Protein Information

Name cytochrome P450 (protein family or complex)
Synonyms cytochrome P450; cytochrome P 450; CYP450; CYP 450

Compound Information

Name hydrogen cyanide
CAS hydrocyanic acid

Reference List

PubMed Abstract RScore(About this table)
3556837 Freeman JJ, Hayes EP: The metabolism of acetonitrile to cyanide by isolated rat hepatocytes. . Fundam Appl Toxicol. 1987 Feb;8(2):263-71.

The metabolism of saturated nitriles, including acetonitrile, has been assumed to occur by a cytochrome P-450-dependent oxidation at the alpha-carbon, yielding a cyanohydrin intermediate which may spontaneously degrade to hydrogen cyanide and an aldehyde.
32(0,1,1,2) Details
6301381 Totani K, Iizuka T, Shimada H, Makino R, Ishimura Y: Proton coupling in the ligand-binding reaction of ferric cytochrome P-450 from Pseudomonas putida. Arch Biochem Biophys. 1983 Apr 1;222(1):207-15.

When a dissociable ligand such as hydrogen cyanide and N-methylimidazole was used, the dissociated form of the ligand had a higher affinity toward the heme than the undissociated form.
3(0,0,0,3) Details
10938360 Bak S, Olsen CE, Halkier BA, Moller BL: Transgenic tobacco and Arabidopsis plants expressing the two multifunctional sorghum cytochrome P450 enzymes, CYP79A1 and CYP71E1, are cyanogenic and accumulate metabolites derived from intermediates in Dhurrin biosynthesis. Plant Physiol. 2000 Aug;123(4):1437-48.

CYP79A1 catalyzes the conversion of tyrosine to p-hydroxyphenylacetaldoxime and CYP71E1, the subsequent conversion to p-hydroxymandelonitrile. p-Hydroxymandelonitrile is labile and dissociates into p-hydroxybenzaldehyde and hydrogen cyanide, the same products released from dhurrin upon cell disruption as a result of pest or herbivore attack.
3(0,0,0,3) Details
6130913 Fenselau C, Lehman JP, Myles A, Brandt J, Yost GS, Friedman OM, Colvin OM: Iminocyclophosphamide as a chemically reactive metabolite of cyclophosphamide. Drug Metab Dispos. 1982 Nov-Dec;10(6):636-40.

Iminocyclophosphamide has been identified among the metabolites produced by incubation of cyclophosphamide with cytochrome P-450 mono-oxygenase immobilized on beaded Sepharose.
The reactive imine was trapped by addition of hydrogen cyanide, and the product, 4-cyanocyclophosphamide, was identified by comparison of its chromatographic and mass-spectral properties with those of a synthetic standard.
1(0,0,0,1) Details
18458107 Olsen KM, Hsu SC, Small LL: Evidence on the molecular basis of the Ac/ac adaptive cyanogenesis polymorphism in white clover (Trifolium repens L). Genetics. 2008 May;179(1):517-26. Epub 2008 May 5.


Here we report evidence that Ac corresponds to a gene encoding a cytochrome P450 of the CYP79D protein subfamily (CYP79D15), and we describe the apparent molecular basis of the Ac/ac polymorphism.
1(0,0,0,1) Details
19954531 Zagrobelny M, Scheibye-Alsing K, Jensen NB, Moller BL, Gorodkin J, Bak S: 454 pyrosequencing based transcriptome analysis of Zygaena filipendulae with focus on genes involved in biosynthesis of cyanogenic glucosides. BMC Genomics. 2009 Dec 2;10:574.

Candidate genes for enzymes functioning in the biosynthesis of cyanogenic glucosides (cytochrome P450 and family 1 glycosyltransferases) were identified based on sequence length, number of copies and presence/absence of close homologs in D. melanogaster, B. mori and the cyanogenic butterfly Heliconius.
They both contain cyanogenic glucosides which liberate toxic hydrogen cyanide upon breakdown.
1(0,0,0,1) Details