KEGG   ORTHOLOGY: K12645Help
Entry
K12645                      KO                                     

Name
CYP170A
Definition
epi-isozizaene 5-monooxygenase / beta-farnesene synthase [EC:1.14.13.106 4.2.3.47]
Pathway
ko00909  Sesquiterpenoid and triterpenoid biosynthesis
ko01130  Biosynthesis of antibiotics
Brite
KEGG Orthology (KO) [BR:ko00001]
 09100 Metabolism
  09109 Metabolism of terpenoids and polyketides
   00909 Sesquiterpenoid and triterpenoid biosynthesis
    K12645  CYP170A; epi-isozizaene 5-monooxygenase / beta-farnesene synthase
 09180 Brite Hierarchies
  09181 Protein families: metabolism
   00199 Cytochrome P450
    K12645  CYP170A; epi-isozizaene 5-monooxygenase / beta-farnesene synthase
Enzymes [BR:ko01000]
 1. Oxidoreductases
  1.14  Acting on paired donors, with incorporation or reduction of molecular oxygen
   1.14.13  With NADH or NADPH as one donor, and incorporation of one atom of oxygen into the other donor
    1.14.13.106  epi-isozizaene 5-monooxygenase
     K12645  CYP170A; epi-isozizaene 5-monooxygenase / beta-farnesene synthase
 4. Lyases
  4.2  Carbon-oxygen lyases
   4.2.3  Acting on phosphates
    4.2.3.47  beta-farnesene synthase
     K12645  CYP170A; epi-isozizaene 5-monooxygenase / beta-farnesene synthase
Cytochrome P450 [BR:ko00199]
 Cytochrome P450, bacteria type
  CYP170 family
   K12645  CYP170A; epi-isozizaene 5-monooxygenase / beta-farnesene synthase
BRITE hierarchy
Other DBs
RN: R08695 R08851 R08852 R08853 R08854 R10072
COG: COG2124
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
 » show all
TaxonomyKoalaUniProt
Reference
  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]
Reference
  Authors
Zhao B, Lei L, Vassylyev DG, Lin X, Cane DE, Kelly SL, Yuan H, Lamb DC, Waterman MR
  Title
Crystal structure of albaflavenone monooxygenase containing a moonlighting terpene synthase active site.
  Journal
J Biol Chem 284:36711-9 (2009)
DOI:10.1074/jbc.M109.064683
  Sequence
[sco:SCO5223]

KEGG   ENZYME: 1.14.13.106Help
Entry
EC 1.14.13.106              Enzyme                                 

Name
epi-isozizaene 5-monooxygenase;
CYP170A1
Class
Oxidoreductases;
Acting on paired donors, with incorporation or reduction of molecular oxygen;
With NADH or NADPH as one donor, and incorporation of one atom of oxygen into the other donor
BRITE hierarchy
Sysname
(+)-epi-isozizaene,NADPH:oxygen oxidoreductase (5-hydroxylating)
Reaction(IUBMB)
(+)-epi-isozizaene + 2 NADPH + 2 H+ + 2 O2 = albaflavenone + 2 NADP+ + 3 H2O (overall reaction) [RN:R10072];
(1a) (+)-epi-isozizaene + NADPH + H+ + O2 = (5S)-albaflavenol + NADP+ + H2O [RN:R08851];
(1b) (5S)-albaflavenol + NADPH + H+ + O2 = albaflavenone + NADP+ + 2 H2O [RN:R08852];
(2a) (+)-epi-isozizaene + NADPH + H+ + O2 = (5R)-albaflavenol + NADP+ + H2O [RN:R08853];
(2b) (5R)-albaflavenol + NADPH + H+ + O2 = albaflavenone + NADP+ + 2 H2O [RN:R08854]
Reaction(KEGG)
Substrate
(+)-epi-isozizaene [CPD:C16269];
NADPH [CPD:C00005];
H+ [CPD:C00080];
O2 [CPD:C00007];
(5S)-albaflavenol [CPD:C17953];
(5R)-albaflavenol [CPD:C17955]
Product
albaflavenone [CPD:C17954];
NADP+ [CPD:C00006];
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 1.14.13.106 created 2008
Pathway
ec00909  Sesquiterpenoid and triterpenoid biosynthesis
ec01130  Biosynthesis of antibiotics
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
 » show all
Taxonomy
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: 1.14.13.106
IUBMB Enzyme Nomenclature: 1.14.13.106
ExPASy - ENZYME nomenclature database: 1.14.13.106
BRENDA, the Enzyme Database: 1.14.13.106
CAS: 1207718-51-1

KEGG   REACTION: R08851Help
Entry
R08851                      Reaction                               

Name
(+)-epi-isozizaene,NADPH:oxygen oxidoreductase (5S-hydroxylating)
Definition
(+)-epi-Isozizaene + NADPH + H+ + Oxygen <=> (5S)-Albaflavenol + NADP+ + H2O
Equation
Reaction class
RC00001  C00005_C00006
RC00723  C16269_C17953
Enzyme
Pathway
rn00909  Sesquiterpenoid and triterpenoid biosynthesis
rn01130  Biosynthesis of antibiotics
Orthology
K12645  epi-isozizaene 5-monooxygenase / beta-farnesene synthase [EC:1.14.13.106 4.2.3.47]
Other DBs
RHEA: 25979

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