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Literature summary for 1.1.1.423 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 1.1.1.423

Application

Application Comment Organism
industry the wide substrate spectrum of these dehydrogenases, combined with their regio- and enantioselectivity, suggests a high potential for the industrial production of valuable chiral compounds Arthrobacter sp. TS-15
synthesis the wide substrate spectrum of these dehydrogenases, combined with their regio- and enantioselectivity, suggests a high potential for the industrial production of valuable chiral compounds Arthrobacter sp. TS-15
synthesis the enzyme catalyzes the oxidation of an isomer of ephedrine and the regio- and enantioselective reduction of sterically demanding substrate 1-phenyl-1,2-propanedione to give (R)-phenylacetylcarbinol Arthrobacter sp. TS-15

Cloned(Commentary)

Cloned (Comment) Organism
expression in Escherichia coli T7 shuffle (DE3) Arthrobacter sp. TS-15

Inhibitors

Inhibitors Comment Organism Structure
1-Phenyl-1,3-butanedione
-
 Arthrobacter sp. TS-15
2-aminoacetophenone
-
 Arthrobacter sp. TS-15
2-chloro-1-phenyl-1-propane
-
 Arthrobacter sp. TS-15
2-chloro-1-phenyl-1-propanone
-
 Arthrobacter sp. TS-15
ethyl 2-chlorobenzoylacetate
-
 Arthrobacter sp. TS-15
methyl benzoylformate
-
 Arthrobacter sp. TS-15

KM Value [mM]

KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
0.01
-
 1-phenyl-1-propanone pH 7.5, 25°C Arthrobacter sp. TS-15
0.02
-
 2-chloro-1-phenyl-1-propanone pH 7.5, 25°C Arthrobacter sp. TS-15
0.02
-
 2-chloro-1-phenyl-1-propane pH 7.5, 25°C Arthrobacter sp. TS-15
0.06
-
 1-phenyl-1,2-propanedione pH 7.5, 25°C Arthrobacter sp. TS-15
0.06
-
 ethyl 2-chlorobenzoylacetate pH 7.5, 25°C Arthrobacter sp. TS-15
0.07
-
 NADH pH 7.5, 25°C Arthrobacter sp. TS-15
0.1
-
 1,2-naphthoquinone pH 7.5, 25°C Arthrobacter sp. TS-15
0.17
-
 4-chlorobenzil pH 7.5, 25°C Arthrobacter sp. TS-15
0.19
-
 methyl benzoylformate 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
0.51
-
 isatin 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-indanedione 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

Molecular Weight [Da]

Molecular Weight [Da] Molecular Weight Maximum [Da] Comment Organism
25930
-
 calculated from sequence Arthrobacter sp. TS-15
27000
-
 SDS-PAGE Arthrobacter sp. TS-15

Natural Substrates/ Products (Substrates)

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

Organism

Organism UniProt Comment Textmining
Arthrobacter sp. TS-15 A0A545BBR2
-
-

Purification (Commentary)

Purification (Comment) Organism
-
 Arthrobacter sp. TS-15

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
(-)-(1R,2S)-ephedrine + NAD+
-
 Arthrobacter sp. TS-15 (S)-2-methylamino-1-phenylpropan-1-one + NADH + H+
-
 ?
(-)-(1R,2S)-ephedrine + NAD+ the enzyme 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 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. (-)-(1R,2S)-ephedrine i.e. (1R,2S)-1-phenyl-1-hydroxy-2-methylaminopropane. (S)-2-methylamino-1-phenylpropan-1-one i.e. (S)-methcathinone Arthrobacter sp. TS-15 (S)-2-methylamino-1-phenylpropan-1-one + NADH + H+
-
 ?
(4-chlorophenyl)-2-pyridinylmethanone + NAD+ specifc activity: 1.74 U/mg. Product: 70% (S) enantiomeric excess Arthrobacter sp. TS-15 (S)-(4-chlorophenyl)(pyridin-2-yl)methanol + NADH + H+
-
 ?
(4-chlorophenyl)-2-pyridinylmethanone + NADH + H+ 2.7% of the activity as compared to 1-phenyl-1,2-propanedione. The (R)-enantiomer is formed with 70% enantiomeric excess Arthrobacter sp. TS-15 (R)-(4-chlorophenyl)(pyridin-2-yl)methanol + NAD+
-
 ?
1,2-indandione + NAD+ specifc 50.05 U/mg Arthrobacter sp. TS-15 ? + NADH + H+
-
 ?
1,2-indanedione + NADH + H+ 78.1% of the activity as compared to 1-phenyl-1,2-propanedione Arthrobacter sp. TS-15 1-hydroxy-1,3-dihydro-2H-inden-2-one + NAD+
-
 ?
1,2-naphthoquinone + NAD+ specifc activity: 13.89 U/mg Arthrobacter sp. TS-15 ? + NADH + H+
-
 ?
1,2-naphthoquinone + NADH + H+ 21.7% of the activity as compared to 1-phenyl-1,2-propanedione Arthrobacter sp. TS-15 1-hydroxynaphthalen-2(1H)-one + NAD+
-
 ?
1-phenyl-1,2-propanedione + NAD+ specifc activity: 64.02 U/mg. Product: 99% (R) enantiomeric excess Arthrobacter sp. TS-15 (R)-phenylacetylcarbinol + NADH + H+
-
 ?
1-phenyl-1,2-propanedione + NADH + H+ substrate with highest activity. Full conversion and enantiomeric excess of more than 99% Arthrobacter sp. TS-15 (R)-phenylacetylcarbinol + NAD+
-
 ?
1-phenyl-1,3-butanedione + NAD+ specifc activity: 13.64 U/mg. Product: 98% (R) enantiomeric excess Arthrobacter sp. TS-15 (4R)-4-hydroxy-4-phenylbutan-2-one + NADH + H+
-
 ?
1-phenyl-1,3-butanedione + NADH + H+ 21.3% of the activity as compared to 1-phenyl-1,2-propanedione. The (R)-enantiomer is formed with 98% enantiomeric excess Arthrobacter sp. TS-15 (4R)-4-hydroxy-4-phenylbutan-2-one + NAD+
-
 ?
1-phenyl-1-propanone + NAD+ specifc activity: 1.55 U/mg. Product: 99% (R) enantiomeric excess Arthrobacter sp. TS-15 (1R)-1-phenylpropan-1-ol + NADH + H+
-
 ?
1-phenyl-1-propanone + NADH + H+ 2.4% of the activity as compared to 1-phenyl-1,2-propanedione. The (R)-enantiomer is formed with 99% enantiomeric excess Arthrobacter sp. TS-15 (1R)-1-phenylpropan-1-ol + NAD+
-
 ?
2,2'-dichlorobenzil + NAD+ specifc activity: 27.91 U/mg. Product: 94% (R) enantiomeric excess Arthrobacter sp. TS-15 (2R)-1,2-bis(2-chlorophenyl)-2-hydroxyethan-1-one + NADH + H+
-
 ?
2,2'-dichlorobenzil + NADH + H+ 43.6% of the activity as compared to 1-phenyl-1,2-propanedione. The (R)-enantiomer is formed with 4% enantiomeric excess Arthrobacter sp. TS-15 (2R)-1,2-bis(2-chlorophenyl)-2-hydroxyethan-1-one + NAD+
-
 ?
2,2'-furil + NAD+ specifc activity: 19.95 U/mg. Product: 99% (R) enantiomeric excess Arthrobacter sp. TS-15 (2R)-1,2-di(furan-2-yl)-2-hydroxyethan + NADH + H+
-
 ?
2,2'-furil + NADH + H+ 20% of the activity as compared to 1-phenyl-1,2-propanedione. The (R)-enantiomer is formed with 99% enantiomeric excess Arthrobacter sp. TS-15 (2R)-1,2-di(furan-2-yl)-2-hydroxyethan-1-one + NAD+
-
 ?
2,2'-thenil + NAD+ specifc activity: 46.77 U/mg. Product: 99% (R) enantiomeric excess Arthrobacter sp. TS-15 (2R)-2-hydroxy-1,2-di(thiophen-2-yl)ethan-1-one + NADH + H+
-
 ?
2,2'-thenil + NADH + H+ 46.8% of the activity as compared to 1-phenyl-1,2-propanedione. The (R)-enantiomer is formed with 99% enantiomeric excess Arthrobacter sp. TS-15 (2R)-2-hydroxy-1,2-di(thiophen-2-yl)ethan-1-one + NAD+
-
 ?
2-aminoacetophenone + NAD+ specifc activity: 25.79 U/mg. Product: 99% (R) enantiomeric excess Arthrobacter sp. TS-15 (1R)-2-amino-1-phenylethan-1-ol + NADH + H+
-
 ?
2-aminoacetophenone + NADH + H+ 40.3% of the activity as compared to 1-phenyl-1,2-propanedione. The (R)-enantiomer is formed with 99% enantiomeric excess Arthrobacter sp. TS-15 (1R)-2-amino-1-phenylethan-1-ol + NAD+
-
 ?
2-bromo-1-(3-chlorophenyl)-1-propanone + NAD+ specifc activity: 5.1 U/mg Arthrobacter sp. TS-15 (R,S)-2-bromo-1-(3-chlorophenyl)propan-1-ol + NADH + H+
-
 ?
2-bromo-1-(3-chlorophenyl)-1-propanone + NADH + H+ 7.9% of the activity as compared to 1-phenyl-1,2-propanedione Arthrobacter sp. TS-15 2-bromo-1-(3-chlorophenyl)propan-1-ol + NAD+
-
 ?
2-bromoacetophenone + NAD+ specifc activity: 9.44 U/mg. Product: 85% (R) enantiomeric excess Arthrobacter sp. TS-15 (1R)-2-bromo-1-phenylethan-1-ol + NADH + H+
-
 ?
2-bromoacetophenone + NADH + H+ 14.8% of the activity as compared to 1-phenyl-1,2-propanedione. The (R)-enantiomer is formed with 85% enantiomeric excess Arthrobacter sp. TS-15 (1R)-2-bromo-1-phenylethan-1-ol + NAD+
-
 ?
2-chloro-1-phenyl-1-propane + NAD+ specifc activity: 8.0 U/mg Arthrobacter sp. TS-15 (R,S)-2-chloro-1-phenylpropan-1-ol + NADH + H+
-
 ?
2-chloro-1-phenyl-1-propanone + NADH + H+ 12.5% of the activity as compared to 1-phenyl-1,2-propanedione Arthrobacter sp. TS-15 2-chloro-1-phenyl-1-propan-1-ol + NAD+
-
 ?
2-chloroacetophenone + NAD+ specifc activity: 8.71 U/mg. Product: 98% (R) enantiomeric excess Arthrobacter sp. TS-15 (1R)-2-chloro-1-phenylethan-1-ol + NADH + H+
-
 ?
2-chloroacetophenone + NADH + H+ 13.6% of the activity as compared to 1-phenyl-1,2-propanedione. The (R)-enantiomer is formed with 98% enantiomeric excess Arthrobacter sp. TS-15 (1R)-2-chloro-1-phenylethan-1-ol + NAD+
-
 ?
2-thenoylacetonitrile + NAD+ specifc activity: 6.87 U/mg. Product: 99% (R) enantiomeric excess Arthrobacter sp. TS-15 (3R)-3-hydroxy-3-(thiophen-2-yl)propanenitril + NADH + H+
-
 ?
2-thenoylacetonitrile + NADH + H+ 6.87% of the activity as compared to 1-phenyl-1,2-propanedione. The (R)-enantiomer is formed with 99% enantiomeric excess Arthrobacter sp. TS-15 (2R)-hydroxy(thiophen-2-yl)acetonitrile + NAD+
-
 ?
3-chloropropiophenone + NAD+ specifc activity: 4.45 U/mg. Product: 99% (R) enantiomeric excess Arthrobacter sp. TS-15 (1R)-3-chloro-1-phenylpropan-1-ol + NADH + H+
-
 ?
3-chloropropiophenone + NADH + H+ 6.9% of the activity as compared to 1-phenyl-1,2-propanedione. The (R)-enantiomer is formed with 99% enantiomeric excess Arthrobacter sp. TS-15 (1R)-3-chloro-1-phenylpropan-1-ol + NAD+
-
 ?
4,4'-difluorobenzil + NAD+ specifc activity: 48.2 U/mg. Product: 99% (R) enantiomeric excess Arthrobacter sp. TS-15 (2R)-1,2-bis(4-fluorophenyl)-2-hydroxyethan-1-one + NADH + H+
-
 ?
4,4'-difluorobenzil + NADH + H+ 75.3% of the activity as compared to 1-phenyl-1,2-propanedione. The (R)-enantiomer is formed with 99% enantiomeric excess Arthrobacter sp. TS-15 (2R)-1,2-bis(4-fluorophenyl)-2-hydroxyethan-1-one + NAD+
-
 ?
4,4'-dimethylbenzil + NAD+ specifc activity: 3.12 U/mg. Product: 99% (R) enantiomeric excess Arthrobacter sp. TS-15 (2R)-2-hydroxy-1,2-bis(4-methylphenyl)ethan-1-one + NADH + H+
-
 ?
4,4'-dimethylbenzil + NADH + H+ 4.8% of the activity as compared to 1-phenyl-1,2-propanedione. The (R)-enantiomer is formed with 99% enantiomeric excess Arthrobacter sp. TS-15 (2R)-1,2-bis(4-methylphenyl)-2-hydroxyethan-1-one + NAD+
-
 ?
4-chlorobenzil + NAD+ specifc activity: 6.5 U/mg. Product: 95% (R) enantiomeric excess Arthrobacter sp. TS-15 ? + NADH + H+
-
 ?
4-chlorobenzil + NADH + H+ 10.2% of the activity as compared to 1-phenyl-1,2-propanedione. The (R)-enantiomer is formed with 58% enantiomeric excess Arthrobacter sp. TS-15 ? + NAD+
-
 ?
benzil + NAD+ specifc activity: 47.06 U/mg. Product: 99% enantiomeric (R) excess Arthrobacter sp. TS-15 (2R)-2-hydroxy-1,2-diphenylethan-1-one + NADH + H+
-
 ?
benzil + NADH + H+ 73.5% of the activity as compared to 1-phenyl-1,2-propanedione. The (R)-enantiomer is formed with 99% enantiomeric excess Arthrobacter sp. TS-15 (2R)-2-hydroxy-1,2-diphenylethan-1-one + NAD+ ? ?
ethyl 2-chlorobenzoylacetate + NAD+ specifc activity: 35.21 U/mg Arthrobacter sp. TS-15 ethyl (R,S)-2-chloro-3-hydroxy-3-phenylpropanoate + NADH + H+
-
 ?
ethyl 2-chlorobenzoylacetate + NADH + H+ 54.9% of the activity as compared to 1-phenyl-1,2-propanedione Arthrobacter sp. TS-15 ethyl 2-chloro-3-hydroxy-3-phenylpropanoate + NAD+
-
 ?
isatin + NAD+ specifc activity: 7.84 U/mg. Product: 52% (R) enantiomeric excess Arthrobacter sp. TS-15 ? + NADH + H+
-
 ?
isatin + NADH + H+ 12.25% of the activity as compared to 1-phenyl-1,2-propanedione. The (R)-enantiomer is formed with 52% enantiomeric excess Arthrobacter sp. TS-15 (3R)-3-hydroxy-1,3-dihydro-2H-indol-2-one + NAD+
-
 ?
methyl benzoylformate + NAD+ specifc activity: 46.56 U/mg. Product: 98% (R) enantiomeric excess Arthrobacter sp. TS-15 methyl (2R)-hydroxy(phenyl)acetate + NADH + H+
-
 ?
methyl benzoylformate + NADH + H+ 72.7% of the activity as compared to 1-phenyl-1,2-propanedione. The (R)-enantiomer is formed with 98% enantiomeric excess Arthrobacter sp. TS-15 methyl (2S)-hydroxy(phenyl)acetate + NAD+
-
 ?
phenyl-2-pyridinylmethanone + NAD+ specifc activity: 2.81 U/mg. Product: 24% (R) enantiomeric excess Arthrobacter sp. TS-15 (R)-phenyl(pyridin-2-yl)methanol + NADH + H+
-
 ?
phenyl-2-pyridinylmethanone + NADH + H+ 4.4% of the activity as compared to 1-phenyl-1,2-propanedione. The (R)-enantiomer is formed with 24% enantiomeric excess Arthrobacter sp. TS-15 (R)-phenyl(pyridin-2-yl)methanol + NAD+
-
 ?
phenylglyoxal + NAD+ specifc activity: 12.1 U/mg. Product: 99% (R) enantiomeric excess Arthrobacter sp. TS-15 (2R)-hydroxy(phenyl)acetaldehyde + NADH + H+
-
 ?
phenylglyoxal + NADH + H+ 18.9% of the activity as compared to 1-phenyl-1,2-propanedione. The (R)-enantiomer is formed with 99% enantiomeric excess Arthrobacter sp. TS-15 (2R)-hydroxy(phenyl)acetaldehyde + NAD+
-
 ?

Subunits

Subunits Comment Organism
dimer 4 * 27000, SDS-PAGE, the smallest oligomeric state seems to be a dimer, the predominant oligomeric state is the tetramer Arthrobacter sp. TS-15
tetramer 4 * 27000, SDS-PAGE, the smallest oligomeric state seems to be a dimer, the predominant oligomeric state is the tetramer Arthrobacter sp. TS-15
tetramer 4 * 27000, the enzyme tends to form higher oligomeric states, up to a hexadecamer, SDS-PAGE 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
70
-
-
 Arthrobacter sp. TS-15

Temperature Range [°C]

Temperature Minimum [°C] Temperature Maximum [°C] Comment Organism
55 75 55°C: about 40% of maximal activity, 75°C: about 75% of maximal activity Arthrobacter sp. TS-15
65 75 65°C: about 55% of maximal activity, 75°C: about 75% of maximal activity Arthrobacter sp. TS-15

Temperature Stability [°C]

Temperature Stability Minimum [°C] Temperature Stability Maximum [°C] Comment Organism
5
-
 half-life: 2.6 h Arthrobacter sp. TS-15
25
-
 half-life: 38.3 h Arthrobacter sp. TS-15
40
-
 half-life: 82.8 h Arthrobacter sp. TS-15

Turnover Number [1/s]

Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Comment Organism Structure
0.77
-
 1-phenyl-1-propanone pH 7.5, 25°C Arthrobacter sp. TS-15
2.54
-
 2-bromo-1-(3-chlorophenyl)-1-propanone pH 7.5, 25°C Arthrobacter sp. TS-15
3.48
-
 4-chlorobenzil pH 7.5, 25°C Arthrobacter sp. TS-15
4.36
-
 isatin pH 7.5, 25°C Arthrobacter sp. TS-15
7.31
-
 2-chloro-1-phenyl-1-propanone pH 7.5, 25°C Arthrobacter sp. TS-15
7.31
-
 2-chloro-1-phenyl-1-propane pH 7.5, 25°C Arthrobacter sp. TS-15
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
15.74
-
 NADH pH 7.5, 25°C Arthrobacter sp. TS-15
27.12
-
 2-aminoacetophenone 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-phenyl-1,2-propanedione pH 7.5, 25°C Arthrobacter sp. TS-15
31.11
-
 1,2-indanedione 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
-
 methyl benzoylformate pH 7.5, 25°C Arthrobacter sp. TS-15

pH Optimum

pH Optimum Minimum pH Optimum Maximum Comment Organism
6
-
-
 Arthrobacter sp. TS-15

pH Stability

pH Stability pH Stability Maximum Comment Organism
7.5 8.5 highest stability Arthrobacter sp. TS-15
7.5 8.5 t1/2: 34-21 h Arthrobacter sp. TS-15

Cofactor

Cofactor Comment Organism Structure
NAD+ no apparent activity with NADP(H)+ and full catalytic activity with NAD(H). The preference for NADH makes the utilization of the enzyme an attractive for industrial applications, since NADH is more stable and less expensive than NADPH under operational reaction conditions Arthrobacter sp. TS-15
NADH no apparent activity with NADP(H)+ and full catalytic activity with NAD(H). The preference for NADH makes the utilization of the enzyme an attractive for industrial applications, since NADH is more stable and less expensive than NADPH under operational reaction conditions 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
0.1
-
 2-chloro-1-phenyl-1-propane 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
-
 methyl benzoylformate pH 7.5, 25°C Arthrobacter sp. TS-15
1.53
-
 2-aminoacetophenone pH 7.5, 25°C Arthrobacter sp. TS-15