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Ligand (R)-2-hydroxybutyric acid

Basic Ligand Information

Molecular Structure

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Roles as Enzyme Ligand

Substrate in Enzyme-catalyzed Reactions (16 results)

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Show Substrate (16 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.1.1.30

(R)-2-hydroxybutanoate + NAD+ = acetoacetate + NADH

668322

-

1.1.1.345

D-2-hydroxybutyrate + NAD+ = 2-oxobutyrate + NADH + H+

672434

-

1.1.2.4

D-2-hydroxybutyrate + cytochrome c = 2-oxobutanoate + ferrocytochrome c

287801, 389623, 389624, 389625, 389626, 389630, 389629

-

1.1.2.4

D-2-hydroxybutyrate + ferricytochrome c = ?

698932

-

1.1.2.4

D-2-hydroxybutyrate + PMS-DCIP = 2-oxobutanoate + reduced PMS-DCIP

763102

-

1.1.2.4

3 entries

1.1.3.15

(R)-2-hydroxybutanoate + 2,6-dichlorophenolindophenol = 2-oxobutanoate + reduced 2,6-dichlorophenolindophenol

761556

-

1.1.5.10

D-2-hydroxybutyrate + ubiquinone-10 = 2-oxobutyrate + ubiquinol-10

763205

-

1.1.5.12

D-2-hydroxybutanoate + 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide = 2-oxobutanoate + reduced 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide

761384

-

1.1.5.12

D-2-hydroxybutyrate + 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide = 2-oxobutanoate + ?

763205

-

1.1.5.12

D-2-hydroxybutyrate + 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide = ? + reduced 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide

763205

-

1.1.5.12

D-2-hydroxybutyrate + ubiquinone-10 = ? + ubiquinol-10

763205

-

1.1.5.12

4 entries

1.1.99.24

D-2-hydroxybutyrate + 2-oxoglutarate = ?

664967

-

1.1.99.6

(R)-2-hydroxybutanoate + 2,6-dichlorophenolindophenol = 2-oxobutanoate + reduced 2,6-dichlorophenolindophenol

761556

-

1.1.99.6

(R)-2-hydroxybutyrate + oxidized 2,6-dichlorophenolindophenol = 2-oxobutyrate + reduced 2,6-dichlorophenolindophenol

693285, 761556

-

1.1.99.6

2(R)-hydroxybutanoate + acceptor = 2-oxobutanoate + reduced acceptor

287840

-

1.1.99.6

3 entries

6.1.2.1

D-Ala + D-2-hydroxybutanoate + ATP = D-Ala-D-2-hydroxybutanoate + ADP + phosphate

707464, 1249, 707463

-

Product in Enzyme-catalyzed Reactions (8 results)

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Show Product (8 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.1.1.272

2-oxobutyrate + NAD(P)H = (2R)-2-hydroxybutyrate + NAD(P)+

0

-

1.1.1.272

2-oxobutyrate + NADH + H+ = (2R)-2-hydroxybutyrate + NAD+

0

-

1.1.1.28

2-oxobutanoate + NADH + H+ = (R)-2-hydroxybutanoate + NAD+

0

-

1.1.1.28

2-oxobutyric acid + NADH + H+ = (R)-2-hydroxybutyric acid + NAD+

0

-

1.1.1.272

2 entries

1.1.1.28

2 entries

1.1.1.345

2-oxobutyrate + NADH + H+ = D-2-hydroxybutyrate + NAD+

0

-

1.1.99.30

(2R)-hydroxy-4-methylpentanoate + 2-oxo-butyrate = 2-oxo-4-methylpentanoate + (2R)-hydroxybutyrate

0

-

3.1.1.25

(R)-alpha-hydroxy-gamma-butyrolactone + H2O = (R)-2-hydroxybutyric acid

0

-

3.8.1.2

(S)-2-chlorobutyric acid + H2O = (R)-2-hydroxybutyric acid + chloride

0

-

Inhibitor in Enzyme-catalyzed Reactions (1 result)

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Show Inhibitors (1 entry)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

5.1.2.2

-

661212

-

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

1.1.2.4

1.467

-

-

698932

1.1.2.4

9.58

-

cosubstrate: ferrocytochrome c, pH 8.35, 25°C

763102

1.1.2.4

10.03

-

cosubstrate: phenazine methosulfate and 2,6-dichlorophenolindophenol, pH 8.35, 25°C

763102

1.1.2.4

3 entries

1.1.5.10

66

-

pH 7.4, 30°C

763205

1.1.5.12

13

-

isolated FAD-containing dehydrogenase domain, pH 7.4. 30°C

761384

1.1.5.12

66

-

pH 7.4. 30°C

761384

1.1.5.12

66

-

pH 7.4, 30°C

763205

1.1.5.12

66

-

pH 7.4, 30°C, acceptor: 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide

763205

6.1.2.1

0.25

-

pH not specified in the publication, temperature not specified in the publication

1249

6.1.2.1

1.8

-

pH 8.6, 25°C

707463

1.1.5.12

4 entries

6.1.2.1

2 entries

K_M Value (13 results)

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Show KM Value (13 entries)

EC NUMBER

KM VALUE [MM]

KM VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

1.1.2.4

0.01102

-

cosubstrate: ferrocytochrome c, pH 8.35, 25°C

763102

1.1.2.4

0.0149

-

cosubstrate: phenazine methosulfate and 2,6-dichlorophenolindophenol, pH 8.35, 25°C

763102

1.1.2.4

0.061

-

-

698932

1.1.2.4

1.34

-

-

389624

1.1.2.4

1.4

-

-

287801, 389623

1.1.2.4

5 entries

1.1.5.10

0.1

-

pH 7.4, 30°C

763205

1.1.5.12

0.1

-

pH 7.4. 30°C

761384

1.1.5.12

0.1

-

pH 7.4, 30°C

763205

1.1.5.12

0.1

-

pH 7.4, 30°C, acceptor: 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide

763205

1.1.5.12

0.17

-

isolated FAD-containing dehydrogenase domain, pH 7.4. 30°C

761384

1.1.5.12

4 entries

1.1.99.24

4.5

-

no activity with L-isomer, 30°C, pH 7.1

664967

6.1.2.1

0.6

-

pH 8.6, 25°C

707463

6.1.2.1

3

-

pH not specified in the publication, temperature not specified in the publication

1249

6.1.2.1

2 entries

K_i Value (2 results)

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Show KI Value (2 entries)

EC NUMBER

KI VALUE [MM]

KI VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

5.1.2.2

17.3

-

wild-type enzyme

661212

5.1.2.2

98

-

mutant enzyme F52W/Y54W

661212

5.1.2.2

2 entries

References & Links

Literature References (21)

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Show Reference (21 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

1249

7957913

Purification and characterization of the VanB ligase associated with type B vancomycin resistance in Enterococcus faecalis V583

1994

Meziane-Cherif, D.; Badet-Denisot, M.A.; Evers, S.; Courvalin, P.; Badet, B.

FEBS Lett.

354

140-142

287801

-

Metal-containing flavoprotein dehydrogenases

1976

Hatefi, Y.; Stiggall, D.L.

The Enzymes, 3rd Ed. (Boyer, P. D. , ed. )

13

175-297

287840

236454

D-2-hydroxy acid dehydrogenase from animal tissue

1975

Cammack, R.

Methods Enzymol.

41

323-329

389623

13950255

The lactic dehydrogenase of yeast. III. D(-)lactic cytochrome c reductase, a zinc-flavoprotein from aerobic yeast

1963

Gregolin, C.; Singer, T.P.

Biochim. Biophys. Acta

67

201-218

389624

13729965

D(-)-lactic cytochrome c reductase, a flavoprotein from yeast

1961

Nygaard, A.P.

J. Biol. Chem.

236

920-925

389625

-

Lactate dehydrogenases of yeast

1963

Nygaard, A.P.

The Enzymes, 2nd Ed (Boyer, P. D. , Lardy, H. , Myrbäck, K. , eds. )

7

557-565

389626

236453

D-lactate dehydrogenase of Peptostreptococcus elsdenii

1975

Brockman, H.L.; Wood, W.A.

Methods Enzymol.

41B

309-312

389629

497163

Suicide inactivation of the flavoenzyme D-lactate dehydrogenase by alpha-hydroxybutynoate

1979

Olson, S.T.; Massey, V.; Ghisla, S.; Whitfield, C.D.

Biochemistry

18

4724-4731

389630

7275946

D-Lactate dehydrogenase of Desulfovibrio vulgaris

1981

Ogata, M.; Arihara, K.; Yagi, T.

J. Biochem.

89

1423-1431

661212

15966725

Perturbing the hydrophobic pocket of mandelate racemase to probe phenyl motion during catalysis

2005

Siddiqi, F.; Bourque, J.R.; Jiang, H.; Gardner, M.; St Maurice, M.; Blouin, C.; Bearne, S.L.

Biochemistry

44

9013-9021

664967

16616524

Identification of the gene encoding hydroxyacid-oxoacid transhydrogenase, an enzyme that metabolizes 4-hydroxybutyrate

2006

Kardon, T.; Noel, G.; Vertommen, D.; Van Schaftingen, E.

FEBS Lett.

580

2347-2350

668322

-

Characterization of two D-b-hydroxybutyrate dehydrogenase populations in heavy and light mitochondria from jerboa (Jaculus orientalis) liver

2006

Mountassif, D.; Kabine, M.; Latruffe, N.; El Kebbaj, M.S.

Comp. Biochem. Physiol. B

143B

285-293

672434

11120357

2-Hydroxyacid dehydrogenase from Haloferax mediteranii, a D-isomer-specific member of the 2-dehydrogenase family

2000

Bonete, M.J.; Ferrer, J.; Pire, C.; Penades, M.; Ruiz, J.L.

Biochimie

82

1143-1150

693285

18691525

A novel flavin adenine dinucleotide (FAD) containing D-lactate dehydrogenase from the thermoacidophilic crenarchaeota Sulfolobus tokodaii strain 7: purification, characterization and expression in Escherichia coli

2008

Satomura, T.; Kawakami, R.; Sakuraba, H.; Ohshima, T.

J. Biosci. Bioeng.

106

16-21

698932

19586914

Two D-2-hydroxy-acid dehydrogenases in Arabidopsis thaliana with catalytic capacities to participate in the last reactions of the methylglyoxal and beta-oxidation pathways

2009

Engqvist, M.; Drincovich, M.F.; Fluegge, U.I.; Maurino, V.G.

J. Biol. Chem.

284

25026-25037

707463

1931965

Molecular basis for vancomycin resistance in Enterococcus faecium BM4147: biosynthesis of a depsipeptide peptidoglycan precursor by vancomycin resistance proteins VanH and VanA

1991

Bugg, T.D.; Wright, G.D.; Dutka-Malen, S.; Arthur, M.; Courvalin, P.; Walsh, C.T.

Biochemistry

30

10408-10415

707464

8756703

Gain of D-alanyl-D-lactate or D-lactyl-D-alanine synthetase activities in three active-site mutants of the Escherichia coli D-alanyl-D-alanine ligase B

1996

Park, I.-S.; Lin, C.-H.; Walsh, C.T.

Biochemistry

35

10464-10471

761384

28847921

A bacterial multidomain NAD-independent D-lactate dehydrogenase utilizes flavin adenine dinucleotide and Fe-S clusters as cofactors and quinone as an electron acceptor for D-lactate oxidization

2017

Jiang, T.; Guo, X.; Yan, J.; Zhang, Y.; Wang, Y.; Zhang, M.; Sheng, B.; Ma, C.; Xu, P.; Gao, C.

J. Bacteriol.

199

e00342

761556

29691195

D-Lactate electrochemical biosensor prepared by immobilization of thermostabledye-linked D-lactate dehydrogenase from Candidatus Caldiarchaeum subterraneum

2018

Satomura, T.; Hayashi, J.; Sakamoto, H.; Nunoura, T.; Takaki, Y.; Takai, K.; Takami, H.; Ohshima, T.; Sakuraba, H.; Suye, S.I.

J. Biosci. Bioeng.

126

425-430

763102

29259615

Silencing of D-lactate dehydrogenase impedes glyoxalase system and leads to methylglyoxal accumulation and growth inhibition in rice

2017

An, B.; Lan, J.; Deng, X.; Chen, S.; Ouyang, C.; Shi, H.; Yang, J.; Li, Y.

Front. Plant Sci.

8

2071

763205

28847921

A bacterial multidomain NAD-independent D-lactate dehydrogenase utilizes flavin adenine dinucleotide and Fe-S clusters as cofactors and quinone as an electron acceptor for D-lactate oxidization

2017

Jiang, T.; Guo, X.; Yan, J.; Zhang, Y.; Wang, Y.; Zhang, M.; Sheng, B.; Ma, C.; Xu, P.; Gao, C.

J. Bacteriol.

199

e00342-17

Links to other databases for (R)-2-hydroxybutyric acid

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ChEBI

PubChem