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Literature summary extracted from

  • Kopecny, D.; Briozzo, P.; Popelkova, H.; Sebela, M.; Koncitikova, R.; Spichal, L.; Nisler, J.; Madzak, C.; Frebort, I.; Laloue, M.; Houba-Herin, N.
    Phenyl- and benzylurea cytokinins as competitive inhibitors of cytokinin oxidase/dehydrogenase: a structural study (2010), Biochimie, 92, 1052-1062.
    View publication on PubMed

Cloned(Commentary)

EC Number Cloned (Comment) Organism
1.5.99.12 expressed in Yarrowia lipolytica Zea mays

Crystallization (Commentary)

EC Number Crystallization (Comment) Organism
1.5.99.12 wild type and L492A mutant enzymes, hanging drop vapor diffusion method Zea mays

Protein Variants

EC Number Protein Variants Comment Organism
1.5.99.12 E381A the mutation mimics the active site composition of naturally occurring isozymes CKO4/6 and CKO2/3 Zea mays
1.5.99.12 E381S the mutation mimics the active site composition of naturally occurring isozymes CKO4/6 and CKO2/3 Zea mays
1.5.99.12 L492A the mutant retains an unchanged pattern of selectivity to variously substituted ureas but it is much more susceptible to the inhibition by phenylureas as IC50 values are 10-50times lower than those for wild type enzyme Zea mays

Inhibitors

EC Number Inhibitors Comment Organism Structure
1.5.99.12 (2,6-dichloro-pyridin-4-yl)-carbamic acid benzyl ester
-
 Zea mays
1.5.99.12 (2-chloro-pyridin-4-yl)-carbamic acid 4-chloro-phenyl ester
-
 Zea mays
1.5.99.12 1-(2-chloro-1-oxidopyridin-4-yl)-3-phenylurea
-
 Zea mays
1.5.99.12 1-imidazo[1,2-a]pyridin-7-yl-3-phenylurea
-
 Zea mays
1.5.99.12 N-(1,2,3-thidiazol-5-yl)-N'-phenylurea
-
 Zea mays
1.5.99.12 N-(2,6-dichloro-pyridin-4-yl)-N'-benzylurea
-
 Zea mays
1.5.99.12 N-(2,6-dichloro-pyridin-4-yl)-N'-phenoxyurea
-
 Zea mays
1.5.99.12 N-(2,6-dichloro-pyridin-4-yl)-N'-phenylurea
-
 Zea mays
1.5.99.12 N-(2,6-dichloropyridin-4-yl)-N'-benzyl-N'-methylurea
-
 Zea mays
1.5.99.12 N-(2-amino-6-chloro-pyridin-4-yl)-N'-benzylurea
-
 Zea mays
1.5.99.12 N-(2-amino-6-chloro-pyridin-4-yl)-N'-phenylurea one of the most potent inhibitors of CKO Zea mays
1.5.99.12 N-(2-amino-pyridin-4-yl)-N'-phenylurea one of the most potent inhibitors of CKO Zea mays
1.5.99.12 N-(2-chloro-6-methoxy-pyridin-4-yl)-N'-benzylurea
-
 Zea mays
1.5.99.12 N-(2-chloro-pyridin-4-yl)-N'-benzylurea
-
 Zea mays
1.5.99.12 N-(2-chloro-pyridin-4-yl)-N'-phenylurea the compound binds in a planar conformation and competes for the same binding site with natural substrates Zea mays

KM Value [mM]

EC Number KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
1.5.99.12 0.0011
-
 N6-(2-isopentenyl)adenine wild type enzyme, pH and temperature not specified in the publication Zea mays
1.5.99.12 0.003
-
 N6-(2-isopentenyl)adenine mutant enzyme E381A, pH and temperature not specified in the publication Zea mays
1.5.99.12 0.0032
-
 N6-(2-isopentenyl)adenine mutant enzyme E381S, pH and temperature not specified in the publication Zea mays

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
1.5.99.12 N6-(2-isopentenyl)adenine + FAD + H2O Zea mays
-
 adenine + 3-methylbut-2-enal + FADH2
-
 ir
1.5.99.12 zeatin + FAD + H2O Zea mays
-
 adenine + 4-hydroxy-3-methylbut-2-enal + FADH2
-
 ir

Organism

EC Number Organism UniProt Comment Textmining
1.5.99.12 Zea mays Q9T0N8
-
-

Purification (Commentary)

EC Number Purification (Comment) Organism
1.5.99.12
-
 Zea mays

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
1.5.99.12 N6-(2-isopentenyl)adenine + 2,6-dichlorophenolindophenol + H2O
-
 Zea mays adenine + 3-methylbut-2-enal + reduced 2,6-dichlorophenolindophenol
-
 ?
1.5.99.12 N6-(2-isopentenyl)adenine + FAD + H2O
-
 Zea mays adenine + 3-methylbut-2-enal + FADH2
-
 ir
1.5.99.12 zeatin + FAD + H2O
-
 Zea mays adenine + 4-hydroxy-3-methylbut-2-enal + FADH2
-
 ir

Synonyms

EC Number Synonyms Comment Organism
1.5.99.12 CKO1
-
 Zea mays
1.5.99.12 cytokinin oxidase/dehydrogenase
-
 Zea mays

Cofactor

EC Number Cofactor Comment Organism Structure
1.5.99.12 FAD
-
 Zea mays

IC50 Value

EC Number IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
1.5.99.12 0.00004
-
 mutant enzyme L492A, pH and temperature not specified in the publication Zea mays N-(2-amino-pyridin-4-yl)-N'-phenylurea
1.5.99.12 0.00004
-
 mutant enzyme L492A, pH and temperature not specified in the publication Zea mays N-(2-amino-6-chloro-pyridin-4-yl)-N'-phenylurea
1.5.99.12 0.00008
-
 mutant enzyme L492A, pH and temperature not specified in the publication Zea mays N-(2,6-dichloro-pyridin-4-yl)-N'-phenylurea
1.5.99.12 0.0001
-
 mutant enzyme L492A, pH and temperature not specified in the publication Zea mays 1-imidazo[1,2-a]pyridin-7-yl-3-phenylurea
1.5.99.12 0.0002
-
 mutant enzyme L492A, pH and temperature not specified in the publication Zea mays (2-chloro-pyridin-4-yl)-carbamic acid 4-chloro-phenyl ester
1.5.99.12 0.0004
-
 mutant enzyme E381A, pH and temperature not specified in the publication Zea mays 1-imidazo[1,2-a]pyridin-7-yl-3-phenylurea
1.5.99.12 0.0004
-
 mutant enzyme E381A, pH and temperature not specified in the publication Zea mays N-(2,6-dichloro-pyridin-4-yl)-N'-phenylurea
1.5.99.12 0.0005
-
 mutant enzyme E381S, pH and temperature not specified in the publication Zea mays N-(2,6-dichloro-pyridin-4-yl)-N'-phenylurea
1.5.99.12 0.0006
-
 mutant enzyme E381A, pH and temperature not specified in the publication Zea mays N-(2-amino-6-chloro-pyridin-4-yl)-N'-phenylurea
1.5.99.12 0.0007
-
 mutant enzyme E381S, pH and temperature not specified in the publication Zea mays N-(2-amino-6-chloro-pyridin-4-yl)-N'-phenylurea
1.5.99.12 0.001
-
 mutant enzyme E381S, pH and temperature not specified in the publication Zea mays 1-imidazo[1,2-a]pyridin-7-yl-3-phenylurea
1.5.99.12 0.0011
-
 mutant enzyme E381A, pH and temperature not specified in the publication Zea mays N-(2,6-dichloropyridin-4-yl)-N'-benzyl-N'-methylurea
1.5.99.12 0.0015
-
 mutant enzyme L492A, pH and temperature not specified in the publication Zea mays N-(2-chloro-pyridin-4-yl)-N'-benzylurea
1.5.99.12 0.0015
-
 mutant enzyme L492A, pH and temperature not specified in the publication Zea mays N-(2,6-dichloropyridin-4-yl)-N'-benzyl-N'-methylurea
1.5.99.12 0.0018
-
 wild type enzyme, pH and temperature not specified in the publication Zea mays N-(2-amino-6-chloro-pyridin-4-yl)-N'-phenylurea
1.5.99.12 0.002
-
 mutant enzyme E381S, pH and temperature not specified in the publication Zea mays N-(2,6-dichloropyridin-4-yl)-N'-benzyl-N'-methylurea
1.5.99.12 0.002
-
 mutant enzyme L492A, pH and temperature not specified in the publication Zea mays N-(2,6-dichloro-pyridin-4-yl)-N'-benzylurea
1.5.99.12 0.002
-
 wild type enzyme, pH and temperature not specified in the publication Zea mays N-(2-amino-pyridin-4-yl)-N'-phenylurea
1.5.99.12 0.002
-
 wild type enzyme, pH and temperature not specified in the publication Zea mays N-(2,6-dichloropyridin-4-yl)-N'-benzyl-N'-methylurea
1.5.99.12 0.003
-
 mutant enzyme E381A, pH and temperature not specified in the publication Zea mays N-(2-chloro-pyridin-4-yl)-N'-benzylurea
1.5.99.12 0.003
-
 mutant enzyme E381A, pH and temperature not specified in the publication Zea mays N-(2,6-dichloro-pyridin-4-yl)-N'-benzylurea
1.5.99.12 0.004
-
 mutant enzyme E381A, pH and temperature not specified in the publication Zea mays (2,6-dichloro-pyridin-4-yl)-carbamic acid benzyl ester
1.5.99.12 0.004
-
 mutant enzyme E381S, pH and temperature not specified in the publication Zea mays N-(2-chloro-pyridin-4-yl)-N'-benzylurea
1.5.99.12 0.004
-
 mutant enzyme E381S, pH and temperature not specified in the publication Zea mays N-(2,6-dichloro-pyridin-4-yl)-N'-benzylurea
1.5.99.12 0.0045
-
 wild type enzyme, pH and temperature not specified in the publication Zea mays N-(2,6-dichloro-pyridin-4-yl)-N'-phenylurea
1.5.99.12 0.005
-
 mutant enzyme E381A, pH and temperature not specified in the publication Zea mays N-(2,6-dichloro-pyridin-4-yl)-N'-phenoxyurea
1.5.99.12 0.005
-
 mutant enzyme L492A, pH and temperature not specified in the publication Zea mays N-(1,2,3-thidiazol-5-yl)-N'-phenylurea
1.5.99.12 0.005
-
 mutant enzyme L492A, pH and temperature not specified in the publication Zea mays 1-(2-chloro-1-oxidopyridin-4-yl)-3-phenylurea
1.5.99.12 0.005
-
 mutant enzyme L492A, pH and temperature not specified in the publication Zea mays N-(2,6-dichloro-pyridin-4-yl)-N'-phenoxyurea
1.5.99.12 0.006
-
 mutant enzyme E381A, pH and temperature not specified in the publication Zea mays (2-chloro-pyridin-4-yl)-carbamic acid 4-chloro-phenyl ester
1.5.99.12 0.006
-
 mutant enzyme E381S, pH and temperature not specified in the publication Zea mays (2-chloro-pyridin-4-yl)-carbamic acid 4-chloro-phenyl ester
1.5.99.12 0.006
-
 mutant enzyme L492A, pH and temperature not specified in the publication Zea mays N-(2-amino-6-chloro-pyridin-4-yl)-N'-benzylurea
1.5.99.12 0.006
-
 mutant enzyme L492A, pH and temperature not specified in the publication Zea mays N-(2-chloro-6-methoxy-pyridin-4-yl)-N'-benzylurea
1.5.99.12 0.006
-
 wild type enzyme, pH and temperature not specified in the publication Zea mays 1-imidazo[1,2-a]pyridin-7-yl-3-phenylurea
1.5.99.12 0.007
-
 mutant enzyme E381S, pH and temperature not specified in the publication Zea mays (2,6-dichloro-pyridin-4-yl)-carbamic acid benzyl ester
1.5.99.12 0.007
-
 mutant enzyme L492A, pH and temperature not specified in the publication Zea mays (2,6-dichloro-pyridin-4-yl)-carbamic acid benzyl ester
1.5.99.12 0.008
-
 mutant enzyme E381S, pH and temperature not specified in the publication Zea mays N-(2,6-dichloro-pyridin-4-yl)-N'-phenoxyurea
1.5.99.12 0.009
-
 wild type enzyme, pH and temperature not specified in the publication Zea mays N-(2,6-dichloro-pyridin-4-yl)-N'-benzylurea
1.5.99.12 0.009
-
 wild type enzyme, pH and temperature not specified in the publication Zea mays (2,6-dichloro-pyridin-4-yl)-carbamic acid benzyl ester
1.5.99.12 0.015
-
 mutant enzyme E381A, pH and temperature not specified in the publication Zea mays N-(1,2,3-thidiazol-5-yl)-N'-phenylurea
1.5.99.12 0.015
-
 mutant enzyme E381A, pH and temperature not specified in the publication Zea mays 1-(2-chloro-1-oxidopyridin-4-yl)-3-phenylurea
1.5.99.12 0.015
-
 mutant enzyme E381A, pH and temperature not specified in the publication Zea mays N-(2-chloro-6-methoxy-pyridin-4-yl)-N'-benzylurea
1.5.99.12 0.017
-
 mutant enzyme E381S, pH and temperature not specified in the publication Zea mays N-(1,2,3-thidiazol-5-yl)-N'-phenylurea
1.5.99.12 0.017
-
 mutant enzyme E381S, pH and temperature not specified in the publication Zea mays 1-(2-chloro-1-oxidopyridin-4-yl)-3-phenylurea
1.5.99.12 0.018
-
 wild type enzyme, pH and temperature not specified in the publication Zea mays N-(2-chloro-pyridin-4-yl)-N'-benzylurea
1.5.99.12 0.02
-
 mutant enzyme E381S, pH and temperature not specified in the publication Zea mays N-(2-chloro-6-methoxy-pyridin-4-yl)-N'-benzylurea
1.5.99.12 0.02
-
 wild type enzyme, pH and temperature not specified in the publication Zea mays N-(2,6-dichloro-pyridin-4-yl)-N'-phenoxyurea
1.5.99.12 0.022
-
 wild type enzyme, pH and temperature not specified in the publication Zea mays N-(2-amino-6-chloro-pyridin-4-yl)-N'-benzylurea
1.5.99.12 0.022
-
 wild type enzyme, pH and temperature not specified in the publication Zea mays N-(2-chloro-6-methoxy-pyridin-4-yl)-N'-benzylurea
1.5.99.12 0.024
-
 mutant enzyme E381A, pH and temperature not specified in the publication Zea mays N-(2-amino-6-chloro-pyridin-4-yl)-N'-benzylurea
1.5.99.12 0.032
-
 mutant enzyme E381A, pH and temperature not specified in the publication Zea mays N-(2-amino-pyridin-4-yl)-N'-phenylurea
1.5.99.12 0.032
-
 mutant enzyme E381S, pH and temperature not specified in the publication Zea mays N-(2-amino-6-chloro-pyridin-4-yl)-N'-benzylurea
1.5.99.12 0.035
-
 mutant enzyme E381S, pH and temperature not specified in the publication Zea mays N-(2-amino-pyridin-4-yl)-N'-phenylurea
1.5.99.12 0.035
-
 mutant enzyme L492A, pH and temperature not specified in the publication Zea mays N-(2-chloro-pyridin-4-yl)-N'-phenylurea
1.5.99.12 0.039
-
 wild type enzyme, pH and temperature not specified in the publication Zea mays (2-chloro-pyridin-4-yl)-carbamic acid 4-chloro-phenyl ester
1.5.99.12 0.042
-
 wild type enzyme, pH and temperature not specified in the publication Zea mays N-(2-chloro-pyridin-4-yl)-N'-phenylurea
1.5.99.12 0.045
-
 mutant enzyme E381A, pH and temperature not specified in the publication Zea mays N-(2-chloro-pyridin-4-yl)-N'-phenylurea
1.5.99.12 0.05
-
 wild type enzyme, pH and temperature not specified in the publication Zea mays N-(1,2,3-thidiazol-5-yl)-N'-phenylurea
1.5.99.12 0.055
-
 mutant enzyme E381S, pH and temperature not specified in the publication Zea mays N-(2-chloro-pyridin-4-yl)-N'-phenylurea
1.5.99.12 0.13
-
 wild type enzyme, pH and temperature not specified in the publication Zea mays 1-(2-chloro-1-oxidopyridin-4-yl)-3-phenylurea

General Information

EC Number General Information Comment Organism
1.5.99.12 physiological function cytokinin oxidase/dehydrogenase irreversibly degrades the plant hormones cytokinins and thereby participates in their homeostasis Zea mays