KEGG ENZYME: 1.14.14.151

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)

R09576 R09577 R10073

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

MEAN:

126681142 126681143

SLY:

101251277

SPEN:

107017184

SOT:	102603519 102603857(CYP71D4)

SSTN:

125856537 125877776

SDUL:

129902541 129902995

CANN:

107868116

LBB:	132614420 132614445

NTA:	107793096 107814513(CYP71D51)

NSY:

104210979

NTO:

104103514

NAU:

109237629

INI:	109147615 109147616 109147619 109147633 109158643 109158692 109189513

ITR:	116001823 116005968 116005969 116005970 116005998 116006057 116006210 116006311 116006362 116006381 116007608 116007666 116007672 116032610

EGT:	105963174 105964617 105975226 105975298 105975392

SSPL:

121743157 121743400 121746146 121750166 121750558 121752413 121754189 121756890 121757276 121757976 121757977 121758417 121759075 121759076 121759080 121759081 121759086 121759088 121761699 121770564 121771349 121779689 121779749 121783560 121783915 121784616 121811461

SMIL:

131000167 131000168 131004834 131012417 131015133 131015134 131015156 131015163 131015164 131015165 131015166 131015167 131018238 131019089 131024881 131024882 131024883 131024884 131024894

SHIS:

125188132 125188135 125188693 125188694 125188695 125188696 125191597 125195624 125195625 125195626 125196687 125197473 125212978 125214595 125215950 125216107 125217106 125222007

APAN:

127255383 127255441 127255451 127255481 127255694 127256012 127265602 127266544

ECAD:

122585186

RVL:	131312856 131312865 131328861

ZOF:	121979433 122019938 122023670

MSIN:

131219493

» show all

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

[ag:ABS00393]

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

All links

Protein sequence (66)   
   UniProt (65)   
   SWISS-PROT (1)   
DNA sequence (2)   
   GenBank (1)   
   EMBL (1)   
Protein domain (5)   
   InterPro (5)   
All databases (73)   

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