Information on EC 1.14.13.47 - (S)-limonene 3-monooxygenase

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The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
1.14.13.47
-
RECOMMENDED NAME
GeneOntology No.
(S)-limonene 3-monooxygenase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
(S)-limonene + NADPH + H+ + O2 = (-)-trans-isopiperitenol + NADP+ + H2O
show the reaction diagram
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
oxidation
-
-
-
-
redox reaction
-
-
-
-
reduction
-
-
-
-
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
menthol biosynthesis
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-
Monoterpenoid biosynthesis
-
-
Biosynthesis of secondary metabolites
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-
SYSTEMATIC NAME
IUBMB Comments
(S)-limonene,NADPH:oxygen oxidoreductase (3-hydroxylating)
High specificity, but NADH can act instead of NADPH, although more slowly. A heme-thiolate protein (P-450).
CAS REGISTRY NUMBER
COMMENTARY hide
138066-92-9
-
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
spearmint
-
-
Manually annotated by BRENDA team
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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 + O2
(+)-trans-isopiperitenol + NADP+ + H2O
show the reaction diagram
(+)-p-menth-1-ene + NADPH + O2
(+)-trans-piperitol + NADP+ + H2O
show the reaction diagram
(-)-(4S)-limonene + NADPH + O2
(-)-trans-(3S,4R)-isopiperitenol + NADP+ + H2O
show the reaction diagram
(-)-(S)-limonene + NADPH + H+ + O2
(+)-trans-isopiperitenol + NADP+ + H2O
show the reaction diagram
(-)-limonene + NADPH + O2
(-)-trans-isopiperitenol + NADP+ + H2O
show the reaction diagram
-
one of the key reactions of oxygenated monoterpenes, biosynthesis of (-)-menthone
-
-
?
(-)-p-menth-1-ene + NADPH + O2
(-)-trans-piperitol + NADP+ + H2O
show the reaction diagram
(S)-limonene + NADPH + H+ + O2
(-)-trans-isopiperitenol + NADP+ + H2O
show the reaction diagram
additional information
?
-
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
(-)-(S)-limonene + NADPH + H+ + O2
(+)-trans-isopiperitenol + NADP+ + H2O
show the reaction diagram
-
the enzyme is involved in biosynthesis of peppermint essential oil monoterpenes
-
-
?
(-)-limonene + NADPH + O2
(-)-trans-isopiperitenol + NADP+ + H2O
show the reaction diagram
-
one of the key reactions of oxygenated monoterpenes, biosynthesis of (-)-menthone
-
-
?
(S)-limonene + NADPH + H+ + O2
(-)-trans-isopiperitenol + NADP+ + H2O
show the reaction diagram
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
cytochrome P450
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NADH
-
14% as effective as NADPH
NADPH
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
5,11-Dimethyl-6H-pyrido[4,3-b]carbazole
-
-
clotrimazole
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i.e. 1-[chloro-alpha,alpha-diphenyl]imidazole, mixed-type, strong
CO
-
CO:O2 ratio of 9:1, photoreversible
cytochrome c
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strong
Metyrapone
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i.e. 2-methyl-1,2-di-3-pyridyl-1-propanone, inhibition
miconazole
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i.e. 1-[2,4-dichloro-beta-([2,4-di-chlorobenzyl]oxy)phenethyl]-imidazole, mixed-type, weak
NADP+
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2 mM
SKF 525A
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i.e. 2-diethylaminoethyl-2,2-diphenylvalerate, moderate
additional information
-
no inhibition: ancymidol, imidazole, up to 5 mM
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
FAD
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plus FMN, 0.005 mM each, activation
FMN
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plus FAD, 0.005 mM each, activation
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.018
(-)-limonene
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-
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.0003333
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-
0.000685
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-
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7.6
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recombinant chimeric mutant enzyme
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6.75 - 8.5
-
half-maximal activity at pH 6.75 and 8.5, recombinant chimeric mutant enzyme
6.9 - 7.9
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about half-maximal activity at pH 6.9 and 7.9
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
additional information
-
enzyme expression with or without growth under UV-B light
Manually annotated by BRENDA team
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
DTT stabilizes during purification
-
EDTA stabilizes during purification
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glycerol stabilizes during purification
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Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
recombinant protein from Escherichia coli
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sonication of secretory cells leads to most active crude extracts
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expression in Escherichia coli
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expression in Escherichia coli and Saccharomyces cerevisiae
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expression of the chimeric protein in Escherichia coli
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EXPRESSION
ORGANISM
UNIPROT
LITERATURE
slight suppressing effect of UV-B light irradiation on the enzyme expression, chemical oil composition of peppermint plants growing in growth chamber and in field after irradiation with UV-B, overview
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ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
-
construction of a chimeric mutant enzyme by fusion of the N-terminal membrane insertion domain of the limonene-3-hydroxylase into limonene 7-hydroxylase. The kinetically competent recombinant protein produces a mixture of C3-, C6- and C7-hydroxylated limonene derivatives with a distribution of 33%, 14% and 53%, respectively
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
agriculture
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cosuppression of limonene-3-hydroxylase in peppermint promotes accumulation of limonene in the essential oil. Pathway engineering can be employed to significantly alter essential oil composition without adverse metabolic consequences