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Ligand (R)-3-hydroxybutyryl-CoA

Basic Ligand Information

Molecular Structure

Show all BRENDA pathways known for (R)-3-hydroxybutyryl-CoA

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Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (4 results)

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Show Natural Substrate (4 entries)

EC NUMBER

LITERATURE

REACTION DIAGRAM

PROVEN IN VIVO REACTION

ENZYME 3D STRUCTURE

1.1.1.36

657366

(R)-3-hydroxybutyryl-CoA + NAD+ = acetoacetyl-CoA + NADH

-

1.1.1.36

761574

(R)-3-hydroxybutyryl-CoA + NAD+ = acetoacetyl-CoA + NADH + H+

-

1.1.1.36

684617, 687159, 689821

(R)-3-hydroxybutyryl-CoA + NADPH + H+ = 3-oxobutyryl-CoA + NADP+

-

1.1.1.36

657366

(R)-3-hydroxybutyryl-CoA = trans-2-butenoyl-CoA + H2O

-

1.1.1.36

4 entries

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

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Show Natural Product (3 entries)

EC NUMBER

LITERATURE

REACTION DIAGRAM

PROVEN IN VIVO REACTION

ENZYME 3D STRUCTURE

1.1.1.36

-

acetoacetyl-CoA + NADH + H+ = (R)-3-hydroxybutyryl-CoA + NAD+

-

1.1.1.36

-

acetoacetyl-CoA + NADPH + H+ = (R)-3-hydroxybutyryl-CoA + NADP+

-

1.1.1.36

-

acetoacetyl-CoA + NADPH = (R)-3-hydroxybutyryl-CoA + NADP+

-

1.1.1.36

3 entries

Substrate in Enzyme-catalyzed Reactions (7 results)

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Show Substrate (7 entries)

EC NUMBER

LITERATURE

REACTION DIAGRAM

REACTION

ENZYME 3D STRUCTURE

1.1.1.36

33732

(R)-3-hydroxybutyryl-CoA + NAD+ = 3-oxobutyryl-CoA + NADH + H+

-

1.1.1.36

657366

(R)-3-hydroxybutyryl-CoA + NAD+ = acetoacetyl-CoA + NADH

-

1.1.1.36

761574

(R)-3-hydroxybutyryl-CoA + NAD+ = acetoacetyl-CoA + NADH + H+

-

1.1.1.36

684617, 687159, 689821

(R)-3-hydroxybutyryl-CoA + NADPH + H+ = 3-oxobutyryl-CoA + NADP+

-

1.1.1.36

657366

(R)-3-hydroxybutyryl-CoA = trans-2-butenoyl-CoA + H2O

-

2.3.1.304

685729, 684663, 685063, 735683, 735496, 685488, 687418, 686489, 688783, 685312, 684662, 685490

(R)-3-hydroxybutyryl-CoA + [(R)-3-hydroxybutanoate]n = [(R)-3-hydroxybutanoate](n+1) + CoA

-

2.3.1.304

685488

(R)-3-hydroxybutyryl-CoA + [3-hydroxybutanoate]n = [(R)-3-hydroxybutanoate](n+1) + CoA

-

1.1.1.36

5 entries

2.3.1.304

2 entries

Product in Enzyme-catalyzed Reactions (7 results)

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Show Product (7 entries)

EC NUMBER

LITERATURE

REACTION DIAGRAM

REACTION

ENZYME 3D STRUCTURE

1.1.1.100

, 285672

acetoacetyl-CoA + NADPH = D-beta-hydroxybutyryl-CoA + NADP+

-

1.1.1.36

-

acetoacetyl-CoA + NADH + H+ = (R)-3-hydroxybutyryl-CoA + NAD+

-

1.1.1.36

-

acetoacetyl-CoA + NADPH + H+ = (R)-3-hydroxybutyryl-CoA + NADP+

-

1.1.1.36

-

acetoacetyl-CoA + NADPH = (R)-3-hydroxybutyryl-CoA + NADP+

-

1.1.1.36

286617,

acetoacetyl-CoA + NADH = D-beta-hydroxybutyryl-CoA + NAD+

-

1.1.1.36

286613, 286625, , 286623

acetoacetyl-CoA + NADPH = D-beta-hydroxybutyryl-CoA + NADP+

-

1.1.1.36

5 entries

3.3.2.12

-

crotonyl-CoA + H2O = (R)-3-hydroxybutyryl-CoA

-

Enzyme Kinetic Parameters

k_cat Value (Turnover Number) (5 results)

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Show Turnover Number (5 entries)

COMMENTARY

EC NUMBER

LITERATURE

TURNOVER NUMBER [1/S]

TURNOVER NUMBER MAXIMUM [1/S]

25°C, pH 7.0, mutant enzyme G4D, based on one catalytic site in a dimeric enzyme

2.3.1.304

688783

26

-

25°C, pH 7.0, wild-type enzyme, based on one catalytic site in a dimeric enzyme

2.3.1.304

688783

44

-

30°C, first phase of reaction

2.3.1.304

684662

65.33

-

30°C, second phase of reaction

2.3.1.304

684662

18.67

-

based on the assumption that 2 PhaC and 2 PhaE subunits comprise one catalytic site

2.3.1.304

685488

320

-

K_M Value (9 results)

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Show KM Value (9 entries)

COMMENTARY

EC NUMBER

KM VALUE [MM]

KM VALUE MAXIMUM [MM]

LITERATURE

-

1.1.1.36

0.03

-

286622, 286623

-

1.1.1.36

0.033

-

286622

-

2.3.1.304

0.056

-

684663

-

2.3.1.304

0.063

-

686489

-

2.3.1.304

0.065

-

685488

-

5 entries

25°C, pH 7.0, mutant enzyme G4D, based on one catalytic site in a dimeric enzyme

2.3.1.304

0.32

-

688783

25°C, pH 7.0, wild-type enzyme, based on one catalytic site in a dimeric enzyme

2.3.1.304

0.19

-

688783

30°C, first phase of reaction

2.3.1.304

0.13

-

684662

30°C, second phase of reaction

2.3.1.304

0.45

-

684662

References & Links

Literature References (24)

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Show Reference (24 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

33732

9003397

Peroxisomal multifunctional enzyme of beta-oxidation metabolizing D-3-hydroxyacyl-CoA esters in rat liver: molecular cloning, expression and characterization

1997

Qin, Y.M.; Poutanen, M.H.; Helander, H.M.; Kvist, A.P.; Siivari, K.M.; Schmitz, W.; Conzelmann, E.; Hellman, U.; Hiltunen, J.K.

Biochem. J.

321

21-28

285672

4381013

Studies on the mechanism of fatty acid synthesis. XV. Preparation and general properties of beta-ketoacyl acyl carrier protein reductase from Escherichia coli

1966

Toomey, R.E.; Wakil, S.J.

Biochim. Biophys. Acta

116

189-197

286613

14004466

Studies on the mechanism of fatty acid synthesis

1962

Wakil, S.J.; Bressler, R.

J. Biol. Chem.

237

687-693

286617

6376489

Rat hepatic microsomal acetoacetyl-CoA reductase. A beta-ketoacyl-CoA reductase distinct from the long chain beta-ketoacyl-CoA reductase component of the microsomal fatty acid chain elongation system

1984

Prasad, M.R.; Cook, L.; Vieth, R.; Cinti, D.L.

J. Biol. Chem.

259

7460-7467

286622

-

Purification and characterization of NADPH-dependent acetoacetyl-CoA reductase from Methylobacterium extorquens

1997

Belova, L.L.; Sokolov, A.P.; Sidorov, I.A.; Trotsenko, Y.A.

FEMS Microbiol. Lett.

156

275-279

286623

-

Methylobacterium rhodesianum MB 126 possesses two acetoacetyl-CoA reductases

1994

Mothes, G.; Babel, W.

Arch. Microbiol.

161

277-280

286625

10550638

Poly(beta-hydroxybutyrate) production in oilseed leukoplasts of Brassica napus

1999

Houmiel, K.L.; Slater, S.; Broyles, D.; Casagrande, L.; Colburn, S.; Gonzalez, K.; Mitsky, T.A.; Reiser, S.E.; Shah, D.; Taylor, N.B.; Tran, M.; Valentin, H.E.; Gruys, K.J.

Planta

209

547-550

657366

12517343

Binary structure of the two-domain (3R)-hydroxyacyl-CoA dehydrogenase from rat peroxisomal multifunctional enzyme type 2 at 2.38 A resolution

2003

Haapalainen, A.M.; Koski, M.K.; Qin, Y.M.; Hiltunen, J.K.; Glumoff, T.

Structure

11

87-97

684617

17609944

Microbial production of R-3-hydroxybutyric acid by recombinant E. coli harboring genes of phbA, phbB, and tesB

2007

Liu, Q.; Ouyang, S.P.; Chung, A.; Wu, Q.; Chen, G.Q.

Appl. Microbiol. Biotechnol.

76

811-818

684662

11566031

Class I and III polyhydroxyalkanoate synthases from Ralstonia eutropha and Allochromatium vinosum: characterization and substrate specificity studies

2001

Yuan, W.; Jia, Y.; Tian, J.; Snell, K.D.; Muh, U.; Sinskey, A.J.; Lambalot, R.H.; Walsh, C.T.; Stubbe, J.

Arch. Biochem. Biophys.

394

87-98

684663

12139978

Biochemical and enzymological properties of the polyhydroxybutyrate synthase from the extremely halophilic archaeon strain 56

2002

Hezayen, F.F.; Steinbuchel, A.; Rehm, B.H.

Arch. Biochem. Biophys.

403

284-291

685063

15938626

Class III polyhydroxybutyrate synthase: involvement in chain termination and reinitiation

2005

Tian, J.; Sinskey, A.J.; Stubbe, J.

Biochemistry

44

8369-8377

685312

11825620

Molecular characterization of the poly(3-hydroxybutyrate) (PHB) synthase from Ralstonia eutropha: in vitro evolution, site-specific mutagenesis and development of a PHB synthase protein model

2002

Rehm, B.H.; Antonio, R.V.; Spiekermann, P.; Amara, A.A.; Steinbuchel, A.

Biochim. Biophys. Acta

1594

178-190

685488

14715006

Poly(hydroxyalkanoic acid) biosynthesis in Ectothiorhodospira shaposhnikovii: characterization and reactivity of a type III PHA synthase

2004

Zhang, S.; Kolvek, S.; Goodwin, S.; Lenz, R.W.

Biomacromolecules

5

40-48

685490

15638509

Synergistic effects of Glu130Asp substitution in the type II polyhydroxyalkanoate (PHA) synthase: enhancement of PHA production and alteration of polymer molecular weight

2005

Matsumoto, K.; Takase, K.; Aoki, E.; Doi, Y.; Taguchi, S.

Biomacromolecules

6

99-104

685729

16049738

Site-directed saturation mutagenesis at residue F420 and recombination with another beneficial mutation of Ralstonia eutropha polyhydroxyalkanoate synthase

2005

Normi, Y.M.; Hiraishi, T.; Taguchi, S.; Sudesh, K.; Najimudin, N.; Doi, Y.

Biotechnol. Lett.

27

705-712

686489

7957260

Purification and characterization of the poly(hydroxyalkanoic acid) synthase from Chromatium vinosum and localization of the enzyme at the surface of poly(hydroxyalkanoic acid) granules

1994

Liebergesell, M.; Sonomoto, K.; Madkour, M.; Mayer, F.; Steinbuchel, A.

Eur. J. Biochem.

226

71-80

687159

-

Biosynthesis of biodegradable polyhydroxyalkanotes biopolymers in genetically modified yeasts

2007

Abd-El-haleem, D.; Amara, A.; Zaki, S.; Abulhamd, A.; Abulreesh, G.

Int. J. Environ. Sci. Technol.

4

513-520

687418

18408025

Genetic and biochemical characterization of the poly(3-hydroxybutyrate-co-3-hydroxyvalerate) synthase in Haloferax mediterranei

2008

Lu, Q.; Han, J.; Zhou, L.; Zhou, J.; Xiang, H.

J. Bacteriol.

190

4173-4180

688783

15768438

Characterization and properties of G4X mutants of Ralstonia eutropha PHA synthase for poly(3-hydroxybutyrate) biosynthesis in Escherichia coli

2005

Normi, Y.M.; Hiraishi, T.; Taguchi, S.; Abe, H.; Sudesh, K.; Najimudin, N.; Doi, Y.

Macromol. Biosci.

5

197-206

689821

-

Production and characterization of terpolyester poly(3-hydroxybutyrate-co-3-hydroxyvalerate-co-3-hydroxyhexanoate) by recombinant Aeromonas hydrophila 4AK4 harboring genes phaAB

2007

Zhao, W.; Chen, G.

Process Biochem.

42

1342-1347

735496

24334666

Alcoholytic cleavage of polyhydroxyalkanoate chains by class IV synthases induced by endogenous and exogenous ethanol

2014

Hyakutake, M.; Tomizawa, S.; Mizuno, K.; Abe, H.; Tsuge, T.

Appl. Environ. Microbiol.

80

1421-1429

735683

25741756

Chemistry with an artificial primer of polyhydroxybutyrate synthase suggests a mechanism for chain termination

2015

Buckley, R.M.; Stubbe, J.

Biochemistry

54

2117-2125

761574

33122026

An NADH preferring acetoacetyl-CoA reductase is engaged in poly-3-hydroxybutyrate accumulation in Escherichia coli

2021

Olavarria, K.; Carnet, A.; van Renselaar, J.; Quakkelaar, C.; Cabrera, R.; Guedes da Silva, L.; Smids, A.L.; Villalobos, P.A.; van Loosdrecht, M.C.M.; Wahl, S.A.

J. Biotechnol.

325

207-216

Links to other databases for (R)-3-hydroxybutyryl-CoA

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Show Links (1 entry)

ChEBI

PubChem

-