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Information on EC 1.14.14.52 - (S)-limonene 7-monooxygenase for references in articles please use BRENDA:EC1.14.14.52
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EC Tree
IUBMB Comments High specificity, but NADH can act instead of NADPH, although more slowly. A heme-thiolate protein (P-450).
The expected taxonomic range for this enzyme is: Bacteria, Eukaryota
Synonyms
(-)-limonene hydroxylase,
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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)
High specificity, but NADH can act instead of NADPH, although more slowly. A heme-thiolate protein (P-450).
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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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LIHY_GEOSE
543
0
61569
Swiss-Prot
CP2C9_HUMAN
490
0
55628
Swiss-Prot
CP2CJ_HUMAN
490
0
55931
Swiss-Prot
A0A259U8N5_9FIRM
633
0
70266
TrEMBL
A0A259U8Y6_9FIRM
707
0
80002
TrEMBL
A0A259U760_9FIRM
467
0
52259
TrEMBL
A0A259UN71_9FIRM
323
0
36551
TrEMBL
A0A0J1FFH0_9FIRM
644
0
71729
TrEMBL
A0A0J1FEM9_9FIRM
500
0
55862
TrEMBL
A0A0X8R3F3_9SPHN
458
0
49632
TrEMBL
A0A259UUL8_9FIRM
474
0
54023
TrEMBL
A0A259UWD0_9FIRM
642
0
70999
TrEMBL
A0A1V4J1A7_9CLOT
574
0
64350
TrEMBL
A0A259UP01_9FIRM
691
0
78477
TrEMBL
A0A1E7RYM6_BUTME
463
0
53108
TrEMBL
A0A1U7MIF3_9FIRM
558
0
62938
TrEMBL
A0A1V4IT54_9CLOT
657
0
74601
TrEMBL
A0A0F0CLP0_9CLOT
636
0
70922
TrEMBL
A0A1F2PFT0_9FIRM
653
0
73459
TrEMBL
A0A259UW73_9FIRM
638
0
72020
TrEMBL
A0A0J1IRY7_9FIRM
652
0
72919
TrEMBL
A0A0F0CK81_9CLOT
647
0
72594
TrEMBL
A0A1J5P3H7_MOOTH
610
0
67937
TrEMBL
A0A1A6ANB9_9CLOT
446
0
51666
TrEMBL
A0A162UF16_9CLOT
466
0
52261
TrEMBL
A0A1U7MB55_9FIRM
627
0
69921
TrEMBL
A0A1U7MIS5_9FIRM
618
0
70067
TrEMBL
A0A151B0V6_9THEO
698
0
77315
TrEMBL
A0A0J1FDP3_9FIRM
584
0
65534
TrEMBL
A0A0J1FBA5_9FIRM
589
0
65831
TrEMBL
A0A1F2PME8_9FIRM
463
0
52583
TrEMBL
A0A161X2B5_9CLOT
642
0
72812
TrEMBL
A0A259U8H2_9FIRM
668
0
74199
TrEMBL
A0A0J1FA13_9FIRM
501
0
56324
TrEMBL
A0A1J5JG26_MOOTH
752
0
83553
TrEMBL
A0A259US84_9FIRM
654
0
74078
TrEMBL
A0A259UNH7_9FIRM
623
0
68840
TrEMBL
A0A0J1FU26_9FIRM
587
0
65920
TrEMBL
A0A083ZX61_9GAMM
591
1
66452
TrEMBL
A0A087A5K8_9BIFI
440
1
47169
TrEMBL
A0A0L6Z833_9CLOT
486
0
55403
TrEMBL
A0A1S8NBP2_CLOSA
636
0
72230
TrEMBL
A0A259UDF5_9FIRM
687
0
76256
TrEMBL
A0A259USU3_9FIRM
622
0
67462
TrEMBL
S5ZZ60_9CLOT
471
0
53489
TrEMBL
A0A259UGG9_9FIRM
511
0
57322
TrEMBL
A0A0H4NV21_9BACI
642
0
73153
TrEMBL
A0A1J5PPM2_9ZZZZ
168
0
18421
TrEMBL
A0A0L6Z6N1_9CLOT
477
0
54405
TrEMBL
A0A151B3G4_9CLOT
431
0
49278
TrEMBL
A0A161WR74_9CLOT
483
0
54662
TrEMBL
A0A1U7M748_TISCR
583
0
66612
TrEMBL
A0A1U7MBW2_9FIRM
638
0
70213
TrEMBL
A0A0L6Z6L1_9CLOT
636
0
71325
TrEMBL
A0A1A6B3W5_9CLOT
471
0
53430
TrEMBL
A0A259U4X5_9FIRM
637
0
70718
TrEMBL
A0A086ZNB2_9BIFI
433
0
46548
TrEMBL
A0A151AMR8_9CLOT
592
0
67745
TrEMBL
A0A1E7RX84_BUTME
469
0
53529
TrEMBL
A0A0J1FH36_9FIRM
614
0
68099
TrEMBL
A0A087DJA4_9BIFI
436
0
46798
TrEMBL
A0A259UT95_9FIRM
478
0
54204
TrEMBL
A0A259UDI7_9FIRM
476
0
53398
TrEMBL
B7QC54_IXOSC
390
1
43763
TrEMBL
A0A162S2Z3_9CLOT
350
0
39831
TrEMBL
A0A259U483_9FIRM
637
0
71729
TrEMBL
A0A1E7RWA3_BUTME
459
0
52842
TrEMBL
A0A1U7M8V9_TISCR
435
0
50088
TrEMBL
A0A1U7MB88_9FIRM
635
0
71335
TrEMBL
A0A0J1FKG9_9FIRM
590
0
66449
TrEMBL
A0A1J5Q123_9ZZZZ
204
0
22453
TrEMBL
A0A0J1IC26_9FIRM
456
0
50510
TrEMBL
A0A0L6Z642_9CLOT
467
0
53231
TrEMBL
A0A0F0C978_9CLOT
633
0
72687
TrEMBL
A0A1A6B3R5_9CLOT
646
0
73047
TrEMBL
A0A1E7S338_BUTME
469
0
53554
TrEMBL
A0A1U7MIU5_9FIRM
601
0
68007
TrEMBL
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48000
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x * 48000, SDS-PAGE
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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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