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Enzyme Nomenclature
Information on EC 1.14.13.47 - (S)-limonene 3-monooxygenase
for references in articles please use BRENDA:EC1.14.13.47
Word Map on EC 1.14.13.47
- 1.14.13.47
- peppermint
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monoterpene
-
mentha
- spearmint
- piperita
- limonene-6-hydroxylase
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regiospecific
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olefin
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monoterpenoids
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4s-limonene
- agriculture
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The enzyme appears in viruses and cellular organisms
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EC NUMBER 
COMMENTARY 
1.14.13.47
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RECOMMENDED NAME
GeneOntology No.
(S)-limonene 3-monooxygenase
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
(S)-limonene + NADPH + H+ + O2 = (-)-trans-isopiperitenol + NADP+ + H2O
mixed-function oxygenase, ring-hydroxylation
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(S)-limonene + NADPH + H+ + O2 = (-)-trans-isopiperitenol + NADP+ + H2O
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-
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-
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
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
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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).
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CAS REGISTRY NUMBER
COMMENTARY
138066-92-9
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
var. cardiaca. Mutant 643 bears a mutation in a regulatory gene that silences the wild-type limonene-6-hydroxylase and promotes the sole expression of a previously quiescent limonene-3-hydroxylase
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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
(-)-limonene + NADPH + O2
(-)-trans-isopiperitenol + NADP+ + H2O
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one of the key reactions of oxygenated monoterpenes, biosynthesis of (-)-menthone
-
-
?
(+)-limonene + NADPH + O2
(+)-trans-isopiperitenol + NADP+ + H2O
-
53% the rate of (-)-limonene hydroxylation
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?
(+)-limonene + NADPH + O2
(+)-trans-isopiperitenol + NADP+ + H2O
-
-
-
-
(+)-limonene + NADPH + O2
(+)-trans-isopiperitenol + NADP+ + H2O
-
-
-
?
(+)-limonene + NADPH + O2
(+)-trans-isopiperitenol + NADP+ + H2O
-
hydroxylation at 50%
-
?
(+)-p-menth-1-ene + NADPH + O2
(+)-trans-piperitol + NADP+ + H2O
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-
-
?
(+)-p-menth-1-ene + NADPH + O2
(+)-trans-piperitol + NADP+ + H2O
-
-
-
?
(+)-p-menth-1-ene + NADPH + O2
(+)-trans-piperitol + NADP+ + H2O
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i.e. (+)-8,9-dihydro-limonene, hydroxylation at 37% the rate of (-)-limonene hydroxylation
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?
(-)-(4S)-limonene + NADPH + O2
(-)-trans-(3S,4R)-isopiperitenol + NADP+ + H2O
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limonene 6-hydroxylase mutant F363I
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-
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(-)-(4S)-limonene + NADPH + O2
(-)-trans-(3S,4R)-isopiperitenol + NADP+ + H2O
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-
-
?
(-)-(4S)-limonene + NADPH + O2
(-)-trans-(3S,4R)-isopiperitenol + NADP+ + H2O
-
-
-
?
(-)-(4S)-limonene + NADPH + O2
(-)-trans-(3S,4R)-isopiperitenol + NADP+ + H2O
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-
-
?
(-)-(4S)-limonene + NADPH + O2
(-)-trans-(3S,4R)-isopiperitenol + NADP+ + H2O
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highly specific, regiospecific and stereospecific reaction
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-
(-)-(4S)-limonene + NADPH + O2
(-)-trans-(3S,4R)-isopiperitenol + NADP+ + H2O
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highly specific, regiospecific and stereospecific reaction
-
?
(-)-(4S)-limonene + NADPH + O2
(-)-trans-(3S,4R)-isopiperitenol + NADP+ + H2O
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highly specific, regiospecific and stereospecific reaction
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?
(-)-(S)-limonene + NADPH + H+ + O2
(+)-trans-isopiperitenol + NADP+ + H2O
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-
-
-
?
(-)-(S)-limonene + NADPH + H+ + O2
(+)-trans-isopiperitenol + NADP+ + H2O
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the enzyme is involved in biosynthesis of peppermint essential oil monoterpenes
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-
?
(-)-p-menth-1-ene + NADPH + O2
(-)-trans-piperitol + NADP+ + H2O
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-
-
?
(-)-p-menth-1-ene + NADPH + O2
(-)-trans-piperitol + NADP+ + H2O
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-
-
?
(-)-p-menth-1-ene + NADPH + O2
(-)-trans-piperitol + NADP+ + H2O
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i.e. (-)-8,9-dihydrolimonene, hydroxylation at 37% the rate of (-)-limonene hydroxylation
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?
(S)-limonene + NADPH + H+ + O2
(-)-trans-isopiperitenol + NADP+ + H2O
-
-
-
-
?
(S)-limonene + NADPH + H+ + O2
(-)-trans-isopiperitenol + NADP+ + H2O
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-
-
-
?
additional information
?
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no substrates: isolimonenes, terpinolene, alpha- or beta-phellandrene, alpha- or beta-terpinene, bicyclic monoterpenes: pinene, sabinene, alpha-thujene, p-cymene, cis- or trans-p-menthane, highly specific, absolute requirement for a reduced pyridine nucleotide and molecular oxygen
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additional information
?
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the kinetically competent recombinant protein produces a mixture of C3-, C6- and C7-hydroxylated limonene derivatives, i.e. (-)-perillyl alcohol, (-)-trans-isopiperitenol, and (-)-trans-carveol, with a distribution of 33%, 14% and 53%, respectively, thus it performs the reaction of EC 1.14.13.47 and 1.14.13.48, overview
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NATURAL SUBSTRATES
NATURAL PRODUCTS
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
(-)-(S)-limonene + NADPH + H+ + O2
(+)-trans-isopiperitenol + NADP+ + H2O
-
the enzyme is involved in biosynthesis of peppermint essential oil monoterpenes
-
-
?
(-)-limonene + NADPH + O2
(-)-trans-isopiperitenol + NADP+ + H2O
-
one of the key reactions of oxygenated monoterpenes, biosynthesis of (-)-menthone
-
-
?
(S)-limonene + NADPH + H+ + O2
(-)-trans-isopiperitenol + NADP+ + H2O
-
-
-
-
?
(S)-limonene + NADPH + H+ + O2
(-)-trans-isopiperitenol + NADP+ + H2O
-
-
-
-
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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INHIBITORS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
clotrimazole
-
i.e. 1-[chloro-alpha,alpha-diphenyl]imidazole, mixed-type, strong
miconazole
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i.e. 1-[2,4-dichloro-beta-([2,4-di-chlorobenzyl]oxy)phenethyl]-imidazole, mixed-type, weak
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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pH RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
6.75 - 8.5
-
half-maximal activity at pH 6.75 and 8.5, recombinant chimeric mutant enzyme
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
additional information
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enzyme expression with or without growth under UV-B light
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LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
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GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
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Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
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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
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
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APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
agriculture
-
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
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LINKS TO OTHER DATABASES (specific for EC-Number 1.14.13.47)
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