Information on EC 1.14.13.49 - (S)-limonene 7-monooxygenase:
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The lowest common taxonomy group for this enzyme is: cellular organisms

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EC NUMBERCOMMENTARY
1.14.13.49-

RECOMMENDED NAMEGeneOntology No.
(S)-limonene 7-monooxygenaseGO:0018676

REACTIONREACTION DIAGRAMCOMMENTARYORGANISM UNIPROT ACCESSION NO.LITERATURE
(S)-limonene + NADPH + H+ + O2 = (-)-perillyl alcohol + NADP+ + H2O
show the reaction diagram		----
(S)-limonene + NADPH + H+ + O2 = (-)-perillyl alcohol + NADP+ + H2O
show the reaction diagram		side-chain hydroxylation, mixed-function oxygenasePerilla frutescens-390083

REACTION TYPEORGANISM UNIPROT ACCESSION NO.COMMENTARYLITERATURE
oxidation----
redox reaction----
reduction----

PATHWAYKEGG LinkMetaCyc Link
perillyl alcohol biosynthesis-PWY-6436

SYSTEMATIC NAMEIUBMB Comments
(S)-limonene,NADPH:oxygen oxidoreductase (7-hydroxylating)High specificity, but NADH can act instead of NADPH, although more slowly. A heme-thiolate protein (P-450).

SYNONYMSORGANISM UNIPROT ACCESSION NO.COMMENTARYLITERATURE
(-)-limonene 7-monooxygenase----
(-)-limonene hydroxylase----
(-)-limonene,NADPH:oxygen oxidoreductase (7-hydroxylating----
oxygenase, (-)-limonene mono-----
(-)-limonene-7-hydroxylasePerilla frutescens--713236
additional informationPerilla frutescens-the enzyme is a cytochrome P450 limonene hydroxylase713236

CAS REGISTRY NUMBERCOMMENTARY
122653-75-2-

ORGANISMCOMMENTARYLITERATURESEQUENCE CODESEQUENCE DB SOURCE
Mycobacterium sp.HXN-1500657606--Manually annotated by BRENDA team
Mycobacterium sp. HXN-1500HXN-1500657606--Manually annotated by BRENDA team
Perilla frutescens-390083, 713236--Manually annotated by BRENDA team

GENERAL INFORMATIONORGANISM UNIPROT ACCESSION NO.COMMENTARYLITERATURE
No entries in this field

SUBSTRATEPRODUCT                      REACTION DIAGRAMORGANISM UNIPROT ACCESSION NO. COMMENTARY/
Substrate		 LITERATURE/
Substrate		 COMMENTARY/
Product		 LITERATURE/
Product		 Reversibility
r=reversible
ir=irreversible
?=not specified
(+)-limonene + NADPH + O2perillyl alcohol + NADP+ + H2O
show the reaction diagram		Perilla frutescens-hydroxylation at the same rate as (-)-limonene390083-390083?
(-)-(S)-limonene + NADPH + O2(-)-perillyl alcohol + NADP+ + H2O
show the reaction diagram		Mycobacterium sp.--657606--?
(-)-limonene + NADPH + O2perillyl alcohol + NADP+ + H2O
show the reaction diagram		Perilla frutescens-highly specific390083-390083?
(-)-limonene + NADPH + O2perillyl alcohol + NADP+ + H2O
show the reaction diagram		Perilla frutescens-one of the key reactions of oxygenated monoterpenes, perillyl aldehyde biosynthesis390083--?
(S)-limonene + NADPH + H+ + O2(-)-perillyl alcohol + NADP+ + H2O
show the reaction diagram		Perilla frutescens--713236--?
additional information?-Perilla frutescens-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, p-menth-1-ene, i.e. 8,9-dihydrolimonene390083---
additional information?-Perilla frutescens-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, overview713236---

NATURAL SUBSTRATESNATURAL PRODUCTSREACTION DIAGRAMORGANISM UNIPROT ACCESSION NO.COMMENTARY SUBSTRATELITERATURE
(Substrate)		COMMENTARY PRODUCTLITERATURE
(Product)
(-)-(S)-limonene + NADPH + O2(-)-perillyl alcohol + NADP+ + H2O
show the reaction diagram		Mycobacterium sp.--657606--
(-)-limonene + NADPH + O2perillyl alcohol + NADP+ + H2O
show the reaction diagram		Perilla frutescens-one of the key reactions of oxygenated monoterpenes, perillyl aldehyde biosynthesis390083--
(S)-limonene + NADPH + H+ + O2(-)-perillyl alcohol + NADP+ + H2O
show the reaction diagram		Perilla frutescens--713236--

COFACTORORGANISM UNIPROT ACCESSION NO.COMMENTARYLITERATUREIMAGE
cytochrome P450Perilla frutescens-heme-thiolate protein, 0.2-0.9 nmol per mg protein390083-
NADHPerilla frutescens-5.3% as effective as NADPH390083 2D-image
NADPHPerilla frutescens--390083, 713236 2D-image

METALS and IONS ORGANISM UNIPROT ACCESSION NO.COMMENTARY LITERATURE
No entries in this field

INHIBITORSORGANISM UNIPROT ACCESSION NO. COMMENTARY LITERATURE IMAGE
5,11-Dimethyl-6H-pyrido[4,3-b]carbazolePerilla frutescens--390083 2D-image
clotrimazolePerilla frutescens-i.e. 1-[chloro-alpha,alpha-diphenyl]imidazole, mixed-type, weak390083 2D-image
COPerilla frutescens-CO:O2 ratio of 9:1, photoreversible390083 2D-image
cytochrome cPerilla frutescens-strong390083 2D-image
MetyraponePerilla frutescens-i.e. 2-methyl-1,2-di-3-pyridyl-1-propanone, moderate390083 2D-image
NADP+Perilla frutescens-2 mM390083 2D-image
SKF 525APerilla frutescens-i.e. 2-diethyl-aminoethyl-2,2-diphenylvalerate, moderate390083 2D-image
MiconazolePerilla frutescens-i.e. 1-[2,4-dichloro-beta-([2,4-di-chlorobenzyl]oxy)phenethyl]-imidazole, mixed-type, weak390083 2D-image
additional informationPerilla frutescens-no inhibition: ancymidol, imidazole, up to 5 mM390083-

ACTIVATING COMPOUNDORGANISM UNIPROT ACCESSION NO. COMMENTARY LITERATURE IMAGE
FADPerilla frutescens-plus FMN, 0.005 mM each, activation390083 2D-image
FMNPerilla frutescens-plus FAD, 0.005 mM each, activation390083 2D-image

KM VALUE [mM]KM VALUE [mM] MaximumSUBSTRATEORGANISM UNIPROT ACCESSION NO. COMMENTARY LITERATURE IMAGE
0.021-(-)-limonenePerilla frutescens--390083 2D-image

TURNOVER NUMBER [1/s] TURNOVER NUMBER MAXIMUM[1/s] SUBSTRATEORGANISM UNIPROT ACCESSION NO. COMMENTARY LITERATURE IMAGE
No entries in this field

kcat/KM VALUE [1/mMs-1]kcat/KM VALUE [1/mMs-1] MaximumSUBSTRATEORGANISM UNIPROT ACCESSION NO. COMMENTARY LITERATURE IMAGE
No entries in this field

Ki VALUE [mM]Ki VALUE [mM] MaximumINHIBITORORGANISM UNIPROT ACCESSION NO. COMMENTARY LITERATURE IMAGE
No entries in this field

IC50 VALUE [mM]IC50 VALUE [mM] MaximumINHIBITORORGANISM UNIPROT ACCESSION NO. COMMENTARY LITERATURE IMAGE
No entries in this field

SPECIFIC ACTIVITY [µmol/min/mg] SPECIFIC ACTIVITY MAXIMUM ORGANISM UNIPROT ACCESSION NO. COMMENTARY LITERATURE
0.0001567-Perilla frutescens--390083

pH OPTIMUMpH MAXIMUMORGANISM UNIPROT ACCESSION NO. COMMENTARYLITERATURE
7-Mycobacterium sp.--657606
7.6-Perilla frutescens-recombinant chimeric mutant enzyme713236
7.8-Perilla frutescens--390083

pH RANGEpH RANGE MAXIMUMORGANISM UNIPROT ACCESSION NO.COMMENTARYLITERATURE
5.58Mycobacterium sp.-almost no activity at pH 5.5 and pH 8.0, respectively657606
6.758.5Perilla frutescens-half-maximal activity at pH 6.75 and 8.5, recombinant chimeric mutant enzyme713236
7.38.3Perilla frutescens-about half-maximal activity at pH 7.3 and 8.3390083

TEMPERATURE OPTIMUMTEMPERATURE OPTIMUM MAXIMUMORGANISM UNIPROT ACCESSION NO.COMMENTARYLITERATURE
32-Perilla frutescens--390083

TEMPERATURE RANGE TEMPERATURE MAXIMUM ORGANISM UNIPROT ACCESSION NO. COMMENTARY LITERATURE
No entries in this field

pI VALUEpI VALUE MAXIMUMORGANISM UNIPROT ACCESSION NO.COMMENTARYLITERATURE
No entries in this field

SOURCE TISSUE ORGANISM UNIPROT ACCESSION NO. COMMENTARY LITERATURE SOURCE
leafPerilla frutescens--713236Manually annotated by BRENDA team
leaf epidermisPerilla frutescens-oil glands on abaxial surface390083Manually annotated by BRENDA team
peltate glandPerilla frutescens--713236Manually annotated by BRENDA team

LOCALIZATION ORGANISM UNIPROT ACCESSION NO. COMMENTARY GeneOntology No. LITERATURE SOURCE
microsomePerilla frutescens---713236Manually annotated by BRENDA team
solubleMycobacterium sp.---657606Manually annotated by BRENDA team

PDBSCOPCATHORGANISM
1og2, downloadSCOP (1og2)CATH (1og2)Homo sapiens
1og5, downloadSCOP (1og5)CATH (1og5)Homo sapiens
4gqs, downloadSCOP (4gqs)CATH (4gqs)Homo sapiens

MOLECULAR WEIGHT MOLECULAR WEIGHT MAXIMUM ORGANISM UNIPROT ACCESSION NO. COMMENTARY LITERATURE
No entries in this field

SUBUNITS ORGANISM UNIPROT ACCESSION NO. COMMENTARY LITERATURE
?Mycobacterium sp.-x * 48000, SDS-PAGE657606

POSTTRANSLATIONAL MODIFICATION ORGANISM UNIPROT ACCESSION NO. COMMENTARY LITERATURE
No entries in this field

Crystallization/COMMENTARY ORGANISM UNIPROT ACCESSION NO. LITERATURE
No entries in this field

pH STABILITYpH STABILITY MAXIMUM ORGANISM UNIPROT ACCESSION NO. COMMENTARY LITERATURE
No entries in this field

TEMPERATURE STABILITYTEMPERATURE STABILITY MAXIMUM ORGANISM UNIPROT ACCESSION NO. COMMENTARYLITERATURE
0-Mycobacterium sp.-50% loss of activity after 6 h657606

GENERAL STABILITYORGANISM UNIPROT ACCESSION NO.LITERATURE
No entries in this field

ORGANIC SOLVENT ORGANISM UNIPROT ACCESSION NO. COMMENTARY LITERATURE
No entries in this field

OXIDATION STABILITY ORGANISM UNIPROT ACCESSION NO. LITERATURE
No entries in this field

STORAGE STABILITY ORGANISM UNIPROT ACCESSION NO. LITERATURE
No entries in this field

Purification/COMMENTARY ORGANISM UNIPROT ACCESSION NO. LITERATURE
ammonium sulfate, phenyl Sepharose, Source Q15Mycobacterium sp.-657606

Cloned/COMMENTARY ORGANISM UNIPROT ACCESSION NO. LITERATURE
expression in n-octane grown Pseudomonas putidaMycobacterium sp.-657606
DNA and amino acid sequence determination and analysis, expression in Escherichia coli as a chimeric protein fused with the N-terminal membrane insertion domain of the limonene-3-hydroxylasePerilla frutescens-713236

EXPRESSION ORGANISM UNIPROT ACCESSION NO. LITERATURE
No entries in this field

ENGINEERINGORGANISM UNIPROT ACCESSION NO.COMMENTARYLITERATURE
additional informationPerilla frutescens-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%, respectively713236

Renatured/COMMENTARYORGANISM UNIPROT ACCESSION NO.LITERATURE
No entries in this field

APPLICATIONORGANISM UNIPROT ACCESSION NO.COMMENTARYLITERATURE
No entries in this field

REF. AUTHORS TITLE JOURNAL VOL. PAGES YEAR ORGANISMLINK TO PUBMEDSOURCE
390083Karp, 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) leavesArch. Biochem. Biophys.276219-2261990Perilla frutescens PubMed
657606van Beilen, J.B.; Holtackers, R.; Luscher, D.; Bauer, U.; Witholt, B.; Duetz, W.A.Biocatalytic production of perillyl alcohol from limonene by using a novel Mycobacterium sp. cytochrome P450 alkane hydroxylase expressed in Pseudomonas putidaAppl. Environ. Microbiol.711737-17442005Mycobacterium sp. PubMed
713236Mau, C.J.; Karp, F.; Ito, M.; Honda, G.; Croteau, R.B.A candidate cDNA clone for (-)-limonene-7-hydroxylase from Perilla frutescensPhytochemistry71373-3792010Perilla frutescens PubMed

LINKS TO OTHER DATABASES (specific for EC-Number 1.14.13.49)
ExplorEnz
ExPASy
KEGG
MetaCyc
NCBI: PubMed, Protein, Nucleotide, Structure, Genome, OMIM
IUBMB Enzyme Nomenclature
PROSITE Database of protein families and domains
SYSTERS
Protein Mutant Database
InterPro (database of protein families, domains and functional sites)