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Ligand 4-dimethylallyl-L-tryptophan

Basic Ligand Information

Molecular Structure

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Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (1 result)

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Show Natural Substrate (1 entry)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

2.1.1.261

S-adenosyl-L-methionine + 4-dimethylallyl-L-tryptophan = S-adenosyl-L-homocysteine + 4-dimethylallyl-L-abrine

736294, 719849, 737281

-

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

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Show Natural Product (2 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

2.5.1.34

dimethylallyl diphosphate + L-tryptophan = diphosphate + 4-(3-methylbut-2-enyl)-L-tryptophan

0

-

2.5.1.34

dimethylallyl diphosphate + L-tryptophan = diphosphate + L-4-(gamma,gamma-dimethylallyl)tryptophan

0

-

2.5.1.34

2 entries

Substrate in Enzyme-catalyzed Reactions (1 result)

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Show Substrate (1 entry)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

2.1.1.261

S-adenosyl-L-methionine + 4-dimethylallyl-L-tryptophan = S-adenosyl-L-homocysteine + 4-dimethylallyl-L-abrine

736294, 719849, 737281

-

Product in Enzyme-catalyzed Reactions (5 results)

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Show Product (5 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

2.5.1.34

dimethylallyl diphosphate + L-Trp = diphosphate + 4-(3-methylbut-2-enyl)-L-Trp

0

-

2.5.1.34

dimethylallyl diphosphate + L-tryptophan = diphosphate + 4-(3-methylbut-2-enyl)-L-tryptophan

0

-

2.5.1.34

dimethylallyl diphosphate + L-tryptophan = diphosphate + 4-dimethylallyl-L-tryptophan

0

-

2.5.1.34

dimethylallyl diphosphate + L-tryptophan = diphosphate + L-4-(3-methylbut-2-enyl)-tryptophan

0

-

2.5.1.34

dimethylallyl diphosphate + L-tryptophan = diphosphate + L-4-(gamma,gamma-dimethylallyl)tryptophan

637462, 0, 637459

-

2.5.1.34

5 entries

Inhibitor in Enzyme-catalyzed Reactions (1 result)

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Show Inhibitors (1 entry)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

2.5.1.34

product inhibition, competitive to dimethylallyl diphosphate, noncompetitive to L-tryptophan

637459

-

Enzyme Kinetic Parameters

k_cat Value (Turnover Number) (1 result)

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Show Turnover Number (1 entry)

EC NUMBER

TURNOVER NUMBER [1/S]

TURNOVER NUMBER MAXIMUM [1/S]

COMMENTARY

LITERATURE

2.1.1.261

2

-

pH 7.5, 37°C, recombinant enzyme

719849

K_M Value (1 result)

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Show KM Value (1 entry)

EC NUMBER

KM VALUE [MM]

KM VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

2.1.1.261

0.12

-

pH 7.5, 37°C, recombinant enzyme

719849

References & Links

Literature References (5)

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Show Reference (5 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

637459

999297

Purification and properties of dimethylallylpyrophosphate:tryptophan dimethylallyl transferase, the first enzyme of ergot alkaloid biosynthesis in Claviceps. sp. SD 58

1976

Lee, S.L.; Floss, H.G.; Heinstein, P.

Arch. Biochem. Biophys.

177

84-94

637462

1605639

Purification and characterization of dimethylallyl tryptophan synthase from Claviceps purpurea

1992

Gebler, J.C.; Poulter, C.D.

Arch. Biochem. Biophys.

296

308-313

719849

18678866

Ergot alkaloid biosynthesis in Aspergillus fumigatus. Overproduction and biochemical characterization of a 4-dimethylallyltryptophan N-methyltransferase

2008

Rigbers, O.; Li, S.M.

J. Biol. Chem.

283

26859-26868

736294

25491167

Identification and structural elucidation of ergotryptamine, a new ergot alkaloid produced by genetically modified Aspergillus nidulans and natural isolates of Epichloe species

2015

Ryan, K.L.; Akhmedov, N.G.; Panaccione, D.G.

J. Agric. Food Chem.

63

61-67

737281

23435153

Partial reconstruction of the ergot alkaloid pathway by heterologous gene expression in Aspergillus nidulans

2013

Ryan, K.L.; Moore, C.T.; Panaccione, D.G.

Toxins

5

445-455

Links to other databases for 4-dimethylallyl-L-tryptophan

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Show Links (1 entry)

ChEBI

PubChem