KEGG ORTHOLOGY: K16265

ORTHOLOGY: K16265

Entry

K16265                      KO

Symbol

CYP71E7

Name

(E)-2-methylbutanal oxime monooxygenase [EC:1.14.14.41]

Pathway

map00460

Cyanoamino acid metabolism

map01100

Metabolic pathways

map01110

Biosynthesis of secondary metabolites

Reaction

R10030

R10034

R11639

R11640

R11641

R11642

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

Genes

HBR:	110649556 110670770

MESC:

110628704 110628705

AG:	AAP57704(CYP71E7)

Reference

PMID:13680228

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

[ag:AAP57704]

Reference

PMID:21736650

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

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

LinkDB

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)

R10030 R10034 R11597 R11598 R11639 R11640 R11641 R11642

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

HBR:	110649556 110670770

MESC:

110628704 110628705

Reference

1 [PMID:21045121]

Authors

Jorgensen K, Morant AV, Morant M, Jensen NB, Olsen CE, Kannangara R, Motawia MS, Moller BL, Bak S

Title

Journal

Plant Physiol 155:282-92 (2011)
DOI:10.1104/pp.110.164053

Sequence

[ag:AAP57704]

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

LinkDB

REACTION: R11641

Entry

R11641                      Reaction

Definition

(Z)-2-Methylpropanal oxime <=> Isobutyronitrile + H2O

Equation

C20315 <=> C02420 + C00001

Comment

the second step of three-step reaction (see R11598, R10034+R11641+R11642)

Reaction class

RC03480

C02420_C20315

Enzyme

1.14.14.41

Pathway

rn00460

Cyanoamino acid metabolism

rn01100

Metabolic pathways

rn01110

Biosynthesis of secondary metabolites

Brite

Enzymatic reactions [BR:br08201]
1. Oxidoreductase reactions
  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
     R11641  (Z)-2-Methylpropanal oxime <=> Isobutyronitrile + H2O

Orthology

K16265

(E)-2-methylbutanal oxime monooxygenase [EC:1.14.14.41]

Other DBs

RHEA:

51963

LinkDB

REACTION: R11642

Entry

R11642                      Reaction

Definition

Isobutyronitrile + [Reduced NADPH---hemoprotein reductase] + Oxygen <=> Acetone cyanohydrin + [Oxidized NADPH---hemoprotein reductase] + H2O

Equation

C02420 + C03024 + C00007 <=> C02659 + C03161 + C00001

Comment

the last step of three-step reaction (see R11598, R10034+R11641+R11642)

Reaction class

RC03495

C02420_C02659

Enzyme

1.14.14.41

Pathway

rn00460

Cyanoamino acid metabolism

rn01100

Metabolic pathways

rn01110

Biosynthesis of secondary metabolites

Brite

Enzymatic reactions [BR:br08201]
1. Oxidoreductase reactions
  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
     R11642  Isobutyronitrile + [Reduced NADPH---hemoprotein reductase] + Oxygen <=> Acetone cyanohydrin + [Oxidized NADPH---hemoprotein reductase] + H2O

Orthology

K16265

(E)-2-methylbutanal oxime monooxygenase [EC:1.14.14.41]

Other DBs

RHEA:

51967

LinkDB

DBGET integrated database retrieval system