KEGG   ENZYME: 1.14.14.151
Entry
EC 1.14.14.151              Enzyme                                 

Name
premnaspirodiene oxygenase;
HPO;
Hyoscymus muticus premnaspirodiene oxygenase;
CYP71D55
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
(-)-vetispiradiene,[reduced NADPH---hemoprotein reductase]:oxygen 2alpha-oxidoreductase
Reaction(IUBMB)
(-)-vetispiradiene + 2 [reduced NADPH---hemoprotein reductase] + 2 O2 = solavetivone + 2 [oxidized NADPH---hemoprotein reductase] + 3 H2O (overall reaction) [RN:R10073];
(1a) (-)-vetispiradiene + [reduced NADPH---hemoprotein reductase] + O2 = solavetivol + [oxidized NADPH---hemoprotein reductase] + H2O [RN:R09576];
(1b) solavetivol + [reduced NADPH---hemoprotein reductase] + O2 = solavetivone + [oxidized NADPH---hemoprotein reductase] + 2 H2O [RN:R09577]
Reaction(KEGG)
Substrate
(-)-vetispiradiene [CPD:C12142];
[reduced NADPH---hemoprotein reductase] [CPD:C03024];
O2 [CPD:C00007];
solavetivol [CPD:C19711]
Product
solavetivone [CPD:C09737];
[oxidized NADPH---hemoprotein reductase] [CPD:C03161];
H2O [CPD:C00001];
solavetivol [CPD:C19711]
Comment
A cytochrome P-450 (heme-thiolate) protein. The enzyme from the plant Hyoscymus muticus also hydroxylates valencene at C-2 to give the alpha-hydroxy compound, nootkatol, and this is converted into nootkatone. 5-Epiaristolochene and epieremophilene are hydroxylated at C-2 to give a 2beta-hydroxy derivatives that are not oxidized further.
History
EC 1.14.14.151 created 2011 as EC 1.14.13.121, transferred 2018 to EC 1.14.14.151
Pathway
ec00909  Sesquiterpenoid and triterpenoid biosynthesis
ec01110  Biosynthesis of secondary metabolites
Orthology
K15472  premnaspirodiene oxygenase
Genes
SLY: 101251277
SPEN: 107017184
SOT: 102603857(CYP71D4)
CANN: 107868116
NTA: 107793096 107814513(CYP71D51)
NSY: 104210979
NAU: 109237629
Reference
1  [PMID:17715131]
  Authors
Takahashi S, Yeo YS, Zhao Y, O'Maille PE, Greenhagen BT, Noel JP, Coates RM, Chappell J
  Title
Functional characterization of premnaspirodiene oxygenase, a cytochrome P450 catalyzing regio- and stereo-specific hydroxylations of diverse sesquiterpene substrates.
  Journal
J Biol Chem 282:31744-54 (2007)
DOI:10.1074/jbc.M703378200
  Sequence
Other DBs
ExplorEnz - The Enzyme Database: 1.14.14.151
IUBMB Enzyme Nomenclature: 1.14.14.151
ExPASy - ENZYME nomenclature database: 1.14.14.151
BRENDA, the Enzyme Database: 1.14.14.151

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