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Ligand D-carnitine

Basic Ligand Information

Molecular Structure

Show all BRENDA pathways known for D-carnitine

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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

1.1.1.254

(S)-3-hydroxy-4-trimethylaminobutyrate + NAD+ = 3-dehydrocarnitine + NADH + H+

285735, 285734

-

1.1.1.254

(S)-carnitine + NAD+ = 3-dehydrocarnitine + NADH + H+

654037

-

1.1.1.254

2 entries

Substrate in Enzyme-catalyzed Reactions (7 results)

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Show Substrate (7 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.1.1.254

(S)-3-hydroxy-4-trimethylaminobutyrate + NAD+ = 3-dehydrocarnitine + NADH + H+

285735, 9589, 285734

-

1.1.1.254

(S)-carnitine + NAD+ = 3-dehydrocarnitine + NADH + H+

654037, 9587, 9588, 9589

-

1.14.11.1

(S)-3-carboxy-2-hydroxy-N,N,N-trimethylpropan-1-aminium + 2-oxoglutarate + O2 = (3S)-3-carboxy-2,3-dihydroxy-N,N,N-trimethylpropan-1-aminium + succinate + CO2

745953

-

1.14.11.1

D-carnitine + 2-oxoglutarate + O2 = 3-carboxy-N,N,N-trimethyl-2-oxopropan-1-aminium + succinate + CO2

439291, 745953

-

1.14.13.239

D-carnitine + NADH + H+ + O2 = (3S)-3-hydroxy-4-oxobutanoate + trimethylamine + NAD+ + H2O

744480

-

1.14.13.239

D-carnitine + NADPH + H+ + O2 = (3S)-3-hydroxy-4-oxobutanoate + trimethylamine + NADP+ + H2O

744480

-

1.1.1.254

2 entries

1.14.11.1

2 entries

1.14.13.239

2 entries

6.2.1.48

ATP + D-carnitine + CoA = AMP + diphosphate + D-carnitinyl-CoA

740589

-

Product in Enzyme-catalyzed Reactions (1 result)

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Show Product (1 entry)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

3.1.1.28

2 palmitoyl-DL-carnitine + 2 H2O = 2 palmitate + L-carnitine + D-carnitine

649489

-

Inhibitor in Enzyme-catalyzed Reactions (8 results)

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Show Inhibitors (8 entries)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

1.14.11.1

uncoupling agent

439287

-

1.3.8.13

-

739868

-

2.3.1.137

-

486295, 486300

-

2.3.1.7

-

487398

-

2.3.1.7

-

486295, 487407

-

2.3.1.7

2 entries

3.1.2.2

inhibits at concentrations over 6 mM

80791

-

3.1.2.20

inhibits at concentrations over 6 mM

80791

-

3.5.1.73

-

288940

-

Enzyme Kinetic Parameters

K_M Value (4 results)

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Show KM Value (4 entries)

EC NUMBER

KM VALUE [MM]

KM VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

1.1.1.254

3.1

-

D-carnitine dehydrogenase

285735

1.1.1.254

5.5

-

-

9589

1.1.1.254

5.5

-

D-carnitine dehydrogenase

9589

1.1.1.254

3 entries

1.14.11.1

0.47

-

-

439291

K_i Value (4 results)

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Show KI Value (4 entries)

EC NUMBER

KI VALUE [MM]

KI VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

2.3.1.137

0.84

-

-

486295

2.3.1.7

1

-

-

486295

2.3.1.7

1.1

-

-

487407

2.3.1.7

2.1

-

-

487398

2.3.1.7

3 entries

References & Links

Literature References (19)

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Show Reference (19 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

9587

-

Production of L-carnitine from D-carnitine by partially purified D- and L-carnitine dehydrogenase of Agrobacterium sp. 525a

1998

Setyahadi, S.; Harada, E.; Mori, N.; Kitamoto, Y.

J. Mol. Catal. , B Enzym.

4

205-209

9588

-

Conversion of D-carnitine into L-carnitine with stereospecific carnitine dehydrogenase

1997

Hanschmann, H.; Kleber, H.P.

Biotechnol. Lett.

19

679-682

9589

9003445

Purification and characterization of D(+)-carnitine dehydrogenase from Agrobacterium sp. - a new enzyme of carnitine metabolism

1997

Hanschmann, H.; Kleber, H.P.

Biochim. Biophys. Acta

1337

133-142

80791

37074

Dual localization of long-chain acyl-CoA hydrolase in rat liver: one in the microsomes and one in the mitochondrial matrix

1979

Berge, R.K.; Farstad, M.

Eur. J. Biochem.

95

89-97

285734

10527494

Enzymatic cycling assay for D-carnitine determination

1999

Obon, J.M.; Buendia, B.; Canovas, M.; Iborra, J.L.

Anal. Biochem.

274

34-39

285735

9214773

Purification and properties of a new enzyme, D-carnitine dehydrogenase from Agrobacterium sp. 525a

1997

Setyahida, S.; Ueyama, T.; Arimoto, T.; Mori, N.; Kitamoto, Y.

Biosci. Biotechnol. Biochem.

61

1055-1058

288940

-

Studies on the kinetics and application of L-carnitine amidase for the production of L-carnitine

1995

Joeres, U.; Bommarius, A.S.; Thoemmes, J.; Kula, M.R.

Biocatal. Biotransform.

12

27-36

439287

7126226

Uncoupling in the gamma-butyrobetaine hydroxylase reaction by D- and L-carnitine

1982

Holme, E.; Lindstedt, S.; Nordin, I.

Biochem. Biophys. Res. Commun.

107

518-524

439291

3378057

Rat liver gamma-butyrobetaine hydroxylase catalyzed reaction: influence of potassium, substrates, and substrate analogues on hydroxylation and decarboxylation

1988

Wehbie, R.S.; Punekar, N.S.; Lardy, H.A.

Biochemistry

27

2222-2228

486295

6436243

Properties of purified carnitine acyltransferases of mouse liver peroxisomes

1984

Farrell, S.O.; Fiol, C.J.; Reddy, J.K.; Bieber, L.L.

J. Biol. Chem.

259

13089-13095

486300

8440734

Properties of the medium chain/long chain carnitine acyltransferase purified from rat liver microsomes

1993

Chung, C.D.; Bieber, L.L.

J. Biol. Chem.

268

4519-4524

487398

14299645

Carnitine acetyltransferase. II. Inhibition by carnitine analogues and by sulfhydryl reagents

1965

Fritz, I.B.; Schultz, S.K.

J. Biol. Chem.

240

2188-2192

487407

6639064

Purification and properties of carnitine acetyltransferases from bovine spermatozoa and heart

1983

Huckle, W.R.; Tamblyn, T.M.

Arch. Biochem. Biophys.

226

94-110

649489

12859986

Purification, molecular cloning, and functional expression of inducible liver acylcarnitine hydrolase in C57BL/6 mouse, belonging to the carboxylesterase multigene family

2003

Furihata, T.; Hosokawa, M.; Nakata, F.; Satoh, T.; Chiba, K.

Arch. Biochem. Biophys.

416

101-109

654037

-

Synthesis of poly-beta-hydroxybutyrate by Agrobacterium radiobacter after growth on D-carnitine

2002

Kluettermann, K.; Tauchert, H.; Kleber, H.P.

Acta Biotechnol.

22

261-269

739868

8060125

Crotonobetaine reductase from Escherichia coli - a new inducible enzyme of anaerobic metabolization of L(-)-carnitine

1994

Roth, S.; Jung, K.; Jung, H.; Hommel, R.; Kleber, H.

Antonie van Leeuwenhoek

65

63-69

740589

18266698

Role of betaine:CoA ligase (CaiC) in the activation of betaines and the transfer of coenzyme A in Escherichia coli

2008

Bernal, V.; Arense, P.; Blatz, V.; Mandrand-Berthelot, M.A.; Canovas, M.; Iborra, J.L.

J. Appl. Microbiol.

105

42-50

744480

8000862

L-carnitine via enzyme-catalyzed oxidative kinetic resolution

1994

Ditullio, D.; Anderson, D.; Chen, C.S.; Sih, C.J.

Bioorg. Med. Chem.

2

415-420

745953

25030770

Comparison of the substrate selectivity and biochemical properties of human and bacterial gamma-butyrobetaine hydroxylase

2014

Rydzik, A.M.; Leung, I.K.; Kochan, G.T.; Loik, N.D.; Henry, L.; McDonough, M.A.; Claridge, T.D.; Schofield, C.J.

Org. Biomol. Chem.

12

6354-6358

Links to other databases for D-carnitine

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ChEBI

PubChem