KEGG   ORTHOLOGY: K16265
Entry
K16265                      KO                                     

Name
CYP71E7
Definition
(E)-2-methylbutanal oxime monooxygenase [EC:1.14.14.41]
Pathway
ko00460  Cyanoamino acid metabolism
ko01100  Metabolic pathways
ko01110  Biosynthesis of secondary metabolites
Brite
KEGG Orthology (KO) [BR:ko00001]
 09100 Metabolism
  09106 Metabolism of other amino acids
   00460 Cyanoamino acid metabolism
    K16265  CYP71E7; (E)-2-methylbutanal oxime monooxygenase
 09180 Brite Hierarchies
  09181 Protein families: metabolism
   00199 Cytochrome P450
    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
Other DBs
RN: R10030 R10034 R11639 R11640 R11641 R11642
Genes
MESC: 110628704
AG: AAP57704(CYP71E7)
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

KEGG   ENZYME: 1.14.14.41
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
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
ec00460  Cyanoamino acid metabolism
ec01100  Metabolic pathways
ec01110  Biosynthesis of secondary metabolites
Orthology
K16265  (E)-2-methylbutanal oxime monooxygenase
Genes
MESC: 110628704
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 155:282-92 (2011)
DOI:10.1104/pp.110.164053
  Sequence
Other DBs
ExplorEnz - The Enzyme Database: 1.14.14.41
IUBMB Enzyme Nomenclature: 1.14.14.41
ExPASy - ENZYME nomenclature database: 1.14.14.41
BRENDA, the Enzyme Database: 1.14.14.41

KEGG   REACTION: R10034
Entry
R10034                      Reaction                               

Definition
(E)-2-Methylpropanal oxime <=> (Z)-2-Methylpropanal oxime
Equation
Comment
spontaneous
the first step of three-step reaction (see R11598, R10034+R11641+R11642)
Reaction class
RC03010  C03219_C20315
Enzyme
Pathway
rn00460  Cyanoamino acid metabolism
rn01100  Metabolic pathways
rn01110  Biosynthesis of secondary metabolites
Orthology
K16265  (E)-2-methylbutanal oxime monooxygenase [EC:1.14.14.41]
Other DBs
RHEA: 51959

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