4-hydroxyphenylacetaldehyde oxime monooxygenase [EC:1.14.14.37]

PMID:9484480

Bak S, Kahn RA, Nielsen HL, Moller BL, Halkier BA

Cloning of three A-type cytochromes P450, CYP71E1, CYP98, and CYP99 from Sorghum  bicolor (L.) Moench by a PCR approach and identification by expression in Escherichia coli of CYP71E1 as a multifunctional cytochrome P450 in the biosynthesis of the cyanogenic glucoside dhurrin.

Plant Mol Biol 36:393-405 (1998)
DOI:10.1023/A:1005915507497

[sbi:SORBI_01g001180]

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

(E)-4-hydroxyphenylacetaldehyde oxime,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase

(E)-4-hydroxyphenylacetaldehyde oxime + [reduced NADPH---hemoprotein reductase] + O2 = (S)-4-hydroxymandelonitrile + [oxidized NADPH---hemoprotein reductase] + 2 H2O (overall reaction) [RN:R05728];
(1a) (E)-4-hydroxyphenylacetaldehyde oxime = (Z)-4-hydroxyphenylacetaldehyde oxime [RN:R11442];
(1b) (Z)-4-hydroxyphenylacetaldehyde oxime = 4-hydroxyphenylacetonitrile + H2O [RN:R04306];
(1c) 4-hydroxyphenylacetonitrile + [reduced NADPH---hemoprotein reductase] + O2 = (S)-4-hydroxymandelonitrile + [oxidized NADPH---hemoprotein reductase] + H2O [RN:R02708]

R02708 R04306 R05728 R11442

(E)-4-hydroxyphenylacetaldehyde oxime [CPD:C04350];
[reduced NADPH---hemoprotein reductase] [CPD:C03024];
O2 [CPD:C00007];
(Z)-4-hydroxyphenylacetaldehyde oxime [CPD:C04353];
4-hydroxyphenylacetonitrile [CPD:C03766]

This cytochrome P-450 (heme thiolate) enzyme is involved in the biosynthesis of the cyanogenic glucoside dhurrin in sorghum. It catalyses three different activities - isomerization of the (E) isomer to the (Z) isomer, dehydration, and C-hydroxylation.

EC 1.14.14.37 created 2000 as EC 1.14.13.68, modified 2005, transferred 2016 to EC 1.14.14.37

1  [PMID:237909]

MacFarlane IJ, Lees EM, Conn EE.

The in vitro biosynthesis of dhurrin, the cyanogenic glycoside of Sorghum bicolor.

J. Biol. Chem. 250 (1975) 4708-13.

2  [PMID:193443]

Shimada M, Conn EE.

The enzymatic conversion of p-hydroxyphenylacetaldoxime to p-hydroxymandelonitrile.

Arch. Biochem. Biophys. 180 (1977) 199-207.

3  [PMID:12114576]

Busk PK, Moller BL.

Dhurrin synthesis in sorghum is regulated at the transcriptional level and induced by nitrogen fertilization in older plants.

Plant. Physiol. 129 (2002) 1222-31.

4  [PMID:15665094]

Kristensen C, Morant M, Olsen CE, Ekstrom CT, Galbraith DW, Moller BL, Bak S.

Metabolic engineering of dhurrin in transgenic Arabidopsis plants with marginal inadvertent effects on the metabolome and transcriptome.

Proc. Natl. Acad. Sci. U. S. A. 102 (2005) 1779-84.

5  [PMID:26361733]

Clausen M, Kannangara RM, Olsen CE, Blomstedt CK, Gleadow RM, Jorgensen K, Bak S, Motawie MS, Moller BL

The bifurcation of the cyanogenic glucoside and glucosinolate biosynthetic pathways.

Plant. J. 84 (2015) 558-73.