KEGG   ENZYME: 1.14.14.149
Entry
EC 1.14.14.149              Enzyme                                 

Name
5-epiaristolochene 1,3-dihydroxylase;
5-epi-aristolochene 1,3-dihydroxylase;
EAH;
CYP71D20
Class
Oxidoreductases;
Acting on paired donors, with incorporation or reduction of molecular oxygen;
With reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen into the other donor
Sysname
5-epiaristolochene,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (1- and 3-hydroxylating)
Reaction(IUBMB)
5-epiaristolochene + 2 [reduced NADPH---hemoprotein reductase] + 2 O2 = capsidiol + 2 [oxidized NADPH---hemoprotein reductase] + 2 H2O [RN:R09573]
Reaction(KEGG)
R09573
Substrate
5-epiaristolochene [CPD:C19708];
[reduced NADPH---hemoprotein reductase] [CPD:C03024];
O2 [CPD:C00007]
Product
capsidiol [CPD:C09627];
[oxidized NADPH---hemoprotein reductase] [CPD:C03161];
H2O [CPD:C00001]
Comment
A cytochrome P-450 (heme-thiolate) protein. Kinetic studies suggest that 1beta-hydroxyepiaristolochene is mainly formed first followed by hydroxylation at C-3. However the reverse order via 3alpha-hydroxyepiaristolochene does occur.
History
EC 1.14.14.149 created 2011 as EC 1.14.13.119, transferred 2018 to EC 1.14.14.149
Pathway
ec00909  Sesquiterpenoid and triterpenoid biosynthesis
Orthology
K15805  5-epiaristolochene 1,3-dihydroxylase
Genes
SOT: 102602839
CANN: 107858875
NTA: 107759261(CYP71D20) 107795237 107825018(CYP71D21)
NSY: 104222453 104247522
NTO: 104116297
NAU: 109231983 109237630
Reference
1  [PMID:11556809]
  Authors
Ralston L, Kwon ST, Schoenbeck M, Ralston J, Schenk DJ, Coates RM, Chappell J
  Title
Cloning, heterologous expression, and functional characterization of 5-epi-aristolochene-1,3-dihydroxylase from tobacco (Nicotiana tabacum).
  Journal
Arch Biochem Biophys 393:222-35 (2001)
DOI:10.1006/abbi.2001.2483
  Sequence
Reference
2  [PMID:15522862]
  Authors
Takahashi S, Zhao Y, O'Maille PE, Greenhagen BT, Noel JP, Coates RM, Chappell J
  Title
Kinetic and molecular analysis of 5-epiaristolochene 1,3-dihydroxylase, a cytochrome P450 enzyme catalyzing successive hydroxylations of sesquiterpenes.
  Journal
J Biol Chem 280:3686-96 (2005)
DOI:10.1074/jbc.M411870200
  Sequence
Other DBs
ExplorEnz - The Enzyme Database: 1.14.14.149
IUBMB Enzyme Nomenclature: 1.14.14.149
ExPASy - ENZYME nomenclature database: 1.14.14.149
BRENDA, the Enzyme Database: 1.14.14.149

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