Deamination of β-alanine induced by hydroxyl radicals and monovalent copper ions. A pulse radiolysis study

Sara Goldstein, Gidon Czapski, Haim Cohen, Dan Meyerstein

Research output: Contribution to journalArticlepeer-review

26 Scopus citations

Abstract

Hydroxyl radicals abstract hydrogen atoms from β-alanine (3-aminopropanoate) at the α position to the carboxylate group with specifc rate constants of (4.5±0.8)×107 and (1.1±0.2)×108 M-1 s-1 at pH 3 and 6.5, respectively. The carbon-centered free radical (3-amino-2-yl-propanoate) reacts with Cu+aq to form an organometallic intermediate with a rate constant of (3.4±0.7×109 M-1 s-1. This intermediate decomposes via a first order reaction with a rate constant of (1.1±0.2)×104 s-1 at pH>3.5 and (2.7±0.3)×104 s-1 at pH≤3. A detailed product analysis shows that the yield of carbon dioxide is insignificant and the final stable product is acrylic acid. It is concluded that the complex with the copper-carbon σ-bond decomposes via a β-elimination of ammonia causing degradation of the amino acid. The spectrum of the organometallic intermediate and the factors affecting the mechanism of its decomposition are discussed.

Original languageEnglish
Pages (from-to)87-93
Number of pages7
JournalInorganica Chimica Acta
Volume192
Issue number1
DOIs
StatePublished - 3 Feb 1992

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Inorganic Chemistry
  • Materials Chemistry

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