KEGG   ORTHOLOGY: K13401
Entry
K13401                      KO                                     

Name
CYP79D1_2
Definition
valine N-monooxygenase [EC:1.14.14.38]
Pathway
ko00460  Cyanoamino acid metabolism
ko00966  Glucosinolate biosynthesis
ko01100  Metabolic pathways
ko01110  Biosynthesis of secondary metabolites
ko01210  2-Oxocarboxylic acid metabolism
Brite
KEGG Orthology (KO) [BR:ko00001]
 09100 Metabolism
  09106 Metabolism of other amino acids
   00460 Cyanoamino acid metabolism
    K13401  CYP79D1_2; valine N-monooxygenase
  09110 Biosynthesis of other secondary metabolites
   00966 Glucosinolate biosynthesis
    K13401  CYP79D1_2; valine N-monooxygenase
 09180 Brite Hierarchies
  09181 Protein families: metabolism
   00199 Cytochrome P450
    K13401  CYP79D1_2; valine N-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
    1.14.14.38  valine N-monooxygenase
     K13401  CYP79D1_2; valine N-monooxygenase
Cytochrome P450 [BR:ko00199]
 Cytochrome P450, plant type
  CYP79 family
   K13401  CYP79D1_2; valine N-monooxygenase
Other DBs
RN: R08663 R10027 R10028 R10029 R10031 R10032 R10033
Genes
RCU: 8273208
JCU: 105641619
HBR: 110641550
MESC: 110627795 110629733
AG: AAF27289(CYP79D1) AAF27290(CYP79D2) AAV97888(CYP79D2) AAV97889(CYP79D1)
Reference
  Authors
Jorgensen K, Bak S, Busk PK, Sorensen C, Olsen CE, Puonti-Kaerlas J, Moller BL
  Title
Cassava plants with a depleted cyanogenic glucoside content in leaves and tubers. Distribution of cyanogenic glucosides, their site of synthesis and transport, and blockage of the biosynthesis by RNA interference technology.
  Journal
Plant Physiol 139:363-74 (2005)
DOI:10.1104/pp.105.065904
  Sequence
Reference
  Authors
Andersen MD, Busk PK, Svendsen I, Moller BL
  Title
Cytochromes P-450 from cassava (Manihot esculenta Crantz) catalyzing the first steps in the biosynthesis of the cyanogenic glucosides linamarin and lotaustralin. Cloning, functional expression in Pichia pastoris, and substrate specificity of the isolated recombinant enzymes.
  Journal
J Biol Chem 275:1966-75 (2000)
DOI:10.1074/jbc.275.3.1966
  Sequence

KEGG   ENZYME: 1.14.14.38
Entry
EC 1.14.14.38               Enzyme                                 

Name
valine N-monooxygenase;
CYP79D1;
CYP79D2
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
L-valine,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (N-hydroxylating)
Reaction(IUBMB)
L-valine + 2 [reduced NADPH---hemoprotein reductase] + 2 O2 = (E)-2-methylpropanal oxime + 2 [oxidized NADPH---hemoprotein reductase] + CO2 + 3 H2O (overall reaction) [RN:R08663];
(1a) L-valine + [reduced NADPH---hemoprotein reductase] + O2 = N-hydroxy-L-valine + [oxidized NADPH---hemoprotein reductase] + H2O [RN:R10031];
(1b) N-hydroxy-L-valine + [reduced NADPH---hemoprotein reductase] + O2 = N,N-dihydroxy-L-valine + [oxidized NADPH---hemoprotein reductase] + H2O [RN:R10032];
(1c) N,N-dihydroxy-L-valine = (E)-2-methylpropanal oxime + CO2 + H2O [RN:R10033]
Reaction(KEGG)
Substrate
L-valine [CPD:C00183];
[reduced NADPH---hemoprotein reductase] [CPD:C03024];
O2 [CPD:C00007];
N-hydroxy-L-valine [CPD:C20313];
N,N-dihydroxy-L-valine [CPD:C20314]
Product
(E)-2-methylpropanal oxime [CPD:C03219];
[oxidized NADPH---hemoprotein reductase] [CPD:C03161];
CO2 [CPD:C00011];
H2O [CPD:C00001];
N-hydroxy-L-valine [CPD:C20313];
N,N-dihydroxy-L-valine [CPD:C20314]
Comment
A cytochrome P-450 (heme-thiolate) protein. This enzyme catalyses two successive N-hydroxylations of L-valine, the committed step in the biosynthesis of the cyanogenic glucoside linamarin in Manihot esculenta (cassava). The product of the two hydroxylations, N,N-dihydroxy-L-valine, is labile and undergoes dehydration and decarboxylation that produce the (E) isomer of the oxime. It is still not known whether the decarboxylation is spontaneous or catalysed by the enzyme. The enzyme can also accept L-isoleucine as substrate, with a lower activity. It is different from EC 1.14.14.39, isoleucine N-monooxygenase, which prefers L-isoleucine.
History
EC 1.14.14.38 created 2010 as EC 1.14.13.118, transferred 2017 to EC 1.14.14.38
Pathway
ec00460  Cyanoamino acid metabolism
ec00966  Glucosinolate biosynthesis
ec01100  Metabolic pathways
ec01110  Biosynthesis of secondary metabolites
Orthology
K13401  valine N-monooxygenase
Genes
RCU: 8273208
JCU: 105641619
HBR: 110641550
MESC: 110627795 110629733
Reference
1  [PMID:10636899]
  Authors
Andersen MD, Busk PK, Svendsen I, Moller BL
  Title
Cytochromes P-450 from cassava (Manihot esculenta Crantz) catalyzing the first steps in the biosynthesis of the cyanogenic glucosides linamarin and lotaustralin. Cloning, functional expression in Pichia pastoris, and substrate specificity of the isolated recombinant enzymes.
  Journal
J Biol Chem 275:1966-75 (2000)
DOI:10.1074/jbc.275.3.1966
  Sequence
Reference
2  [PMID:15122013]
  Authors
Forslund K, Morant M, Jorgensen B, Olsen CE, Asamizu E, Sato S, Tabata S, Bak S
  Title
Biosynthesis of the nitrile glucosides rhodiocyanoside A and D and the cyanogenic glucosides lotaustralin and linamarin in Lotus japonicus.
  Journal
Plant Physiol 135:71-84 (2004)
DOI:10.1104/pp.103.038059
Other DBs
ExplorEnz - The Enzyme Database: 1.14.14.38
IUBMB Enzyme Nomenclature: 1.14.14.38
ExPASy - ENZYME nomenclature database: 1.14.14.38
BRENDA, the Enzyme Database: 1.14.14.38

KEGG   REACTION: R10032
Entry
R10032                      Reaction                               

Name
N-hydroxy-L-valine,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (N-hydroxylating)
Definition
N-Hydroxy-L-valine + Oxygen + [Reduced NADPH---hemoprotein reductase] <=> N,N-Dihydroxy-L-valine + [Oxidized NADPH---hemoprotein reductase] + H2O
Equation
Comment
the second step of three-step reaction (see R08663, R10031+R10032+R10033)
Reaction class
RC00001  C00005_C00006
RC01918  C20313_C20314
Enzyme
Pathway
rn00460  Cyanoamino acid metabolism
rn01100  Metabolic pathways
rn01110  Biosynthesis of secondary metabolites
Orthology
K13401  valine N-monooxygenase [EC:1.14.14.38]
K14984  isoleucine N-monooxygenase [EC:1.14.14.39]
Other DBs
RHEA: 30498

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