EC 1.14.14.37 - 4-hydroxyphenylacetaldehyde oxime monooxygenase

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IntEnz Enzyme Nomenclature
EC 1.14.14.37

Names

Accepted name:
4-hydroxyphenylacetaldehyde oxime monooxygenase
Other names:
4-hydroxybenzeneacetaldehyde oxime monooxygenase
NADPH-cytochrome P450 reductase (CYP71E1)
cytochrome P450II-dependent monooxygenase
4-hydroxyphenylacetaldehyde oxime,NADPH:oxygen oxidoreductase
CYP71E1
Systematic name:
(E)-4-hydroxyphenylacetaldehyde oxime,[reduced NADPH—hemoprotein reductase]:oxygen oxidoreductase

Reaction

Cofactor

Comments:

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. This enzyme is involved in the biosynthesis of the cyanogenic glucoside dhurrin in sorghum, along with EC 1.14.13.41, tyrosine N-monooxygenase and EC 2.4.1.85, cyanohydrin β-glucosyltransferase.

Links to other databases

Enzymes and pathways: NC-IUBMB , BRENDA , DIAGRAM , ExplorEnz , ENZYME@ExPASy , KEGG , MetaCyc , UniPathway
Protein domains and families: PROSITE:PDOC00081
Structural data: CSA , EC2PDB
Gene Ontology: GO:0050592
UniProtKB/Swiss-Prot:

References

  1. MacFarlane, I.J., Lees, E.M. and Conn, E.E.
    The in vitro biosynthesis of dhurrin, the cyanogenic glycoside of Sorghum bicolor.
    J. Biol. Chem. 250: 4708-4713 (1975). [PMID: 237909]
  2. Shimada, M. and Conn, E.E.
    The enzymatic conversion of p-hydroxyphenylacetaldoxime to p-hydroxymandelonitrile.
    Arch. Biochem. Biophys. 180: 199-207 (1977). [PMID: 193443]
  3. Busk, P.K. and Møller, B.L.
    Dhurrin synthesis in sorghum is regulated at the transcriptional level and induced by nitrogen fertilization in older plants.
    Plant Physiol. 129: 1222-1231 (2002). [PMID: 12114576]
  4. Kristensen, C., Morant, M., Olsen, C.E., Ekstrøm, C.T., Galbraith, D.W., Møller, B.L. and Bak, S.
    Metabolic engineering of dhurrin in transgenic Arabidopsis plants with marginal inadvertent effects on the metabolome and transcriptome.
    Proc. Natl. Acad. Sci. USA 102: 1779-1784 (2005). [PMID: 15665094]
  5. Clausen, M., Kannangara, R. M., Olsen, C. E., Blomstedt, C. K., Gleadow, R. M., Jørgensen, K., Bak, S., Motawie, M. S., Møller, B. L.
    The bifurcation of the cyanogenic glucoside and glucosinolate biosynthetic pathways.
    Plant J. 84: 558-573 (2015). [PMID: 26361733]

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