Information on EC 1.14.13.48 - (S)-limonene 6-monooxygenase

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The expected taxonomic range for this enzyme is: Eukaryota, Bacteria

EC NUMBER
COMMENTARY hide
1.14.13.48
-
RECOMMENDED NAME
GeneOntology No.
(S)-limonene 6-monooxygenase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
(S)-limonene + NADPH + H+ + O2 = (-)-trans-carveol + NADP+ + H2O
show the reaction diagram
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-
-
-
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
oxidation
-
-
-
-
redox reaction
-
-
-
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reduction
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-
-
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
(4R)-carvone biosynthesis
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Monoterpenoid biosynthesis
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Limonene and pinene degradation
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Biosynthesis of secondary metabolites
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SYSTEMATIC NAME
IUBMB Comments
(S)-limonene,NADPH:oxygen oxidoreductase (6-hydroxylating)
High specificity, but NADH can act instead of NADPH, but more slowly. A heme-thiolate protein (P-450).
CAS REGISTRY NUMBER
COMMENTARY hide
138066-93-0
-
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
scotch spearmint, wild type
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-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
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
(+)-cis-carveol + NADP+ + H2O
show the reaction diagram
(+)-p-menth-1-ene + NADPH + O2
(+)-cis-carvotanacetol + NADP+ + H2O
show the reaction diagram
(-)-(4S)-limonene + NADPH + O2
(-)-(4R,6S)-trans-carveol + NADP+ + H2O
show the reaction diagram
(-)-(4S)-limonene + NADPH + O2
(-)-trans-isopiperitenol + NADP+ + H2O
show the reaction diagram
-
mutant F363I
mutant F363I
?
(-)-(S)-limonene + NADPH + O2
(-)-trans-carveol + NADP+
show the reaction diagram
(-)-limonene + NADPH + O2
(-)-trans-carveol + NADP+ + H2O
show the reaction diagram
-
one of the key reactions of oxygenated monoterpenes, biosynthesis of (-)-carvone
-
-
-
(-)-p-menth-1-ene + NADPH + O2
(-)-trans-carvotanacetol + NADP+ + H2O
show the reaction diagram
(S)-limonene + NADPH + H+ + O2
(-)-trans-carveol + 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 + O2
(-)-trans-carveol + NADP+
show the reaction diagram
-
-
-
-
?
(-)-limonene + NADPH + O2
(-)-trans-carveol + NADP+ + H2O
show the reaction diagram
-
one of the key reactions of oxygenated monoterpenes, biosynthesis of (-)-carvone
-
-
-
(S)-limonene + NADPH + H+ + O2
(-)-trans-carveol + NADP+ + H2O
show the reaction diagram
additional information
?
-
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
cytochrome P450
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NADPH
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
5,11-Dimethyl-6H-pyrido[4,3-b]-carbazole
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clotrimazole
CO
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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, moderate
miconazole
NADP+
-
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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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.02
(-)-limonene
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-
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.00068
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0.0007
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7.1
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assay at
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
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
25
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assay at
30
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assay at
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
-
secretory cells of peltate glandular trichomes
Manually annotated by BRENDA team
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
-
overview
GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
DTT stabilizes during purification
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EDTA stabilizes during purification
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glycerol stabilizes during purification
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Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
overview
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partial
partial; sonication of secretory cells leads to most active crude extracts
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protein expressed in Escherichia coli; protein expressed in Saccharomyces cerevisiae
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expression in Escherichia coli and in Saccharomyces cerevisiae
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expression in Escherichia coli. Systematic attempt to install the multistep pathway from isopentenyl diphosphate and dimethylallyl diphosphate to (-) carvone in Escherichia coli, limitations when using microbial hosts that are not otherwise enhanced for isoprenoid production
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overexpression in Saccharomyces cerevisiae
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overview
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ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
Show AA Sequence (159 entries)
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