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• • In Vivo Substrate
  • In Vivo Product
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  • Activator
  • Inhibitor
  • Metals and Ions
  • 3D Structure (PDB)
• Enzyme Kinetic Parameters
• • k_cat Value (Turnover Number)
  • K_M Value
  • K_i Value
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Ligand acetophenone

Basic Ligand Information

Molecular Structure

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Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (3 results)

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Show Natural Substrate (3 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.1.1.213

acetophenone + NADPH = 1-phenylethanol + NADP+

673101

-

1.1.1.B4

(R)-1-phenylethanol + NAD+ = acetophenone + NADH + H+

742305, 725726, 723841

-

6.4.1.8

2 ATP + acetophenone + HCO3- + H2O + H+ = 2 ADP + 2 phosphate + 3-oxo-3-phenylpropanoate

708932

-

In Vivo Product in Enzyme-catalyzed Reactions (5 results)

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Show Natural Product (5 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.1.1.311

(S)-1-phenylethanol + NAD+ = acetophenone + NADH + H+

-

-

1.1.1.71

(RS)-1-phenylethanol + NAD+ = 1-phenylethanone + NADH + H+

-

-

1.1.1.71

(RS)-1-phenylethanol + NADP+ = 1-phenylethanone + NADPH + H+

-

-

1.1.1.71

2 entries

1.1.1.B3

(S)-1-phenylethanol + NAD+ = acetophenone + NADH + H+

-

-

1.1.1.B4

(R)-1-phenylethanol + NAD+ = acetophenone + NADH + H+

-

-

Substrate in Enzyme-catalyzed Reactions (55 results)

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Show Substrate (55 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.1.1.1

acetophenone + NADH = (R)-alpha-phenyl ethanol + NAD+

654294

-

1.1.1.1

acetophenone + NADH + H+ = (R)-1-phenylethanol + NAD+

667255

-

1.1.1.1

acetophenone + NADH + H+ = 1-phenylethanol + NAD+

722888, 718681, 721868, 688442, 687850

-

1.1.1.1

acetophenone + NADPH + H+ = 1-phenylethanol + NADP+

684556

-

1.1.1.1

acetophenone + NADH + H+ = (S)-(-)-1-phenylethanol + NAD+

684583

-

1.1.1.1

acetophenone + NADH + H+ = (S)-1-phenylethanol + NAD+

684583

-

1.1.1.1

6 entries

1.1.1.100

acetophenone + NADPH = ? + NADP+

701783

-

1.1.1.153

acetophenone + NADPH = ?

286021

-

1.1.1.184

acetophenone + NADPH + H+ = (1S)-1-phenylethanol + (1R)-1-phenylethanol + NADP+

689309

-

1.1.1.184

1-phenylethanone + NADPH + H+ = (S)-1-phenylethanol + NADP+

726512

-

1.1.1.2

acetophenone + NADPH = (R)-1-phenylethanol + NADP+

655106

1zk1, 3D-view

1.1.1.2

acetophenone + NADPH = (R)-1-phenylethanol + NADP+

655106

1zk4, 3D-view

1.1.1.2

acetophenone + NADPH = 1-phenylethanol + NADP+

656514

1zk1, 3D-view

1.1.1.2

acetophenone + NADPH = 1-phenylethanol + NADP+

656514

1zk4, 3D-view

1.1.1.2

acetophenone + NADPH + H+ = (S)-1-phenylethanol + NADP+

668054

1zk1, 3D-view

1.1.1.2

acetophenone + NADPH + H+ = (S)-1-phenylethanol + NADP+

668054

1zk4, 3D-view

1.1.1.2

acetophenone + NADH + H+ = 1-phenylethanol + NAD+

675348

1zk1, 3D-view

1.1.1.2

acetophenone + NADH + H+ = 1-phenylethanol + NAD+

675348

1zk4, 3D-view

1.1.1.2

acetophenone + NADPH + H+ = 1-phenylethanol + NADP+

675348

1zk1, 3D-view

1.1.1.2

acetophenone + NADPH + H+ = 1-phenylethanol + NADP+

675348

1zk4, 3D-view

1.1.1.213

acetophenone + NADPH = 1-phenylethanol + NADP+

673101

-

1.1.1.213

1-acetophenone + NADPH = 1-phenylethanol + NADP+

685529

-

1.1.1.184

2 entries

1.1.1.2

10 entries

1.1.1.213

2 entries

1.1.1.311

acetophenone + NADH + H+ = (S)-1-phenylethanol + NAD+

739947

-

1.1.1.50

1-acetophenone + NADPH = 1-phenylethanol + NADP+

685529

-

1.1.1.71

acetophenone + NADH + H+ = 1-phenylethan-1-ol + NAD+

740200

-

1.1.1.72

1-phenylethanone + NADPH + H+ = 1-phenylethanol + NADP+

711743

-

1.1.1.73

1-phenylethan-1-one + NADH + H+ = 1-phenylethan-1-ol + NAD+

739937

-

1.1.1.91

(R)-1-phenylethanol + NAD+ = 1-phenylacetaldehyde + NADH + H+

737897

-

1.1.1.91

acetophenone + NADPH + H+ = ?

735498

-

1.1.1.B3

(R)-1-phenylethanol + NAD+ = 1-phenylethanone + NADH + H+

685643

-

1.1.1.B3

acetophenone + NADH + H+ = (1S)-1-phenylethanol + NAD+

689823

-

1.1.1.B3

acetophenone + NADH + H+ = (S)-1-phenylethanol + NAD+

685078, 684583, 741747

-

1.1.1.B3

acetophenone + NADH + H+ = alpha-phenylethanol + NAD+

684588

-

1.1.1.B4

acetophenone + NADH + H+ = 1-phenylethanol + NAD+

743703

-

1.1.1.B4

acetophenone + NADPH + H+ = 1-phenylethanol + NADP+

741784

-

1.1.1.B4

1-phenylethanone + NADH = (1R)-1-phenylethanol + NAD+

688571

-

1.1.1.B4

acetophenone + NADH + H+ = phenylethanol + NAD+

711860, 688747

-

1.1.1.B4

acetophenone + NADPH + H+ = phenylethanol + NADP+

711860

-

1.1.1.B4

(R)-1-phenylethanol + NAD+ = acetophenone + NADH + H+

742305, 725726, 723841

-

1.1.1.91

2 entries

1.1.1.B3

4 entries

1.1.1.B4

6 entries

1.1.3.47

(R)-1-phenylethanol + O2 = acetophenone + H2O2

739768

-

1.1.99.36

acetophenone + 1-propanol = ?

707345

-

1.1.99.36

acetophenone + cyclohexanol = ?

707345

-

1.1.99.36

acetophenone + ethanol = ?

707345

-

1.1.99.36

3 entries

1.14.13.22

acetophenone + NADPH + H+ + O2 = ?

741605

-

1.14.13.84

acetophenone + NADPH + H+ + O2 = phenyl acetate + NADP+ + H2O

644553, 649387, 651670

-

1.14.13.84

acetophenone + NADPH + H+ + O2 = ? + NADP+ + H2O

695775

-

1.14.13.84

2 entries

1.14.14.155

acetophenone + FMNH2 + O2 = ?

717141

-

2.6.1.21

1-phenylethanone + D-alanine = (1R)-1-phenylethanamine + pyruvate

721250

-

4.1.2.10

HCN + acetophenone = 2-hydroxyphenylpropionitrile

695075

-

4.1.2.10

cyanide + 1-phenylethanone = (2R)-2-hydroxy-2-phenylpropanenitrile

653959

-

4.1.2.10

cyanide + 1-phenylethanone = 2-hydroxy-2-phenylpropanenitrile

749351

-

4.1.2.10

cyanide + acetophenone = (2R)-hydroxyphenylpropionitrile

746785

-

4.1.2.47

Acetophenone + cyanide = 3-Hydroxy-3-phenylpropionitrile

5160

-

4.1.2.47

cyanide + 1-phenylethanone = (2S)-2-hydroxy-2-phenylpropanenitrile

650854

-

4.1.2.10

4 entries

4.1.2.47

2 entries

6.4.1.8

2 ATP + acetophenone + HCO3- + H2O + H+ = 2 ADP + 2 phosphate + 3-oxo-3-phenylpropanoate

659062, 708932

-

Product in Enzyme-catalyzed Reactions (65 results)

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Show Product (65 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.1.1.1

R-(+)-1-phenylethanol + NAD+ = 1-phenylethanone + NADH

-

-

1.1.1.1

S-(-)-1-phenylethanol + NAD+ = 1-phenylethanone + NADH

-

-

1.1.1.1

1-phenylethanol + NAD+ = 1-phenylethanone + NADH

-

-

1.1.1.1

acetophenone + NADH + H+ = (R)-1-phenylethanol + NAD+

-

-

1.1.1.1

1-phenylethanol + NAD+ = 1-phenylethanone + NADH + H+

-

-

1.1.1.1

1-phenylethanol + NAD+ = acetophenone + NADH + H+

-

-

1.1.1.1

acetylacetone + NADH + H+ = acetophenone + NADH + H+

-

-

1.1.1.1

(S)-1-phenylethanol + NAD+ = 1-phenylethanone + NADH + H+

-

-

1.1.1.1

1-phenylethanol + NADP+ = 1-phenylethanone + NADPH + H+

-

-

1.1.1.1

9 entries

1.1.1.183

phenylethylalcohol + NADP+ = 1-phenylethan-1-one + NADPH + H+

-

-

1.1.1.2

acetophenone + NADPH = (R)-1-phenylethanol + NADP+

-

1zk1, 3D-view

1.1.1.2

acetophenone + NADPH = (R)-1-phenylethanol + NADP+

-

1zk4, 3D-view

1.1.1.2

2 entries

1.1.1.311

(S)-1-phenylethanol + NAD+ = acetophenone + NADH + H+

-

-

1.1.1.320

sec-phenethyl alcohol + NADP+ = 1-phenylethanone + NADPH + H+

-

-

1.1.1.6

1-phenylethanol + NAD+ = acetophenone + NADH + H+

-

-

1.1.1.71

1-phenylethanol + NADP+ = acetophenone + NADPH + H+

-

-

1.1.1.71

1-phenylethanol + NADP+ = 1-phenylethanone + NADPH + H+

-

-

1.1.1.71

(RS)-1-phenylethanol + NAD+ = 1-phenylethanone + NADH + H+

-

-

1.1.1.71

(RS)-1-phenylethanol + NADP+ = 1-phenylethanone + NADPH + H+

-

-

1.1.1.71

rac-1-phenylethanol + NAD(P)+ = acetophenone + (R)-1-phenylethanol + NAD(P)H + H+

-

-

1.1.1.71

rac-1-phenylethanol + NAD(P)+ = acetophenone + (R)-1-phenylethanol + NAD(P)H + H+

-

-

1.1.1.71

rac-1-phenylethanol + NADP+ = (R)-1-phenylethanol + (S)-1-phenylethanol + NADPH + H+

-

-

1.1.1.71

7 entries

1.1.1.76

(S)-1-phenylethanol + NAD+ = acetophenone + NADH + H+

-

-

1.1.1.91

(R)-1-phenylethanol + NAD+ = 1-phenylacetaldehyde + NADH + H+

-

-

1.1.1.91

(S)-1-phenylethanol + NADP+ = 1-phenylacetaldehyde + NADPH + H+

-

-

1.1.1.B3

(R)-1-phenylethanol + NAD+ = 1-phenylethanone + NADH + H+

-

-

1.1.1.B3

(S)-1-phenylethanol + NAD+ = acetophenone + NADH + H+

-

-

1.1.1.B3

(S)-1-phenylethanol + NAD+ = 1 phenylethanone + NADH + H+

-

-

1.1.1.91

2 entries

1.1.1.B3

3 entries

1.1.1.B4

(R)-1-phenylethanol + NAD+ = acetophenone + NADH + H+

-

-

1.1.3.18

sec-phenethyl alcohol + O2 = 1-phenylethanone + H2O2

-

-

1.1.3.47

(R)-1-phenylethanol + O2 = acetophenone + H2O2

-

-

1.1.3.47

(S)-1-phenylethanol + O2 = acetophenone + H2O2

-

-

1.1.3.47

2 entries

1.11.2.1

ethylbenzene + H2O2 = (R)-1-phenylethanol

-

-

1.14.12.12

ethylbenzene + NADH + H+ + O2 = (S)-1-phenylethanol + (R)-1-phenylethanol + NAD+

-

-

1.14.14.1

ethylbenzene + [reduced NADPH-hemoprotein reductase] + O2 = (R)-1-phenylethanol + 1-phenylethanone + [oxidized NADPH-hemoprotein reductase] + H2O

-

-

1.14.14.1

ethylbenzene + [reduced NADPH-hemoprotein reductase] + O2 = (R)-1-phenylethanol + 1-phenylethanone + [oxidized NADPH-hemoprotein reductase] + H2O

-

-

1.14.14.1

ethylbenzene + [reduced NADPH-hemoprotein reductase] + H+ + O2 = (1S)-1-phenylethan-1-ol + 1-phenylethan-1-one + [oxidized NADPH-hemoprotein reductase] + ?

-

-

1.14.14.1

3 entries

1.2.3.1

acetophenone oxime + H2O + 2-hydroxypyrimidine = acetophenone + NH3

390388

-

1.4.3.12

1-phenylethanamine + O2 + H2O = 1-phenylacetaldehyde + NH3 + H2O2

-

-

1.4.3.12

1-phenylethanamine + O2 + H2O = 1-phenylethanone + NH3 + H2O2

-

-

1.4.3.12

(1R)-1-phenylethan-1-amine + H2O + O2 = 1-phenylacetaldehyde + NH3 + H2O2

-

-

1.4.3.12

(1S)-1-phenylethan-1-amine + H2O + O2 = 1-phenylacetaldehyde + NH3 + H2O2

-

-

2.6.1.18

(S)-alpha-methylbenzylamine + pyruvate = acetophenone + alanine

-

-

2.6.1.18

butyraldehyde + (S)-alpha-methylbenzylamine = ? + acetophenone

-

-

2.6.1.18

glyoxylate + (S)-alpha-methylbenzylamine = glycine + acetophenone

-

-

2.6.1.18

propion aldehyde + (S)-alpha-methylbenzylamine = ? + acetophenone

-

-

2.6.1.18

pyruvic aldehyde + (S)-alpha-methylbenzylamine = ? + acetophenone

-

-

2.6.1.18

(S)-alpha-methylbenzylamine + pyruvate = acetophenone + L-alanine

-

-

2.6.1.18

1-phenylethanamine + 2-oxobutyrate = acetophenone + D-homoalanine

-

-

2.6.1.18

1-phenylethanamine + 2-oxobutyrate = acetophenone + L-homoalanine

-

-

2.6.1.18

1-phenylethanamine + pyruvate = acetophenone + alanine

-

-

2.6.1.18

1-phenylethylamine + pyruvate = acetophenone + L-alanine

-

-

2.6.1.18

3-fluoropyruvate + (1S)-1-phenyl-ethanamine = (R)-3-fluoroalanine + acetophenone

-

-

1.4.3.12

4 entries

2.6.1.18

11 entries

2.6.1.42

(R)-alpha-methylbenzylamine + pyruvate = alpha-methylbenzaldehyde + L-alanine

-

-

2.6.1.77

(S)-1-methylbenzylamine + pyruvate = acetophenone + L-alanine

-

-

2.6.1.B16

2-phenylpropionaldehyde + (S)-1-phenylethylamine = 2-phenylpropylamine + acetophenone

-

-

2.6.1.B16

cinnamaldehyde + (S)-1-phenylethylamine = (2E)-3-phenylprop-2-en-1-amine + acetophenone

-

-

2.6.1.B16

propanal + (S)-1-phenylethylamine = propylamine + acetophenone

-

-

2.6.1.B16

pyruvate + (S)-1-phenylethylamine = L-alanine + acetophenone

-

-

3.1.1.3

(RS)-1-phenylethyl acetate + H2O = (R)-1-phenylethanol + acetate + (R)-1-phenylethyl acetate

651025

-

3.1.1.3

(RS)-1-phenylethanol + vinyl acetate = (S)-1-phenylethyl acetate + acetaldehyde + (R)-1-phenylethanol

-

-

3.2.1.149

(R)-1-phenylethyl beta-D-glucopyranoside + H2O = (R)-1-phenylethanol + beta-D-glucopyranose

-

-

3.2.1.149

(R)-1-phenylethyl beta-primeveroside + H2O = (R)-1-phenylethanol + beta-primeverose

-

-

2.6.1.B16

4 entries

3.1.1.3

2 entries

3.2.1.149

2 entries

3.7.1.7

1-phenyl-1,3-butanedione + H2O = acetic acid + acetophenone

210617

-

4.1.1.4

2-Oxo-3-phenylpropionic acid = Acetophenone + CO2

-

-

Inhibitor in Enzyme-catalyzed Reactions (9 results)

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Show Inhibitors (9 entries)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

1.1.1.311

0.05 mM, 50% inhibition of acetophenone reduction activity

685078

-

1.1.1.311

oxidation of (S)-1-phenylethanol is completely inhibited in the presence of tenfold higher concentrations of (R)-1-phenylethanol

707292

-

1.1.1.B3

-

685078

-

1.1.1.B3

inhibitory above 0.02 mM, 75% of maximum activty at 1 mM

685078

-

1.1.1.311

2 entries

1.1.1.B3

2 entries

1.13.11.2

-

439587

-

1.14.18.1

-

685530

-

2.4.2.30

IC50: 2.3 mM

637997

-

2.6.1.18

is a poor inhibitor which reduces enzyme activity by 10% at 25 mM

658326

-

2.6.1.18

in the presence of 5 mM acetophenone, the reactivity of the enzyme towards F-pyruvate decreased by 78%

721893

-

2.6.1.18

2 entries

3D Structure of Enzyme-Ligand-Complex (PDB) (2 results)

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Show 3D Structure of Enzyme-Ligand-Complex (PDB) (2 entries)

EC NUMBER

ENZYME 3D STRUCTURE

1.1.1.2

1zk1, 3D-view

1.1.1.2

1zk4, 3D-view

1.1.1.2

2 entries

Enzyme Kinetic Parameters

k_cat Value (Turnover Number) (14 results)

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Show Turnover Number (14 entries)

EC NUMBER

TURNOVER NUMBER [1/S]

TURNOVER NUMBER MAXIMUM [1/S]

COMMENTARY

LITERATURE

1.1.1.1

211

-

pH 6.0, 37°C, recombinant enzyme expressed from Hansenula polymorpha

722888

1.1.1.1

259

-

pH 6.0, 37°C, recombinant enzyme expressed from Saccharomyces cerevisiae

722888

1.1.1.1

288

-

pH 6.0, 37°C, recombinant enzyme expressed from Arxula adeninivorans

722888

1.1.1.2

35.7

-

cofactor NADH, reduction, recombinant mutant G37Dm 30°C, pH 7.0

675348

1.1.1.2

44.5

-

cofactor NADPH, reduction, recombinant wild-type, 30°C, pH 7.0

675348

1.1.1.1

3 entries

1.1.1.2

2 entries

1.1.1.311

1.6

-

pH 8, 30°C

707292

1.1.1.91

0.0047

-

wild-type, pH 8.3, 30°C

737897

1.1.1.B4

8.2

-

pH 6.5, 50°C, mutant I86A

741784

1.1.1.B4

15.8

-

pH 6.5, 50°C, wild-type enzyme

741784

1.14.13.22

0.1

-

pH 7.0, 25°C

741605

1.14.13.22

0.4

-

pH 7.0, 25°C

741605

1.14.13.84

4.5

-

pH 8, 30°C

644553

1.14.13.84

13.2

-

pH 7.5, 30°C

649387

1.14.13.84

16.3

-

312 microM NADPH, 50 mM Tris-HCl, pH 8.0, 30°C

695775

1.1.1.B4

2 entries

1.14.13.22

2 entries

1.14.13.84

3 entries

K_M Value (19 results)

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Show KM Value (19 entries)

EC NUMBER

KM VALUE [MM]

KM VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

1.1.1.1

0.2

-

pH 6.0, 37°C, recombinant enzyme expressed from Hansenula polymorpha

722888

1.1.1.1

0.4

-

pH 6.0, 37°C, recombinant enzyme expressed from Arxula adeninivorans

722888

1.1.1.1

0.66

-

pH 6.0, 37°C, recombinant enzyme expressed from Saccharomyces cerevisiae

722888

1.1.1.1

3 entries

1.1.1.100

46.92

-

with 4 mM NADPH, in 0.1 M sodium phosphate buffer, pH 7.0

701783

1.1.1.153

1.1

-

-

286021

1.1.1.2

0.034

-

-

668054

1.1.1.2

2.8

-

cofactor NADPH, reduction, recombinante wild-type, 30°C, pH 7.0

675348

1.1.1.2

10.9

-

cofactor NADH, reduction, recombinante mutant G37D, 30°C, pH 7.0

675348

1.1.1.2

3 entries

1.1.1.311

0.001

-

pH 8, 30°C

707292

1.1.1.91

5.5

-

wild-type, pH 8.3, 30°C

737897

1.1.1.B3

0.0113

-

pH 7.8, 25°C

685078

1.1.1.B3

0.153

-

pH 7.0, 25°C

689823

1.14.13.22

5

-

pH 7.0, 25°C

741605

1.14.13.22

13

-

pH 7.0, 25°C

741605

1.14.13.84

0.384

-

pH 8, 30°C

651670

1.14.13.84

0.393

-

312 microM NADPH, 50 mM Tris-HCl, pH 8.0, 30°C

695775

1.14.13.84

2.27

-

pH 8, 30°C

644553

1.14.13.84

2.3

-

pH 7.5, 30°C

649387

1.1.1.B3

2 entries

1.14.13.22

2 entries

1.14.13.84

4 entries

6.4.1.8

0.033

-

pH 6.5, 30°C

708932

K_i Value (1 result)

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Show KI Value (1 entry)

EC NUMBER

KI VALUE [MM]

KI VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

1.13.11.2

0.21

-

-

439587

IC₅₀ Value (2 results)

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Show IC50 Value (2 entries)

EC NUMBER

IC50 VALUE

IC50 VALUE MAXIMUM

COMMENTARY

LITERATURE

1.14.18.1

0.85

-

-

685530

2.4.2.30

2.3

-

IC50: 2.3 mM

637997

References & Links

Literature References (64)

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Show Reference (64 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

5160

8958123

Enantioselective synthesis of aliphatic (S)-cyanohydrins in organic solvents using hydroxynitrile lyase from Manihot esculenta

1996

Wajant, H.; Foerster, S.; Spauer, A.; Effenberger, F.; Pfizenmaier, K.

Ann. N. Y. Acad. Sci.

799

771-776

210617

-

Degradation mechanism of poly(vinyl alcohol) by successive reactions of secondary alcohol oxidase and beta-diketone hydrolase from Pseudomonas sp.

1986

Sakai, K.; Hamada, N.; Watanabe, Y.

Agric. Biol. Chem.

50

989-996

286021

3904835

Carbonyl reductase activity of sepiapterin reductase from rat erythrocytes

1985

Sueoka, T.; Katoh, S.

Biochim. Biophys. Acta

843

193-198

390388

3566284

Oxime-metabolizing activity of liver aldehyde oxidase

1987

Tatsumi, K.; Ishigai, M.

Arch. Biochem. Biophys.

253

413-418

439587

8163017

Aliphatic and aromatic inhibitors binding to the active site of catechol 2,3-dioxygenase from Pseudomonas putida mt-2

1994

Bertini, I.; Briganti, F.; Scozzafava, A.

FEBS Lett.

343

56-60

637997

1530940

Specific inhibitors of poly(ADP-ribose) synthetase and mono(ADP-ribosyl)transferase

1992

Banasik, M.; Komura, H.; Shimoyama, M.; Ueda, K.

J. Biol. Chem.

267

1569-1575

644553

11322873

4- Hydroxyacetophenone monooxygenase from Pseudomonas fluorescens ACB: a novel flavoprotein catalyzing Baeyer-Villiger oxidation of aromatic compounds

2001

Kamerbeek, N.M.; Moonen, M.J.; van der Ven, J.G.; van Berkel, W.J.H.; Fraaije, M.W.; Janssen, D.B.

Eur. J. Biochem.

268

2547-2557

649387

12514023

Substrate specificity and enantioselectivity of 4-hydroxyacetophenone monooxygenase

2003

Kamerbeek, N.M.; Olsthoorn, A.J.J.; Fraaije, M.W.; Janssen, D.B.

Appl. Environ. Microbiol.

69

419-426

650854

12616635

Substrate specificity of mutants of the hydroxynitrile lyase from Manihot esculenta

2003

Bühler, H.; Effenberger, F.; Förster, S.; Roos, J.; Wajant, H.

ChemBioChem

4

211-216

651025

-

Biochemical characterization of a recombinant thermoalkalophilic lipase and assessment of its substrate enantioselectivity

2002

Sunna, A.; Hunter, L.; Hutton, C.A.; Bergquist, P.L.

Enzyme Microb. Technol.

31

472-476

651670

11073896

Conversion of 4-hydroxyacetophenone into 4-phenyl acetate by a flavin adenine dinucleotide-containing Baeyer-Villiger-type monooxygenase

2000

Tanner, A.; Hopper, D.J.

J. Bacteriol.

182

6565-6569

653959

-

Enzymic synthesis of (R)-cyanohydrins by three (R)-oxynitrilase sources in micro-aqueous organic medium

1999

Lin, G.; Han, S.; Li, Z.

Tetrahedron

55

3531-3540

654294

12172614

Cloning, functional expression and biochemical characterization of a stereoselective alcohol dehydrogenase from Pseudomonas fluorescens DSM50106

2002

Hildebrandt, P.; Musidlowska, A.; Bornscheuer, U.T.; Altenbuchner, J.

Appl. Microbiol. Biotechnol.

59

483-487

655106

15604828

Improved synthesis of chiral alcohols with Escherichia coli cells co-expressing pyridine nucleotide transhydrogenase, NADP(+)-dependent alcohol dehydrogenase and NAD(+)-dependent formate dehydrogenase

2004

Weckbecker, A.; Hummel, W.

Biotechnol. Lett.

26

1739-1744

656514

12628239

The crystal structure of R-specific alcohol dehydrogenase from Lactobacillus brevis suggests the structural basis of its metal dependency

2003

Niefind, K.; Muller, J.; Riebel, B.; Hummel, W.; Schomburg, D.

J. Mol. Biol.

327

317-328

658326

12882012

Simultaneous synthesis of enantiomerically pure (R)-1-phenylethanol and (R)-alpha-methylbenzylamine from racemic alpha-methylbenzylamine using omega-transaminase/alcohol dehydrogenase/glucose dehydrogenase coupling reaction

2003

Yun, H.; Yang, Y.H.; Cho, B.K.; Hwang, B.Y.; Kim, B.G.

Biotechnol. Lett.

25

809-814

659062

15687214

Substrate-dependent regulation of anaerobic degradation pathways for toluene and ethylbenzene in a denitrifying bacterium, strain EbN1

2005

Kuhner, S.; Wohlbrand, L.; Fritz, I.; Wruck, W.; Hultschig, C.; Hufnagel, P.; Kube, M.; Reinhardt, R.; Rabus, R.

J. Bacteriol.

187

1493-1503

667255

16000771

Purification and characterization of a novel alcohol dehydrogenase from Leifsonia sp. strain S749: a promising biocatalyst for an asymmetric hydrogen transfer bioreduction

2005

Inoue, K.; Makino, Y.; Itoh, N.

Appl. Environ. Microbiol.

71

3633-3641

668054

16132858

Kinetic modeling of acetophenone reduction catalyzed by alcohol dehydrogenase from Thermoanaerobacter sp.

2005

Findrik, Z.; Vasic-Racki, D.; Luetz, S.; Daussmann, T.; Wandrey, C.

Biotechnol. Lett.

27

1087-1095

673101

16113996

Purification and characterization of rat liver enzyme catalyzing stereoselective reduction of acetylpyridines

2005

Uwai, K.; Konno, N.; Kitamura, S.; Ohta, S.; Takeshita, M.

Chirality

17

494-500

675348

15896805

Atomic resolution of R-specific alcohol dehydrogenase from Lactobacillus brevis provide the structual bases of its substrate and cosubstrate specificity

2005

Schlieben, N.H.; Niefind, K.; Mueller, J.; Riebel, B.; Hummel, W.; Schomburg, D.

J. Mol. Biol.

349

801-813

684556

17435004

Purification, characterization, gene cloning, and expression of a novel alcohol dehydrogenase with anti-prelog stereospecificity from Candida parapsilosis

2007

Nie, Y.; Xu, Y.; Mu, X.Q.; Wang, H.Y.; Yang, M.; Xiao, R.

Appl. Environ. Microbiol.

73

3759-3764

684583

18456852

Purification and characterization of a novel recombinant highly enantioselective short-chain NAD(H)-dependent alcohol dehydrogenase from Thermus thermophilus

2008

Pennacchio, A.; Pucci, B.; Secundo, F.; La Cara, F.; Rossi, M.; Raia, C.A.

Appl. Environ. Microbiol.

74

3949-3958

684588

12719937

Cloning, sequence analysis, and heterologous expression of the gene encoding a (S)-specific alcohol dehydrogenase from Rhodococcus erythropolis DSM 43297

2003

Abokitse, k.; Hummel, w.

Appl. Microbiol. Biotechnol.

62

380-386

685078

16388583

Crystal structure and enzyme kinetics of the (S)-specific 1-phenylethanol dehydrogenase of the denitrifying bacterium strain EbN1

2006

Hoeffken, H.W.; Duong, M.; Friedrich, T.; Breuer, M.; Hauer, B.; Reinhardt, R.; Rabus, R.; Heider, J.

Biochemistry

45

82-93

685529

18006320

Electronic effects of para-substitution on acetophenones in the reaction of rat liver 3alpha-hydroxysteroid dehydrogenase

2008

Uwai, K.; Konno, N.; Yasuta, Y.; Takeshita, M.

Bioorg. Med. Chem.

16

1084-1089

685530

18326070

1-(1-Arylethylidene)thiosemicarbazide derivatives: a new class of tyrosinase inhibitors

2008

Liu, J.; Yi, W.; Wan, Y.; Ma, L.; Song, H.

Bioorg. Med. Chem.

16

1096-1102

685643

10586501

NAD+-Dependent (S)-specific secondary alcohol dehydrogenase involved in stereoinversion of 3-pentyn-2ol catalyzed by Nocardia fusca AKU 2123

1999

Xie, S.-X.; Ogawa, J.; Shimizu, S.

Biosci. Biotechnol. Biochem.

63

1721-1729

687850

17368401

Purification and characterization of alcohol dehydrogenase reducing N-benzyl-3-pyrrolidinone from Geotrichum capitatum

2007

Yamada-Onodera, K.; Fukui, M.; Tani, Y.

J. Biosci. Bioeng.

103

174-178

688442

-

Characterization of novel alcohol dehydrogenase of Devosia riboflavina involved in stereoselective reduction of 3-pyrrolidinone derivatives

2008

Kizaki, N.; Yasohara, Y.; Nagashima, N.; Hasegawa, J.

J. Mol. Catal. B

51

73-80

688571

-

A Pseudomonas sp. alcohol dehydrogenase with broad substrate specificity and unusual stereospecificity for organic synthesis

1992

Bradshaw, C.W.; Fu, H.; Shen, G.-J.; Wong, C.-H

J. Org. Chem.

57

1526-1532

688747

17451525

A novel NADH-dependent carbonyl reductase with unusual stereoselectivity for (R)-specific reduction from an (S)-1-phenyl-1,2-ethanediol-producing micro-organism: purification and characterization

2007

Nie, Y.; Xu, Y.; Yang, M.; Mu, X.Q.

Lett. Appl. Microbiol.

44

555-562

689309

18205368

Inverting the enantioselectivity of a carbonyl reductase via substrate-enzyme docking-guided point mutation

2008

Zhu, D.; Yang, Y.; Majkowicz, S.; Pan, T.H.; Kantardjieff, K.; Hua, L.

Org. Lett.

10

525-528

689823

-

Purification and characterization of an enantioselective carbonyl reductase from Candida viswanathii MTCC 5158

2007

Soni, P.; Kansal, H.; Banerjee, U.C.

Process Biochem.

42

1632-1640

695075

-

Biosynthesis of chiral methyl ketone cyanohydrins catalyzed by oxynitrilase in Chaenomeles speciosa seed meal

2008

Fang, F.; Ji, A.; Meng, Z.

React. Kinet. Catal. Lett.

93

233-239

695775

19251889

Cloning, expression, characterization, and biocatalytic investigation of the 4-hydroxyacetophenone monooxygenase from Pseudomonas putida JD1

2009

Rehdorf, J.; Zimmer, C.L.; Bornscheuer, U.T.

Appl. Environ. Microbiol.

75

3106-3114

701783

18791006

Identification, cloning, and characterization of a novel ketoreductase from the cyanobacterium Synechococcus sp. strain PCC 7942

2008

Hoelsch, K.; Havel, J.; Haslbeck, M.; Weuster-Botz, D.

Appl. Environ. Microbiol.

74

6697-6702

707292

11479712

(S)-1-Phenylethanol dehydrogenase of Azoarcus sp. strain EbN1, an enzyme of anaerobic ethylbenzene catabolism

2001

Kniemeyer, O.; Heider, J.

Arch. Microbiol.

176

129-135

707345

-

Scope and limitations of the use of nicotinoprotein alcohol dehydrogenase for the coenzyme-free production of enantiopure fine-chemicals

2001

Schenkels, P.; De Vries, S.; Straathof, A.J.J.

Biocatal. Biotransform.

19

191-212

708932

20047908

ATP-dependent carboxylation of acetophenone by a novel type of carboxylase

2010

Jobst, B.; Schühle, K.; Linne, U.; Heider, J.

J. Bacteriol.

192

1387-1394

711743

19579248

Characterisation of a recombinant NADP-dependent glycerol dehydrogenase from Gluconobacter oxydans and its application in the production of L-glyceraldehyde

2009

Richter, N.; Neumann, M.; Liese, A.; Wohlgemuth, R.; Eggert, T.; Hummel, W.

ChemBioChem

10

1888-1896

711860

-

Cofactor engineering of Lactobacillus brevis alcohol dehydrogenase by computational design

2009

Machielsen, R.; Looger, L.; Raedts, J.; Dijkhuizen, S.; Hummel, W.; Henneman, H.; Daussmann, T.; van der Oost, J.

Eng. Life Sci.

9

38-44

717141

22286514

Completing the series of BVMOs involved in camphor metabolism of Pseudomonas putida NCIMB 10007 by identification of the two missing genes, their functional expression in E. coli, and biochemical characterization

2012

Kadow, M.; Loschinski, K.; Sass, S.; Schmidt, M.; Bornscheuer, U.

Appl. Microbiol. Biotechnol.

96

419-429

718681

22805786

Biochemical and structural characterization of recombinant short-chain NAD(H)-dependent dehydrogenase/reductase from Sulfolobus acidocaldarius highly enantioselective on diaryl diketone benzil

2013

Pennacchio, A.; Sannino, V.; Sorrentino, G.; Rossi, M.; Raia, C.A.; Esposito, L.

Appl. Microbiol. Biotechnol.

97

3949-3964

721250

-

Enzymatic asymmetric synthesis of enantiomerically pure aliphatic, aromatic and arylaliphatic amines with (R)-selective amine transaminases

2011

Schätzle, S.; Steffen-Munsberg, F.; Thontowi, A.; Höhne, M.; Robins, K.; Bornscheuer, U.

Adv. Synth. Catal.

353

2439-2445

721868

21670533

Purification and characterization of an NADH-dependent alcohol dehydrogenase from Candida maris for the synthesis of optically active 1-(pyridyl)ethanol derivatives

2011

Kawano, S.; Yano, M.; Hasegawa, J.; Yasohara, Y.

Biosci. Biotechnol. Biochem.

75

1055-1060

721893

-

Asymmetric synthesis of (R)-3-fluoroalanine from 3-fluoropyruvate using omega-transaminase

2011

Bea, H.; Lee, S.; Yun, H.

Biotechnol. Bioprocess Eng.

16

291-296

722888

22584819

Production of a thermostable alcohol dehydrogenase from Rhodococcus ruber in three different yeast species using the Xplor2 transformation/expression platform

2012

Giersberg, M.; Degelmann, A.; Bode, R.; Piontek, M.; Kunze, G.

J. Ind. Microbiol. Biotechnol.

39

1385-1396

723841

20606285

Crystallization and preliminary X-ray diffraction analysis of the Thermoanaerobacter ethanolicus secondary alcohol dehydrogenase I86A mutant

2010

Protsko, C.; Vieille, C.; Laivenieks, M.; Prasad, L.; Sanders, D.A.; Delbaere, L.T.

Acta Crystallogr. Sect. F

66

831-833

725726

-

Deracemization of aryl secondary alcohols via enantioselective oxidation and stereoselective reduction with tandem whole-cell biocatalysts

2010

Li, Y.; Xu, J.; Xu, Y.

J. Mol. Catal. B

64

48-52

726512

-

Highly enantioselective double reduction of phenylglyoxal to (R)-1-phenyl-1,2-ethanediol by one NADPH-dependent yeast carbonyl reductase with a broad substrate profile

2013

Li, Z.; Liu, W.; Chen, X.; Jia, S.; Wu, Q.; Zhu, D.; Ma, Y.

Tetrahedron

69

3561-3564

735498

24509923

Characterization of an allylic/benzyl alcohol dehydrogenase from Yokenella sp. strain WZY002, an organism potentially useful for the synthesis of alpha,beta-unsaturated alcohols from allylic aldehydes and ketones

2014

Ying, X.; Wang, Y.; Xiong, B.; Wu, T.; Xie, L.; Yu, M.; Wang, Z.

Appl. Environ. Microbiol.

80

2399-2409

737897

23686719

Crystallographic analysis and structure-guided engineering of NADPH-dependent Ralstonia sp. alcohol dehydrogenase toward NADH cosubstrate specificity

2013

Lerchner, A.; Jarasch, A.; Meining, W.; Schiefner, A.; Skerra, A.

Biotechnol. Bioeng.

110

2803-2814

739768

-

Structure-based enzyme tailoring of 5-hydroxymethylfurfural oxidase

2015

Dijkman, W.; Binda, C.; Fraaije, M.; Mattevi, A.

ACS Catal.

5

1833-1839

739937

23274959

Novel chiral tool, (R)-2-octanol dehydrogenase, from Pichia finlandica: Purification, gene cloning, and application for optically active alpha-haloalcohols

2013

Yamamoto, H.; Kudoh, M.

Appl. Microbiol. Biotechnol.

97

8087-8096

739947

25549618

Asymmetric reduction of ketones and beta-keto esters by (S)-1-phenylethanol dehydrogenase from denitrifying bacterium Aromatoleum aromaticum

2015

Dudzik, A.; Snoch, W.; Borowiecki, P.; Opalinska-Piskorz, J.; Witko, M.; Heider, J.; Szaleniec, M.

Appl. Microbiol. Biotechnol.

99

5055-5069

740200

23381774

Biochemical characterization of an alcohol dehydrogenase from Ralstonia sp.

2013

Kulig, J.; Frese, A.; Kroutil, W.; Pohl, M.; Rother, D.

Biotechnol. Bioeng.

110

1838-1848

741605

27873437

Characterization and crystal structure of a robust cyclohexanone monooxygenase

2016

Romero, E.; Castellanos, J.R.; Mattevi, A.; Fraaije, M.W.

Angew. Chem. Int. Ed. Engl.

55

15852-15855

741747

25549618

Asymmetric reduction of ketones and beta-keto esters by (S)-1-phenylethanol dehydrogenase from denitrifying bacterium Aromatoleum aromaticum

2015

Dudzik, A.; Snoch, W.; Borowiecki, P.; Opalinska-Piskorz, J.; Witko, M.; Heider, J.; Szaleniec, M.

Appl. Microbiol. Biotechnol.

99

5055-5069

741784

27495738

I86A/C295A mutant secondary alcohol dehydrogenase from Thermoanaerobacter ethanolicus has broadened substrate specificity for aryl ketones

2016

Nealon, C.M.; Welsh, T.P.; Kim, C.S.; Phillips, R.S.

Arch. Biochem. Biophys.

606

151-156

742305

-

Continuous preparation of (R)-phenyl-ethanediol by catalysis of nanoparticles immobilized bi-enzyme coupling system

2016

Peng, Y.; Zhang, Y.

Chin. J. Proc. Engin.

16

286-291

743703

-

Purification and characterization of a novel carbonyl reductase involved in oxidoreduction of aromatic beta-amino ketones/alcohols

2014

He, S.; Wang, Z.; Zou, Y.; Chen, S.; Xu, X.

Process Biochem.

49

1107-1112

746785

26310798

Enantioselective synthesis of various cyanohydrins using covalently immobilized preparations of hydroxynitrile lyase from Prunus dulcis

2015

Alagoez, D.; Tuekel, S.S.; Yildirim, D.

Appl. Biochem. Biotechnol.

177

1348-1363

749351

28466867

Enzyme discovery beyond homology a unique hydroxynitrile lyase in the Bet v1 superfamily

2017

Lanfranchi, E.; Pavkov-Keller, T.; Koehler, E.M.; Diepold, M.; Steiner, K.; Darnhofer, B.; Hartler, J.; Van Den Bergh, T.; Joosten, H.J.; Gruber-Khadjawi, M.; Thallinger, G.G.; Birner-Gruenberger, R.; Gruber, K.; Winkler, M.; Glieder, A.

Sci. Rep.

7

46738

Links to other databases for acetophenone

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Show Links (1 entry)

ChEBI

PubChem