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Ligand vinyl acetate

Basic Ligand Information

Molecular Structure

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Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (1 result)

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Show Natural Substrate (1 entry)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

3.1.1.3

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

663726

-

Substrate in Enzyme-catalyzed Reactions (42 results)

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Show Substrate (42 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

2.3.1.167

vinyl acetate + 10-deacetylbaccatin III = vinyl alcohol + baccatin III

757640, 755829

-

2.7.2.7

ATP + vinyl acetate = ADP + vinylacetyl phosphate

642344

-

3.1.1.1

vinyl acetate + H2O = vinyl alcohol + acetate

664198, 668463, 677663, 653767, 727066

-

3.1.1.113

vinyl acetate + H2O = ethenol + acetate

754005

-

3.1.1.3

(5R,6R)-6-hydroxy-5,6-dihydro-1,10-phenanthrolin-5-yl acetate + vinyl acetate = (5S,6S)-6-hydroxy-5,6-dihydro-1,10-phenanthrolin-5-yl acetate + (5R,6R)-5,6-dihydro-1,10-phenanthroline-5,6-diyl diacetate + ethenol

695170

-

3.1.1.3

(R,S)-mandelonitrile + vinyl acetate = (S)-cyano(phenyl)methyl acetate + (R)-mandelonitrite

691762

-

3.1.1.3

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

663726

-

3.1.1.3

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

691448

-

3.1.1.3

2-[2-(2,4-difluoro-phenyl)-allyl]-propane-1,3-diol + vinyl acetate = (S)-acetic acid 4-(2,4-difluoro-phenyl)-2-hydroxymethyl-pent-4-enyl ester + acetic acid 2-acetoxymethyl-4-(2,4-difluoro-phenyl)-pent-4-enyl-ester

659774

-

3.1.1.3

6-azido-5,6-dihydro-1,10-phenanthrolin-5-ol + vinyl acetate = (5S,6S)-6-azido-5,6-dihydro-1,10-phenanthrolin-5-ol + (5R,6R)-6-azido-5,6-dihydro-1,10-phenanthrolin-5-yl acetate + ethenol

695170

-

3.1.1.3

dextran T40 + vinyl acetate = ?

715683

-

3.1.1.6

3-O-methyl-D-glucopyranoside + vinyl acetate = 6-O-acetyl-3-O-methyl-D-glucopyranoside + vinyl alcohol

715029

-

3.1.1.6

4-nitrophenyl beta-D-glucopyranoside + vinyl acetate = 4-nitrophenyl 3-O-acetyl-beta-D-glucopyranoside + vinyl alcohol

666091

-

3.1.1.6

alpha,alpha-trehalose + vinyl acetate = ? + vinyl alcohol

715029

-

3.1.1.6

cellobiose + vinyl acetate = ? + vinyl alcohol

715029

-

3.1.1.6

D-galactose + vinyl acetate = ? + vinyl alcohol

715029

-

3.1.1.6

D-glucopyranosyl beta-(1,3)-xylopyranoside + vinyl acetate = ? + vinyl alcohol

715029

-

3.1.1.6

D-glucopyranosyl beta-(1,4)-xylopyranoside + vinyl acetate = ? + vinyl alcohol

715029

-

3.1.1.6

D-glucose + vinyl acetate = 6-O-acetyl-D-glucopyranose + vinyl alcohol

715029

-

3.1.1.6

D-mannose + vinyl acetate = 6-O-acetyl-D-mannopyranose + vinyl alcohol

715029

-

3.1.1.6

D-xylopyranosyl beta-(1,4)-D-glucopyranoside + vinyl acetate = ? + vinyl alcohol

715029

-

3.1.1.6

kojic acid + vinyl acetate = 7-O-acetyl-kojic acid + vinyl alcohol

666091

-

3.1.1.6

methyl 2-O-methyl-beta-D-glucopyranoside + vinyl acetate = ? + vinyl alcohol

715029

-

3.1.1.6

methyl 4-O-methyl-alpha-D-glucopyranoside + vinyl acetate = ? + vinyl alcohol

715029

-

3.1.1.6

methyl alpha-D-glucopyranoside + vinyl acetate = ? + vinyl alcohol

715029

-

3.1.1.6

methyl beta-D-glucopyranoside + vinyl acetate = ? + vinyl alcohol

715029

-

3.1.1.6

methyl beta-D-glucopyranoside + vinyl acetate = methyl 3-O-acetyl-beta-D-glucopyranoside + vinyl alcohol

666091

-

3.1.1.6

xylobiose + vinyl acetate = ? + vinyl alcohol

715029

-

3.1.1.72

methyl beta-cellobiose + vinyl acetate = ?

650392

-

3.1.1.72

methyl beta-xylopyranoside + vinyl acetate = ?

650392

-

3.1.1.73

1-(1,1'-biphenyl)-4-yl-1-ethanol + vinyl acetate = ?

669895

-

3.1.1.73

1-(3-methylphenyl)-1-ethanol + vinyl acetate = ?

669895

-

3.1.1.73

1-(4-isopropylphenyl)-1-ethanol + vinyl acetate = ?

669895

-

3.1.1.73

1-(4-methoxyphenyl)-1-ethanol + vinyl acetate = ?

669895

-

3.1.1.73

1-(4-pyridinyl)-1-ethanol + vinyl acetate = 1-pyridin-4-ylethylacetate + prop-2-en-1-ol

669895

-

3.1.1.73

1-phenyl-1-ethanol + vinyl acetate = ?

669895

-

3.1.1.73

1-phenyl-1-propanol + vinyl acetate = ?

669895

-

3.1.1.73

vinyl acetate + H2O = vinyl alcohol + acetate

729036

-

3.1.1.3

7 entries

3.1.1.6

17 entries

3.1.1.72

2 entries

3.1.1.73

8 entries

3.1.1.74

tyrosol + vinyl acetate = tyrosyl acetate + vinyl alcohol

751346

-

3.1.1.79

vinyl acetate + H2O = acetate + ethylenol

664198

-

3.1.1.79

vinyl acetate + H2O = vinyl alcohol + acetate

654765

-

3.1.1.79

2 entries

3.5.1.11

allopurinol + vinyl acetate = 1-(4-oxo-4,5-dihydro-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl acetate

668240

-

Enzyme Kinetic Parameters

k_cat Value (Turnover Number) (10 results)

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Show Turnover Number (10 entries)

EC NUMBER

TURNOVER NUMBER [1/S]

TURNOVER NUMBER MAXIMUM [1/S]

COMMENTARY

LITERATURE

2.3.1.167

0.0224

-

mutant enzyme D390H, pH 7.2, 37°C

757640

2.3.1.167

0.0224

-

wild-type enzyme, pH 7.2, 37°C

757640

2.3.1.167

0.0236

-

mutant enzyme I43T, pH 7.2, 37°C

757640

2.3.1.167

0.0244

-

mutant enzyme I43S, pH 7.2, 37°C

757640

2.3.1.167

0.0259

-

mutant enzyme D390R, pH 7.2, 37°C

757640

2.3.1.167

0.0263

-

mutant enzyme I43S/D390R, pH 7.2, 37°C

757640

3.1.1.1

50

-

pH 7.5, 25°C

664198

3.1.1.1

110

-

pH 7.5, 25°C

664198

3.1.1.1

140

-

pH 7.5, 25°C

664198

2.3.1.167

6 entries

3.1.1.1

3 entries

3.1.1.79

170

-

-

664198

K_M Value (11 results)

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Show KM Value (11 entries)

EC NUMBER

KM VALUE [MM]

KM VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

2.3.1.167

0.046

-

mutant enzyme I43S/D390R, pH 7.2, 37°C

757640

2.3.1.167

0.065

-

mutant enzyme D390R, pH 7.2, 37°C

757640

2.3.1.167

0.065

-

mutant enzyme I43T, pH 7.2, 37°C

757640

2.3.1.167

0.066

-

mutant enzyme I43S, pH 7.2, 37°C

757640

2.3.1.167

0.128

-

wild-type enzyme, pH 7.2, 37°C

757640

2.3.1.167

0.134

-

mutant enzyme D390H, pH 7.2, 37°C

757640

3.1.1.1

2.5

-

pH 7.5, 25°C

664198

3.1.1.1

4

-

pH 7.5, 25°C

664198

3.1.1.1

170

-

pH 7.5, 25°C

664198

3.1.1.79

170

-

37°C, pH 8.0

654765

3.1.1.79

315

-

-

664198

2.3.1.167

6 entries

3.1.1.1

3 entries

3.1.1.79

2 entries

References & Links

Literature References (23)

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Show Reference (23 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

642344

3027059

Butyrate kinase from Clostridium acetobutylicum

1987

Hartmanis, M.G.N.

J. Biol. Chem.

262

617-621

650392

14572903

Transacetylations to carbohydrates catalyzed by acetylxylan esterase in the presence of organic solvent

2003

Biely, P.; Wong, K.K.; Suckling, I.D.; Spanikova, S.

Biochim. Biophys. Acta

1623

62-71

653767

12880765

Cloning, heterologous expression, renaturation, and characterization of a cold-adapted esterase with unique primary structure from a psychrotroph Pseudomonas sp. strain B11-1

2003

Suzuki, T.; Nakayama, T.; Choo, D.W.; Hirano, Y.; Kurihara, T.; Nishino, T.; Esaki, N.

Protein Expr. Purif.

30

171-178

654765

15260473

Might the kinetic behavior of hormone-sensitive lipase reflect the absence of the lid domain?

2004

Ben Ali, Y.; Chahinian, H.; Petry, S.; Muller, G.; Carriere, F.; Verger, R.; Abousalham, A.

Biochemistry

43

9298-9306

659774

-

Enzymatic desymmetrization of prochiral 2-substituted-1,3-propanediols: A practical chemoenzymatic synthesis of a key precursor of SCH51048, a broad-spectrum orally active antifungal agent

1997

MOrgan, B.; Dodds, D.R.; Zaks, A.; Andrews, D.R.; Klesse, R.

J. Org. Chem.

62

7736-7743

663726

15052375

Enantioselective transesterification using immobilized Aspergillus oryzae overexpressing lipase

2004

Kaieda, M.; Nagayoshi, M.; Hama, S.; Kondo, A.; Fukuda, H.

Appl. Microbiol. Biotechnol.

65

301-305

664198

16325466

Substrate specificity and kinetic properties of enzymes belonging to the hormone-sensitive lipase family: comparison with non-lipolytic and lipolytic carboxylesterases

2005

Chahinian, H.; Ali, Y.B.; Abousalham, A.; Petry, S.; Mandrich, L.; Manco, G.; Canaan, S.; Sarda, L.

Biochim. Biophys. Acta

1738

29-36

666091

-

Trichoderma reesei acetyl esterase catalyzes transesterification in water

2004

Kremnicky, L.; Mastihuba, V.; Cote, G.L.

J. Mol. Catal. B

30

229-239

668240

15877124

Penicillin G acylase catalyzed Markovnikov addition of allopurinol to vinyl ester

2005

Wu, W.B.; Wang, N.; Xu, J.M.; Wu, Q.; Lin, X.F.

Chem. Commun. (Camb.)

2005

2348-2350

668463

15373841

Expression and characterization of the protein Rv1399c from Mycobacterium tuberculosis. A novel carboxyl esterase structurally related to the HSL family

2004

Canaan, S.; Maurin, D.; Chahinian, H.; Pouilly, B.; Durousseau, C.; Frassinetti, F.; Scappuccini-Calvo, L.; Cambillau, C.; Bourne, Y.

Eur. J. Biochem.

271

3953-3961

669895

-

Ferulic acid esterase from Humicola Insolens catalyzes enantioselective transesterification of secondary alcohols

2003

Hatzakis, N.S.; Daphnomili, D.; Smonou, I.

J. Mol. Catal. B

21

309-311

677663

16672512

Isolation and biochemical characterization of two novel metagenome-derived esterases

2006

Elend, C.; Schmeisser, C.; Leggewie, C.; Babiak, P.; Carballeira, J.D.; Steele, H.L.; Reymond, J.; Jaeger, K.; Streit, W.R.

Appl. Environ. Microbiol.

72

3637-3645

691448

18777014

Wheat germ lipase catalyzed kinetic resolution of secondary alcohols in non-aqueous media

2009

Xia, X.; Wang, Y.H.; Yang, B.; Wang, X.

Biotechnol. Lett.

31

83-87

691762

-

Kinetic study of lipase catalyzed asymmetric transesterification of mandelonitrile in solvent-free system

2008

Xiong, J.; Wu, J.; Xu, G.; Yang, L.

Chem. Eng. J.

138

258-263

695170

-

Lipase-catalyzed kinetic resolution as the key step in the synthesis of a new class of optically active 5,6-trans-9,10-dihydrophenanthroline derivatives

2008

Sanfilippo, C.; Nicolosi, G.

Tetrahedron Asymmetry

19

2171-2176

715029

19968989

Carbohydrate esterases of family 2 are 6-O-deacetylases

2010

Topakas, E.; Kyriakopoulos, S.; Biely, P.; Hirsch, J.; Vafiadi, C.; Christakopoulos, P.

FEBS Lett.

584

543-548

715683

21602099

Lipase-catalyzed synthesis of hydrophobically modified dextrans: activity and regioselectivity of lipase from Candida rugosa

2011

Kaewprapan, K.; Wongkongkatep, J.; Panbangred, W.; Phinyocheep, P.; Marie, E.; Durand, A.; Inprakhon, P.

J. Biosci. Bioeng.

112

124-129

727066

19303051

First evidence for the salt-dependent folding and activity of an esterase from the halophilic archaea Haloarcula marismortui

2009

Müller-Santos, M.; de Souza, E.M.; Pedrosa, Fde O.; Mitchell, D.A., Longhi, S.; Carrière, F.; Canaan, S.; Krieger, N.

Biochim. Biophys. Acta

1791

719-729

729036

23793626

Characterization of a feruloyl esterase from Lactobacillus plantarum

2013

Esteban-Torres, M.; Reveron, I.; Mancheno, J.M.; de Las Rivas, B.; Munoz, R.

Appl. Environ. Microbiol.

79

5130-5136

751346

-

Cutinase from Fusarium oxysporum catalyzes the acylation of tyrosol in an aqueous medium Optimization and thermodynamic study of the reaction

2016

Nikolaivits, E.; Norra, G.; Voutsas, E.; Topakas, E.

J. Mol. Catal. B

129

29-36

754005

17351032

Degradation of alkyl methyl ketones by Pseudomonas veronii MEK700

2007

Onaca, C.; Kieninger, M.; Engesser, K.; Altenbuchner, J.

J. Bacteriol.

189

3759-3767

755829

29797298

Activity essential residue analysis of taxoid 10beta-O-acetyl transferase for enzymatic synthesis of baccatin

2018

You, L.; Wei, T.; Zheng, Q.; Lin, J.; Guo, L.; Jiang, B.; Huang, J.

Appl. Biochem. Biotechnol.

186

949-959

757640

29796788

Bio-production of baccatin III, an important precursor of paclitaxel by a cost-effective approach

2018

Lin, S.L.; Wei, T.; Lin, J.F.; Guo, L.Q.; Wu, G.P.; Wei, J.B.; Huang, J.J.; Ouyang, P.L.

Mol. Biotechnol.

60

492-505

Links to other databases for vinyl acetate

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ChEBI

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