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Ligand 5-guanidino-2-oxopentanoate

Basic Ligand Information

Molecular Structure

Pathway Source

Pathways

BRENDA

arginine metabolism

KEGG

Arginine and proline metabolism, D-Amino acid metabolism

MetaCyc

3-methylarginine biosynthesis, D-arginine degradation, L-arginine degradation IX (arginine:pyruvate transaminase pathway), L-arginine degradation VIII (arginine oxidase pathway), L-arginine degradation XI, L-arginine degradation XII more

Show all BRENDA pathways known for 5-guanidino-2-oxopentanoate

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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

2.1.1.243

S-adenosyl-L-methionine + 5-guanidino-2-oxopentanoate = S-adenosyl-L-homocysteine + 5-guanidino-3-methyl-2-oxopentanoate

717120

-

4.1.1.75

5-Guanidino-2-oxopentanoate = ?

288074, 4829

-

In Vivo Product in Enzyme-catalyzed Reactions (10 results)

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Show Natural Product (10 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.4.3.14

L-arginine + O2 + H2O = 5-carbamidamido-2-oxopentanoate + NH3 + H2O2

0

-

1.4.3.2

L-Arg + H2O + O2 = 2-oxo-5-guanidinopentanoic acid + NH3 + H2O2

0

-

1.4.3.2

L-arginine + H2O + O2 = 2-oxo-5-guanidinopentanoic acid + NH3 + H2O2

0

-

1.4.3.2

L-Arg + H2O + O2 = 2-oxo-5-guanidinovaleric acid + NH3 + H2O2

0

-

1.4.3.2

L-Arg + H2O + O2 = 5-guanidino-2-oxopentanoic acid + NH3 + H2O2

0

-

1.4.3.2

4 entries

1.4.3.25

L-arginine + H2O + O2 = 5-guanidino-2-oxopentanoate + NH3 + H2O2

0

-

1.4.3.3

D-Arg + H2O + O2 = 5-guanidino-2-oxopentanoate + NH3 + H2O2

0

-

1.4.3.3

D-Arg + H2O + O2 = 5-guanidino-2-oxopentanoic acid + NH3 + H2O2

0

-

1.4.3.3

D-arginine + H2O + O2 = 5-guanidino-2-oxopentanoic acid + NH3 + H2O2

0

-

1.4.3.3

3 entries

2.6.1.84

L-arginine + pyruvate = 5-guanidino-2-oxopentanoate + L-alanine

0

-

Substrate in Enzyme-catalyzed Reactions (5 results)

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Show Substrate (5 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.4.1.25

5-guanidino-2-oxopentanoate + NH3 + NAD(P)H + H+ = L-arginine + H2O + NAD(P)+

706547

-

2.1.1.243

S-adenosyl-L-methionine + 5-guanidino-2-oxopentanoate = S-adenosyl-L-homocysteine + 5-guanidino-3-methyl-2-oxopentanoate

717120

-

2.6.1.9

L-histidinol phosphate + 2-oxo-5-guanidinopentanoate = 3-(imidazol-4-yl)-2-oxopropyl phosphate + L-arginine

637142

-

4.1.1.75

5-Guanidino-2-oxopentanoate = 4-Guanidinobutyraldehyde + CO2

669134, 4829, 288074

-

4.1.1.75

5-Guanidino-2-oxopentanoate = ?

288074, 4829

-

4.1.1.75

2 entries

Product in Enzyme-catalyzed Reactions (35 results)

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Show Product (35 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.13.12.2

L-arginine + phenazine methosulfate = 2-keto-5-guanidinovalerate + NH3 + reduced phenazine methosulfate

440265

-

1.4.1.25

L-arginine + H2O + NAD(P)+ = 5-guanidino-2-oxopentanoate + NH3 + NAD(P)H + H+

0

-

1.4.3.14

L-arginine + O2 + H2O = 5-carbamidamido-2-oxopentanoate + NH3 + H2O2

0

-

1.4.3.14

L-arginine + O2 + H2O = 5-guanidino-2-oxopentanoate + NH3 + H2O2

391746, 391748, 391751, 391749, 0

-

1.4.3.2

L-arginine + H2O + O2 = 2-oxo-5-guanidinopentanoate + NH3 + H2O2

0

-

1.4.3.2

L-Arg + H2O + O2 = 2-oxo-5-guanidinopentanoic acid + NH3 + H2O2

0

-

1.4.3.2

L-arginine + H2O + O2 = 2-oxo-5-guanidinopentanoic acid + NH3 + H2O2

0

-

1.4.3.2

L-Arg + H2O + O2 = 2-oxo-5-guanidinovaleric acid + NH3 + H2O2

0

-

1.4.3.2

L-arginine + H2O + O2 = 2-oxo-5-guanidinovaleric acid + NH3 + H2O2

0, 651026

-

1.4.3.2

L-Arg + H2O + O2 = 5-carbamidamido-2-oxopentanoate + NH3 + H2O2

0

-

1.4.3.2

L-arginine + H2O + O2 = 5-carbamidamido-2-oxopentanoate + NH3 + H2O2

0

-

1.4.3.2

L-arginine + H2O + O2 = 5-guanidino-2-oxopentanoate + NH3 + H2O2

0

-

1.4.3.2

L-Arg + H2O + O2 = 5-guanidino-2-oxopentanoic acid + NH3 + H2O2

0

-

1.4.3.14

2 entries

1.4.3.2

9 entries

1.4.3.25

L-arginine + H2O + O2 = 5-guanidino-2-oxopentanoate + NH3 + H2O2

0

-

1.4.3.3

D-Arg + H2O + O2 = 5-guanidino-2-oxopentanoate + NH3 + H2O2

0

-

1.4.3.3

D-arginine + H2O + O2 = 5-guanidino-2-oxopentanoate + NH3 + H2O2

0

-

1.4.3.3

D-Arg + H2O + O2 = 5-guanidino-2-oxopentanoic acid + NH3 + H2O2

0

-

1.4.3.3

D-arginine + H2O + O2 = 5-guanidino-2-oxopentanoic acid + NH3 + H2O2

0

-

1.4.5.1

D-arginine + oxidized 2,6-dichlorophenolindophenol + H2O = 2-oxo-5-guanidinopentanoate + NH3 + reduced 2,6-dichlorophenolindophenol

0

-

1.4.5.1

D-arginine + oxidized acceptor + H2O = 2-oxo-5-guanidinopentanoate + NH3 + reduced acceptor

0

-

1.4.99.6

D-arginine + H2O + FAD = 5-guanidino-2-oxopentanoate + NH3 + FADH2

0

-

1.4.99.6

D-arginine + H2O + iodonitrotetrazolium chloride = 5-guanidino-2-oxopentanoate + NH3 + reduced iodonitrotetrazolium chloride

0

-

1.4.99.6

D-arginine + phenazine methosulfate + H2O = 5-guanidino-2-oxopentanoate + NH3 + reduced phenazine methosulfate

0

-

1.4.99.6

D-arginine + phenazine methosulfate = 5-guanidino-2-oxopentanoate + NH3 + reduced phenazine methosulfate

0

-

1.4.3.3

4 entries

1.4.5.1

2 entries

1.4.99.6

4 entries

1.4.99.B3

L-arginine + H2O + 2 cytochrome b = 2-oxo-5-guanidinopentanoic acid + NH3 + 2 reduced cytochrome b

0

-

1.5.99.13

D-arginine + oxidized 2,6-dichloroindophenol + H2O = 2-oxo-5-guanidinopentanoate + NH3 + reduced 2,6-dichloroindophenol

0

-

2.6.1.40

arginine + pyruvate = 2-oxo-5-guanidinovaleric acid + L-alanine

0

-

2.6.1.42

L-arginine + 2-oxoglutarate = 2-oxo-5-guanidinopentanoate + L-glutamate

0

-

2.6.1.43

L-arginine + 4,5-dioxopentanoate = 5-aminolevulinate + 5-guanidino-2-oxopentanoate

0

-

2.6.1.44

L-arginine + pyruvate = 5-guanidino-2-oxopentanoate + L-alanine

0

-

2.6.1.51

arginine + pyruvate = 5-guanidino-2-oxopentanoate + L-alanine

0

-

2.6.1.64

L-arginine + pyruvate = 5-guanidino-2-oxopentanoate + L-alanine

0

-

2.6.1.84

L-arginine + pyruvate = 5-guanidino-2-oxopentanoate + L-alanine

0

-

2.6.1.9

3-(imidazol-4-yl)-2-oxopropyl phosphate + L-arginine = L-histidinol phosphate + 2-oxo-5-guanidinopentanoate

0

-

4.4.1.14

L-arginine + pyridoxal 5'-phosphate = 2-oxo-5-guanidinopentanoate + pyridoxamine 5'-phosphate

649945

-

Activator in Enzyme-catalyzed Reactions (1 result)

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Show Activating Compound (1 entry)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

4.1.1.12

activates

3955

-

Inhibitor in Enzyme-catalyzed Reactions (1 result)

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Show Inhibitors (1 entry)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

3.5.3.1

-

172127

-

3D Structure of Enzyme-Ligand-Complex (PDB) (3 results)

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

EC NUMBER

ENZYME 3D STRUCTURE

1.1.1.79

6p35, 3D-view

1.1.1.81

6p35, 3D-view

1.14.11.41

6mp9, 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

4.1.1.75

167

-

-

288074

References & Links

Literature References (15)

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Show Reference (15 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

3955

4950473

L-Aspartate-beta-decarboxylase. Structure, catalytic activities, and allosteric regulation

1971

Tate, S.S.; Meister, A.

Adv. Enzymol. Relat. Areas Mol. Biol.

35

503-543

4829

1194237

Physiological consequences of starvation in Pseudomonas putida: degradation of intracellular protein and loss of activity of the inducible enzymes of L-arginine catabolism

1975

Fan, C.L.; Rodwell, V.W.

J. Bacteriol.

124

1302-1311

172127

2029528

Characterization of arginase from the extreme thermophile Bacillus caldovelox

1991

Patchett, M.L.; Daniel, R.M.; Morgan, H.W.

Biochim. Biophys. Acta

1077

291-298

288074

237915

Intermediates and enzymes between alpha-ketoarginine and gamma-guanidinobutyrate in the L-arginine catabolic pathway of Pseudomonas putida

1975

Vanderbilt, A.S.; Gaby, N.S.; Rodwell, V.W.

J. Biol. Chem.

250

5322-5329

391746

6101334

A new antitumor enzyme, L-lysine alpha-oxidase from Trichoderma viride. Purification and enzymological properties

1980

Kusakabe, H.; Kodama, K.; Kuninaka, A.; Yoshino, H.; Misono, H.; Soda, K.

J. Biol. Chem.

255

976-981

391748

-

Occurence of a novel enzyme, L-lysine oxidase with antitumor activity in culture of Trichoderma viride

1979

Kusakabe, H.; Kodama, K.; Machida, H.; Midorikawa, Y.; Kuninaka, A.; Misono, H.; Soda, K.

Agric. Biol. Chem.

43

337-343

391749

-

Purification and characterization of L-lysine oxidase from Trichoderma pseudokonigii and its effect on growth of mouse erythroleukemia cells

1994

Hu, H.M.; Cheng, S.W.; Huang, M.C.; Tang, S.J.; Chang, M.C.; Tsai, Y.C.

Zhongguo Nongye Huaxue Huizhi

32

361-371

391751

-

L-Lysine alpha-oxidase from Trichoderma viride i4. Purification and characterization

1994

Weber, E.; Tonder, K.; Reinbothe, C.; Unverhau, K.; Weide, H.; Aurich, H.

J. Basic Microbiol.

34

265-276

440265

818961

A dehydrogenase reaction catalyzed by lysine monooxygenase, a flavooxygenase

1976

Maruyama, K.; Yamauchi, T.; Yamamoto, S.; Hayaishi, O.

Arch. Biochem. Biophys.

173

480-489

637142

13319331

Biosynthesis of histidine: imidazoleacetol phosphate transaminase

1956

Ames, B.N.; Horecker, B.L.

J. Biol. Chem.

220

113-128

649945

11106504

Aminotransferase activity and bioinformatic analysis of 1-aminocyclopropane-1-carboxylate synthase

2000

Feng, L.; Geck, M.K.; Eliot, A.C.; Kirsch, J.F.

Biochemistry

39

15242-15249

651026

-

A new bacterial L-amino acid oxidase with a broad substrate specificity: purification and characterization

2002

Geueke, B.; Hummel, W.

Enzyme Microb. Technol.

31

77-87

669134

17416670

Functional genomics enables identification of genes of the arginine transaminase pathway in Pseudomonas aeruginosa

2007

Yang, Z.; Lu, C.D.

J. Bacteriol.

189

3945-3953

706547

19139398

Arginine racemization by coupled catabolic and anabolic dehydrogenases

2009

Li, C.; Lu, C.D.

Proc. Natl. Acad. Sci. USA

106

906-911

717120

20190091

Identification of the biosynthetic gene cluster for 3-methylarginine, a toxin produced by Pseudomonas syringae pv. syringae 22d/93

2010

Braun, S.D.; Hofmann, J.; Wensing, A.; Ullrich, M.S.; Weingart, H.; Voelksch, B.; Spiteller, D.

Appl. Environ. Microbiol.

76

2500-2508

Links to other databases for 5-guanidino-2-oxopentanoate

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Show Links (1 entry)

ChEBI

PubChem