Hydroxyl Radical Induced Decarboxylation and Deamination of 2-Methylalanine Catalyzed by Copper Ions

Sara Goldstein, Gidon Czapski, Haim Cohen, Dan Meyerstein

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43 Scopus citations

Abstract

Using the pulse radiolysis technique, the rate constants of the reactions of CH2C(CH3)(NH3+)COO- (the radical derived via H-abstraction from 2-methylalanine) with Cu2+aq and Cu+aq to form unstable intermediates with a copper-carbon -bond have been determined to be (1.3 ± 0.3) × 107 and (1.3 ± 0.2) × 109 M-1 s-1, respectively. In the case of cupric ions, the transient decomposes via a β-carboxyl elimination reaction yielding Cu+ aq, CH3COCH3, and CO2, whereas in the case of cuprous ions it decomposes via a β-amine elimination reaction yielding Cu2+ aq, CH2=C(CH3)COO-, and NH3. A reaction mechanism for aliphatic radical induced amino acid damage catalyzed by copper ions in different oxidation states is suggested. This mechanism describes a plausible new pathway for biological damage induced by free radicals.

Original languageEnglish
Pages (from-to)2439-2444
Number of pages6
JournalInorganic Chemistry
Volume31
Issue number12
DOIs
StatePublished - 1 Jan 1992

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