KEGG   ENZYME: 1.14.15.39
Entry
EC 1.14.15.39               Enzyme                                 
Name
epi-isozizaene 5-monooxygenase;
CYP170A1
Class
Oxidoreductases;
Acting on paired donors, with incorporation or reduction of molecular oxygen;
With reduced iron-sulfur protein as one donor, and incorporation of one atom of oxygen into the other donor
Sysname
(+)-epi-isozizaene,reduced-ferredoxin:oxygen oxidoreductase (5-hydroxylating)
Reaction(IUBMB)
(+)-epi-isozizaene + 4 reduced [2Fe-2S] ferredoxin + 4 H+ + 2 O2 = albaflavenone + 4 oxidized [2Fe-2S] ferredoxin + 3 H2O (overall reaction) [RN:R10072];
(1a) (+)-epi-isozizaene + 2 reduced [2Fe-2S] ferredoxin + 2 H+ + O2 = (5S)-albaflavenol + 2 oxidized [2Fe-2S] ferredoxin + H2O [RN:R08851];
(1b) (5S)-albaflavenol + 2 reduced [2Fe-2S] ferredoxin + 2 H+ + O2 = albaflavenone + 2 oxidized [2Fe-2S] ferredoxin + 2 H2O [RN:R08852];
(2a) (+)-epi-isozizaene + 2 reduced [2Fe-2S] ferredoxin + 2 H+ + O2 = (5R)-albaflavenol + 2 oxidized [2Fe-2S] ferredoxin + H2O [RN:R08853];
(2b) (5R)-albaflavenol + 2 reduced [2Fe-2S] ferredoxin + 2 H+ + O2 = albaflavenone + 2 oxidized [2Fe-2S] ferredoxin + 2 H2O [RN:R08854]
Reaction(KEGG)
Substrate
(+)-epi-isozizaene [CPD:C16269];
reduced [2Fe-2S] ferredoxin [CPD:C22150];
H+ [CPD:C00080];
O2 [CPD:C00007];
(5S)-albaflavenol [CPD:C17953];
(5R)-albaflavenol [CPD:C17955]
Product
albaflavenone [CPD:C17954];
oxidized [2Fe-2S] ferredoxin [CPD:C22151];
H2O [CPD:C00001];
(5S)-albaflavenol [CPD:C17953];
(5R)-albaflavenol [CPD:C17955]
Comment
This cytochrome-P-450 enzyme, from the soil-dwelling bacterium Streptomyces coelicolor A3(2), catalyses two sequential allylic oxidation reactions. The substrate epi-isozizaene, which is formed by the action of EC 4.2.3.37, epi-isozizaene synthase, is first oxidized to yield the epimeric intermediates (5R)-albaflavenol and (5S)-albaflavenol, which can be further oxidized to yield the sesquiterpenoid antibiotic albaflavenone.
History
EC 1.14.15.39 created 2008 as EC 1.14.13.106, transferred 2021 to EC 1.14.15.39
Pathway
ec00909  Sesquiterpenoid and triterpenoid biosynthesis
ec01110  Biosynthesis of secondary metabolites
Orthology
K12645  epi-isozizaene 5-monooxygenase / beta-farnesene synthase
Genes
SCOSCO5223(SC7E4.20)
SALBXNR_1579
SMASAVERM_3031(cyp14)
SHYSHJG_6336
SHOSHJGH_6097
SDVBN159_3154
SALSSLNWT_2071
SCIB446_24615
SLVSLIV_12250
SGUSGLAU_22465
SCWTU94_21770
SAMBSAM23877_5011
SCXAS200_17630
SRWTUE45_05743
STRFASR50_23825
SLEsle_25170(sle_25170)
SPAVSpa2297_22090
STRTA8713_21095
SGSAVL59_06870
STSIA4E84_26815
SKYD0C37_09630
SALWCP975_23795
SGMGCM10017557_26710
SCADDN051_14270
SPHWNFX46_06120
SLSSLINC_5615
SPLULK06_022340
STRDNI25_13050
SSIAA7J05_12560
SPUNBFF78_14830
SALFSMD44_05800
SFKKY5_5349
SNZDC008_23215
SGEDWG14_02916
SRJSRO_2585
SDXC4B68_13425
SGDELQ87_13270
SCYAEJ357_30820
SASTCD934_10765
SNQCP978_22470
SKACP970_14415
SHAWCEB94_27440
SGALCP966_24285
SFYGFH48_14920
SAQUEJC51_32140
SGFHEP81_02793
SSEOD0Z67_19540
SFUGCNQ36_23700
SPACB1H29_12435
SCHACP983_14565
SCOECP976_28740
SSPBCP982_27725
SBROGQF42_28700
STUIGCM10017668_47530
SCHFIPT68_24090
SCYGS1361_25900
SFEUIM697_37485
SVDCP969_25545
SPRACP972_23865
SROIIAG44_13190
SXNIAG42_11635
SHKJ2N69_24780
SDDD9753_11940
SACTDMT42_26025
SLFJEQ17_16410
SAOVG3H79_11730
SDURM4V62_15475
 » show all
Reference
1  [PMID:18234666]
  Authors
Zhao B, Lin X, Lei L, Lamb DC, Kelly SL, Waterman MR, Cane DE
  Title
Biosynthesis of the sesquiterpene antibiotic albaflavenone in Streptomyces coelicolor A3(2).
  Journal
J Biol Chem 283:8183-9 (2008)
DOI:10.1074/jbc.M710421200
  Sequence
[sco:SCO5223]
Other DBs
ExplorEnz - The Enzyme Database: 1.14.15.39
IUBMB Enzyme Nomenclature: 1.14.15.39
ExPASy - ENZYME nomenclature database: 1.14.15.39
BRENDA, the Enzyme Database: 1.14.15.39
CAS: 1207718-51-1

DBGET integrated database retrieval system