Information on EC 1.17.3.4 - juglone 3-hydroxylase

for references in articles please use BRENDA:EC1.17.3.4
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The expected taxonomic range for this enzyme is: Pseudomonas putida

EC NUMBER
COMMENTARY hide
1.17.3.4
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RECOMMENDED NAME
GeneOntology No.
juglone 3-hydroxylase
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REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
2 juglone + 2 H2O = 2 naphthalene-1,2,4,8-tetrol
show the reaction diagram
(1a)
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2 juglone + O2 = 2 3,5-dihydroxy-1,4-naphthoquinone
show the reaction diagram
overall reaction
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2 naphthalene-1,2,4,8-tetrol + O2 = 2 3,5-dihydroxy-1,4-naphthoquinone + 2 H2O
show the reaction diagram
(1b)
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
hydroxylation
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oxidation
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redox reaction
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reduction
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
juglone degradation
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SYSTEMATIC NAME
IUBMB Comments
5-hydroxy-1,4-naphthoquinone,water:oxygen oxidoreductase (3-hydroxylating)
Even though oxygen is consumed, molecular oxygen is not incorporated into the product. Catalysis starts by incorporation of an oxygen atom from a water molecule into the substrate. The naphthalene-1,2,4,8-tetrol intermediate is then oxidized by molecular oxygen, which is reduced to water. Also acts on 1,4-naphthoquinone, naphthazarin and 2-chloro-1,4-naphthoquinone.
CAS REGISTRY NUMBER
COMMENTARY hide
98865-54-4
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
two isofunctional enzymes named enzyme 1, present in induced and non-induced cells and enzyme 2, present only in juglone-induced cells
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Manually annotated by BRENDA team
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
1,4-naphthoquinone + O2
2-hydroxy-1,4-naphthoquinone + H2O
show the reaction diagram
2-chloro-1,4-naphthoquinone + O2
2-chloro-3-hydroxy-1,4-naphthoquinone + H2O
show the reaction diagram
5,8-dihydroxy-1,4-naphthoquinone + O2
2,5,8-trihydroxy-1,4-naphthoquinone + H2O
show the reaction diagram
5-hydroxy-1,4-naphthoquinone + O2
3,5-dihydroxy-1,4-naphthoquinone + H2O
show the reaction diagram
5-hydroxy-2-methyl-1,4-naphthoquinone + O2
3,5-dihydroxy-2-methyl-1,4-naphthoquinone + H2O
show the reaction diagram
additional information
?
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hydroxyl substituent at C-5 is indispensable for induction of juglone hydroxylase
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NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
5-hydroxy-1,4-naphthoquinone + O2
3,5-dihydroxy-1,4-naphthoquinone + H2O
show the reaction diagram
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Fe
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0.39 atoms per subunit for enzyme 1, 0.04 atoms per subunit for enzyme 2
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
3,3'-dithiobis(6-nitrobenzoate)
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weak inhibition
HgCl2
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at 0.5 mM complete inhibition of enzyme 1 and enzyme 2
p-chloromercuribenzoate
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complete inhibition of enzyme 1 and enzyme 2
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0042 - 0.0185
5-hydroxy-1,4-naphthoquinone
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7.5 - 8.5
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enzyme 1 and enzyme 2
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
23500
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2 * 23500, enzyme 2, SDS-PAGE
25000
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2 * 25000, enzyme 1, SDS-PAGE
56000
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enzyme 2, gel filtration
59000
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enzyme 1, gel filtration
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
enzyme 1 is not stable in potassium phosphate buffer pH 7.5, 10 vol% methanol, ethanol or propanol stabilizes
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enzyme 2 is most stable in imidazole/HCl buffer, 10 vol% acetone stabilizes
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Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE