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Information on EC 1.14.15.11 - pentalenic acid synthase for references in articles please use BRENDA:EC1.14.15.11
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EC Tree
IUBMB Comments A heme-thiolate enzyme (P-450). Isolated from the bacterium Streptomyces avermitilis. The product, pentalenate, is a co-metabolite from pentalenolactone biosynthesis.
The enzyme appears in viruses and cellular organisms
Synonyms
CYP105D7, CYP28, pentalenic acid synthase,
sav7469 ,
SAV_7469 ,
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CYP105D7
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pentalenic acid synthase
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pentalenic acid synthase
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SAV_7469
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1-deoxypentalenate + reduced ferredoxin + O2 = pentalenate + oxidized ferredoxin + H2O
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1-deoxypentalenate,reduced ferredoxin:O2 oxidoreductase
A heme-thiolate enzyme (P-450). Isolated from the bacterium Streptomyces avermitilis. The product, pentalenate, is a co-metabolite from pentalenolactone biosynthesis.
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1-deoxypentalenic acid + reduced ferredoxin + O2
pentalenic acid + oxidized ferredoxin + H2O
compactin + reduced ferredoxin + O2
pravastatin + oxidized ferredoxin + H2O
compactin + reduced putidaredoxin + O2
pravastatin + oxidized putidaredoxin + H2O
diclofenac + reduced ferredoxin + O2
4'-hydroxydiclofenac + oxidized ferredoxin + H2O
diclofenac + reduced putidaredoxin + O2
4'-hydroxydiclofenac + oxidized putidaredoxin + H2O
additional information
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1-deoxypentalenic acid + reduced ferredoxin + O2
pentalenic acid + oxidized ferredoxin + H2O
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1-deoxypentalenic acid + reduced ferredoxin + O2
pentalenic acid + oxidized ferredoxin + H2O
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compactin + reduced ferredoxin + O2
pravastatin + oxidized ferredoxin + H2O
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compactin + reduced ferredoxin + O2
pravastatin + oxidized ferredoxin + H2O
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compactin + reduced putidaredoxin + O2
pravastatin + oxidized putidaredoxin + H2O
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compactin + reduced putidaredoxin + O2
pravastatin + oxidized putidaredoxin + H2O
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diclofenac + reduced ferredoxin + O2
4'-hydroxydiclofenac + oxidized ferredoxin + H2O
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diclofenac + reduced ferredoxin + O2
4'-hydroxydiclofenac + oxidized ferredoxin + H2O
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diclofenac + reduced putidaredoxin + O2
4'-hydroxydiclofenac + oxidized putidaredoxin + H2O
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diclofenac + reduced putidaredoxin + O2
4'-hydroxydiclofenac + oxidized putidaredoxin + H2O
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additional information
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enzyme additionally catalyzes the hydroxylation of daidzein to 7,3',4'-trihydroxyisoflavone with apparent Km and kcat values for daidzein of 21.83 mM and 15.01 per min in the presence of putidaredoxin and putidaredoxin reductase, respectively
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additional information
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no substrates: pentalenene, 1-deoxy-11beta-hydroxypentalenic acid, 1-deoxy-11-oxopentalenic acid, or the corresponding methyl esters of 1-deoxy-11beta-hydroxypentalenic acid, 1-deoxy-11-oxopentalenic acid and 1-deoxypentalenic acid, respectively
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additional information
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enzyme additionally catalyzes the hydroxylation of daidzein to 7,3',4'-trihydroxyisoflavone with apparent Km and kcat values for daidzein of 21.83 mM and 15.01 per min in the presence of putidaredoxin and putidaredoxin reductase, respectively
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0.027
1-deoxypentalenic acid
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pH 8.0, 25°C
0.039
Compactin
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pH 7.4, 30°C
0.19
diclofenac
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pH 7.4, 30°C
additional information
diclofenac
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CYP105D7 binds diclofenac in a slightly cooperative manner with an affinity of 65 microM and a Hill coefficient of 1.16, pH not specified in the publication, temperature not specified in the publication
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0.018
Compactin
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pH 7.4, 30°C
0.36
diclofenac
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pH 7.4, 30°C
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0.48
Compactin
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pH 7.4, 30°C
1.9
diclofenac
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pH 7.4, 30°C
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UniProt
brenda
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UniProt
brenda
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UniProt
brenda
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physiological function
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disruption of the sav7469 gene encoding pentalenic acid synthase abolishes production of pentalenic acid. The deletion mutant accumulates 1-deoxypentalenic acid. Recombinant enzyme prepared from Escherichia coli catalyzes the oxidative conversion of 1-deoxypentalenic acid to pentalenic acid in the presence of the electron-transport partners, ferredoxin and ferredoxin reductase, both in vivo and in vitro
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CYP28_STRAW
Streptomyces avermitilis (strain ATCC 31267 / DSM 46492 / JCM 5070 / NBRC 14893 / NCIMB 12804 / NRRL 8165 / MA-4680)
402
0
44113
Swiss-Prot
A0A1Y2MLN9_PSEAH
399
0
44150
TrEMBL
A0A1V2RC73_9ACTN
401
0
45011
TrEMBL
A0A433DRC3_9ACTN
407
0
45300
TrEMBL
A0A387HPL8_9ACTN
424
0
47219
TrEMBL
A0A2K8QWX7_9ACTN
399
0
44198
TrEMBL
A0A5B7V818_9ACTN
408
0
44979
TrEMBL
A0A3N6F9N6_9ACTN
406
0
45349
TrEMBL
A0A1Y2NG16_STRPT
408
0
44773
TrEMBL
A0A1Y2NL66_STRPT
395
0
43904
TrEMBL
A0A3N6GZG9_9ACTN
406
0
45632
TrEMBL
A0A0B8NDN6_9NOCA
406
0
44487
TrEMBL
A0A2P8A9R8_9ACTN
412
0
45272
TrEMBL
A0A5B7V3A5_9ACTN
430
0
47674
TrEMBL
A0A1Y2NB83_STRPT
428
0
45920
TrEMBL
A0A178X0S7_9PSEU
393
0
42557
TrEMBL
A0A2K8PNY1_STRLA
395
0
43761
TrEMBL
A0A2N9BKY9_STRCX
398
0
44258
TrEMBL
A0A433DWB5_9ACTN
416
0
45807
TrEMBL
A0A3N6G9Z4_9ACTN
392
0
44342
TrEMBL
A0A3N6DUM1_9ACTN
408
0
44926
TrEMBL
A0A3G4VP63_9ACTN
395
0
43717
TrEMBL
A0A100JE39_9ACTN
406
0
44485
TrEMBL
A0A1K2FLF7_9ACTN
409
0
45208
TrEMBL
A0A178WU10_9PSEU
396
0
42999
TrEMBL
A0A178WVD2_9PSEU
155
0
16880
TrEMBL
A0A1Q2ZLZ3_9ACTN
406
0
44470
TrEMBL
A0A1Y5TTC4_9PROT
392
0
44662
TrEMBL
A0A2P9FFI1_9ACTN
396
0
43089
TrEMBL
A0A3N6FF75_9ACTN
408
0
45595
TrEMBL
A0A168IQ27_9ACTN
404
0
44012
TrEMBL
A0A3N6HHY7_9ACTN
393
0
44301
TrEMBL
A0A178WYH9_9PSEU
406
0
43723
TrEMBL
A0A1D8BYU9_9PSEU
408
0
43546
TrEMBL
A0A3N6EMM2_9ACTN
405
0
44849
TrEMBL
A0A221WAP2_9PSEU
405
0
44933
TrEMBL
A0A100JAG8_9ACTN
398
0
43948
TrEMBL
A0A1V2RS67_9ACTN
397
0
42817
TrEMBL
A0A433DRG1_9ACTN
406
0
45587
TrEMBL
A0A1B2GNK8_STRNR
395
0
44033
TrEMBL
A0A445NB50_STRNE
410
0
45045
TrEMBL
A0A5B7V9R5_9ACTN
256
0
27692
TrEMBL
A0A3N6GBS9_9ACTN
397
0
43632
TrEMBL
A0A1D2IFC0_9ACTN
423
0
46572
TrEMBL
A0A178XD47_9PSEU
395
0
43226
TrEMBL
A0A3N6IA41_9ACTN
398
0
43901
TrEMBL
A0A3N6CXJ5_9ACTN
395
0
43774
TrEMBL
A0A221W573_9PSEU
401
0
44641
TrEMBL
A0A1L7F9Z8_9PSEU
420
0
46386
TrEMBL
A0A3N6IS14_9ACTN
412
0
45111
TrEMBL
A0A1Y2NIU8_STRPT
404
0
44899
TrEMBL
A0A2P9FCH1_9ACTN
406
0
44785
TrEMBL
A0A168IKZ7_9ACTN
398
0
43334
TrEMBL
A0A0Q0HH78_9GAMM
398
0
44934
TrEMBL
A0A2K8RJQ7_9ACTN
420
0
46384
TrEMBL
A0A5B7V2W8_9ACTN
397
0
44041
TrEMBL
A0A3N6F7D9_9ACTN
388
0
42759
TrEMBL
A0A3N6FFF0_9ACTN
398
0
43754
TrEMBL
A0A1V2MT02_9ACTN
416
0
45781
TrEMBL
A0A3N6GPH9_9ACTN
391
0
44899
TrEMBL
A0A117E6X6_9ACTN
410
0
45464
TrEMBL
A0A2S6X4H8_9ACTN
427
0
46826
TrEMBL
A0A2K8RH03_9ACTN
407
0
45367
TrEMBL
A0A445NFA4_STRNE
420
0
45864
TrEMBL
A0A178X0D7_9PSEU
404
0
44351
TrEMBL
A0A3N6H8Z1_9ACTN
422
0
46789
TrEMBL
A0A4P7C9Z4_9PSEU
394
0
43052
TrEMBL
A0A1Q2ZEA0_9ACTN
395
0
43827
TrEMBL
A0A385ZGL3_9ACTN
399
0
44220
TrEMBL
A0A5B7V368_9ACTN
401
0
43772
TrEMBL
A0A3G4VM45_9ACTN
408
0
44970
TrEMBL
A0A231GVG8_9NOCA
408
0
45127
TrEMBL
A0A221W545_9PSEU
406
0
44951
TrEMBL
A0A1K2G2S5_9ACTN
404
0
43928
TrEMBL
A0A3N6ENL5_9ACTN
401
0
44175
TrEMBL
A0A1L7F9X4_9PSEU
408
0
45376
TrEMBL
A0A5B7V9R9_9ACTN
302
0
32746
TrEMBL
A0A1Y2NHD1_STRPT
408
0
45632
TrEMBL
A0A100J4D7_9ACTN
395
0
43923
TrEMBL
A0A1Q2ZB40_9ACTN
401
0
43903
TrEMBL
A0A2Z5KD24_9ACTN
401
0
44461
TrEMBL
A0A3N6J259_9ACTN
410
0
44545
TrEMBL
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Streptomyces avermitilis (strain ATCC 31267 / DSM 46492 / JCM 5070 / NBRC 14893 / NCIMB 12804 / NRRL 8165 / MA-4680)
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?
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x * 45000, SDS-PAGE, recombinant protein with His-tag
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x * 45000, SDS-PAGE, recombinant protein
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x * 45000, SDS-PAGE, recombinant protein; x * 45000, SDS-PAGE, recombinant protein with His-tag
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in complex with diclofenac, at 2.2 A resolution. The distal pocket of CYP105D7 contains two diclofenac molecules. The C3' and C4' atoms of the dichlorophenyl ring of one diclofenac molecule are positioned near the heme iron
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molecular docking of compactin, compactin is directly hydrogen bonded with residues Thr79, Arg81, Leu178, Thr391, and Ile392 and its C6 position is proximate to the heme group. Molecular docking of diclofenac
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expression in Escheirchia coli
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expression in Escherichia coli
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Pandey, B.P.; Roh, C.; Choi, K.Y.; Lee, N.; Kim, E.J.; Ko, S.; Kim, T.; Yun, H.; Kim, B.G.
Regioselective hydroxylation of daidzein using P450 (CYP105D7) from Streptomyces avermitilis MA4680
Biotechnol. Bioeng.
105
697-704
2010
Streptomyces avermitilis (Q825I8), Streptomyces avermitilis, Streptomyces avermitilis MA-4680 (Q825I8)
brenda
Takamatsu, S.; Xu, L.H.; Fushinobu, S.; Shoun, H.; Komatsu, M.; Cane, D.E.; Ikeda, H.
Pentalenic acid is a shunt metabolite in the biosynthesis of the pentalenolactone family of metabolites: hydroxylation of 1-deoxypentalenic acid mediated by CYP105D7 (SAV_7469) of Streptomyces avermitilis
J. Antibiot.
64
65-71
2011
Streptomyces avermitilis (Q825I8), Streptomyces avermitilis
brenda
Xu, L.; Ikeda, H.; Liu, L.; Arakawa, T.; Wakagi, T.; Shoun, H.; Fushinobu, S.
Structural basis for the 4'-hydroxylation of diclofenac by a microbial cytochrome P450 monooxygenase
Appl. Microbiol. Biotechnol.
99
3081-3091
2015
Streptomyces avermitilis (Q825I8), Streptomyces avermitilis, Streptomyces avermitilis DSM 46492 (Q825I8)
brenda
Yao, Q.; Ma, L.; Liu, L.; Ikeda, H.; Fushinobu, S.; Li, S.; Xu, L.H.
Hydroxylation of Compactin (ML-236B) by CYP105D7 (SAV_7469) from Streptomyces avermitilis
J. Microbiol. Biotechnol.
27
956-964
2017
Streptomyces avermitilis (Q825I8), Streptomyces avermitilis, Streptomyces avermitilis DSM 46492 (Q825I8)
brenda
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Enzyme Nomenclature
1.14.15.11 pentalenic acid synthase
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