Chemistry:Aminoacetone
Aminoacetone is the organic compound with the formula CH3C(O)CH2NH2. Although stable in the gaseous form, once condensed it reacts with itself. The protonated derivative forms isolable salts, e.g. aminoacetone hydrochloride ([CH3C(O)CH2NH3]Cl)). The semicarbazone of the hydrochloride is another bench-stable precursor.[1] Aminoacetone is a metabolite that is implicated in the biosynthesis of methylglyoxal.[2]
Aminoacetone is also produced during catabolism of the amino acid threonine. Threonine is first dehydrogenated to 2-amino-3-oxobutyrate, which is unstable and spontaneously decarboxylates to aminoacetone. Aminoacetone is then oxidized and deaminated, giving 2-oxopropanal (methylglyoxal), which is in turn oxidized to pyruvate. This pathway is the most important catabolic pathway of threonine in mammals.[3]
See also
- Propanolamines
- Aminoaldehydes and aminoketones
References
- ↑ John D. Hepworth (1965). "Aminoacetone Semicarbazone Hydrochloride". Organic Syntheses 45: 1. doi:10.15227/orgsyn.045.0001.
- ↑ Bechara, Etelvino J.H.; Dutra, Fernando; Cardoso, Vanessa E.S.; Sartori, Adriano; Olympio, Kelly P.K.; Penatti, Carlos A.A.; Adhikari, Avishek; Assunção, Nilson A. (2007). "The dual face of endogenous α-aminoketones: Pro-oxidizing metabolic weapons". Comparative Biochemistry and Physiology Part C: Toxicology & Pharmacology 146 (1–2): 88–110. doi:10.1016/j.cbpc.2006.07.004. PMID 16920403.
- ↑ Dobrota, Dušan (2016) (in sk). Lekárska biochémia (2nd ed.). Martin: Osveta. pp. 316—317. ISBN 978-80-8063-444-5.
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