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Information on EC 1.14.14.51 - (S)-limonene 6-monooxygenase and Organism(s) Mentha spicata and UniProt Accession Q9XHE8

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IUBMB Comments
A cytochrome P-450 (heme thiolate) enzyme. The enzyme participates in the biosynthesis of (-)-carvone, which is responsible for the aroma of spearmint.
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This record set is specific for:
Mentha spicata
UNIPROT: Q9XHE8
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Word Map
The taxonomic range for the selected organisms is: Mentha spicata
The expected taxonomic range for this enzyme is: Bacteria, Eukaryota
Synonyms
limonene-6-hydroxylase, limonene hydroxylase, (-)-(4s)-limonene-6-hydroxylase, more
SYNONYM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
(-)-(4S)-limonene-6-hydroxylase
-
-
(-)-limonene 6-hydroxylase
-
-
-
-
(-)-limonene 6-monooxygenase
-
-
-
-
(-)-limonene,NADPH:oxygen oxidoreductase (6-hydroxylating)
-
-
-
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(-)-limonene-6-hydroxylase
-
-
4S-limonene-6-hydroxylase
-
-
limonene-6-hydroxylase
-
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oxygenase, (-)-limonene 6-mono-
-
-
-
-
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
redox reaction
-
-
-
-
oxidation
-
-
-
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reduction
-
-
-
-
SYSTEMATIC NAME
IUBMB Comments
(S)-limonene,[reduced NADPH-hemoprotein reductase]:oxygen oxidoreductase (6-hydroxylating)
A cytochrome P-450 (heme thiolate) enzyme. The enzyme participates in the biosynthesis of (-)-carvone, which is responsible for the aroma of spearmint.
CAS REGISTRY NUMBER
COMMENTARY hide
138066-93-0
-
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(-)-(4S)-limonene + NADPH + O2
(-)-(4R,6S)-trans-carveol + NADP+ + H2O
show the reaction diagram
-
-
?
(+)-limonene + NADPH + O2
(+)-cis-carveol + NADP+ + H2O
show the reaction diagram
-
hydroxylation at 25% the rate of (-)-limonene
-
?
(+)-p-menth-1-ene + NADPH + O2
(+)-cis-carvotanacetol + NADP+ + H2O
show the reaction diagram
-
i.e. (+)-8,9-dihydrolimonene, hydroxylation at 30% the rate of (-)-limonene
-
-
?
(-)-(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
-
i.e. (-)-8,9-dihydrolimonene, hydroxylation at 74% the rate of (-)-limonene
-
-
?
additional information
?
-
NATURAL SUBSTRATE
NATURAL PRODUCT
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
-
-
?
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
cytochrome P450
-
-
cytochrome P450
-
average content of 0.0005 mmol/mg protein
-
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
5,11-Dimethyl-6H-pyrido[4,3-b]-carbazole
-
-
clotrimazole
-
i.e. 1-[chloro-alpha,alpha-diphenyl]imidazole, mixed-type, strong
CO
-
CO:O2 ratio of 9:1, photoreversible
cytochrome c
-
strong
Metyrapone
-
i.e. 2-methyl-1,2-di-3-pyridyl-1-propanone, moderate
miconazole
-
i.e. 1-[2,4-dichloro-beta-([2,4-di-chlorobenzyl]oxy)phenethyl]-imidazole, mixed-type, strong
NADP+
-
2 mM
SKF 525A
-
i.e. 2-diethylaminoethyl-2,2-diphenylvalerate, moderate
additional information
-
no inhibition: ancymidol, imidazole, up to 5 mM
-
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.02
(-)-limonene
-
-
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.00068
-
-
0.0007
-
-
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6.9 - 7.9
-
about half-maximal activity at pH 6.9 and 7.9
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
30
-
assay at
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
spearmint
Uniprot
Manually annotated by BRENDA team
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
oil glands on upper and lower surface
Manually annotated by BRENDA team
-
secretory cells of peltate glandular trichomes
Manually annotated by BRENDA team
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION?
C71DI_MENSP
496
1
56149
Swiss-Prot
Secretory Pathway (Reliability: 4)
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
57000
SDS-PAGE
57000
-
SDS-PAGE, recombinant protein expressed in Saccharomyces cerevisiae
additional information
-
overview
GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
DTT stabilizes during purification
-
EDTA stabilizes during purification
-
glycerol stabilizes during purification
-
PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
overview
-
protein expressed in Escherichia coli
-
protein expressed in Saccharomyces cerevisiae
-
sonication of secretory cells leads to most active crude extracts
-
CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
expression in Escherichia coli and in Saccharomyces cerevisiae
-
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
-
overexpression in Saccharomyces cerevisiae
-
overview
-
REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Gershenzon, J.; Maffei, M.; Croteau, R.
Biochemical and histochemical localization of monoterpene biosynthesis in the glandular trichomes of spearmint (Mentha spicata)
Plant Physiol.
89
1351-1357
1989
Mentha spicata
Manually annotated by BRENDA team
Karp, F.; Mihaliak, C.A.; Harris, J.L.; Croteau, R.
Monoterpene biosynthesis: specificity of the hydroxylations of (-)-limonene by enzyme preparations from peppermint (Mentha piperita), spearmint (Mentha spicata), and perilla (Perilla frutescens) leaves
Arch. Biochem. Biophys.
276
219-226
1990
Mentha spicata
Manually annotated by BRENDA team
Gershenzon, J.; McCaskill, D.; Rajaonarivony, J.I.; Mihaliak, C.; Karp, F.; Croteau, R.
Isolation of secretory cells from plant glandular trichomes and their use in biosynthetic studies of monoterpenes and other gland products
Anal. Biochem.
200
130-138
1992
Mentha spicata
Manually annotated by BRENDA team
Schalk, M.; Croteau, R.
A single amino acid substitution (F363I) converts the regiochemistry of the spearmint (-)-limonene hydroxylase from a C6- to a C3-hydroxylase
Proc. Natl. Acad. Sci. USA
97
11948-11953
2000
Mentha spicata
Manually annotated by BRENDA team
Lupien, S.; Karp, F.; Wildung, M.; Croteau, R.
Regiospecific cytochrome P450 limonene hydroxylases from mint (Mentha) species: cDNA isolation, characterization, and functional expression of (-)-4S-limonene-3-hydroxylase and (-)-4S-limonene-6-hydroxylase
Arch. Biochem. Biophys.
368
181-192
1999
Mentha spicata (Q9XHE8), Mentha spicata
Manually annotated by BRENDA team
Haudenschild, C.; Schalk, M.; Karp, F.; Croteau, R.
Functional expression of regiospecific cytochrome P450 limonene hydroxylases from mint (Mentha spp.) in Escherichia coli and Saccharomyces cerevisiae
Arch. Biochem. Biophys.
379
127-136
2000
Mentha spicata
Manually annotated by BRENDA team
Wust, M.; Little, D.B.; Schalk, M.; Croteau, R.
Hydroxylation of limonene enantiomers and analogs by recombinant (-)-limonene 3- and 6-hydroxylases from Mint (Mentha) species: Evidence for catalysis within sterically constrained active sites
Arch. Biochem. Biophys.
387
125-136
2001
Mentha spicata
Manually annotated by BRENDA team
Wuest, M.; Croteau, R.B.
Hydroxylation of specifically deuterated limonene enantiomers by cytochrome P450 limonene-6-hydroxylase reveals the mechanism of multiple product formation
Biochemistry
41
1820-1827
2002
Mentha spicata
Manually annotated by BRENDA team
Lupien, S.; Karp, F.; Ponnamperuma, K.; Wildung, M.; Croteau, R.
Cytochrome P450 limonene hydroxylases of Mentha species
Drug Metabol. Drug Interact.
12
245-260
1995
Mentha spicata
Manually annotated by BRENDA team
Carter, O.A.; Peters, R.J.; Croteau, R.
Monoterpene biosynthesis pathway construction in Escherichia coli
Phytochemistry
64
425-433
2003
Mentha spicata
Manually annotated by BRENDA team
Turner, G.W.; Croteau, R.
Organization of monoterpene biosynthesis in Mentha. Immunocytochemical localizations of geranyl diphosphate synthase, limonene-6-hydroxylase, isopiperitenol dehydrogenase, and pulegone reductase
Plant Physiol.
136
4215-4227
2004
Mentha spicata
Manually annotated by BRENDA team