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Information on EC 1.14.14.39 - isoleucine N-monooxygenase

for references in articles please use BRENDA:EC1.14.14.39
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IUBMB Comments
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.
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The enzyme appears in viruses and cellular organisms
Synonyms
CYP79D1, CYP79D2, CYP79D3, CYP79D4, valine N-monooxygenase, more
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
L-isoleucine + 2 [reduced NADPH-hemoprotein reductase] + 2 O2 = (1E,2S)-2-methylbutanal oxime + 2 [oxidized NADPH-hemoprotein reductase] + CO2 + 3 H2O
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overall reaction
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L-isoleucine + [reduced NADPH-hemoprotein reductase] + O2 = N-hydroxy-L-isoleucine + [oxidized NADPH-hemoprotein reductase] + H2O
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(1a)
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N,N-dihydroxy-L-isoleucine = (1E,2S)-2-methylbutanal oxime + CO2 + H2O
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spontaneous
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N-hydroxy-L-isoleucine + [reduced NADPH-hemoprotein reductase] + O2 = N,N-dihydroxy-L-isoleucine + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
(1b)
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