Information on EC 1.14.14.51 - (S)-limonene 6-monooxygenase

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

EC NUMBER
COMMENTARY hide
1.14.14.51
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RECOMMENDED NAME
GeneOntology No.
(S)-limonene 6-monooxygenase
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REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
(S)-limonene + [reduced NADPH-hemoprotein reductase] + O2 = (-)-trans-carveol + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
oxidation
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redox reaction
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reduction
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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,[reduced NADPH-hemoprotein reductase]: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
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
variant Karzo
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
scotch spearmint, wild type
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
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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
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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
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one of the key reactions of oxygenated monoterpenes, biosynthesis of (-)-carvone
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(-)-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
(S)-limonene + [reduced NADH-hemoprotein reductase] + O2
(-)-trans-carveol + [oxidized NADH-hemoprotein reductase] + H2O
show the reaction diagram
(S)-limonene + [reduced NADPH-hemoprotein reductase] + O2
(-)-trans-carveol + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
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?
3-cyclohexene 1-methanol + NAD+
3-cyclohexenylaldehyde + NADH
show the reaction diagram
4-isopropyl benzyl alcohol + NAD+
4-isopropylbenzyl aldehyde + NADH
show the reaction diagram
4-mrthyl benzyl alcohol + NAD+
? + NADH
show the reaction diagram
17.1% activity compared to perillyl alcohol
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?
benzyl alcohol + NAD+
benzaldehyde + NADH
show the reaction diagram
carveol + NAD+
? + NADH
show the reaction diagram
86% activity compared to perillyl alcohol
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?
cyclohexyl methanol + NAD+
cyclohexylaldehyde + NADH
show the reaction diagram
15.8% activity compared to perillyl alcohol
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?
myrtenol + NAD+
myrtenal + NADH
show the reaction diagram
4.0% activity compared to perillyl alcohol
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?
perillyl alcohol + NAD+
perillyl aldehyde + NADH
show the reaction diagram
perillyl aldehyde + NADH
perillyl alcohol + NAD+
show the reaction diagram
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r
additional information
?
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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
(-)-(S)-limonene + NADPH + O2
(-)-trans-carveol + NADP+
show the reaction diagram
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?
(-)-limonene + NADPH + O2
(-)-trans-carveol + NADP+ + H2O
show the reaction diagram
-
one of the key reactions of oxygenated monoterpenes, biosynthesis of (-)-carvone
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(S)-limonene + NADPH + H+ + O2
(-)-trans-carveol + NADP+ + H2O
show the reaction diagram
(S)-limonene + [reduced NADH-hemoprotein reductase] + O2
(-)-trans-carveol + [oxidized NADH-hemoprotein reductase] + H2O
show the reaction diagram
(S)-limonene + [reduced NADPH-hemoprotein reductase] + O2
(-)-trans-carveol + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
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?
additional information
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
cytochrome P450
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NAD+
stimulates the dehydrogenase reaction
NADH
stimulates the hydroxylation reaction
NADPH
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
5,11-Dimethyl-6H-pyrido[4,3-b]-carbazole
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clotrimazole
cytochrome c
Metyrapone
miconazole
NADP+
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2 mM
SKF 525A
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i.e. 2-diethylaminoethyl-2,2-diphenylvalerate, moderate
additional information
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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
6.3 - 8.4
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half-maximal activities at pH 6.3 and 8.4
7.1
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assay at
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
5.5 - 10
about 40% activity at pH 5.5, about 75% activity at pH 6.5, about 90% activity at pH 7.0, 100% activity at 8.0, about 75% activity at pH 9.0, about 40% activity at pH 10.0
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
TEMPERATURE RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
30 - 55
about 35% activity at 30°C, about 55% activity at 37°C, about 90% activity at 40°C, 100% activity at 45°C, about 75% activity at 50°C, about 30% activity at 55°C
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
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Manually annotated by BRENDA team
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secretory cells of peltate glandular trichomes
Manually annotated by BRENDA team
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
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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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STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-80°C, enzyme in microsomal pellet, over 1 year, no loss of activity
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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
expressed in Escherichia coli BL21(DE3) cells
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 (356 entries)
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