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Ligand 5-methyl-L-tryptophan

Basic Ligand Information

Molecular Structure

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Roles as Enzyme Ligand

Substrate in Enzyme-catalyzed Reactions (11 results)

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Show Substrate (11 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.13.11.52

5-methyl-tryptophan + O2 = 4-(2-amino-5-methylphenyl)-2-(formylamino)-4-oxobutanoic acid

685239

-

1.13.11.52

5-methyltryptophan + O2 = ?

696151

-

1.13.11.52

2 entries

1.13.12.3

5-methyltryptophan + O2 = 5-methylindole-3-acetamide + CO2 + H2O

439342

-

1.14.16.4

5-methyltryptophan + 6-methyltetrahydropterin + O2 = 5-hydroxymethyltryptophan + 5-hydroxy-4-methyltryptophan + 6-methyldihydropterin + H2O

438674

-

1.14.19.9

5-methyl-L-tryptophan + FADH2 + chloride + O2 + H+ = 7-chloro-5-methyl-L-tryptophan + FAD + 2 H2O

744712

-

2.1.1.106

S-adenosyl-L-methionine + L-5-methyl-tryptophan = S-adenosyl-L-homocysteine + L-2,5-dimethyltryptophan

757761

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2.5.1.34

dimethylallyl diphosphate + 5-methyl-L-tryptophan = diphosphate + 4-(3-methylbut-2-enyl)-5-methyl-L-tryptophan

687716

-

2.5.1.34

dimethylallyl diphosphate + 5-methyltryptophan = diphosphate + 4-(3-methylbut-2-enyl)-5-methyl-L-tryptophan

637459

-

2.5.1.34

2 entries

2.6.1.57

L-5-methyltryptophan + 2-oxoglutarate = 3-indole-2-oxopropanoate + L-glutamate

636665

-

4.1.99.1

5-methyl-L-Trp + H2O = ?

37356, 37363, 37349

-

6.1.1.2

ATP + 5-methyltryptophan + tRNATrp = AMP + diphosphate + 5-methyltryptophyl-tRNATrp

691148

-

Product in Enzyme-catalyzed Reactions (4 results)

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Show Product (4 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

4.1.99.1

5-methylindole + L-Cys = 5-methyl-L-Trp + ?

0

-

4.1.99.1

5-methylindole + S-methyl-L-Cys = 5-methyl-L-Trp + ?

0

-

4.2.1.20

L-serine + 5-methylindole = 5-methyl-L-tryptophan + H2O

0

-

4.2.1.20

L-serine + 5-methylindole = 5-methyltryptophan + H2O

0

-

4.1.99.1

2 entries

4.2.1.20

2 entries

Inhibitor in Enzyme-catalyzed Reactions (5 results)

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Show Inhibitors (5 entries)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

2.4.2.18

0.32 mM

638680

-

4.1.3.27

79% inhibition at 0.05 mM

682452

-

4.1.3.27

less effective inhibitor than 4-methylindole or 7-methyl-DL-tryptophan

682362

-

4.1.3.27

2 entries

4.2.1.51

-

33885

-

6.1.1.2

ATP-diphosphate exchange, weak

299

-

3D Structure of Enzyme-Ligand-Complex (PDB) (1 result)

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Show 3D Structure of Enzyme-Ligand-Complex (PDB) (1 entry)

EC NUMBER

ENZYME 3D STRUCTURE

1.4.3.23

6fw8, 3D-view

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

1.13.11.52

3.78

-

-

685239

K_M Value (3 results)

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Show KM Value (3 entries)

EC NUMBER

KM VALUE [MM]

KM VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

1.13.11.52

0.098

-

-

685239

2.6.1.57

1.2

-

-

636665

4.1.99.1

1.8

-

alpha,beta-elimination

37352

References & Links

Literature References (19)

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Show Reference (19 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

299

-

Tryptophanyl-tRNA synthetase from beef pancreas

1979

Kisselev, L.L.; Favorova, O.O.; Kovaleva, G.K.

Methods Enzymol.

54

234-257

33885

-

Regulatory properties of prephenate dehydrogenase and prephenate dehydratase from Corynebacterium glutamicum

1974

Hagino, H.; Nakayama, K.

Agric. Biol. Chem.

38

2367-2376

37349

-

Purification, crystallization and properties of tryptophanase from Proteus rettgeri

1974

Yoshida, H.; Utagawa, T.; Kumagai, H.; Yamada, H.

Agric. Biol. Chem.

38

2065-2072

37352

-

Catalytic properties of tryptophanase from Proteus rettgeri

1974

Yoshida, H.; Kumagai, H.; Yamada, H.

Agric. Biol. Chem.

38

463-464

37356

4698211

Catalytic studies on tryptophanase from Bacillus alvei

1973

O'Neill Hoch, S.; DeMoss, R.D.

J. Bacteriol.

114

341-350

37363

1368766

Purification and properties of thermostable tryptophanase from an obligately symbiotic thermophile, Symbiobacterium thermophilum

1991

Suzuki, S.; Hirahara, T.; Horinouchi, S.; Beppu, T.

Agric. Biol. Chem.

55

3059-3066

438674

10587452

Influence of steric bulk and electrostatics on the hHydroxylation regiospecificity of tryptophan hydroxylase: characterization of methyltryptophans and azatryptophans as substrates

1999

Moran, G.R.; Phillips, R.S.; Fitzpatrick, P.F.

Biochemistry

38

16283-16289

439342

7204339

Involvement of plasmid deoxyribonucleic acid in indoleacetic acid synthesis in Pseudomonas savastanoi

1980

Comai, L.; Kosuge, T.

J. Bacteriol.

143

950-957

636665

8868238

Purification and properties of aromatic amino acid aminotransferases from Azospirillum brasilense UAP 14 strain

1996

Soto-Urzua, L.; Xochinua-Corona, Y.G.; Flores-Encarnacion, M.; Baca, B.E.

Can. J. Microbiol.

42

294-298

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

638680

8534114

Mutations in the trpD gene of Corynebacterium glutamicum confer 5-methyltryptophan resistance by encoding a feedback-resistant anthranilate phosphoribosyltransferase

1995

O'Gara, J.P.; Dunican, L.K.

Appl. Environ. Microbiol.

61

4477-4479

682362

18060408

Use of 4-methylindole or 7-methyl-DL-tryptophan in a transformant selection system based on the feedback-insensitive anthranilate synthase alpha-subunit of tobacco (ASA2)

2008

Barone, P.; Widholm, J.M.

Plant Cell Rep.

27

509-517

682452

100105581

Accumulation of free tryptophan in azuki bean (Vigna angularis) induced by expression of a gene (OASA1D) for a modified ?-subunit of rice anthranilate synthase

2006

Hanafy, M.S.; Rahman, S.M.; Khalafalla, M.M.; El-Shemy, H.A.; Nakamoto, Y.; Ishimoto, M.; Wakasa, K.

Plant Sci.

171

670-676

685239

18370401

A kinetic, spectroscopic, and redox study of human tryptophan 2,3-dioxygenase

2008

Basran, J.; Rafice, S.A.; Chauhan, N.; Efimov, I.; Cheesman, M.R.; Ghamsari, L.; Raven, E.L.

Biochemistry

47

4752-4760

687716

18390548

Molecular analysis of a 4-dimethylallyltryptophan synthase from Malbranchea aurantiaca

2008

Ding, Y.; Williams, R.M.; Sherman, D.H.

J. Biol. Chem.

283

16068-16076

691148

18713004

Docking of tryptophanyl [corrected tryptophan] analogs to trytophanyl-tRNA synthetase: implications for non-canonical amino acid incorporations

2008

Azim, M.K.; Budisa, N.

Biol. Chem.

389

1173-1182

696151

19290871

Oxidation of L-tryptophan in biology: a comparison between tryptophan 2,3-dioxygenase and indoleamine 2,3-dioxygenase

2009

Rafice, S.A.; Chauhan, N.; Efimov, I.; Basran, J.; Raven, E.L.

Biochem. Soc. Trans.

37

408-412

744712

-

Regioselective enzymatic halogenation of substituted tryptophan derivatives using the FAD-dependent halogenase RebH

2014

Frese, M.; Guzowska, P.; Voss, H.; Sewald, N.

ChemCatChem

6

1270-1276

757761

26456915

The thiostrepton A tryptophan methyltransferase TsrM catalyses a cob(II)alamin-dependent methyl transfer reaction

2015

Benjdia, A.; Pierre, S.; Gherasim, C.; Guillot, A.; Carmona, M.; Amara, P.; Banerjee, R.; Berteau, O.

Nat. Commun.

6

8377

Links to other databases for 5-methyl-L-tryptophan

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ChEBI

PubChem