KEGG   ENZYME: 1.14.19.69
Entry
EC 1.14.19.69               Enzyme                                 
Name
biflaviolin synthase;
CYP158A2 (gene name);
cytochrome P450 158A2
Class
Oxidoreductases;
Acting on paired donors, with incorporation or reduction of molecular oxygen;
With oxidation of a pair of donors resulting in the reduction of O2 to two molecules of water
Sysname
flaviolin,reduced ferredoxin:oxygen oxidoreductase
Reaction(IUBMB)
(1) 2 flaviolin + 2 reduced ferredoxin [iron-sulfur] cluster + 2 H+ + O2 = 3,3'-biflaviolin + 2 oxidized ferredoxin [iron-sulfur] cluster + 2 H2O [RN:R08912];
(2) 2 flaviolin + 2 reduced ferredoxin [iron-sulfur] cluster + 2 H+ + O2 = 3,8'-biflaviolin + 2 oxidized ferredoxin [iron-sulfur] cluster + 2 H2O [RN:R08913]
Reaction(KEGG)
R08912 R08913
Substrate
flaviolin [CPD:C18012];
reduced ferredoxin [iron-sulfur] cluster [CPD:C00138];
H+ [CPD:C00080];
O2 [CPD:C00007]
Product
3,3'-biflaviolin [CPD:C18013];
oxidized ferredoxin [iron-sulfur] cluster [CPD:C00139];
H2O [CPD:C00001];
3,8'-biflaviolin [CPD:C18014]
Comment
This cytochrome-P-450 (heme-thiolate) enzyme, from the soil-dwelling bacterium Streptomyces coelicolor A3(2), catalyses a phenol oxidation C-C coupling reaction, which results in the polymerization of flaviolin to form biflaviolin or triflaviolin without the incorporation of oxygen into the product [1,3]. The products are highly conjugated pigments that protect the bacterium from the deleterious effects of UV irradiation [1].
History
EC 1.14.19.69 created 2008 as EC 1.14.21.7, transferred 2018 to EC 1.14.19.69
Orthology
K13074  biflaviolin synthase
K19628  biflaviolin synthase
Genes
SCOSCO1207(2SCG58.07) SCO6998(SC8F11.24c)
SMASAVERM_7130(cyp25)
SHYSHJG_2646 SHJG_6732
SHOSHJGH_2410 SHJGH_6492
SVESVEN_0292 SVEN_5366
SDVBN159_1508 BN159_7378(cyp25)
SCIB446_03420 B446_06315 B446_31265
SLVSLIV_04255 SLIV_31760
SAMBSAM23877_1287
SRWTUE45_01598 TUE45_06139
SRNA4G23_00271 A4G23_05455
SPAVSpa2297_04360
STRTA8713_04010 A8713_28145
SGSAVL59_15725 AVL59_31510
SGMGCM10017557_72050(cyp158a2)
SLSSLINC_1367 SLINC_7316
SPLULK06_002085 LK06_002215
STRDNI25_04195 NI25_33215
SSIAA7J05_03050
SPUNBFF78_05845 BFF78_35590
SLAUSLA_0187 SLA_5576
SRJSRO_1057 SRO_6250
SDXC4B68_35490
SGDELQ87_04520 ELQ87_33735
SNQCP978_05720 CP978_32540
STIRDDW44_24845 DDW44_24855
SGZC0216_11395 C0216_11405
SVNCP980_05715 CP980_05725
SHAWCEB94_06405 CEB94_36095
SRKFGW37_13515 FGW37_13520 FGW37_29145
SFICEIZ62_00760 EIZ62_06600
SSPODDQ41_26480 DDQ41_26495
SFYGFH48_17515 GFH48_34415
SAQUEJC51_08475 EJC51_40200
SGFHEP81_01023 HEP81_06601
SSEOD0Z67_03145 D0Z67_28205
SBYH7H31_02850
SBROGQF42_08485 GQF42_38225
STUIGCM10017668_08030
SCHFIPT68_05175
SCYGS1361_06200 S1361_27985
SLIAHA039_01305 HA039_03435
SFBCP974_01420 CP974_29035
SROIIAG44_34390 IAG44_34940
SXNIAG42_30910 IAG42_33830
SHKJ2N69_10825
SDDD9753_09915 D9753_30940
SACTDMT42_33155
SLFJEQ17_39905
SSPNLXH13_05465 LXH13_34165
SCIRSTRCI_001131 STRCI_007007
SARGHKX69_09470 HKX69_30290
SJNRI060_05125 RI060_36660
SCYNN8I84_06605
SKGKJK29_03605 KJK29_33430
SCOAQU709_03860 QU709_37870
SROCRGF97_07810 RGF97_31845 RGF97_31855
SCHGNRO40_02080 NRO40_28110
SINNABB07_04420 ABB07_32760
SCTSCAT_5028
SCYSCATT_50200
SENSACE_1242(cyp25)
SACGFDZ84_31495 FDZ84_36320
KBUQ4V64_06690
KPHYAOZ06_26080 AOZ06_26100
 » show all
Reference
1  [PMID:15659395]
  Authors
Zhao B, Guengerich FP, Bellamine A, Lamb DC, Izumikawa M, Lei L, Podust LM, Sundaramoorthy M, Kalaitzis JA, Reddy LM, Kelly SL, Moore BS, Stec D, Voehler M, Falck JR, Shimada T, Waterman MR
  Title
Binding of two flaviolin substrate molecules, oxidative coupling, and crystal structure of Streptomyces coelicolor A3(2) cytochrome P450 158A2.
  Journal
J Biol Chem 280:11599-607 (2005)
DOI:10.1074/jbc.M410933200
  Sequence
[sco:SCO1207]
Reference
2  [PMID:16239228]
  Authors
Zhao B, Guengerich FP, Voehler M, Waterman MR
  Title
Role of active site water molecules and substrate hydroxyl groups in oxygen activation by cytochrome P450 158A2: a new mechanism of proton transfer.
  Journal
J Biol Chem 280:42188-97 (2005)
DOI:10.1074/jbc.M509220200
  Sequence
[sco:SCO1207]
Reference
3  [PMID:17614370]
  Authors
Zhao B, Lamb DC, Lei L, Kelly SL, Yuan H, Hachey DL, Waterman MR
  Title
Different binding modes of two flaviolin substrate molecules in cytochrome P450 158A1 (CYP158A1) compared to CYP158A2.
  Journal
Biochemistry 46:8725-33 (2007)
DOI:10.1021/bi7006959
  Sequence
[sco:SCO6998]
Other DBs
ExplorEnz - The Enzyme Database: 1.14.19.69
IUBMB Enzyme Nomenclature: 1.14.19.69
ExPASy - ENZYME nomenclature database: 1.14.19.69
BRENDA, the Enzyme Database: 1.14.19.69

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