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Ligand (E)-4-(trimethylammonio)but-2-enoyl-CoA

Basic Ligand Information

Molecular Structure

Show all BRENDA pathways known for (E)-4-(trimethylammonio)but-2-enoyl-CoA

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Roles as Enzyme Ligand

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

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Show Natural Substrate (3 entries)

EC NUMBER

LITERATURE

REACTION DIAGRAM

PROVEN IN VIVO REACTION

ENZYME 3D STRUCTURE

1.3.8.13

724139

crotonobetainyl-CoA + reduced electron-transfer flavoprotein = gamma-butyrobetainyl-CoA + electron-transfer flavoprotein

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4.2.1.149

724139

(E)-4-(trimethylammonio)but-2-enoyl-CoA + H2O = L-carnitinyl-CoA

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4.2.1.149

726932

crotonobetainyl-CoA + H2O = L-carnitinyl-CoA

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4.2.1.149

2 entries

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

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Show Natural Product (2 entries)

EC NUMBER

LITERATURE

REACTION DIAGRAM

PROVEN IN VIVO REACTION

ENZYME 3D STRUCTURE

4.2.1.149

-

L-carnitinyl-CoA = (E)-4-(trimethylammonio)but-2-enoyl-CoA + H2O

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4.2.1.149

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L-carnitinyl-CoA = crotonobetainyl-CoA + H2O

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4.2.1.149

2 entries

Substrate in Enzyme-catalyzed Reactions (6 results)

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Show Substrate (6 entries)

EC NUMBER

LITERATURE

REACTION DIAGRAM

REACTION

ENZYME 3D STRUCTURE

1.3.8.13

740036, 724139

crotonobetainyl-CoA + reduced benzylviologen = gamma-butyrobetainyl-CoA + oxidized benzylviologen

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1.3.8.13

724139

crotonobetainyl-CoA + reduced electron-transfer flavoprotein = gamma-butyrobetainyl-CoA + electron-transfer flavoprotein

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2.8.3.21

724265, 726830

(E)-4-(trimethylammonio)but-2-enoyl-CoA + L-carnitine = (E)-4-(trimethylammonio)but-2-enoate + L-carnitinyl-CoA

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2.8.3.21

726932, 724139

crotonobetainyl-CoA + L-carnitine = crotonobetaine + L-carnitinyl-CoA

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4.2.1.149

724139

(E)-4-(trimethylammonio)but-2-enoyl-CoA + H2O = L-carnitinyl-CoA

-

4.2.1.149

726932

crotonobetainyl-CoA + H2O = L-carnitinyl-CoA

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1.3.8.13

2 entries

2.8.3.21

2 entries

4.2.1.149

2 entries

Product in Enzyme-catalyzed Reactions (4 results)

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Show Product (4 entries)

EC NUMBER

LITERATURE

REACTION DIAGRAM

REACTION

ENZYME 3D STRUCTURE

1.3.8.13

-

gamma-butyrobetainyl-CoA + electron-transfer flavoprotein = crotonobetainyl-CoA + reduced electron-transfer flavoprotein

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4.2.1.149

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L-carnitinyl-CoA = (E)-4-(trimethylammonio)but-2-enoyl-CoA + H2O

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4.2.1.149

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L-carnitinyl-CoA = crotonobetainyl-CoA + H2O

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4.2.1.149

2 entries

6.2.1.48

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ATP + crotonobetaine + CoA = AMP + diphosphate + crotonobetainyl-CoA

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Enzyme Kinetic Parameters

K_M Value (2 results)

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Show KM Value (2 entries)

COMMENTARY

EC NUMBER

KM VALUE [MM]

KM VALUE MAXIMUM [MM]

LITERATURE

37°C, pH 7.5

4.2.1.149

0.043

-

724139

at pH 7.5 and 37°C

4.2.1.149

0.012

-

726932

References & Links

Literature References (5)

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Show Reference (5 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

724139

15731894

Identification and functional characterisation of genes and corresponding enzymes involved in carnitine metabolism of Proteus sp.

2005

Engemann, C.; Elssner, T.; Pfeifer, S.; Krumbholz, C.; Maier, T.; Kleber, H.P.

Arch. Microbiol.

183

176-189

724265

15518548

Crystal structure of CaiB, a type-III CoA transferase in carnitine metabolism

2004

Stenmark, P.; Gurmu, D.; Nordlund, P.

Biochemistry

43

13996-14003

726830

11409545

Biotransformation of crotonobetaine to L(-)-carnitine in Proteus sp.

2001

Engemann, C.; Elssner, T.; Kleber, H.P.

Arch. Microbiol.

175

353-359

726932

11551212

Involvement of coenzyme A esters and two new enzymes, an enoyl-CoA hydratase and a CoA-transferase, in the hydration of crotonobetaine to L-carnitine by Escherichia coli

2001

Elssner, T.; Engemann, C.; Baumgart, K.; Kleber, H.P.

Biochemistry

40

11140-11148

740036

10978161

Isolation, identification, and synthesis of gamma-butyrobetainyl-CoA and crotonobetainyl-CoA, compounds involved in carnitine metabolism of E. coli

2000

Elssner, T.; Hennig, L.; Frauendorf, H.; Haferburg, D.; Kleber, H.P.

Biochemistry

39

10761-10769

Links to other databases for (E)-4-(trimethylammonio)but-2-enoyl-CoA

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Show Links (1 entry)

ChEBI

PubChem

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