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Literature summary for 1.5.1.18 extracted from

  • Shanati, T.; Lockie, C.; Beloti, L.; Grogan, G.; Ansorge-Schumacher, M.B.
    Two enantiocomplementary ephedrine dehydrogenases from Arthrobacter sp. TS-15 with broad substrate specificity (2019), ACS Catal., 9, 6202-6211 .
No PubMed abstract available
Search for more literature for 1.5.1.18

Application

Application Comment Organism
synthesis the wide substrate spectrum of the dehydrogenase, combined with its regio- and enantioselectivity, suggests a high potential for the industrial production of valuable chiral compounds Arthrobacter sp. TS-15

Inhibitors

Inhibitors Comment Organism Structure
1-Phenyl-1,3-butanedione substrate inhibition Arthrobacter sp. TS-15
2-aminoacetophenone substrate inhibition Arthrobacter sp. TS-15
2-chloro-1-phenyl-1-propanone substrate inhibition Arthrobacter sp. TS-15
ethyl 2-chlorobenzoylacetate substrate inhibition Arthrobacter sp. TS-15
methylbenzoyl formate substrate inhibition Arthrobacter sp. TS-15

KM Value [mM]

KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
0.06
-
 ethyl 2-chlorobenzoylacetate pH 7.5, 25°C Arthrobacter sp. TS-15
0.06
-
 1-phenylpropan-1,2-dione pH 7.5, 25°C Arthrobacter sp. TS-15
0.1
-
 1,2-naphthoquinone pH 7.5, 25°C Arthrobacter sp. TS-15
0.19
-
 methylbenzoyl formate pH 7.5, 25°C Arthrobacter sp. TS-15
0.2
-
 1-Phenyl-1,3-butanedione pH 7.5, 25°C Arthrobacter sp. TS-15
0.6
-
 2-aminoacetophenone pH 7.5, 25°C Arthrobacter sp. TS-15
2.29
-
 1,2-indandione pH 7.5, 25°C Arthrobacter sp. TS-15
5.67
-
 Phenylglyoxal pH 7.5, 25°C Arthrobacter sp. TS-15

Natural Substrates/ Products (Substrates)

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

Organism

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

Specific Activity [micromol/min/mg]

Specific Activity Minimum [µmol/min/mg] Specific Activity Maximum [µmol/min/mg] Comment Organism
64.02
-
 1-phenylpropan-1,2-dione, pH 10.0, 25°C Arthrobacter sp. TS-15

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
(R,R)-(-)-pseudoephedrine + NAD+
-
 Arthrobacter sp. TS-15 (R)-2-methylimino-1-phenylpropan-1-ol + NADH + H+
-
 r
(R,S)-(-)-ephedrine + NAD+
-
 Arthrobacter sp. TS-15 (R)-2-methylimino-1-phenylpropan-1-ol + NADH + H+
-
 r
1,2-indandione + NADH + H+
-
 Arthrobacter sp. TS-15 ?
-
 r
1,2-naphthoquinone + NADH + H+
-
 Arthrobacter sp. TS-15 ?
-
 r
1-phenyl-1,3-butanedione + NADH + H+
-
 Arthrobacter sp. TS-15 ?
-
 r
1-phenylpropan-1,2-dione + NADH + H+ high activity Arthrobacter sp. TS-15 (R)-phenylacetylcarbinol + NAD+
-
 r
2,2'-dichlorobenzil + NADH + H+
-
 Arthrobacter sp. TS-15 ?
-
 r
2,2'-furil + NADH + H+
-
 Arthrobacter sp. TS-15 ?
-
 r
2,2'-thenil + NADH + H+
-
 Arthrobacter sp. TS-15 ?
-
 r
2-aminoacetophenone + NADH + H+
-
 Arthrobacter sp. TS-15 ?
-
 r
2-bromoacetophenone + NADH + H+ low activity Arthrobacter sp. TS-15 ?
-
 r
4,4'-difluorobenzil + NADH + H+
-
 Arthrobacter sp. TS-15 ?
-
 r
benzil + NADH + H+
-
 Arthrobacter sp. TS-15 ?
-
 r
ethyl 2-chlorobenzoylacetate + NADH + H+
-
 Arthrobacter sp. TS-15 ?
-
 r
ethyl 2-chlorobenzyolacetate + NADH + H+ low activity Arthrobacter sp. TS-15 ?
-
 r
methylbenzoyl formate + NADH + H+
-
 Arthrobacter sp. TS-15 ?
-
 r
additional information enzyme EDH is specific for the enantioselective oxidation of (-)-(R) N-(pseudo)ephedrine. Prelog-specific EDH 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 acetophenone, poor activity with 4,4-dimethylbenzil, 2-thenoylacetonitrile, 4-(chlorophenyl)-2-pyridinylmethanone, phenyl-2-pyridinylmethanone, 2-chloroacetophenone, 3-chloropropiophenone, 1-phenyl-1-propanone, 4-chlorobenzil, 2-chloro-1-phenyl-1-propanone, 2-bromo-1-(3-chlorophenyl)-1-propanone, and isatin Arthrobacter sp. TS-15 ?
-
-
phenylglyoxal + NADH + H+
-
 Arthrobacter sp. TS-15 ?
-
 r

Synonyms

Synonyms Comment Organism
EDH
-
 Arthrobacter sp. TS-15

Temperature Optimum [°C]

Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
70
-
 reduction of 1-phenyl-1,2-propanedione Arthrobacter sp. TS-15

Temperature Range [°C]

Temperature Minimum [°C] Temperature Maximum [°C] Comment Organism
25 75 activity range, profile overview Arthrobacter sp. TS-15

Temperature Stability [°C]

Temperature Stability Minimum [°C] Temperature Stability Maximum [°C] Comment Organism
15 25 EDH has a half-life of 36-38 h Arthrobacter sp. TS-15
40
-
 EDH has a half-life of 76 h Arthrobacter sp. TS-15
50
-
 EDH has a half-life of about 5 h Arthrobacter sp. TS-15

Turnover Number [1/s]

Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Comment Organism Structure
7.94
-
 1,2-naphthoquinone pH 7.5, 25°C Arthrobacter sp. TS-15
9.49
-
 Phenylglyoxal pH 7.5, 25°C Arthrobacter sp. TS-15
15.37
-
 1-Phenyl-1,3-butanedione pH 7.5, 25°C Arthrobacter sp. TS-15
27.13
-
 2-aminoacetophenone pH 7.5, 25°C Arthrobacter sp. TS-15
30.43
-
 1-phenylpropan-1,2-dione pH 7.5, 25°C Arthrobacter sp. TS-15
31.11
-
 1,2-indandione pH 7.5, 25°C Arthrobacter sp. TS-15
37.38
-
 ethyl 2-chlorobenzoylacetate pH 7.5, 25°C Arthrobacter sp. TS-15
40.05
-
 methylbenzoyl formate pH 7.5, 25°C Arthrobacter sp. TS-15

pH Optimum

pH Optimum Minimum pH Optimum Maximum Comment Organism
6
-
 reduction activity Arthrobacter sp. TS-15
10
-
 oxidation activity Arthrobacter sp. TS-15

pH Stability

pH Stability pH Stability Maximum Comment Organism
7.5 8.5 half-life is about 38 h at pH 8.0, and about 10 h at pH 7.0 and pH 9.0, profile overview Arthrobacter sp. TS-15

Cofactor

Cofactor Comment Organism Structure
NAD+
-
 Arthrobacter sp. TS-15
NADH
-
 Arthrobacter sp. TS-15

Ki Value [mM]

Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
0.1
-
 2-chloro-1-phenyl-1-propanone pH 7.5, 25°C Arthrobacter sp. TS-15
0.16
-
 ethyl 2-chlorobenzoylacetate pH 7.5, 25°C Arthrobacter sp. TS-15
0.26
-
 1-Phenyl-1,3-butanedione pH 7.5, 25°C Arthrobacter sp. TS-15
1.46
-
 methylbenzoyl formate pH 7.5, 25°C Arthrobacter sp. TS-15
1.53
-
 2-aminoacetophenone pH 7.5, 25°C Arthrobacter sp. TS-15

General Information

General Information Comment Organism
evolution ephedrine dehydrogenase (EDH) from Arthrobacter sp. TS-15 is an NADH-dependent member of the oxidoreductase superfamily of short-chain dehydrogenases/reductases (SDRs) Arthrobacter sp. TS-15