropan-1-ol + NADH + H+
-
 ?
1-phenylpropan-1,2-dione + NAD+
-
 Arthrobacter sp. TS-15 phenylacetylcarbinol + NADH + H+
-
 ?
1-phenylpropan-1,2-dione + NAD+ 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 Arthrobacter sp. TS-15 phenylacetylcarbinol + NADH + H+
-
 ?
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 Arthrobacter sp. TS-15 ?
-
-
additional information enzyme EDH exhibits a strict enantioselectivity for the oxidation of (R,S)-(-)-ephedrine and (R,R)-(-)-pseudoephedrine Arthrobacter sp. TS-15 ?
-
-

Synonyms

Synonyms Comment Organism
EDH
-
 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
2.06
-
 (R,R)-(-)-pseudoephedrine pH 7.8, 25°C Arthrobacter sp. TS-15
2.62
-
 (R,S)-(-)-ephedrine 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+ the enzyme is strictly NAD+-dependent Arthrobacter sp. TS-15

Ki Value [mM]

Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
1.78
-
 (R,R)-(-)-pseudoephedrine pH 7.8, 25°C Arthrobacter sp. TS-15
4.61
-
 (R,S)-(-)-ephedrine pH 7.8, 25°C Arthrobacter sp. TS-15

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
21.92
-
 (R,R)-(-)-pseudoephedrine pH 7.8, 25°C Arthrobacter sp. TS-15
72.78
-
 (R,S)-(-)-ephedrine pH 7.8, 25°C Arthrobacter sp. TS-15