KEGG   ORTHOLOGY: K16265Help
Entry
K16265                      KO                                     

Name
CYP71E7
Definition
(E)-2-methylbutanal oxime monooxygenase [EC:1.14.14.41]
Pathway
Cyanoamino acid metabolism
Brite
KEGG Orthology (KO) [BR:ko00001]
 Metabolism
  Metabolism of other amino acids
   00460 Cyanoamino acid metabolism
    K16265  CYP71E7; (E)-2-methylbutanal oxime monooxygenase
Enzymes [BR:ko01000]
 1. Oxidoreductases
  1.14  Acting on paired donors, with incorporation or reduction of molecular oxygen
   1.14.14  With reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen into the other donor
    1.14.14.41  (E)-2-methylbutanal oxime monooxygenase
     K16265  CYP71E7; (E)-2-methylbutanal oxime monooxygenase
Cytochrome P450 [BR:ko00199]
 Cytochrome P450, plant type
  CYP71 family
   K16265  CYP71E7; (E)-2-methylbutanal oxime monooxygenase
BRITE hierarchy
Genes
AG: 
AAP57704(CYP71E7)
TaxonomyKoalaUniProt
Reference
  Authors
Zhang P, Bohl-Zenger S, Puonti-Kaerlas J, Potrykus I, Gruissem W
  Title
Two cassava promoters related to vascular expression and storage root formation.
  Journal
Planta 218:192-203 (2003)
DOI:10.1007/s00425-003-1098-0
  Sequence
Reference
  Authors
Kannangara R, Motawia MS, Hansen NK, Paquette SM, Olsen CE, Moller BL, Jorgensen K
  Title
Characterization and expression profile of two UDP-glucosyltransferases, UGT85K4  and UGT85K5, catalyzing the last step in cyanogenic glucoside biosynthesis in cassava.
  Journal
Plant J 68:287-301 (2011)
DOI:10.1111/j.1365-313X.2011.04695.x
Reference
  Authors
Jorgensen K, Morant AV, Morant M, Jensen NB, Olsen CE, Kannangara R, Motawia MS, Moller BL, Bak S
  Title
Biosynthesis of the cyanogenic glucosides linamarin and lotaustralin in cassava:  isolation, biochemical characterization, and expression pattern of CYP71E7, the oxime-metabolizing cytochrome P450 enzyme.
  Journal
Plant Physiol 155:282-92 (2011)
DOI:10.1104/pp.110.164053
  Sequence
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KEGG   ENZYME: 1.14.14.41Help
Entry
EC 1.14.14.41               Enzyme                                 

Name
(E)-2-methylbutanal oxime monooxygenase;
CYP71E7 (gene name)
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
BRITE hierarchy
Sysname
(E)-2-methylbutanal oxime,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase
Reaction(IUBMB)
(1) (E)-2-methylbutanal oxime + [reduced NADPH---hemoprotein reductase] + O2 = 2-hydroxy-2-methylbutanenitrile + [oxidized NADPH---hemoprotein reductase] + 2 H2O (overall reaction) [RN:R11597];
(1a) (E)-2-methylbutanal oxime = (Z)-2-methylbutanal oxime [RN:R10030];
(1b) (Z)-2-methylbutanal oxime = 2-methylbutanenitrile + H2O [RN:R11639];
(1c) 2-methylbutanenitrile + [reduced NADPH---hemoprotein reductase] + O2 = 2-hydroxy-2-methylbutanenitrile + [oxidized NADPH---hemoprotein reductase] + H2O [RN:R11640];
(2) (E)-2-methylpropanal oxime + [reduced NADPH---hemoprotein reductase] + O2 = 2-hydroxy-2-methylpropanenitrile + [oxidized NADPH---hemoprotein reductase] + 2 H2O (overall reaction) [RN:R11598];
(2a) (E)-2-methylpropanal oxime = (Z)-2-methylpropanal oxime [RN:R10034];
(2b) (Z)-2-methylpropanal oxime = 2-methylpropanenitrile + H2O [RN:R11641];
(2c) 2-methylpropanenitrile + [reduced NADPH---hemoprotein reductase] + O2 = 2-hydroxy-2-methylpropanenitrile + [oxidized NADPH---hemoprotein reductase] + H2O [RN:R11642]
Reaction(KEGG)
Substrate
(E)-2-methylbutanal oxime [CPD:C19491];
[reduced NADPH---hemoprotein reductase] [CPD:C03024];
O2 [CPD:C00007];
(Z)-2-methylbutanal oxime [CPD:C20312];
2-methylbutanenitrile [CPD:C21525];
(E)-2-methylpropanal oxime [CPD:C03219];
(Z)-2-methylpropanal oxime [CPD:C20315];
2-methylpropanenitrile [CPD:C02420]
Product
2-hydroxy-2-methylbutanenitrile [CPD:C18796];
[oxidized NADPH---hemoprotein reductase] [CPD:C03161];
H2O [CPD:C00001];
(Z)-2-methylbutanal oxime [CPD:C20312];
2-methylbutanenitrile [CPD:C21525];
2-hydroxy-2-methylpropanenitrile [CPD:C02659];
(Z)-2-methylpropanal oxime [CPD:C20315];
2-methylpropanenitrile [CPD:C02420]
Comment
This cytochrome P-450 (heme thiolate) enzyme is involved in the biosynthesis of the cyanogenic glucosides lotaustralin and linamarin. It catalyses three different activities - isomerization of its substrate, the (E) isomer, to the (Z) isomer, dehydration, and C-hydroxylation.
History
EC 1.14.14.41 created 2017
Pathway
Cyanoamino acid metabolism
Biosynthesis of secondary metabolites
Orthology
K16265  
(E)-2-methylbutanal oxime monooxygenase
Reference
1  [PMID:21045121]
  Authors
Jorgensen K, Morant AV, Morant M, Jensen NB, Olsen CE, Kannangara R, Motawia MS, Moller BL, Bak S
  Title
Biosynthesis of the cyanogenic glucosides linamarin and lotaustralin in cassava:  isolation, biochemical characterization, and expression pattern of CYP71E7, the oxime-metabolizing cytochrome P450 enzyme.
  Journal
Plant. Physiol. 155 (2011) 282-92.
  Sequence
Other DBs
ExplorEnz - The Enzyme Database: 
IUBMB Enzyme Nomenclature: 
ExPASy - ENZYME nomenclature database: 
BRENDA, the Enzyme Database: 
LinkDB All DBs

KEGG   REACTION: R10038Help
Entry
R10038                      Reaction                               

Definition
(Z)-2-Methylpropanal oxime + NADPH + H+ + Oxygen <=> Acetone cyanohydrin + NADP+ + 2 H2O
Equation
Comment
CYP736A2
Reaction class
C00005_C00006
C02659_C20315
Pathway
Cyanoamino acid metabolism
Biosynthesis of secondary metabolites
LinkDB All DBs

KEGG   REACTION: R11641Help
Entry
R11641                      Reaction                               

Definition
(Z)-2-Methylpropanal oxime <=> Isobutyronitrile + H2O
Equation
Comment
second step of three-step reaction (see R11598, R10034+R11641+R11642)
Enzyme
Pathway
Cyanoamino acid metabolism
Biosynthesis of secondary metabolites
LinkDB All DBs

KEGG   REACTION: R11642Help
Entry
R11642                      Reaction                               

Definition
Isobutyronitrile + [Reduced NADPH---hemoprotein reductase] + Oxygen <=> Acetone cyanohydrin + [Oxidized NADPH---hemoprotein reductase] + H2O
Equation
Comment
last step of three-step reaction (see R11598, R10034+R11641+R11642)
Enzyme
Pathway
Cyanoamino acid metabolism
Biosynthesis of secondary metabolites
LinkDB All DBs

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