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
SCO: SCO5223(SC7E4.20)
SALB: XNR_1579
SMA: SAVERM_3031(cyp14)
SHY: SHJG_6336
SHO: SHJGH_6097
SDV: BN159_3154
SALS: SLNWT_2071
SCI: B446_24615
SLV: SLIV_12250
SGU: SGLAU_22465
SLE: sle_25170(sle_25170)
STRD: NI25_13050
SFK: KY5_5349
SRJ: SRO_2585
 » 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

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