KEGG ENZYME: 1.14.14.42

ENZYME: 1.14.14.42

Entry

EC 1.14.14.42 Enzyme

Name

homomethionine N-monooxygenase;
CYP79F1 (gene name);
CYP79F2 (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-homomethionine,[NADPH---hemoprotein reductase]:oxygen oxidoreductase

Reaction(IUBMB)

an L-polyhomomethionine + 2 [reduced NADPH---hemoprotein reductase] + 2 O2 = an omega-(methylthio)-(E)-alkanal oxime + 2 [oxidized NADPH---hemoprotein reductase] + CO2 + 3 H2O (overall reaction) [RN:R11646];
(1a) an L-polyhomomethionine + [reduced NADPH---hemoprotein reductase] + O2 = an L-N-hydroxypolyhomomethionine + [oxidized NADPH---hemoprotein reductase] + H2O [RN:R11647];
(1b) an L-N-hydroxypolyhomomethionine + [reduced NADPH---hemoprotein reductase] + O2 = an L-N,N-dihydroxypolyhomomethionine + [oxidized NADPH---hemoprotein reductase] + H2O [RN:R11648];
(1c) an L-N,N-dihydroxypolyhomomethionine = omega-(methylthio)-(E)-alkanal oxime + CO2 + H2O [RN:R11649]

Reaction(KEGG)

R11646 > R08665 R08670 R08672 R08673 R08674 R08675;
R11647 R11648 R11649

Substrate

L-polyhomomethionine [CPD:C21534];
[reduced NADPH---hemoprotein reductase] [CPD:C03024];
O2 [CPD:C00007];
L-N-hydroxypolyhomomethionine [CPD:C21536];
L-N,N-dihydroxypolyhomomethionine [CPD:C21537]

Product

omega-(methylthio)-(E)-alkanal oxime [CPD:C21535];
[oxidized NADPH---hemoprotein reductase] [CPD:C03161];
CO2 [CPD:C00011];
H2O [CPD:C00001];
L-N-hydroxypolyhomomethionine [CPD:C21536];
L-N,N-dihydroxypolyhomomethionine [CPD:C21537]

Comment

This plant cytochrome P-450 (heme thiolate) enzyme is involved in methionine-derived aliphatic glucosinolates biosynthesis. It catalyses two successive N-hydroxylations, which are followed by dehydration and decarboxylation. CYP79F1 from Arabidopsis thaliana can metabolize homo-, di-, tri-, tetra-, penta-, and hexahomomethionine to their corresponding aldoximes, while CYP79F2 from the same plant can only metabolize penta- and hexahomomethionine.

History

EC 1.14.14.42 created 2017

Pathway

ec00966	Glucosinolate biosynthesis
ec01110	Biosynthesis of secondary metabolites

Orthology

K12154	homomethionine N-monooxygenase
K12155	homomethionine N-monooxygenase

Genes

ATH:	AT1G16400(CYP79F2) AT1G16410(CYP79F1)
ALY:	ARALYDRAFT_312617 ARALYDRAFT_889032
CRB:	CARUB_v10010983mg CARUB_v10011470mg
EUS:	EUTSA_v10007301mg
BRP:	103872429(CYP79F1)
BNA:	106367453(CYP79F1)
THJ:	104812394

Reference

1 [PMID:11133994]

Authors

Hansen CH, Wittstock U, Olsen CE, Hick AJ, Pickett JA, Halkier BA.

Title

Cytochrome p450 CYP79F1 from arabidopsis catalyzes the conversion of dihomomethionine and trihomomethionine to the corresponding aldoximes in the biosynthesis of aliphatic glucosinolates.

Journal

J. Biol. Chem. 276 (2001) 11078-85.

Reference

2 [PMID:12609033]

Authors

Chen S, Glawischnig E, Jorgensen K, Naur P, Jorgensen B, Olsen CE, Hansen CH, Rasmussen H, Pickett JA, Halkier BA

Title

CYP79F1 and CYP79F2 have distinct functions in the biosynthesis of aliphatic glucosinolates in Arabidopsis.

Journal

Plant. J. 33 (2003) 923-37.

Sequence

[ath:AT1G16410 AT1G16400]