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Ligand 2,5-dihydroxypyridine

Basic Ligand Information

Molecular Structure

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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

1.13.11.9

2,5-dihydroxypyridine + O2 + H2O = maleamate + formate

392543, 396334

7cn3, 3D-view

1.13.11.9

2,5-dihydroxypyridine + O2 = N-formylmaleamic acid

710759, 742294, 764843, 765451, 763873, 700940

7cn3, 3D-view

1.13.11.9

2 entries

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

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Show Natural Product (3 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.14.13.114

6-hydroxynicotinate + NADH + H+ + O2 = 2,5-dihydroxypyridine + NAD+ + H2O + CO2

0

-

1.14.13.163

4-(6-hydroxypyridin-3-yl)-4-oxobutanoate + 2 NADH + 2 H+ + O2 = 2,5-dihydroxypyridine + succinate semialdehyde + 2 NAD+ + H2O

0

-

1.14.99.26

2-hydroxypyridine + NADH + O2 = 2,5-dihydroxypyridine + NAD+ + H2O

0

-

Substrate in Enzyme-catalyzed Reactions (2 results)

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Show Substrate (2 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.13.11.9

2,5-dihydroxypyridine + O2 + H2O = maleamate + formate

392543, 396333, 396336, 396334, 396335

7cn3, 3D-view

1.13.11.9

2,5-dihydroxypyridine + O2 = N-formylmaleamic acid

710759, 742294, 764843, 765451, 763873, 700940

7cn3, 3D-view

1.13.11.9

2 entries

Product in Enzyme-catalyzed Reactions (4 results)

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Show Product (4 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.14.13.114

6-hydroxynicotinate + NADH + H+ + O2 = 2,5-dihydroxypyridine + NAD+ + H2O + CO2

0

-

1.14.13.163

4-(6-hydroxypyridin-3-yl)-4-oxobutanoate + 2 NADH + 2 H+ + O2 = 2,5-dihydroxypyridine + succinate semialdehyde + 2 NAD+ + H2O

0

-

1.14.13.163

6-hydroxy-3-succinoylpyridine + 2 NADH + 2 H+ + O2 = 2,5-dihydroxypyridine + succinate semialdehyde + 2 NAD+ + H2O

0

-

1.14.13.163

2 entries

1.14.99.26

2-hydroxypyridine + NADH + O2 = 2,5-dihydroxypyridine + NAD+ + H2O

0

-

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

1.13.11.9

7cn3, 3D-view

Enzyme Kinetic Parameters

K_M Value (2 results)

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Show KM Value (2 entries)

EC NUMBER

KM VALUE [MM]

KM VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

1.13.11.9

0.07

-

25°C

700940

1.13.11.9

0.07

-

pH 8.0, 25°C, strict substrate specificity

700940

1.13.11.9

2 entries

References & Links

Literature References (11)

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Show Reference (11 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

392543

13475371

The bacterial oxidation of nicotinic acid

1957

Behrman, E.J.; Stanier, R.Y.

J. Biol. Chem.

228

923-945

396333

-

Nonheme iron dioxygenase

1974

Nozaki, M.

Mol. Mech. Oxygen Activ. (Hayaishi, O., ed.) Academic Press, New York

-

135-165

396334

5578917

The metabolism of nicotinic acid. I. Purification and properties of 2,5-dihydroxypyridine oxygenase from Pseudomonas putida N-9

1971

Gauthier, J.J.; Rittenberg, S.C.

J. Biol. Chem.

246

3737-3742

396335

4342498

The bacterial oxidation of picolinamide, a photolytic product of Diquat

1972

Orpin, C.G.; Knight, M.; Evans, W.C.

Biochem. J.

127

819-831

396336

4455192

Microbial metabolism of the pyridine ring. Metabolism of 2- and 3-hydroxypyridines by the maleamate pathway in Achromobacter sp

1974

Cain, R.B.; Houghton, C.; Wright, K.A.

Biochem. J.

140

293-300

700940

18678916

Deciphering the genetic determinants for aerobic nicotinic acid degradation: The nic cluster from Pseudomonas putida KT2440

2008

Jimenez, J.; Canales, A.; Jimenez-Barbero, J.; Ginalski, K.; Rychlewski, L.; Garcia, J.; Diaz, E.

Proc. Natl. Acad. Sci. USA

105

11329-11334

710759

20445257

A preliminary crystallographic study of recombinant NicX, an Fe2+-dependent 2,5-dihydroxypyridine dioxygenase from Pseudomonas putida KT2440

2010

Jimenez, J.I.; Acebron, I.; Garcia, J.L.; Diaz, E.; Mancheno, J.M.

Acta Crystallogr. Sect. F

66

549-553

742294

-

Isolation and characterization of novel pyridine dicarboxylic acid-degrading microorganisms

2016

Kutanovas, S.; Karvelis, L.; Vaitekunas, J.; Stankeviciute, J.; Gasparaviciute, R.; Meskys, R.

Chemija

27

74-83

763873

31102032

Isolation of a 3-hydroxypyridine degrading bacterium, Agrobacterium sp. DW-1, and its proposed degradation pathway

2019

Zhao, S.; Hu, C.; Guo, L.; Li, K.; Yu, H.

AMB Express

9

65

764843

35060702

Mechanistic insights into pyridine ring degradation catalyzed by 2,5-dihydroxypyridine dioxygenase NicX

2022

Wei, J.; Wang, Y.; Li, X.; Zhang, X.; Liu, Y.

Inorg. Chem.

61

2517-2529

765451

33637718

Structure-guided insights into heterocyclic ring-cleavage catalysis of the non-heme Fe (II) dioxygenase NicX

2021

Liu, G.; Zhao, Y.L.; He, F.; Zhang, P.; Ouyang, X.; Tang, H.; Xu, P.

Nat. Commun.

12

1301

Links to other databases for 2,5-dihydroxypyridine

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Show Links (1 entry)

ChEBI

PubChem