KEGG   ORTHOLOGY: K14984
Entry
K14984                      KO                                     
Symbol
CYP79D3_4
Name
isoleucine N-monooxygenase [EC:1.14.14.39]
Pathway
map00460  Cyanoamino acid metabolism
map00966  Glucosinolate biosynthesis
map01100  Metabolic pathways
map01110  Biosynthesis of secondary metabolites
map01210  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: Lj0g3v0137329.1(Lj0g3v0137329.1) Lj3g3v0744720.1(Lj3g3v0744720.1) Lj3g3v0755150.1(Lj3g3v0755150.1)
EGT: 105961699
ZOF: 121972575 122010758 122010762 122013737 122013740
AG: AAT11920(CYP79D3) AAT11921(CYP79D4)
Reference
PMID:15122013 (CYP79D3 CYP79D4)
  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
[ag:AAT11920 AAT11921]
LinkDB

KEGG   ORTHOLOGY: K13401
Entry
K13401                      KO                                     
Symbol
CYP79D1_2
Name
valine N-monooxygenase [EC:1.14.14.38]
Pathway
map00460  Cyanoamino acid metabolism
map00966  Glucosinolate biosynthesis
map01100  Metabolic pathways
map01110  Biosynthesis of secondary metabolites
map01210  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 105650274
HBR: 110641550 110660829
MESC: 110627795 110629733
ZOF: 121973513 122013704
AG: AAF27289(CYP79D1) AAF27290(CYP79D2) AAV97888(CYP79D2) AAV97889(CYP79D1)
Reference
PMID:16126856 (CYP79D2 CYP79D1)
  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
[ag:AAV97888 AAV97889]
Reference
PMID:10636899 (CYP79D1 CYP79D2)
  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
[ag:AAF27289 AAF27290]
LinkDB

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)
R08663 R10031 R10032 R10033;
(other) R10027 R10028 R10029
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 105650274
HBR: 110641550 110660829
MESC: 110627795 110629733
ZOF: 121973513 122013704
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
[ag:AAF27289 AAF27290]
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
LinkDB

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)
R09403 R10027 R10028 R10029;
(other) R10031 R10032 R10033
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: Lj0g3v0137329.1(Lj0g3v0137329.1) Lj3g3v0744720.1(Lj3g3v0744720.1) Lj3g3v0755150.1(Lj3g3v0755150.1)
EGT: 105961699
ZOF: 121972575 122010758 122010762 122013737 122013740
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
[ag:AAT11920 AAT11921]
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
LinkDB

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
C20313 + C00007 + C03024 <=> C20314 + C03161 + C00001
Comment
the second step of three-step reaction (see R08663, R10031+R10032+R10033)
Reaction class
RC00001  C00005_C00006
RC01918  C20313_C20314
Enzyme
1.14.14.38      1.14.14.39
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
LinkDB

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