KEGG   ORTHOLOGY: K14984
Entry
K14984                      KO                                     

Name
CYP79D3_4
Definition
isoleucine N-monooxygenase [EC:1.14.14.39]
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
    K14984  CYP79D3_4; isoleucine N-monooxygenase
  09110 Biosynthesis of other secondary metabolites
   00966 Glucosinolate biosynthesis
    K14984  CYP79D3_4; isoleucine N-monooxygenase
 09180 Brite Hierarchies
  09181 Protein families: metabolism
   00199 Cytochrome P450
    K14984  CYP79D3_4; isoleucine 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
    1.14.14.39  isoleucine N-monooxygenase
     K14984  CYP79D3_4; isoleucine N-monooxygenase
Cytochrome P450 [BR:ko00199]
 Cytochrome P450, plant type
  CYP79 family
   K14984  CYP79D3_4; isoleucine N-monooxygenase
Other DBs
RN: R09403 R10027 R10028 R10029 R10031 R10032 R10033
Genes
LJA: Lj3g3v0755150.1(Lj3g3v0755150.1)
AG: AAT11920(CYP79D3) AAT11921(CYP79D4)
Reference
  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
  Sequence

KEGG   ENZYME: 1.14.14.39
Entry
EC 1.14.14.39               Enzyme                                 

Name
isoleucine N-monooxygenase;
CYP79D3 (gene name);
CYP79D4 (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
L-isoleucine,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (N-hydroxylating)
Reaction(IUBMB)
L-isoleucine + 2 [reduced NADPH---hemoprotein reductase] + 2 O2 = (1E,2S)-2-methylbutanal oxime + 2 [oxidized NADPH---hemoprotein reductase] + CO2 + 3 H2O (overall reaction) [RN:R09403];
(1a) L-isoleucine + [reduced NADPH---hemoprotein reductase] + O2 = N-hydroxy-L-isoleucine + [oxidized NADPH---hemoprotein reductase] + H2O [RN:R10027];
(1b) N-hydroxy-L-isoleucine + [reduced NADPH---hemoprotein reductase] + O2 = N,N-dihydroxy-L-isoleucine + [oxidized NADPH---hemoprotein reductase] + H2O [RN:R10028];
(1c) N,N-dihydroxy-L-isoleucine = (1E,2S)-2-methylbutanal oxime + CO2 + H2O (spontaneous) [RN:R10029]
Reaction(KEGG)
Substrate
L-isoleucine [CPD:C00407];
[reduced NADPH---hemoprotein reductase] [CPD:C03024];
O2 [CPD:C00007];
N-hydroxy-L-isoleucine [CPD:C20310];
N,N-dihydroxy-L-isoleucine [CPD:C20311]
Product
(1E,2S)-2-methylbutanal oxime;
[oxidized NADPH---hemoprotein reductase] [CPD:C03161];
CO2 [CPD:C00011];
H2O [CPD:C00001];
N-hydroxy-L-isoleucine [CPD:C20310];
N,N-dihydroxy-L-isoleucine [CPD:C20311]
Comment
This cytochrome P-450 (heme-thiolate) enzyme, found in plants, catalyses two successive N-hydroxylations of L-isoleucine, the committed step in the biosynthesis of the cyanogenic glucoside lotaustralin. The product of the two hydroxylations, N,N-dihydroxy-L-isoleucine, is labile and undergoes dehydration followed by decarboxylation, producing the oxime. It is still not known whether the decarboxylation is spontaneous or catalysed by the enzyme. The enzyme can also accept L-valine, but with a lower activity. cf. EC 1.14.14.38, valine N-monooxygenase.
History
EC 1.14.14.39 created 2010 as EC 1.14.13.117, transferred 2017 to EC 1.14.14.39
Pathway
ec00460  Cyanoamino acid metabolism
ec00966  Glucosinolate biosynthesis
ec01100  Metabolic pathways
ec01110  Biosynthesis of secondary metabolites
Orthology
K14984  isoleucine N-monooxygenase
Genes
LJA: Lj3g3v0755150.1(Lj3g3v0755150.1)
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
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
  Sequence
Other DBs
ExplorEnz - The Enzyme Database: 1.14.14.39
IUBMB Enzyme Nomenclature: 1.14.14.39
ExPASy - ENZYME nomenclature database: 1.14.14.39
BRENDA, the Enzyme Database: 1.14.14.39

KEGG   REACTION: R10029
Entry
R10029                      Reaction                               

Definition
N,N-Dihydroxy-L-isoleucine <=> (E)-2-Methylbutanal oxime + CO2 + H2O
Equation
Comment
the last step of three-step reaction (see R09403, R10027+R10028+R10029)
Reaction class
RC03009  C19491_C20311
Enzyme
Pathway
rn00460  Cyanoamino acid metabolism
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: 30490

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