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Aminooxyacetic acid

Hydroxylamineacetic acid U-7524 Aminooxyacetic acid, often abbreviated AOA or AOAA, is a compound that inhibits 4-aminobutyrate aminotransferase (GABA-T) activity in vitro and in vivo, leading to less gamma-aminobutyric acid (GABA) being broken down.{{Cite journal

Aminooxyacetic acid is a general inhibitor of pyridoxal phosphate (PLP)-dependent enzymes (this includes GABA-T).{{Cite journal | doi-access = free

Aminooxyacetic acid inhibits aspartate aminotransferase, another PLP-dependent enzyme, which is an essential part of the malate-aspartate shuttle. Also in the nerve terminals, aminooxyacetic acid prevents the mitochondria from utilizing pyruvate generated from glycolysis, thus leading to a bioenergetic state similar to that of hypoglycemia. Aminooxyacetic acid has been shown to cause excitotoxic lesions of the striatum, similar to Huntington's disease, potentially due to its impairment of mitochondrial energy metabolism.{{Cite journal

Aminooxyacetic acid has been studied as a treatment for tinnitus.{{Cite journal

Aminooxyacetic acid also has anticonvulsant properties.{{Cite journal

Aminooxyacetic acid can also inhibit 1-aminocyclopropane-1-carboxylate synthase preventing ethylene synthesis, which can increase the vase life of cut flowers.

History

Aminooxyacetic acid was first described by Werner in 1893, and was prepared by the hydrolysis of ethylbenzhydroximinoacetic acid. In 1936, Anchel and Shoenheimer used aminooxyacetic acid to isolate ketones from natural sources.

References

References

  1. (1989). "Use of Inhibitors of γ-Aminobutyric Acid (GABA) Transaminase for the Estimation of GABA Turnover in Various Brain Regions of Rats: A Reevaluation of Aminooxyacetic Acid". Journal of Neurochemistry.
  2. (1987). "Aminooxyacetic acid inhibits the malate-aspartate shuttle in isolated nerve terminals and prevents the mitochondria from utilizing glycolytic substrates". Biochimica et Biophysica Acta (BBA) - Molecular Cell Research.
  3. (2008). "Targeting aspartate aminotransferase in breast cancer". Breast Cancer Research.
  4. (1981). "Aminooxyacetic acid as an inhibitor of ethylenesynthesis and senescence in carnation flowers". Scientia Horticulturae.
  5. Werner, A.. (1893). "Ueber Hydroxylaminessigsäure und Derivate derselben". [[Chemische Berichte.
  6. (1894). "Ueber Hydroxylaminessigsäure und α-Hydroxylaminpropionsäure". Berichte der Deutschen Chemischen Gesellschaft.
  7. (1936). "Reagents for the isolation of carbonyl compounds from unsaponifiable material". Journal of Biological Chemistry.
  8. (1936). "Carboxymethoxylamine". Journal of the American Chemical Society.
  9. (1936). "Studies on a Diamino Acid, Canavanin, IV. The Constitution of Canavanin and Canalin". Journal of Biochemistry.
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