4-hydroxyphenylacetaldehyde oxime monooxygenase

4-hydroxyphenylacetaldehyde oxime monooxygenase
Identifiers
EC no.	1.14.13.68
Databases
IntEnz	IntEnz view
BRENDA	BRENDA entry
ExPASy	NiceZyme view
KEGG	KEGG entry
MetaCyc	metabolic pathway
PRIAM	profile
PDB structures	RCSB PDB PDBe PDBsum
Gene Ontology	AmiGO / QuickGO
Search PMC articles PubMed articles NCBI proteins

In enzymology, a 4-hydroxyphenylacetaldehyde oxime monooxygenase (EC 1.14.13.68) is an enzyme that catalyzes the chemical reaction

(Z)-4-hydroxyphenylacetaldehyde oxime + NADPH + H⁺ + O₂${\displaystyle \rightleftharpoons }$ (S)-4-hydroxymandelonitrile + NADP⁺ + 2 H₂O

The 4 substrates of this enzyme are (Z)-4-hydroxyphenylacetaldehyde oxime, NADPH, H⁺, and O₂, whereas its 3 products are (S)-4-hydroxymandelonitrile, NADP⁺, and H₂O.

This enzyme belongs to the family of oxidoreductases, specifically those acting on paired donors, with O2 as oxidant and incorporation or reduction of oxygen. The oxygen incorporated need not be derived from O2 with NADH or NADPH as one donor, and incorporation of one atom o oxygen into the other donor. The systematic name of this enzyme class is (Z)-4-hydroxyphenylacetaldehyde oxime,NADPH:oxygen oxidoreductase. Other names in common use include 4-hydroxybenzeneacetaldehyde oxime monooxygenase, cytochrome P450II-dependent monooxygenase, NADPH-cytochrome P450 reductase (CYP71E1), CYP71E1, and 4-hydroxyphenylacetaldehyde oxime,NADPH:oxygen oxidoreductase. This enzyme participates in tyrosine metabolism.

References

• MacFarlane IJ, Lees EM, Conn EE (1975). "The in vitro biosynthesis of dhurrin, the cyanogenic glycoside of Sorghum bicolor". J. Biol. Chem. 250 (12): 4708–13. doi: 10.1016/S0021-9258(19)41359-8 . PMID   237909.
• Shimada M, Conn EE (1977). "The enzymatic conversion of p-hydroxyphenylacetaldoxime to p-hydroxymandelonitrile". Arch. Biochem. Biophys. 180 (1): 199–207. doi:10.1016/0003-9861(77)90026-1. PMID   193443.
• Busk PK, Moller BL (2002). "Dhurrin synthesis in sorghum is regulated at the transcriptional level and induced by nitrogen fertilization in older plants". Plant Physiol. 129 (3): 1222–31. doi:10.1104/pp.000687. PMC   166516 . PMID   12114576.
• BL, Bak S; Morant, M; Olsen, CE; Ekstrøm, CT; Galbraith, DW; Møller, BL; Bak, S (2005). "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 (5): 1779–84. Bibcode:2005PNAS..102.1779K. doi: 10.1073/pnas.0409233102 . PMC   545087 . PMID   15665094.