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Chemical Compound Review

Acetaldoxime     (NZ)-N-ethylidenehydroxylamine

Synonyms: NSC-4974, CHEBI:50719, NSC4974, WLN: QNU2, AC1NT4XO, ...
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Disease relevance of acetaldehyde oxime


High impact information on acetaldehyde oxime

  • The substrate specificity of AcsA was similar to those of aldoxime dehydratase, NHase, and amidase, the genes of which coexist in the same orientation in the gene cluster [5].
  • Two open reading frames (nhpS and acsA) were identified immediately downstream of the previously described Pseudomonas chlororaphis B23 nitrile hydratase (NHase) gene cluster (encoding aldoxime dehydratase, amidase, the two NHase subunits, and an uncharacterized protein) [5].
  • We report that cytochrome P450 CYP79F1 catalyzes aldoxime formation in the biosynthesis of aliphatic glucosinolates in Arabidopsis thaliana [6].
  • CYP79A2 is the first enzyme shown to catalyze the conversion of an amino acid to the aldoxime in the biosynthesis of glucosinolates [7].
  • Wild-type BuChE and mutants were inhibited by di-isopropylfluorophosphate at pH 8.0 and 25 degrees C. Di-isopropyl-phosphorylated enzymes were incubated with the nucleophilic oxime 2-pyridine aldoxime methiodide and their reactivatability was determined [8].

Chemical compound and disease context of acetaldehyde oxime


Biological context of acetaldehyde oxime


Anatomical context of acetaldehyde oxime


Associations of acetaldehyde oxime with other chemical compounds


Gene context of acetaldehyde oxime

  • A P450 complex characterized by a Soret peak at 442 nm was detected during these reactions; its disappearance was found to be concomitant with the consumption of the aldoxime and the formation of the corresponding nitrile [21].
  • Effects of 2-pyridine aldoxime methochloride on cerebral acetylcholinesterase activity and respiration in cats poisoned with sarin [22].
  • The cluster was composed of genes coding for aldoxime dehydratase (Oxd), nitrile hydratase (NHase), NHase activator, amidase, acyl-CoA ligase, and some regulatory and functionally unknown proteins, which were similar to proteins appearing in the "aldoxime-nitrile pathway" gene cluster from strains having Fe-containing NHase [23].

Analytical, diagnostic and therapeutic context of acetaldehyde oxime

  • The combination of site-directed mutagenesis of OxdA (mutation of all conserved histidines in the aldoxime dehydratase superfamily), estimation of the heme contents and specific activities of the mutants, and CD and resonance Raman spectroscopic analyses led to the identification of the proximal and distal histidines in this unique enzyme [24].
  • Together with these findings, Western blotting analysis of the extracts using anti-OxdA antiserum revealed that OxdA is responsible for the metabolism of aldoxime in vivo in this strain [2].
  • Determination of some pyridinium aldoxime compounds by means of ion-pair reversed-phase high-performance liquid chromatography: application in biological material [25].
  • Polymerase chain reaction for identification of aldoxime dehydratase in aldoxime- or nitrile-degrading microorganisms [26].


  1. Discovery of a reaction intermediate of aliphatic aldoxime dehydratase involving heme as an active center. Konishi, K., Ohta, T., Oinuma, K., Hashimoto, Y., Kitagawa, T., Kobayashi, M. Proc. Natl. Acad. Sci. U.S.A. (2006) [Pubmed]
  2. Novel aldoxime dehydratase involved in carbon-nitrogen triple bond synthesis of Pseudomonas chlororaphis B23. Sequencing, gene expression, purification, and characterization. Oinuma, K., Hashimoto, Y., Konishi, K., Goda, M., Noguchi, T., Higashibata, H., Kobayashi, M. J. Biol. Chem. (2003) [Pubmed]
  3. Substituent effects on the antibacterial activity of nitrogen-carbon-linked (azolylphenyl)oxazolidinones with expanded activity against the fastidious gram-negative organisms Haemophilus influenzae and Moraxella catarrhalis. Genin, M.J., Allwine, D.A., Anderson, D.J., Barbachyn, M.R., Emmert, D.E., Garmon, S.A., Graber, D.R., Grega, K.C., Hester, J.B., Hutchinson, D.K., Morris, J., Reischer, R.J., Ford, C.W., Zurenko, G.E., Hamel, J.C., Schaadt, R.D., Stapert, D., Yagi, B.H. J. Med. Chem. (2000) [Pubmed]
  4. Nitrile hydratase involved in aldoxime metabolism from Rhodococcus sp. strain YH3-3 purification and characterization. Kato, Y., Tsuda, T., Asano, Y. Eur. J. Biochem. (1999) [Pubmed]
  5. Nitrile pathway involving acyl-CoA synthetase: overall metabolic gene organization and purification and characterization of the enzyme. Hashimoto, Y., Hosaka, H., Oinuma, K., Goda, M., Higashibata, H., Kobayashi, M. J. Biol. Chem. (2005) [Pubmed]
  6. Cytochrome p450 CYP79F1 from arabidopsis catalyzes the conversion of dihomomethionine and trihomomethionine to the corresponding aldoximes in the biosynthesis of aliphatic glucosinolates. Hansen, C.H., Wittstock, U., Olsen, C.E., Hick, A.J., Pickett, J.A., Halkier, B.A. J. Biol. Chem. (2001) [Pubmed]
  7. Cytochrome P450 CYP79A2 from Arabidopsis thaliana L. Catalyzes the conversion of L-phenylalanine to phenylacetaldoxime in the biosynthesis of benzylglucosinolate. Wittstock, U., Halkier, B.A. J. Biol. Chem. (2000) [Pubmed]
  8. Aging of di-isopropyl-phosphorylated human butyrylcholinesterase. Masson, P., Fortier, P.L., Albaret, C., Froment, M.T., Bartels, C.F., Lockridge, O. Biochem. J. (1997) [Pubmed]
  9. Purification and properties of S-adenosylmethionine: aldoxime O-methyltransferase from Pseudomonas sp. N.C.I.B. 11652. Harper, D.B., Kennedy, J.T. Biochem. J. (1985) [Pubmed]
  10. Synthesis of pyrrolo[2,1-f][1,2,4]triazine C-nucleosides. Isosteres of sangivamycin, tubercidin, and toyocamycin. Nishimura, N., Kato, A., Maeba, I. Carbohydr. Res. (2001) [Pubmed]
  11. The unusual effect of pKM101 on the mutagenicity of acetaldehyde oxime in Salmonella typhimurium. Prival, M.J. Mutat. Res. (2003) [Pubmed]
  12. Degradation of three related bis(pyridinium)aldoximes in aqueous solutions at high concentrations: examples of unexpectedly rapid amide group hydrolysis. Korte, W.D., Shih, M.L. Journal of pharmaceutical sciences. (1993) [Pubmed]
  13. Disposition kinetics and urinary excretion of 2-pyridine aldoxime methiodide in sheep. Srivastava, A.K., Malik, J.K. Vet. Rec. (1989) [Pubmed]
  14. Platelet aggregation inhibitors. II - N-heterocyclic aldoxime methiodides (1). Antonini, I., Franchetti, P., Grifantini, M., Gulini, U., Martelli, S., Petrelli, F. Il Farmaco; edizione scientifica. (1976) [Pubmed]
  15. Oxidative effects in human erythrocytes caused by some oximes and hydroxylamine. Palmen, N.G., Evelo, C.T. Arch. Toxicol. (1998) [Pubmed]
  16. The effects of some cholinesterase reactivators on contractility of the isolated guinea-pig heart atria. Fusek, J., Patocka, J. Acta Biol. Med. Ger. (1976) [Pubmed]
  17. Alteration in calcium metabolism as a mechanism for pyridine aldoxime methochloride (2-PAM) cardiac action in rabbit atria. Carrier, G.O., Peters, T., Bishop, V.S. J. Pharmacol. Exp. Ther. (1975) [Pubmed]
  18. Reactions of p-coumaric acid with nitrite: product isolation and mechanism studies. Torres y Torres, J.L., Rosazza, J.P. J. Agric. Food Chem. (2001) [Pubmed]
  19. Pharmacokinetics and dosage regimen of 2-pyridine aldoxime in Bubalus bubalis intoxicated with fenitrothion. Srivastava, A.K., Malik, J.K. J. Vet. Pharmacol. Ther. (2001) [Pubmed]
  20. Atropine sulfate and 2-pyridine aldoxime methylchloride elicit stress-induced convulsions and lethality in mice and guinea pigs. Donzanti, B.A., Green, M.D., Shores, E.I. Drug and chemical toxicology. (1985) [Pubmed]
  21. Dehydration of alkyl- and arylaldoximes as a new cytochrome P450-catalyzed reaction: mechanism and stereochemical characteristics. Boucher, J.L., Delaforge, M., Mansuy, D. Biochemistry (1994) [Pubmed]
  22. Effects of 2-pyridine aldoxime methochloride on cerebral acetylcholinesterase activity and respiration in cats poisoned with sarin. Murtha, E.F., Harris, L.W. Life Sci. (1980) [Pubmed]
  23. Molecular and enzymatic analysis of the "aldoxime-nitrile pathway" in the glutaronitrile degrader Pseudomonas sp. K-9. Kato, Y., Asano, Y. Appl. Microbiol. Biotechnol. (2006) [Pubmed]
  24. Identification of crucial histidines involved in carbon-nitrogen triple bond synthesis by aldoxime dehydratase. Konishi, K., Ishida, K., Oinuma, K., Ohta, T., Hashimoto, Y., Higashibata, H., Kitagawa, T., Kobayashi, M. J. Biol. Chem. (2004) [Pubmed]
  25. Determination of some pyridinium aldoxime compounds by means of ion-pair reversed-phase high-performance liquid chromatography: application in biological material. Benschop, H.P., Konings, K.A., Kossen, S.P., Ligtenstein, D.A. J. Chromatogr. (1981) [Pubmed]
  26. Polymerase chain reaction for identification of aldoxime dehydratase in aldoxime- or nitrile-degrading microorganisms. Kato, Y., Yoshida, S., Asano, Y. FEMS Microbiol. Lett. (2005) [Pubmed]
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