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Ligand 3-Hydroxy-2-methylpyridine-5-carboxylate

Basic Ligand Information

Molecular Structure

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Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (5 results)

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Show Natural Substrate (5 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.14.13.242

2-methyl-3-hydroxypyridine-5-carboxylic acid + NADH + O2 + H+ = 2-(acetamidomethylene)succinate + NAD+

742939

-

1.14.13.242

3-hydroxy-2-methylpyridine-5-carboxylate + NAD(P)H + H+ + O2 = 2-(acetamidomethylidene)succinate + NAD(P)+

763846

-

1.14.13.242

3-hydroxy-2-methylpyridine-5-carboxylate + NADH + H+ + O2 = 2-(acetamidomethylene)succinate + NAD+

742939

-

1.14.13.242

3-hydroxy-2-methylpyridine-5-carboxylate + NADH + O2 = 2-(acetamidomethylene)succinate + NAD+

439054, 439060

-

1.14.13.242

3-hydroxy-2-methylpyridine-5-carboxylate + NADPH + H+ + O2 = 2-(acetamidomethylene)succinate + NADP+

742494

-

1.14.13.242

5 entries

Substrate in Enzyme-catalyzed Reactions (10 results)

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Show Substrate (10 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.14.13.241

3-hydroxy-2-methylpyridine-5-carboxylic acid + NADH = 2-[(acetylamino)methylene]succinate + NAD+ + H2O

439055

-

1.14.13.242

2-methyl-3-hydroxypyridine-5-carboxylic acid + NADH + O2 + H+ = 2-(acetamidomethylene)succinate + NAD+

742939

-

1.14.13.242

3-hydroxy-2-methylpyridine-5-carboxylate + NAD(P)H + H+ + O2 = 2-(acetamidomethylene)succinate + NAD(P)+

654133, 654745

-

1.14.13.242

3-hydroxy-2-methylpyridine-5-carboxylate + NAD(P)H + H+ + O2 = 2-(acetamidomethylidene)succinate + NAD(P)+

763846

-

1.14.13.242

3-hydroxy-2-methylpyridine-5-carboxylate + NADH + H+ + O2 = 2-(acetamidomethylene)succinate + NAD+

742939

-

1.14.13.242

3-hydroxy-2-methylpyridine-5-carboxylate + NADH + H+ + O2 = 2-(acetamidomethylene)succinate + NAD+ + H2O

742939

-

1.14.13.242

3-hydroxy-2-methylpyridine-5-carboxylate + NADH + O2 + H+ = 2-(acetamidomethylene)succinate + NAD+

745404

-

1.14.13.242

3-hydroxy-2-methylpyridine-5-carboxylate + NADH + O2 = 2-(acetamidomethylene)succinate + NAD(P)+

439054, 439056, 439057, 439061, 439062, 439059, 439060

-

1.14.13.242

3-hydroxy-2-methylpyridine-5-carboxylate + NADH + O2 = 2-(acetamidomethylene)succinate + NAD+

439054, 439060

-

1.14.13.242

3-hydroxy-2-methylpyridine-5-carboxylate + NADPH + H+ + O2 = 2-(acetamidomethylene)succinate + NADP+

742494

-

1.14.13.242

9 entries

Product in Enzyme-catalyzed Reactions (1 result)

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Show Product (1 entry)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

4.1.1.51

3-Hydroxy-2-methylpyridine-4,5-dicarboxylate = 3-Hydroxy-2-methylpyridine-5-carboxylate + CO2

4700, 0

-

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

1.14.13.242

11.8

-

pH 8.0, 25°C

745404

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

1.14.13.242

0.0254

-

pH 8.0, 25°C

745404

References & Links

Literature References (15)

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Show Reference (15 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

4700

-

Die bakterielle Oxydation des Vitamin B6. Die enzymatische Decarboxylierung von 2-Methyl-3-hydroxy-pyridin-4,5-dicarbonsaeure

1964

Snell, E.E.; Smucker, A.A.; Ringelmann, E.; Lynen, F.

Biochem. Z.

341

109-119

439054

4306031

The bacterial oxidation of vitamin B6. VII. Purification, properties, and mechanism of action of an oxygenase which cleaves the 3-hydroxypyridine ring

1969

Sparrow, L.G.; Ho, P.P.K.; Sundaram, T.K.; Zach, D.; Nyns, E.J.; Snell, E.E.

J. Biol. Chem.

244

2590-2600

439055

3771566

Enzymes of vitamin B6 degradation. Purification and properties of 5-pyridoxic-acid oxygenase from Arthrobacter sp

1986

Nelson, M.J.K.; Snell, E.E.

J. Biol. Chem.

261

15115-15120

439056

7217081

Interaction of 2-methyl-3-hydroxypyridine-5-carboxylic acid oxygenase with FAD, substrates, and analogues. Spectral and fluorescence investigations

1981

Kishore, G.M.; Snell, E.E.

J. Biol. Chem.

256

4234-4240

439057

7217080

Kinetic investigations on a flavoprotein oxygenase, 2-methyl-3-hydroxypyridine-5-carboxylic acid oxygenase

1981

Kishore, G.M.; Snell, E.E.

J. Biol. Chem.

256

4228-4233

439059

9207074

Gene cloning, sequence analysis, and expression of 2-methyl-3-hydroxypyridine-5-carboxylic acid oxygenase

1997

Chaiyen, P.; Ballou, D.P.; Massey, V.

Proc. Natl. Acad. Sci. USA

94

7233-7238

439060

9374863

Reaction of 2-methyl-3-hydroxypyridine-5-carboxylic acid (MHPC) oxygenase with N-methyl-5-hydroxynicotinic acid: studies on the mode of binding, and Protonation Status of the Substrate

1997

Chaiyen, P.; Brissette, P.; Ballou, D.P.; Massey, V.

Biochemistry

36

13856-13864

439061

9201954

Unusual mechanism of oxygen atom transfer and product rearrangement in the catalytic reaction of 2-methyl-3-hydroxypyridine-5-carboxylic acid oxygenase

1997

Chaiyen, P.; Brissette, P.; Ballou, D.P.; Massey, V.

Biochemistry

36

8060-8070

439062

9054568

Thermodynamics and reduction kinetics properties of 2-methyl-3-hydroxypyridine-5-carboxylic acid oxygenase

1997

Chaiyen, P.; Brissette, P.; Ballou, D.P.; Massey, V.

Biochemistry

36

2612-2621

654133

16511028

Crystallization and preliminary x-ray crystallographic analysis of 2-methyl-3-hydroxypyridine-5-carboxylic acid (MHPC) oxygenase from Pseudomonas sp. MA-1

2005

Oonanant, W.; Sucharitakul, J.; Yuvaniyama, J.; Chaiyen, P.

Acta Crystallogr. Sect. F

61

312-314

654745

15049701

Use of 8-substituted-FAD analogues to investigate the hydroxylation mechanism of the flavoprotein 2-methyl-3-hydroxypyridine-5-carboxylic acid oxygenase

2004

Chaiyen, P.; Sucharitakul, J.; Svasti, J.; Entsch, B.; Massey, V.; Ballou, D.P.

Biochemistry

43

3933-3943

742494

25639849

Selectivity of substrate binding and ionization of 2-methyl-3-hydroxypyridine-5-carboxylic acid oxygenase

2015

Luanloet, T.; Sucharitakul, J.; Chaiyen, P.

FEBS J.

282

3107-3125

742939

27568368

Role of the Tyr270 residue in 2-methyl-3-hydroxypyridine-5-carboxylic acid oxygenase from Mesorhizobium loti

2017

Kobayashi, J.; Yoshida, H.; Yagi, T.; Kamitori, S.; Hayashi, H.; Mizutani, K.; Takahashi, N.; Mikami, B.

J. Biosci. Bioeng.

123

154-162

745404

17270714

Molecular cloning, identification and characterization of 2-methyl-3-hydroxypyridine-5-carboxylic-acid-dioxygenase-coding gene from the nitrogen-fixing symbiotic bacterium Mesorhizobium loti

2006

Yuan, B.; Yokochi, N.; Yoshikane, Y.; Ohnishi, K.; Yagi, T.

J. Biosci. Bioeng.

102

504-510

763846

31282871

Structural comparison of p-hydroxybenzoate hydroxylase (PobA) from Pseudomonas putida with PobA from other Pseudomonas spp. and other monooxygenases

2019

Lazar, J.T.; Shuvalova, L.; Rosas-Lemus, M.; Kiryukhina, O.; Satchell, K.J.F.; Minasov, G.

Acta Crystallogr. Sect. F

75

507-514

Links to other databases for 3-Hydroxy-2-methylpyridine-5-carboxylate

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Show Links (1 entry)

ChEBI

PubChem