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Information on EC 1.5.99.12 - cytokinin dehydrogenase
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1.5.99.12 cytokinin dehydrogenaseIUBMB Comments
A flavoprotein (FAD). Catalyses the oxidation of cytokinins, a family of N6-substituted adenine derivatives that are plant hormones, where the substituent is a prenyl group. Although this activity was previously thought to be catalysed by a hydrogen-peroxide-forming oxidase, this enzyme does not require oxygen for activity and does not form hydrogen peroxide. 2,6-Dichloroindophenol, methylene blue, nitroblue tetrazolium, phenazine methosulfate and copper(II) in the presence of imidazole can act as acceptors. This enzyme plays a part in regulating rice-grain production, with lower levels of the enzyme resulting in enhanced grain production .
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Word Map
- 1.5.99.12
- trans-zeatin
- riboside
- cis-zeatin
-
isopentenyltransferase
-
cytokinin-deficient
- agriculture
The expected taxonomic range for this enzyme is: Eukaryota, Bacteria
Reaction Schemes
Synonyms
cytokinin oxidase, cytokinin oxidase/dehydrogenase, cytokinin dehydrogenase, osckx2, hvckx1, zmckx1, zmcko1, atckx2, atckx7, atckx3, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
AtCKX2
CKO
CKX
CKX1
CKX2
CKX3
CKX5
CKX6
CKX7
CKX8
CKX9
cytokinin oxidase
cytokinin oxidase/dehydrogenase
isopentenyladenosine oxidase
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-
-
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N6-(D2-isopentenyl)adenosine oxidase
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-
-
-
N6-isopentenylaldenine oxidase
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-
-
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zeatin oxidase
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-
-
-
additional information
AtCKX2
-
seven distinct genes AtCKX1 to AtCKX7, AtCKX2 is subject of the study
cytokinin oxidase
-
-
-
-
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
N6-dimethylallyladenine + acceptor + H2O = adenine + 3-methylbut-2-enal + reduced acceptor
N6-dimethylallyladenine + acceptor + H2O = adenine + 3-methylbut-2-enal + reduced acceptor
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-
-
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N6-dimethylallyladenine + acceptor + H2O = adenine + 3-methylbut-2-enal + reduced acceptor
reaction might also be catalyzed by a different enzyme in Dictyostelium discoideum, since no related sequence has been found
-
N6-dimethylallyladenine + acceptor + H2O = adenine + 3-methylbut-2-enal + reduced acceptor
reaction scheme and mechanism, reduction of N6-(2-isopentenyl)adenine is rapidly performed, the reaction with O2 is slowly
N6-dimethylallyladenine + acceptor + H2O = adenine + 3-methylbut-2-enal + reduced acceptor
reaction scheme and mechanism, the substrate displays a plug-into-socket binding mode that seals the catalytic site and precisely positions the carbon atom undergoing oxidation in close contact with the reactive locus of the flavin, bipartite architecture of the catalytic centre, which consists of a funnel-shaped region on the protein surface and an internal cavity lined by the flavin ring, the 3 active site regions are connected by a pore of about 4 A diameter
N6-dimethylallyladenine + acceptor + H2O = adenine + 3-methylbut-2-enal + reduced acceptor
Asp162 and Glu275 involved in substrate binding
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
oxidation
-
-
-
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redox reaction
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-
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reduction
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-
-
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PATHWAY SOURCE
PATHWAYS
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SYSTEMATIC NAME
IUBMB Comments
N6-dimethylallyladenine:acceptor oxidoreductase
A flavoprotein (FAD). Catalyses the oxidation of cytokinins, a family of N6-substituted adenine derivatives that are plant hormones, where the substituent is a prenyl group. Although this activity was previously thought to be catalysed by a hydrogen-peroxide-forming oxidase, this enzyme does not require oxygen for activity and does not form hydrogen peroxide. 2,6-Dichloroindophenol, methylene blue, nitroblue tetrazolium, phenazine methosulfate and copper(II) in the presence of imidazole can act as acceptors. This enzyme plays a part in regulating rice-grain production, with lower levels of the enzyme resulting in enhanced grain production [2].
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CAS REGISTRY NUMBER
COMMENTARY
55326-39-1
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
cis-zeatin + electron acceptor
(2Z)-4-hydroxy-3-methylbut-2-enal + adenine + reduced electron acceptor
cytokinin + 2,3-dimethoxy-5-methyl-1,4-benzoquinone
? + reduced 2,3-dimethoxy-5-methyl-1,4-benzoquinone
-
-
-
?
cytokinin riboside + 2,3-dimethoxy-5-methyl-1,4-benzoquinone
? + reduced 2,3-dimethoxy-5-methyl-1,4-benzoquinone
-
-
-
?
isopentenyladenine + 2,6-dichlorophenolindophenol
adenine + 3-methylbut-2-enal + reduced 2,6-dichlorophenolindophenol
isopentenyladenine 9-glucoside + 2,6-dichlorophenolindophenol
adenine 9-glucoside + 3-methylbut-2-enal + reduced 2,6-dichlorophenolindophenol
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-
-
?
isopentenyladenosine + 2,6-dichlorophenolindophenol
adenosine + 3-methylbut-2-enal + reduced 2,6-dichlorophenolindophenol
-
-
-
?
isopentenyladenosine monophosphate + 2,6-dichlorophenolindophenol
adenosine monophosphate + 3-methylbut-2-enal + reduced 2,6-dichlorophenolindophenol
-
-
-
?
kinetin + 2,3-dimethoxy-5-methyl-1,4-benzoquinone + H2O
?
-
-
-
?
kinetin + electron acceptor
2-furaldehyde + adenine + reduced electron acceptor
-
-
-
-
?
kinetin riboside + 2,3-dimethoxy-5-methyl-1,4-benzoquinone + H2O
?
-
-
-
?
m-topolin + 2,3-dimethoxy-5-methyl-p-benzoquinone
?
-
very low activity
-
-
?
N-benzyladenine + electron acceptor
benzaldehyde + adenine + reduced electron acceptor
-
-
-
-
?
N6-(2-butynyl)adenine + 2,6-dichlorophenol indophenol
?
very effective electron acceptor
-
-
?
N6-(2-isopentenyl)adenine + 1,4-naphthoquinone
?
-
very effective electron acceptor
-
-
?
N6-(2-isopentenyl)adenine + 1,4-naphthoquinone
adenine + 3-methylbut-2-enal + reduced 1,4-naphthoquinone
-
-
-
?
N6-(2-isopentenyl)adenine + 2,2'-azino-bis-(3-ethylbenzothiazoline-6-sulfonic acid) radical + H2O
adenine + 3-methylbut-2-enal + ?
-
-
-
-
?
N6-(2-isopentenyl)adenine + 2,3-dimethoxy-5-methyl-1,4-benzoquinone
adenine + 3-methylbut-2-enal + reduced 2,3-dimethoxy-5-methyl-1,4-benzoquinone
i.e. coenzyme Q0
-
-
?
N6-(2-isopentenyl)adenine + 2,3-dimethoxy-5-methyl-1,4-benzoquinone + H2O
adenine + 3-methylbut-2-enal + 2,3-dimethoxy-5-methyl-1,4-benzoquinol
-
4-nitrosoresorcinol-1-monomethyl ether serves as a weak electron acceptor of CKX
-
-
?
N6-(2-isopentenyl)adenine + 2,3-dimethoxy-5-methyl-1,4-benzoquinone + H2O
adenine + 3-methylbut-2-enal + ?
-
-
-
?
N6-(2-isopentenyl)adenine + 2,6-dichlorophenolindophenol
adenine + 3-methylbut-2-enal + reduced 2,6-dichlorophenolindophenol
N6-(2-isopentenyl)adenine + 2,6-dichlorophenolindophenol + H2O
adenine + 3-methylbut-2-enal + reduced 2,6-dichlorophenolindophenol
N6-(2-isopentenyl)adenine + 4-nitrosoresorcinol-1-monomethyl ether + H2O
adenine + 3-methylbut-2-enal + reduced 4-nitrosoresorcinol-1-monomethyl ether
-
4-nitrosoresorcinol-1-monomethyl ether serves as a weak electron acceptor of CKX
-
-
?
N6-(2-isopentenyl)adenine + acceptor + H2O
?
-
preferred substrate of isozyme AtCKX4
-
-
?
N6-(2-isopentenyl)adenine + caffeic acid
adenine + 3-methylbut-2-enal + ?
-
-
-
?
N6-(2-isopentenyl)adenine + coenzyme Q1
adenine + 3-methylbut-2-enal + reduced coenzyme Q1
-
-
-
?
N6-(2-isopentenyl)adenine + cytochrome c
adenine + 3-methylbut-2-enal + reduced cytochrome c
-
-
-
?
N6-(2-isopentenyl)adenine + daphnoretin
adenine + 3-methylbut-2-enal + ?
-
-
-
?
N6-(2-isopentenyl)adenine + electron acceptor
adenine + 3-methylbut-2-enal + reduced electron acceptor
-
-
-
-
?
N6-(2-isopentenyl)adenine + FAD + H2O
adenine + 3-methylbut-2-enal + FADH2
-
-
-
ir
N6-(2-isopentenyl)adenine + hydroxamic acid 2,4-dihydroxy-7-methoxy-1,4-benzoxazin-one + H2O
adenine + 3-methylbut-2-enal + reduced hydroxamic acid 2,4-dihydroxy-7-methoxy-1,4-benzoxazin-one
-
CKX1 is able to use hydroxamic acid 2,4-dihydroxy-7-methoxy-1,4-benzoxazin-one as a poor electron acceptor at neutral pH levels, but not in acidic pH levels
-
-
?
N6-(2-isopentenyl)adenine + o-coumaric acid
adenine + 3-methylbut-2-enal + ?
-
-
-
?
N6-(2-isopentenyl)adenine + O2
adenine + 3-methylbut-2-enal + H2O2
oxidative degradation of cytokinins, slow reaction, low substrate specificity
-
-
?
N6-(2-isopentenyl)adenine + plantacyanine
adenine + 3-methylbut-2-enal + reduced plantacyanine
electron acceptor from spinach
-
-
?
N6-(2-isopentenyl)adenine + potassium ferricyanide
?
-
low activity
-
-
?
N6-(2-isopentenyl)adenine + rosmarinic acid
adenine + 3-methylbut-2-enal + ?
-
-
-
?
N6-(2-isopentenyl)adenine + scopoletin
adenine + 3-methylbut-2-enal + ?
-
-
-
?
N6-(2-isopentenyl)adenine + spinach plantacyanine
adenine + 3-methylbut-2-enal + reduced spinach plantacyanine
-
-
-
r
N6-(2-isopentenyl)adenine + vitamin K1
adenine + 3-methylbut-2-enal + reduced vitamin K1
-
-
-
?
N6-(2-isopentenyl)adenine + vitamin K3
adenine + 3-methylbut-2-enal + reduced vitamin K3
-
-
-
?
N6-(2-isopentenyl)adenine 9-beta-D-glucoside + 3',5'-dimethoxy-4'-hydroxyacetophenone + H2O
adenine 9-beta-D-glucoside + 3-methylbut-2-enal + ?
i.e. iP9G, best substrate for isozyme AtCKX1 at pH 5.0, 3',5'-dimethoxy-4-hydroxyacetophenone is the best acceptor
-
-
?
N6-(2-isopentenyl)adenine 9-beta-D-riboside + 2,3,5-triphenyl-tetrazolium chloride + H2O
adenine 9-beta-D-riboside + 3-methylbut-2-enal + ?
-
-
-
?
N6-(2-isopentenyl)adenine 9-beta-D-riboside + 2,3-dimethoxy-5-methyl-1,4-benzoquinone + H2O
adenine 9-beta-D-riboside + 3-methylbut-2-enal + ?
-
-
-
?
N6-(2-isopentenyl)adenine 9-beta-D-riboside + 3',5'-dimethoxy-4'-hydroxyacetophenone + H2O
adenine 9-beta-D-riboside + 3-methylbut-2-enal + ?
-
-
-
?
N6-(2-isopentenyl)adenine 9-beta-D-riboside + ferricyanide + H2O
adenine 9-beta-D-riboside + 3-methylbut-2-enal + ferrocyanide
-
-
-
?
N6-(2-isopentenyl)adenine 9-beta-D-riboside + ferricytochrome c + H2O
adenine 9-beta-D-riboside + 3-methylbut-2-enal + ferrocytochrome c
-
-
-
?
N6-(2-isopentenyl)adenine 9-beta-D-riboside + NAD+ + H2O
adenine 9-beta-D-riboside + 3-methylbut-2-enal + ?
-
-
-
?
N6-(2-isopentenyl)adenine 9-beta-D-riboside + O2 + H2O
adenine 9-beta-D-riboside + 3-methylbut-2-enal + ?
-
-
-
?
N6-(2-isopentenyl)adenine 9-beta-D-riboside + oxidized 2,6-dichlorophenolindophenol + H2O
adenine 9-beta-D-riboside + 3-methylbut-2-enal + reduced 2,6-dichlorophenolindophenol
-
-
-
?
N6-(2-isopentenyl)adenine 9-beta-D-riboside 5'-phosphate + 2,3-dimethoxy-5-methyl-1,4-benzoquinone + H2O
adenine 9-beta-D-riboside 5'-phosphate + 3-methylbut-2-enal + ?
-
-
-
?
N6-(2-isopentenyl)adenine 9-glucoside + 2,3-dimethoxy-5-methyl-p-benzoquinone
?
-
low activity
-
-
?
N6-(2-isopentenyl)adenine 9-riboside-5'-monophosphate + 2,3-dimethoxy-5-methyl-p-benzoquinone
?
-
low activity
-
-
?
N6-(2-isopentenyl)adenose + 2,6-dichlorophenolindophenol
adenosine + 3-methylbut-2-enal + reduced 2,6-dichlorophenolindophenol
-
-
-
-
?
N6-(2-isopentenyl)adenosine + 2,6-dichlorophenol indophenol
?
very effective electron acceptor
-
-
?
N6-(2-isopentenyl)adenosine + FAD
adenosine + 3-methylbut-2-enal + FADH2
-
-
-
?
N6-(4-hydroxy-2-butynyl)adenine + 2,6-dichlorophenol indophenol
?
very effective electron acceptor
-
-
?
N6-(DELTA2-isopentenyl)adenine + 2,3-dimetoxy-5-methyl-1,4-benzoquinone + H2O
?
-
-
-
?
N6-(DELTA2-isopentenyl)adenine + 2,6-dichlorophenolindophenol + H2O
adenine + 3-methylbut-2-enal + reduced 2,6-dichlorophenolindophenol
N6-(DELTA2-isopentenyl)adenine + 4-methylcatechol + H2O
adenine + 3-methylbut-2-enal + reduced 4-methylcatechol
-
-
-
?
N6-(DELTA2-isopentenyl)adenine + acceptor + H2O
adenine + 3-methylbut-2-enal + reduced acceptor
-
-
-
-
?
N6-(DELTA2-isopentenyl)adenine + acetosyringone + H2O
adenine + 3-methylbut-2-enal + reduced acetosyringone
-
-
-
?
N6-(DELTA2-isopentenyl)adenine + CuCl2 + H2O
adenine + 3-methyl-2-butenal + CuCl + Cl-
-
-
-
-
?
N6-(DELTA2-isopentenyl)adenine + guaiacol + H2O
adenine + 3-methylbut-2-enal + reduced guaiacol
-
-
-
?
N6-(DELTA2-isopentenyl)adenine-9-beta-D-glucoside + 2,6-dichlorophenolindophenol + H2O
?
-
-
-
?
N6-(DELTA2-isopentenyl)adenosine + 2,6-dichlorophenolindophenol + H2O
?
-
-
-
?
N6-(DELTA2-isopentenyl)adenosine + 2,6-dichlorophenolindophenol + H2O
adenosine + 3-methylbut-2-enal + reduced 2,6-dichlorophenolindophenol
artificial electron acceptor
-
-
?
N6-(DELTA2-isopentenyl)adenosine + 4-methylcatechol + H2O
adenosine + 3-methylbut-2-enal + reduced 4-methylcatechol
-
-
-
?
N6-(DELTA2-isopentenyl)adenosine + acetosyringone + H2O
adenosine + 3-methylbut-2-enal + reduced acetosyringone
-
-
-
?
N6-(DELTA2-isopentenyl)adenosine + guaiacol + H2O
adenosine + 3-methylbut-2-enal + reduced guaiacol
-
-
-
?
N6-(DELTA2-isopentenyl)adenosine-5'-monophosphate + 2,6-dichlorophenolindophenol + H2O
?
-
-
-
?
N6-dimethylallyladenine + 2,6-dichlorophenolindophenol
adenine + 3-methylbut-2-enal + reduced 2,6-dichlorophenolindophenol
-
i.e. isopentenyladenine, reaction via an imine intermediate
-
-
?
N6-dimethylallyladenine + FAD + H2O2
adenine + 3-methylbut-2-enal + FADH2 + O2
-
i.e. isopentenyladenine
-
-
?
N6-dimethylallyladenosine + FAD + H2O
adenosine + 3-methylbut-2-enal + FADH2
i.e. isopentenyladenosine
-
-
ir
N6-hexyladenine + electron acceptor
hexanal + adenine + reduced electron acceptor
-
-
-
-
?
N6-isopentenyl-2-(2-hydroxyethylamino)-9-methyladenine + electron acceptor
3-methyl-2-butenal + 2-hydroxyethylamino-9-methyladenine + reduced electron acceptor
-
-
-
-
?
N6-isopentenyl-2-methylthioadenine + electron acceptor
3-methyl-2-butenal + 2-methylthioadenine + reduced electron acceptor
-
-
-
-
?
N6-isopentenyladenine + 2,3-dimethoxy-5-methyl-1,4-benzoquinone
?
-
-
-
?
N6-isopentenyladenine + 2,6-dichlorophenolindophenol
adenine + 3-methyl-2-butenal + reduced 2,6-dichlorophenolindophenol
-
-
-
?
N6-isopentenyladenine + CuCl2
adenine + 3-methyl-2-butenal + reduced electron acceptor
-
-
-
?
N6-isopentenyladenine + dichlorophenolindophenol + H2O
adenine + 3-methylbut-2-enal + reduced dichlorophenolindophenol
-
-
-
?
N6-isopentenyladenine + electron acceptor
adenine + 3-methyl-2-butenal + reduced electron acceptor
N6-isopentenyladenine + oxidized 2,6-dichlorophenolindophenol
adenine + 3-methylbut-2-enol + reduced 2,6-dichlorophenolindophenol
N6-isopentenyladenine 9-beta-D-glucoside + oxidized 2,6-dichlorophenolindophenol
adenine 9-beta-D-glucoside + 3-methylbut-2-enol + reduced 2,6-dichlorophenolindophenol
-
-
-
?
N6-isopentenyladenine-9-beta-D-glucoside + 2,3-dimethoxy-5-methyl-1,4-benzoquinone
?
-
-
-
?
N6-isopentenyladenosine + 2,6-dichlorophenolindophenol
3-methylbut-2-enal + adenosine + reduced 2,6-dichlorophenolindophenol
-
-
-
?
N6-isopentenyladenosine + electron acceptor
3-methylbut-2-enal + adenosine + reduced electron acceptor
N6-isopentenyladenosine + oxidized 2,6-dichlorophenolindophenol
adenosine + 3-methylbut-2-enol + reduced 2,6-dichlorophenolindophenol
-
-
-
?
N6-methyl-isopentenyladenine + 2,3-dimethoxy-5-methyl-p-benzoquinone
?
-
very low activity
-
-
?
O-beta-D-glucosyl-trans-zeatin + oxidized 2,6-dichlorophenolindophenol
?
-
-
-
?
o-topolin + 2,3-dimethoxy-5-methyl-p-benzoquinone
?
-
very low activity
-
-
?
p-topolin + 2,3-dimethoxy-5-methyl-p-benzoquinone
?
-
very low activity
-
-
?
trans-zeatin + 2,3-dimethoxy-5-methyl-1,4-benzoquinone + H2O
?
-
-
-
?
trans-zeatin + 2,3-dimethoxy-5-methyl-p-benzoquinone
?
-
very effective substrate
-
-
?
trans-zeatin + 2,6-dichlorophenolindophenol
? + reduced 2,6-dichlorophenolindophenol
cis-zeatin is utilized only by some tissue-specific forms but not by HvCKX2
-
-
?
trans-zeatin + electron acceptor
(2E)-4-hydroxy-3-methylbut-2-enal + adenine + reduced electron acceptor
-
-
-
-
?
trans-zeatin 9-glucoside + 2,3-dimethoxy-5-methyl-p-benzoquinone
?
-
low activity
-
-
?
trans-zeatin 9-riboside + 2,3-dimethoxy-5-methyl-p-benzoquinone
?
-
very effective substrate
-
-
?
trans-zeatin O-glucoside + 2,6-dichlorophenolindophenol
? + reduced 2,6-dichlorophenolindophenol
-
-
-
?
trans-zeatin riboside + 2,6-dichlorophenolindophenol
? + reduced 2,6-dichlorophenolindophenol
-
-
-
?
trans-zeatin riboside + 2,6-dichlorophenolindophenol + H2O
?
most favorable substrate
-
-
?
trans-zeatin riboside O-glucoside + 2,6-dichlorophenolindophenol
? + reduced 2,6-dichlorophenolindophenol
-
-
-
?
trans-zeatin ribotide + 2,6-dichlorophenolindophenol
? + reduced 2,6-dichlorophenolindophenol
-
-
-
?
trans-zeatin-9-glucoside + 2,6-dichlorophenolindophenol
? + reduced 2,6-dichlorophenolindophenol
-
-
-
?
zeatin + 2,6-dichlorophenolindophenol
4-hydroxy-3-methylbut-2-enal + adenine + reduced 2,6-dichlorophenolindophenol
-
-
-
?
zeatin + electron acceptor
4-hydroxy-3-methylbut-2-enal + adenine + reduced electron acceptor
cis-zeatin + electron acceptor
(2Z)-4-hydroxy-3-methylbut-2-enal + adenine + reduced electron acceptor
-
-
-
-
?
cis-zeatin + electron acceptor
(2Z)-4-hydroxy-3-methylbut-2-enal + adenine + reduced electron acceptor
-
-
-
-
?