Literature summary for 1.5.99.12 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.

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Cloned(Commentary)

Cloned (Comment)	Organism
expressed in Yarrowia lipolytica	Zea mays

Crystallization (Commentary)

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

Protein Variants

Protein Variants	Comment	Organism
E381A	the mutation mimics the active site composition of naturally occurring isozymes CKO4/6 and CKO2/3	Zea mays
E381S	the mutation mimics the active site composition of naturally occurring isozymes CKO4/6 and CKO2/3	Zea mays
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

Inhibitors	Comment	Organism
(2,6-dichloro-pyridin-4-yl)-carbamic acid benzyl ester	-	Zea mays
(2-chloro-pyridin-4-yl)-carbamic acid 4-chloro-phenyl ester	-	Zea mays
1-(2-chloro-1-oxidopyridin-4-yl)-3-phenylurea	-	Zea mays
1-imidazo[1,2-a]pyridin-7-yl-3-phenylurea	-	Zea mays
N-(1,2,3-thidiazol-5-yl)-N'-phenylurea	-	Zea mays
N-(2,6-dichloro-pyridin-4-yl)-N'-benzylurea	-	Zea mays
N-(2,6-dichloro-pyridin-4-yl)-N'-phenoxyurea	-	Zea mays
N-(2,6-dichloro-pyridin-4-yl)-N'-phenylurea	-	Zea mays
N-(2,6-dichloropyridin-4-yl)-N'-benzyl-N'-methylurea	-	Zea mays
N-(2-amino-6-chloro-pyridin-4-yl)-N'-benzylurea	-	Zea mays
N-(2-amino-6-chloro-pyridin-4-yl)-N'-phenylurea	one of the most potent inhibitors of CKO	Zea mays
N-(2-amino-pyridin-4-yl)-N'-phenylurea	one of the most potent inhibitors of CKO	Zea mays
N-(2-chloro-6-methoxy-pyridin-4-yl)-N'-benzylurea	-	Zea mays
N-(2-chloro-pyridin-4-yl)-N'-benzylurea	-	Zea mays
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]

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

Natural Substrates/ Products (Substrates)

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

Organism

Organism	UniProt	Comment	Textmining
Zea mays	Q9T0N8	-	-

Purification (Commentary)

Purification (Comment)	Organism
-	Zea mays

Substrates and Products (Substrate)

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

Synonyms

Synonyms	Comment	Organism
CKO1	-	Zea mays
cytokinin oxidase/dehydrogenase	-	Zea mays

Cofactor

Cofactor	Comment	Organism	Structure
FAD	-	Zea mays

IC50 Value

IC50 Value	IC50 Value Maximum	Comment	Organism	Inhibitor
0.00004	-	mutant enzyme L492A, pH and temperature not specified in the publication	Zea mays	N-(2-amino-pyridin-4-yl)-N'-phenylurea
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
0.00008	-	mutant enzyme L492A, pH and temperature not specified in the publication	Zea mays	N-(2,6-dichloro-pyridin-4-yl)-N'-phenylurea
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
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
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
0.0004	-	mutant enzyme E381A, pH and temperature not specified in the publication	Zea mays	N-(2,6-dichloro-pyridin-4-yl)-N'-phenylurea
0.0005	-	mutant enzyme E381S, pH and temperature not specified in the publication	Zea mays	N-(2,6-dichloro-pyridin-4-yl)-N'-phenylurea
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
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
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
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
0.0015	-	mutant enzyme L492A, pH and temperature not specified in the publication	Zea mays	N-(2-chloro-pyridin-4-yl)-N'-benzylurea
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
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
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
0.002	-	mutant enzyme L492A, pH and temperature not specified in the publication	Zea mays	N-(2,6-dichloro-pyridin-4-yl)-N'-benzylurea
0.002	-	wild type enzyme, pH and temperature not specified in the publication	Zea mays	N-(2-amino-pyridin-4-yl)-N'-phenylurea
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
0.003	-	mutant enzyme E381A, pH and temperature not specified in the publication	Zea mays	N-(2-chloro-pyridin-4-yl)-N'-benzylurea
0.003	-	mutant enzyme E381A, pH and temperature not specified in the publication	Zea mays	N-(2,6-dichloro-pyridin-4-yl)-N'-benzylurea
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
0.004	-	mutant enzyme E381S, pH and temperature not specified in the publication	Zea mays	N-(2-chloro-pyridin-4-yl)-N'-benzylurea
0.004	-	mutant enzyme E381S, pH and temperature not specified in the publication	Zea mays	N-(2,6-dichloro-pyridin-4-yl)-N'-benzylurea
0.0045	-	wild type enzyme, pH and temperature not specified in the publication	Zea mays	N-(2,6-dichloro-pyridin-4-yl)-N'-phenylurea
0.005	-	mutant enzyme E381A, pH and temperature not specified in the publication	Zea mays	N-(2,6-dichloro-pyridin-4-yl)-N'-phenoxyurea
0.005	-	mutant enzyme L492A, pH and temperature not specified in the publication	Zea mays	N-(1,2,3-thidiazol-5-yl)-N'-phenylurea
0.005	-	mutant enzyme L492A, pH and temperature not specified in the publication	Zea mays	1-(2-chloro-1-oxidopyridin-4-yl)-3-phenylurea
0.005	-	mutant enzyme L492A, pH and temperature not specified in the publication	Zea mays	N-(2,6-dichloro-pyridin-4-yl)-N'-phenoxyurea
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
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
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
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
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
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
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
0.008	-	mutant enzyme E381S, pH and temperature not specified in the publication	Zea mays	N-(2,6-dichloro-pyridin-4-yl)-N'-phenoxyurea
0.009	-	wild type enzyme, pH and temperature not specified in the publication	Zea mays	N-(2,6-dichloro-pyridin-4-yl)-N'-benzylurea
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
0.015	-	mutant enzyme E381A, pH and temperature not specified in the publication	Zea mays	N-(1,2,3-thidiazol-5-yl)-N'-phenylurea
0.015	-	mutant enzyme E381A, pH and temperature not specified in the publication	Zea mays	1-(2-chloro-1-oxidopyridin-4-yl)-3-phenylurea
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
0.017	-	mutant enzyme E381S, pH and temperature not specified in the publication	Zea mays	N-(1,2,3-thidiazol-5-yl)-N'-phenylurea
0.017	-	mutant enzyme E381S, pH and temperature not specified in the publication	Zea mays	1-(2-chloro-1-oxidopyridin-4-yl)-3-phenylurea
0.018	-	wild type enzyme, pH and temperature not specified in the publication	Zea mays	N-(2-chloro-pyridin-4-yl)-N'-benzylurea
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
0.02	-	wild type enzyme, pH and temperature not specified in the publication	Zea mays	N-(2,6-dichloro-pyridin-4-yl)-N'-phenoxyurea
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
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
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
0.032	-	mutant enzyme E381A, pH and temperature not specified in the publication	Zea mays	N-(2-amino-pyridin-4-yl)-N'-phenylurea
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
0.035	-	mutant enzyme E381S, pH and temperature not specified in the publication	Zea mays	N-(2-amino-pyridin-4-yl)-N'-phenylurea
0.035	-	mutant enzyme L492A, pH and temperature not specified in the publication	Zea mays	N-(2-chloro-pyridin-4-yl)-N'-phenylurea
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
0.042	-	wild type enzyme, pH and temperature not specified in the publication	Zea mays	N-(2-chloro-pyridin-4-yl)-N'-phenylurea
0.045	-	mutant enzyme E381A, pH and temperature not specified in the publication	Zea mays	N-(2-chloro-pyridin-4-yl)-N'-phenylurea
0.05	-	wild type enzyme, pH and temperature not specified in the publication	Zea mays	N-(1,2,3-thidiazol-5-yl)-N'-phenylurea
0.055	-	mutant enzyme E381S, pH and temperature not specified in the publication	Zea mays	N-(2-chloro-pyridin-4-yl)-N'-phenylurea
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

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