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Ligand tributyrin

Basic Ligand Information

Molecular Structure

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Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (2 results)

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Show Natural Substrate (2 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

3.1.1.1

tributyrin + H2O = ?

653084

-

3.1.1.3

tributyrin + H2O = dibutyrin + butyrate

650524, 666217, 677728, 666825

6tp8, 3D-view

Substrate in Enzyme-catalyzed Reactions (32 results)

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Show Substrate (32 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

3.1.1.1

glyceryl tributyrate + H2O = ?

669844

-

3.1.1.1

tributyrin + H2O = ?

670779, 664198, 667838, 668463, 653084, 653767, 678016, 715403, 729647, 749825, 721900, 725032

-

3.1.1.1

tributyrin + H2O = butanoate + glycerol

677732, 690570, 677663, 680960, 692396

-

3.1.1.1

tributyrylglycerol + H2O = butyrate + glycerol

170991, 170993, 171006, 171000, 170986, 171027, 171029

-

3.1.1.13

tributyrin + H2O = dibutyrin + butyrate

650388, 702443

-

3.1.1.13

tributyrin + H2O = dibutyrylglycerol + butanoic acid

133852

-

3.1.1.1

4 entries

3.1.1.13

2 entries

3.1.1.2

tributyrin + H2O = dibutyrin + butyrate

692889

-

3.1.1.23

tributyrylglycerol + H2O = ?

94273

-

3.1.1.26

tributyrin + H2O = ?

664182, 691901, 691003

-

3.1.1.3

glyceryl tributanoate + H2O = glycerol + butanoate

742676

6tp8, 3D-view

3.1.1.3

glyceryl tributyrate + H2O = glyceryl dibutyrate + butyric acid

650306

6tp8, 3D-view

3.1.1.3

tributyrin + 3 H2O = glycerol + 3 butyrate

748394, 692424

6tp8, 3D-view

3.1.1.3

tributyrin + H2O = ?

729305, 730743, 678397, 730877

6tp8, 3D-view

3.1.1.3

tributyrin + H2O = butyric acid + ?

80846, 80854, 80811, 80816, 80836, 80862, 80827, 80826, 80858

6tp8, 3D-view

3.1.1.3

tributyrin + H2O = dibutyrin + butyrate

651027, 665746, 681263, 690730, 650654, 694531, 651022, 680528, 666381, 664236, 680948, 682667, 650524, 650367, 651141, 692905, 679795, 682990, 666217, 651019, 691892, 666789, 716527, 691439, 677728, 682646, 714072, 666825, 678491, 663907, 682608, 650429, 666368, 665175, 664191, 678497, 679311, 664965, 677808, 679881, 679894, 681355, 679885, 691405, 694532, 682678, 749967, 652958, 652591, 651516, 653758, 650660, 653102, 664788, 664815, 664964, 650688, 651396, 651018, 692122, 715393, 716082

6tp8, 3D-view

3.1.1.3

tributyrin + H2O = dibutyrin + butyric acid

653203

6tp8, 3D-view

3.1.1.32

tributyrin + H2O = ?

94342

-

3.1.1.32

tributyrin + H2O = butyric acid + 1,2-dibutyrylglycerol

751202

-

3.1.1.34

tributyrin + H2O = ?

652702, 80906, 80885

-

3.1.1.34

tributyrin + H2O = butanoate + dibutyrin

652457

-

3.1.1.3

7 entries

3.1.1.32

2 entries

3.1.1.34

2 entries

3.1.1.47

tributyrylglycerol + H2O = dibutyrylglycerol + butyrate

650057

-

3.1.1.5

tributyrin + H2O = ?

94384, 94388

-

3.1.1.6

tributyrin + H2O = ?

715950, 699069

-

3.1.1.73

tributyrin + H2O = ?

729036

-

3.1.1.74

tributyrin + H2O = ?

729653, 715944, 750578, 710477, 707267, 750134

-

3.1.1.74

tributyrin + H2O = butyric acid + 1,2-dibutyrylglycerol

729450, 749726

-

3.1.1.74

2 entries

3.1.1.76

1,2,3-tributyryl-sn-glycerol + H2O = ?

680871

-

3.1.1.79

tributanoyl glycerol + H2O = dibutanoylglycerol + butanoate

654765

-

3.1.1.79

tributanoylglycerol + H2O = dibutanoylglycerol + butanoate

655415

-

3.1.1.79

tributyrin + H2O = dibutanoylglycerol + butanoate

664198

-

3.1.1.79

tributyrin + H2O = dibutyrin + butyrate

750177

-

3.1.1.79

tributyrylglycerol + H2O = ?

677872

-

3.1.1.79

5 entries

3D Structure of Enzyme-Ligand-Complex (PDB) (1 result)

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Show 3D Structure of Enzyme-Ligand-Complex (PDB) (1 entry)

EC NUMBER

ENZYME 3D STRUCTURE

3.1.1.3

6tp8, 3D-view

Enzyme Kinetic Parameters

k_cat Value (Turnover Number) (21 results)

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Show Turnover Number (21 entries)

EC NUMBER

TURNOVER NUMBER [1/S]

TURNOVER NUMBER MAXIMUM [1/S]

COMMENTARY

LITERATURE

3.1.1.1

18

-

pH 7.5, 25°C

664198

3.1.1.1

23

-

pH 2.0, 50°C

729647

3.1.1.1

95

-

pH 7.5, 25°C

664198

3.1.1.1

1290

-

pH 7.5, 25°C

664198

3.1.1.1

4 entries

3.1.1.13

179

-

pH 7.0, 37°C

650388

3.1.1.3

30

-

pH 8.0, 37°C, recombinant mutant G311K

682678

3.1.1.3

75.8

-

pH 8.0, 37°C, recombinant mutant G311D

682678

3.1.1.3

250

-

pH 8.0, 37°C, recombinant mutant G311L

682678

3.1.1.3

1200

-

pH 8.5, 37°C, recombinant His-tagged mutant D290A

682646

3.1.1.3

1500

-

pH 8.0, 37°C, recombinant wild-type enzyme

682678

3.1.1.3

1500

-

pH 8.5, 37°C, recombinant His-tagged wild-type enzyme

682646

3.1.1.3

1900

-

pH 8.5, 37°C, native wild-type enzyme

682646

3.1.1.3

4333

-

at pH 8.5 and 37°C

691892

3.1.1.3

5370

-

pH 9.0, 37°C

664191

3.1.1.6

6.2

-

wild type enzyme, in 20 mM phosphate buffer (pH 7.1), at 30°C

715950

3.1.1.6

6.9

-

mutant enzyme R48K, in 20 mM phosphate buffer (pH 7.1), at 30°C

715950

3.1.1.6

9.3

-

mutant enzyme R48E, in 20 mM phosphate buffer (pH 7.1), at 30°C

715950

3.1.1.6

17.4

-

mutant enzyme R48A, in 20 mM phosphate buffer (pH 7.1), at 30°C

715950

3.1.1.6

17.5

-

mutant enzyme R48S, in 20 mM phosphate buffer (pH 7.1), at 30°C

715950

3.1.1.3

9 entries

3.1.1.6

5 entries

3.1.1.74

238

-

pH 7.5, 30°C, recombinant enzyme

729653

3.1.1.79

18

-

-

664198

K_M Value (27 results)

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Show KM Value (27 entries)

EC NUMBER

KM VALUE [MM]

KM VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

3.1.1.1

0.05

-

pH 7.5, 25°C

664198

3.1.1.1

0.07

-

pH 7.5, 25°C

664198

3.1.1.1

0.4

-

pH 7.5, 25°C

664198

3.1.1.1

2.22

-

pH 7.5, 22°C

680960

3.1.1.1

7.4

-

pH 2.0, 50°C

729647

3.1.1.1

5 entries

3.1.1.13

9.9

-

pH 7.0, 37°C

650388

3.1.1.23

40

-

-

94273

3.1.1.3

4.7

-

pH 8.0, 37°C, recombinant mutant G311D

682678

3.1.1.3

5

-

pH 7.5, 30°C

651516

3.1.1.3

5.5

-

at pH 8.5 and 37°C

691892

3.1.1.3

13.9

-

pH 8.0, 37°C, recombinant mutant G311K

682678

3.1.1.3

16.6

-

at pH 7 and 37°C

691405

3.1.1.3

17

-

pH 9.0, 37°C

664191

3.1.1.3

18.9

-

pH 8.0, 37°C, recombinant mutant G311L

682678

3.1.1.3

20.4

-

pH 8.0, 37°C, recombinant wild-type enzyme

682678

3.1.1.3

20.4

-

pH 8.5, 37°C, recombinant His-tagged wild-type enzyme

682646

3.1.1.3

31.25

-

pH 8.5, 37°C, native wild-type enzyme

682646

3.1.1.3

34

-

at 45°C

692424

3.1.1.3

34.5

-

pH 8.5, 37°C, recombinant His-tagged mutant D290A

682646

3.1.1.3

12 entries

3.1.1.47

0.136

-

plasma isozyme, pH 7.5, 22°C

650057

3.1.1.6

0.015

-

mutant enzyme R48S, in 20 mM phosphate buffer (pH 7.1), at 30°C

715950

3.1.1.6

0.018

-

mutant enzyme R48A, in 20 mM phosphate buffer (pH 7.1), at 30°C

715950

3.1.1.6

0.047

-

mutant enzyme R48K, in 20 mM phosphate buffer (pH 7.1), at 30°C

715950

3.1.1.6

0.052

-

wild type enzyme, in 20 mM phosphate buffer (pH 7.1), at 30°C

715950

3.1.1.6

0.073

-

mutant enzyme R48E, in 20 mM phosphate buffer (pH 7.1), at 30°C

715950

3.1.1.79

0.4

-

37°C, pH 8.0

654765

3.1.1.79

0.4

-

-

664198

3.1.1.6

5 entries

3.1.1.79

2 entries

References & Links

Literature References (138)

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Show Reference (138 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

80811

-

Hydrolysis of emulsified tributyrin by porcine pancreatic lipase

1988

O'Connor, K.C.; Bailey, J.E.

Enzyme Microb. Technol.

10

352-356

80816

7278671

Triglyceride lipase from porcine pancreas

1981

Brockmann, H.L.

Methods Enzymol.

71

619-627

80826

-

Crystallization and characterization of lipase from Penicillium cyclopium

1988

Isobe, K.; Akiba, T.; Yamaguchi, S.

Agric. Biol. Chem.

52

41-47

80827

3382677

Purification, characterization and kinetic properties of the rabbit gastric lipase

1988

Moreau, H.; Gargouri, Y.; Lecat, D.; Junien, J.L.; Verger, R.

Biochim. Biophys. Acta

960

286-293

80836

3922786

Irreversible inhibition of pancreatic lipase by bis-p-nitrophenyl methylphosphonate

1985

Sikk, P.; Osa, A.; Aaviksaar, A.

FEBS Lett.

184

193-196

80846

8409770

Functional characterization of a chimeric lipase genetically engineered from human lipoprotein lipase and human hepatic lipase

1993

Dichek, H.L.; Parrott, C.; Ronan, R.; Brunzell, J.D.; Brewer, H.B.; Santamarina-Fojo, S.

J. Lipid Res.

34

1393-1401

80854

9631512

Human pancreatic triglyceride lipase expressed in yeast cells: purification and characterization

1998

Yang, Y.; Lowe, M.E.

Protein Expr. Purif.

13

36-40

80858

9590625

Biochemical and structural characterization of triacylglycerol lipase from Penicillium cyclopium

1998

Ibrik, A.; Chahinian, H.; Rugani, N.; Sarda, L.; Comeau, L.C.

Lipids

33

377-384

80862

9799112

Purification and molecular cloning of porcine intestinal glycerol-ester hydrolase--evidence for its identity with carboxylesterase

1998

David, L.; Guo, X.J.; Villard, C.; Moulin, A.; Puigserver, A.

Eur. J. Biochem.

257

142-148

80885

8995362

Mutation of tryptophan residues in lipoprotein lipase. Effects on stability, immunoreactivity, and catalytic properties

1997

Lookene, A.; Groot, N.B.; Kastelein, J.J.P.; Olivecrona, G.; Bruin, T.

J. Biol. Chem.

272

766-772

80906

4370169

Lipoprotein lipase: comparative properties of the membrane-supported and solubilized enzyme species

1974

Fielding, C.J.; Higgins, J.M.

Biochemistry

13

4324-4330

94273

889853

Purification and characterization of rat liver microsomal monoacylglycerol lipase in comparison to the other esterases

1977

Ikeda, Y.; Okamura, K.; Fujii, S.

Biochim. Biophys. Acta

488

128-139

94342

6691999

Substrate specificity of two cationic lipases with high phospholipase A1 activity purified from guinea pig pancreas

1984

Fauvel, J.; Chap, H.; Roques, V.; Sarda, L.; Douste-Blazy, L.

Biochim. Biophys. Acta

792

65-71

94384

4693498

Studies on lysophospholipases. II. Substrate specificity of a lysolecithin hydrolyzing carboxylesterase from beef pancreas

1973

De Jong, J.G.N.; van den Bosch, H.; Aarsman, A.J.; van Deenen, L.L.M.

Biochim. Biophys. Acta

296

105-115

94388

4421163

Studies on lysophospholipases. III. The complete purification of two proteins with lysophospholipase activity from beef liver

1974

De Jong, J.G.N.; van den Bosch, H.; Rijken, D.; van Deenen, L.L.M.

Biochim. Biophys. Acta

369

50-63

133852

3828371

Isolation of two forms of carboxylester lipase (cholesterol esterase) from porcine pancreas

1987

Rudd, E.A.; Mizuno, N.K.; Brockman, H.L.

Biochim. Biophys. Acta

918

106-114

170986

3597342

Purification and characterization of a carboxylesterase from rabbit liver lysosomes

1987

Tanaka, M.; Lio, T.; Tabata, T.

J. Biochem.

101

619-624

170991

6417119

Human liver carboxylesterase. Properties and comparison with human serum carboxylesterase

1983

Tsujita, T.; Okuda, H.

J. Biochem.

94

793-797

170993

7074137

Purification and some properties of carboxylesterase of rat adipose tissue

1982

Tsujita, T.; Okuda, H.; Yamasaki, N.

Biochim. Biophys. Acta

715

181-188

171000

446478

Characterization of the isoenzymes of pig-liver esterase. 2. Kinetic studies

1979

Junge, W.; Heymann, E.

Eur. J. Biochem.

95

519-525

171006

870055

Purification and characterization of two types of esterase from rat liver microsomes

1977

Ikeda, Y.; Okamura, K.; Arima, T.; Fujii, S.

Biochim. Biophys. Acta

487

189-203

171027

7764864

Purification and characterization of a carboxylesterase from Pseudomonas sp. KWI-56

1994

Sugihara, A.; Shimada, Y.; Nagao, T.; Iizumi, T.; Nakamura, K.; Fukase, T.; Tominaga, Y.

Biosci. Biotechnol. Biochem.

58

752-755

171029

-

Purification and some properties of carboxylesterase from Arthrobacter globiformis stereoselective hydrolysis of ethyl chrysanthemate

1993

Nishizawa, M.; Gomi, H.; Kishimoto, F.

Biosci. Biotechnol. Biochem.

57

594-598

650057

11294621

Platelet-activating factor acetylhydrolases: broad substrate specificity and lipoprotein binding does not modulate the catalytic properties of the plasma enzyme

2001

Min, J.H.; Wilder, C.; Aoki, J.; Arai, H.; Inoue, K.; Paul, L.; Gelb, M.H.

Biochemistry

40

4539-4549

650306

10825531

Overproduction in Escherichia coli, purification and characterization of a family I.3 lipase from Pseudomonas sp. MIS38

2000

Amada, K.; Haruki, M.; Imanaka, T.; Morikawa, M.; Kanaya, S.

Biochim. Biophys. Acta

1478

201-210

650367

12117564

Expression and characterization of Ca2+-independent lipase from Bacillus pumilus B26

2002

Kim, H.K.; Choi, H.J.; Kim, M.H.; Sohn, C.B.; Oh, T.K.

Biochim. Biophys. Acta

1583

205-212

650388

12479402

Production, isolation and characterization of a sterol esterase from Ophiostoma piceae

2002

Calero-Rueda, O.; Plou, F.J.; Ballesteros, A.; Martinez, A.T.; Martinez, M.J.

Biochim. Biophys. Acta

1599

28-35

650429

11698108

Biochemical and molecular characterization of Staphylococcus simulans lipase

2001

Sayari, A.; Agrebi, N.; Jaoua, S.; Gargouri, Y.

Biochimie

83

863-871

650524

12614891

Purification and characterization of an alkaline lipase from a newly isolated Pseudomonas mendocina PK-12CS and chemoselective hydrolysis of fatty acid ester

2003

Jinwal, U.K.; Roy, U.; Chowdhury, A.R.; Bhaduri, A.P.; Roy, P.K.

Bioorg. Med. Chem.

11

1041-1046

650654

14550014

Production, purification, characterization, and applications of lipases

2001

Sharma, R.; Chisti, Y.; Banerjee, U.C.

Biotechnol. Adv.

19

627-662

650660

10814595

Purification and properties of a lipase from Cephaloleia presignis (Coleoptera, Chrysomelidae)

2000

Arreguin-Espinosa, R.; Arreguin, B.; Gonzalez, C.

Biotechnol. Appl. Biochem.

31

239-244

650688

-

Properties of recombinant Rhizomucor miehei lipase with amino acid substitutions of Phe94 in the substrate binding domain

2001

Oh, S.W.; Gaskin, D.J.H.; Kwon, D.Y.; Vulfson, E.N.

Biotechnol. Lett.

23

563-568

651018

-

Purification and characterization of two distinct thermostable lipases from the gram-positive thermophilic bacterium Bacillus thermoleovorans ID-1

2001

Lee, D.W.; Kim, H.W.; Lee, K.W.; Kim, B.C.; Choe, E.A.; Lee, H.S.; Kim, D.S.; Pyun, Y.R.

Enzyme Microb. Technol.

29

363-371

651019

-

Substrate specificity and effects of water-miscible solvents on the activity and stability of extracellular lipase from Streptomyces rimosus

2001

Lescic, I.; Vukelic, B.; Majeric-Elenkov, M.; Saenger, W.; Abramic, M.

Enzyme Microb. Technol.

29

548-553

651022

-

Biochemical characterization and kinetic properties of a purified lipase from Aspergillus niger in bulk phase and monomolecular films

2002

van Heerden, E.; Litthauer, D.; Verger, R.

Enzyme Microb. Technol.

30

902-909

651027

-

Can lipases hydrolyze a peptide bond?

2003

Maruyama, T.; Nakajima, M.; Kondo, H.; Kawasaki, K.; Seki, M.; Goto, M.

Enzyme Microb. Technol.

32

655-657

651141

12444965

Purification and properties of the extracellular lipase, LipA, of Acinetobacter sp. RAG-1

2002

Snellman, E.A.; Sullivan, E.R.; Colwell, R.R.

Eur. J. Biochem.

269

5771-5779

651396

11040182

The specific activities of human digestive lipases measured from the in vivo and in vitro lipolysis of test meals

2000

Carriere, F.; Renou, C.; Lopez, V.; De Caro, J.; Ferrato, F.; Lengsfeld, H.; De Caro, A.; Laugier, R.; Verger, R.

Gastroenterology

119

949-960

651516

100138638

Purification and characterization of an extracellular tributyrin esterase produced by a cheese isolate, Micrococcus sp. INIA 528

2004

Fernandez, J.; Mohedano, A.F.; Fernandez-Garcia, E.; Medina, M.; Nunez, M.

Int. Dairy J.

14

135-142

652457

12855707

1,1'-bis(anilino)-4-,4'-bis(naphtalene)-8,8'-disulfonate acts as an inhibitor of lipoprotein lipase and competes for binding with apolipoprotein CII

2003

Lookene, A.; Zhang, L.; Tougu, V.; Olivecrona, G.

J. Biol. Chem.

278

37183-37194

652591

16233513

Purification and characterization of the lipase from Pseudomonas fluorescens HU380

2003

Kojima, Y.; Shimizu, S.

J. Biosci. Bioeng.

96

219-226

652702

11483618

Novel site in lipoprotein lipase (LPL415-438) essential for substrate interaction and dimer stability

2001

Keiper, T.; Schneider, J.G.; Dugi, K.A.

J. Lipid Res.

42

1180-1186

652958

-

Purification and properties of thermostable lipase from a thermophilic Bacillus stearothermophilus MC7

2003

Kambourova, M.; Kirilova, N.; Mandeva, R.; Derekova, A.

J. Mol. Catal. B

22

307-313

653084

-

Cloning and characterization of an esterase from Propionibacterium freudenreichii ssp. shermanii

2002

Suoniemi, A.; Tynkkynen, S.

Lait

82

81-89

653102

11337984

Purification and characterization of an extracellular lipase from Penicillium candidum

2001

Ruiz, B.; Farres, A.; Langley, E.; Masso, F.; Sanchez, S.

Lipids

36

283-289

653203

10839198

Purification, characterization and thermostability of lipase from a thermophilic Bacillus sp. J33

2000

Nawani, N.; Kaur, J.

Mol. Cell. Biochem.

206

91-96

653758

12651113

High-level expression of a lipase from Bacillus thermocatenulatus BTL2 in Pichia pastoris and some properties of the recombinant lipase

2003

Quyen, D.T.; Schmidt-Dannert, C.; Schmid, R.D.

Protein Expr. Purif.

28

102-110

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

655415

11277912

Structure-function relationships of hormone-sensitive lipase

2001

Osterlund, T.

Eur. J. Biochem.

268

1899-1907

663907

-

Activity and stability of a crude lipase from Penicillium aurantiogriseum in aqueous media and organic solvents

2004

Lima, V.M.G.; Krieger, N.; Mitchell, D.A.; Fontana, J.D.

Biochem. Eng. J.

18

65-71

664182

15450178

Characterization of pancreatic lipase-related protein 2 isolated from human pancreatic juice

2004

De Caro, J.; Sias, B.; Grandval, P.; Ferrato, F.; Halimi, H.; Carriere, F.; De Caro, A.

Biochim. Biophys. Acta

1701

89-99

664191

16154275

Purification and characterization of a novel lipase from the digestive glands of a primitive animal: The scorpion

2005

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

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Analysis of Bacillus megaterium lipolytic system and cloning of LipA, a novel subfamily I.4 bacterial lipase

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Biochemical and molecular characterization of a lipase produced by Rhizopus oryzae

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Molecular cloning and characterization of thermostable esterase and lipase from Geobacillus thermoleovorans YN isolated from desert soil in Egypt

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Expression, purification, and characterization of His-tagged Staphylococcus xylosus lipase wild-type and its mutant Asp 290 Ala

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Structure of human pancreatic lipase-related protein 2 with the lid in an open conformation

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Purification and properties of the alkaline lipase from Burkholderia cepacia A.T.C.C. 25609

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Cloning, purification and characterization of two lipases from Streptomyces coelicolor A3(2)

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Esterase SeE of Streptococcus equi ssp. equi is a novel nonspecific carboxylic ester hydrolase

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An extra-cellular alkaline metallolipase from Bacillus licheniformis MTCC 6824: Purification and biochemical characterization

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Purification and characterization of the first reptile pancreatic lipase: the turtle

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Purification and characterization of the enantioselective esterase from Kluyveromyces marxianus CBS 1553

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The putative lipase, AF1763, from Archaeoglobus fulgidus is a carboxylesterase with a very high pH optimum

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Thiol-functionalization of acrylic ester monomers catalyzed by immobilized Humicola insolens cutinase

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