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Química Nova

Print version ISSN 0100-4042On-line version ISSN 1678-7064


DUTRA, Fernando  and  BECHARA, Etelvino J. H.. Biochemistry and cytotoxicity of a-aminoketones. Quím. Nova [online]. 2005, vol.28, n.3, pp.483-491. ISSN 1678-7064.

a-Aminoketones are expected to undergo enolization and subsequent aerobic oxidation yielding oxyradicals and highly toxic a-oxoaldehydes. Our interest has been focused on two endogenous a-aminoketones: 5-aminolevulinic acid (ALA) and aminoacetone (AA), accumulated in porphyrias and diabetes mellitus, respectively, and recently implicated as contributing sources of oxyradicals in these diseases. The final oxidation product of ALA, 4,5-dioxovaleric acid (DOVA), is able to alkylate DNA guanine moieties and expected to promote protein cross-linking. Methylglyoxal (MG), the final oxidation product of AA, is also highly cytotoxic and able to aggregate protein molecules. This review covers chemical and biochemical aspects of these a-aminoketones and their putative roles in the oxidative stress associated with porphyric disorders and diabetes.

Keywords : 5-aminolevulinic acid; aminoacetone; hexosamines.

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