Information on EC 1.14.13.80 - (R)-limonene 6-monooxygenase

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The expected taxonomic range for this enzyme is: Carum carvi

EC NUMBER
COMMENTARY hide
1.14.13.80
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RECOMMENDED NAME
GeneOntology No.
(R)-limonene 6-monooxygenase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
(R)-limonene + NADPH + H+ + O2 = (+)-trans-carveol + NADP+ + H2O
show the reaction diagram
The reaction is stereospecific with over 95% yield of (+)-trans-carveol from (R)-limonene. (S)-Limonene, the substrate for EC 1.14.13.48, (S)-limonene 6-monooxygenase, is not a substrate. Forms part of the carvone biosynthesis pathway in Carum carvi (caraway) seeds
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
oxidation
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-
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redox reaction
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-
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reduction
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-
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
(4S)-carvone biosynthesis
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Biosynthesis of secondary metabolites
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Limonene and pinene degradation
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Monoterpenoid biosynthesis
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SYSTEMATIC NAME
IUBMB Comments
(R)-limonene,NADPH:oxygen oxidoreductase (6-hydroxylating)
The reaction is stereospecific with over 95% yield of (+)-trans-carveol from (R)-limonene. (S)-Limonene, the substrate for EC 1.14.13.48, (S)-limonene 6-monooxygenase, is not a substrate. Forms part of the carvone biosynthesis pathway in Carum carvi (caraway) seeds.
CAS REGISTRY NUMBER
COMMENTARY hide
221461-49-0
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
var Karzo, annual caraway, var Beija, biennial caraway
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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
(+)-limonene + NADPH + H+ + O2
(+)-trans-carveol + NADP+ + H2O
show the reaction diagram
(-)-limonene + NADPH + H+ + O2
(-)-cis-carveol + NADP+ + H2O
show the reaction diagram
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hydroxylation at 10% the rate of (+)-limonene
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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
(+)-limonene + NADPH + H+ + O2
(+)-trans-carveol + NADP+ + H2O
show the reaction diagram
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intermediate in biosynthesis of (+)-carvone
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?
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
cytochrome P-450
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-
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NADP+
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
clotrimazole
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less than 0.001 mM, 50% inhibition
cytochrome c
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less than 0.01 mM, 50% inhibition
metapyrone
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1.5 mM, 50% inhibition
miconazole
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0.048 mM, 50% inhibition
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0114 - 0.0149
(+)-limonene
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7.2 - 7.4
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pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6.3 - 8.4
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
30
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assay at
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
polyvinylpyrrolidone, NaHsO3, sodium diethyldithiocarbamate, leupeptin, EGTA, catalase, and glutathione stabilize microsomal extract
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STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-80 C, microsomal preparation, 1 year, no loss of activity
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