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. 1977 Aug 1;165(2):409–411. doi: 10.1042/bj1650409

Aldolase-like imine formation in the mechanism of action of phosphonoacetaldehyde hydrolase.

J M La Nauze, J R Coggins, H B Dixon
PMCID: PMC1164914  PMID: 200222

Abstract

Phosphonoacetaldehyde hydrolase (EC 3.11.1.1), the bacterial enzyme that catalyses the reaction HCO-CH2-PO(OH)2+H2O leads to HCO-CH3+Pi, is inactivated by borohydride if either phosphonoacetaldehyde or acetaldehyde is present. This supports the suggestion that the substrate forms an imine with an amino group of the enzyme. Such imine formation would labilize the C-P bond in the same way that aldolase and related enzymes labilize C-C and C-H bonds (Scheme 1a).

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Selected References

These references are in PubMed. This may not be the complete list of references from this article.

  1. Dixon H. B., Sparkes M. J. Phosphonomethyl analogues of phosphate ester glycolytic intermediates. Biochem J. 1974 Sep;141(3):715–719. doi: 10.1042/bj1410715. [DOI] [PMC free article] [PubMed] [Google Scholar]
  2. Dunathan H. C. Conformation and reaction specificity in pyridoxal phosphate enzymes. Proc Natl Acad Sci U S A. 1966 Apr;55(4):712–716. doi: 10.1073/pnas.55.4.712. [DOI] [PMC free article] [PubMed] [Google Scholar]
  3. Feeney R. E., Blankenhorn G., Dixon H. B. Carbonyl-amine reactions in protein chemistry. Adv Protein Chem. 1975;29:135–203. doi: 10.1016/s0065-3233(08)60412-x. [DOI] [PubMed] [Google Scholar]
  4. La Nauze J. M., Rosenberg H., Shaw D. C. The enzymic cleavage of the carbon-phosphorus bond: purification and properties of phosphonatase. Biochim Biophys Acta. 1970 Aug 15;212(2):332–350. doi: 10.1016/0005-2744(70)90214-7. [DOI] [PubMed] [Google Scholar]
  5. La Nauze J. M., Rosenberg H. The identification of 2-phosphonoacetaldehyde as an intermediate in the degradation of 2-aminoethylphosphonate by Bacillus cereus. Biochim Biophys Acta. 1968 Oct 15;165(3):438–447. doi: 10.1016/0304-4165(68)90223-7. [DOI] [PubMed] [Google Scholar]
  6. Lai C. Y., Horecker B. L. Aldolase: a model for enzyme structure-function relationships. Essays Biochem. 1972;8:149–178. [PubMed] [Google Scholar]
  7. Nandi D. L., Shemin D. Delta-aminolevulinic acid dehydratase of Rhodopseudomonas spheroides. 3. Mechanism of porphobilinogen synthesis. J Biol Chem. 1968 Mar 25;243(6):1236–1242. [PubMed] [Google Scholar]

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