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EC Tree
IUBMB Comments A cytochrome P-450 (heme thiolate) enzyme. The enzyme, characterized from the plant Perilla frutescens, participates in the biosynthesis of perillyl aldehyde, the major constituent of the essential oil that accumulates in the glandular trichomes of this plant. Some forms of the enzyme also catalyse the oxidation of (-)-perillyl alcohol to (-)-perillyl aldehyde.
The expected taxonomic range for this enzyme is: Bacteria, Eukaryota
Synonyms
(-)-limonene 7-monooxygenase, (-)-limonene hydroxylase, (-)-limonene,NADPH:oxygen oxidoreductase (7-hydroxylating, (-)-limonene-7-hydroxylase, More, oxygenase, (-)-limonene mono-,
more
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(-)-limonene 7-monooxygenase
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(-)-limonene hydroxylase
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(-)-limonene,NADPH:oxygen oxidoreductase (7-hydroxylating
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(-)-limonene-7-hydroxylase
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oxygenase, (-)-limonene mono-
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additional information
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the enzyme is a cytochrome P450 limonene hydroxylase
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(S)-limonene + [reduced NADPH-hemoprotein reductase] + O2 = (-)-perillyl alcohol + [oxidized NADPH-hemoprotein reductase] + H2O
(S)-limonene + [reduced NADPH-hemoprotein reductase] + O2 = (-)-perillyl alcohol + [oxidized NADPH-hemoprotein reductase] + H2O
side-chain hydroxylation, mixed-function oxygenase
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(S)-limonene + [reduced NADPH-hemoprotein reductase] + O2 = (-)-perillyl alcohol + [oxidized NADPH-hemoprotein reductase] + H2O
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(S)-limonene,[reduced NADPH-hemoprotein reductase]:oxygen oxidoreductase (7-hydroxylating)
A cytochrome P-450 (heme thiolate) enzyme. The enzyme, characterized from the plant Perilla frutescens, participates in the biosynthesis of perillyl aldehyde, the major constituent of the essential oil that accumulates in the glandular trichomes of this plant. Some forms of the enzyme also catalyse the oxidation of (-)-perillyl alcohol to (-)-perillyl aldehyde.
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(+)-limonene + NADPH + O2
perillyl alcohol + NADP+ + H2O
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hydroxylation at the same rate as (-)-limonene
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(-)-(S)-limonene + NADPH + O2
(-)-perillyl alcohol + NADP+ + H2O
(-)-limonene + NADPH + O2
perillyl alcohol + NADP+ + H2O
(S)-limonene + NADPH + H+ + O2
(-)-perillyl alcohol + NADP+ + H2O
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additional information
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(-)-(S)-limonene + NADPH + O2
(-)-perillyl alcohol + NADP+ + H2O
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(-)-(S)-limonene + NADPH + O2
(-)-perillyl alcohol + NADP+ + H2O
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(-)-limonene + NADPH + O2
perillyl alcohol + NADP+ + H2O
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highly specific
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(-)-limonene + NADPH + O2
perillyl alcohol + NADP+ + H2O
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one of the key reactions of oxygenated monoterpenes, perillyl aldehyde biosynthesis
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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, p-menth-1-ene, i.e. 8,9-dihydrolimonene
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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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(-)-(S)-limonene + NADPH + O2
(-)-perillyl alcohol + NADP+ + H2O
(-)-limonene + NADPH + O2
perillyl alcohol + NADP+ + H2O
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one of the key reactions of oxygenated monoterpenes, perillyl aldehyde biosynthesis
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(S)-limonene + NADPH + H+ + O2
(-)-perillyl alcohol + NADP+ + H2O
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(-)-(S)-limonene + NADPH + O2
(-)-perillyl alcohol + NADP+ + H2O
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(-)-(S)-limonene + NADPH + O2
(-)-perillyl alcohol + NADP+ + H2O
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cytochrome P450
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heme-thiolate protein, 0.2-0.9 nmol per mg protein
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NADH
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5.3% as effective as NADPH
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5,11-Dimethyl-6H-pyrido[4,3-b]carbazole
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clotrimazole
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i.e. 1-[chloro-alpha,alpha-diphenyl]imidazole, mixed-type, weak
CO
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CO:O2 ratio of 9:1, photoreversible
Metyrapone
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i.e. 2-methyl-1,2-di-3-pyridyl-1-propanone, moderate
miconazole
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i.e. 1-[2,4-dichloro-beta-([2,4-di-chlorobenzyl]oxy)phenethyl]-imidazole, mixed-type, weak
SKF 525A
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i.e. 2-diethyl-aminoethyl-2,2-diphenylvalerate, moderate
additional information
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no inhibition: ancymidol, imidazole, up to 5 mM
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FAD
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plus FMN, 0.005 mM each, activation
FMN
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plus FAD, 0.005 mM each, activation
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7.6
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recombinant chimeric mutant enzyme
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5.5 - 8
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almost no activity at pH 5.5 and pH 8.0, respectively
6.75 - 8.5
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half-maximal activity at pH 6.75 and 8.5, recombinant chimeric mutant enzyme
7.3 - 8.3
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about half-maximal activity at pH 7.3 and 8.3
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HXN-1500
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brenda
HXN-1500
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brenda
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brenda
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brenda
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oil glands on abaxial surface
brenda
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brenda
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brenda
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brenda
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brenda
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CP2C9_HUMAN
490
0
55628
Swiss-Prot
Secretory Pathway (Reliability: 1 )
CP2CJ_HUMAN
490
0
55931
Swiss-Prot
Secretory Pathway (Reliability: 1 )
LIHY_GEOSE
543
0
61569
Swiss-Prot
-
A0A259U483_9FIRM
637
0
71729
TrEMBL
-
A0A259U8N5_9FIRM
633
0
70266
TrEMBL
-
A0A1U7MBW2_9FIRM
638
0
70213
TrEMBL
-
A0A086ZNB2_9BIFI
433
0
46548
TrEMBL
-
A0A0L6Z7Q9_9CLOT
474
0
53971
TrEMBL
-
A0A0L6Z6L1_9CLOT
636
0
71325
TrEMBL
-
A0A259UBX6_9FIRM
634
0
70751
TrEMBL
-
A0A1U7M748_TISCR
583
0
66612
TrEMBL
-
A0A0J1I1L5_9FIRM
701
0
77563
TrEMBL
-
A0A0F0CK81_9CLOT
647
0
72594
TrEMBL
-
A0A259UE55_9FIRM
683
0
76771
TrEMBL
-
A0A259UT95_9FIRM
478
0
54204
TrEMBL
-
A0A259U8H2_9FIRM
668
0
74199
TrEMBL
-
A0A1U7MB88_9FIRM
635
0
71335
TrEMBL
-
A0A1E7RX84_BUTME
469
0
53529
TrEMBL
-
A0A1A6B3W5_9CLOT
471
0
53430
TrEMBL
-
A0A0H4NV21_9BACI
642
0
73153
TrEMBL
-
A0A0J1IC26_9FIRM
456
0
50510
TrEMBL
-
A0A0J1FFH0_9FIRM
644
0
71729
TrEMBL
-
A0A151B3G4_9CLOT
431
0
49278
TrEMBL
-
A0A1E7RYM6_BUTME
463
0
53108
TrEMBL
-
A0A1U7MIS5_9FIRM
618
0
70067
TrEMBL
-
S5ZZ60_9CLOT
471
0
53489
TrEMBL
-
A0A151AMR8_9CLOT
592
0
67745
TrEMBL
-
A0A1V4J1A7_9CLOT
574
0
64350
TrEMBL
-
A0A1V4IT54_9CLOT
657
0
74601
TrEMBL
-
A0A259US84_9FIRM
654
0
74078
TrEMBL
-
A0A259U760_9FIRM
467
0
52259
TrEMBL
-
A0A1S8NBP2_CLOSA
636
0
72230
TrEMBL
-
A0A0J1FBA5_9FIRM
589
0
65831
TrEMBL
-
A0A259UDF5_9FIRM
687
0
76256
TrEMBL
-
A0A259UP01_9FIRM
691
0
78477
TrEMBL
-
B7QC54_IXOSC
390
1
43763
TrEMBL
Secretory Pathway (Reliability: 4 )
A0A162UF16_9CLOT
466
0
52261
TrEMBL
-
A0A1U7MB55_9FIRM
627
0
69921
TrEMBL
-
A0A1U7MIU5_9FIRM
601
0
68007
TrEMBL
-
A0A0X8R3F3_9SPHN
458
0
49632
TrEMBL
-
A0A259UUL8_9FIRM
474
0
54023
TrEMBL
-
A0A259U8U6_9FIRM
695
0
77743
TrEMBL
-
A0A1J5PPM2_9ZZZZ
168
0
18421
TrEMBL
other Location (Reliability: 3 )
A0A0L6Z833_9CLOT
486
0
55403
TrEMBL
-
A0A0X8R6A2_9SPHN
342
0
37559
TrEMBL
-
A0A259UGW2_9FIRM
641
0
71585
TrEMBL
-
A0A1S8NJ43_CLOSA
646
0
73161
TrEMBL
-
A0A0J1FEM9_9FIRM
500
0
55862
TrEMBL
-
A0A259UDW0_9FIRM
714
0
80579
TrEMBL
-
A0A161X2B5_9CLOT
642
0
72812
TrEMBL
-
A0A0L6Z642_9CLOT
467
0
53231
TrEMBL
-
A0A259UWD0_9FIRM
642
0
70999
TrEMBL
-
A0A151ALB6_9CLOT
446
0
51062
TrEMBL
-
A0A087A5K8_9BIFI
440
1
47169
TrEMBL
-
A0A0F0C978_9CLOT
633
0
72687
TrEMBL
-
A0A259UNH7_9FIRM
623
0
68840
TrEMBL
-
A0A259UN71_9FIRM
323
0
36551
TrEMBL
-
A0A1J5Q123_9ZZZZ
204
0
22453
TrEMBL
other Location (Reliability: 2 )
A0A1J5P3H7_MOOTH
610
0
67937
TrEMBL
-
A0A259U8Y6_9FIRM
707
0
80002
TrEMBL
-
A0A259U4X5_9FIRM
637
0
70718
TrEMBL
-
A0A1U7MCR5_9FIRM
637
0
70818
TrEMBL
-
A0A0F0CLP0_9CLOT
636
0
70922
TrEMBL
-
A0A1F2PFT0_9FIRM
653
0
73459
TrEMBL
-
A0A0J1FH36_9FIRM
614
0
68099
TrEMBL
-
A0A1F2PME8_9FIRM
463
0
52583
TrEMBL
-
A0A161WR74_9CLOT
483
0
54662
TrEMBL
-
A0A083ZX61_9GAMM
591
1
66452
TrEMBL
-
A0A259UDI7_9FIRM
476
0
53398
TrEMBL
-
A0A0J1FKG9_9FIRM
590
0
66449
TrEMBL
-
A0A259UW73_9FIRM
638
0
72020
TrEMBL
-
A0A1A6ANB9_9CLOT
446
0
51666
TrEMBL
-
A0A0J1FA13_9FIRM
501
0
56324
TrEMBL
-
A0A087DJA4_9BIFI
436
0
46798
TrEMBL
-
A0A162S2Z3_9CLOT
350
0
39831
TrEMBL
-
A0A259URT8_9FIRM
600
0
67811
TrEMBL
-
A0A1U7M8V9_TISCR
435
0
50088
TrEMBL
-
A0A0J1IRY7_9FIRM
652
0
72919
TrEMBL
-
A0A1A6B3R5_9CLOT
646
0
73047
TrEMBL
-
A0A259USU3_9FIRM
622
0
67462
TrEMBL
-
CP2C9_HUMAN
490
0
55628
Swiss-Prot
Secretory Pathway (Reliability: 1 )
CP2CJ_HUMAN
490
0
55931
Swiss-Prot
Secretory Pathway (Reliability: 1 )
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48000
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x * 48000, SDS-PAGE
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?
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x * 48000, SDS-PAGE
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x * 48000, SDS-PAGE
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additional information
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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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0
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50% loss of activity after 6 h
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ammonium sulfate, phenyl Sepharose, Source Q15
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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-hydroxylase
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expression in n-octane grown Pseudomonas putida
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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
Perilla frutescens
brenda
van 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 putida
Appl. Environ. Microbiol.
71
1737-1744
2005
Mycobacterium sp., Mycobacterium sp. HXN-1500
brenda
Mau, C.J.; Karp, F.; Ito, M.; Honda, G.; Croteau, R.B.
A candidate cDNA clone for (-)-limonene-7-hydroxylase from Perilla frutescens
Phytochemistry
71
373-379
2010
Perilla frutescens
brenda
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