Bulletin of the Chemical Society of Japan p. 3403 - 3407 (1984)
Update date:2022-08-16
Topics:
Tanaka, Masako
Sakuma, Hiroshi
Kohanawa, Osamu
Fukaya, Seijun
Katayama, Meiseki
The reaction of (R)-4-amino-3-isoxazolidinone (cycloserine) with OH radicals was studied in aqueous solutions by optical pulse radiolysis at pHs 6.5-12.It was concluded, from a comparison of the transient spectra with those obtained in a reaction with N3 radicals, that OH radicals attacked at the dissociated peptide group, -N-CO-, and an oxidized radical, -N.CO-, was produced through one-electron oxidation.From a kinetic analysis, the reaction was considered to have proceeded by two steps: The first step was the formation of OH adducts, where the rate constant, k(OH+cycloserine), was 8X109 mol-1dm3s-1 for the zwitterion form of cycloserine at pH 6.5 and 1.2X1010mol-1dm3s-1 for anion form at pHs 8-10.The second step was the formation of oxidized radicals at a rate of 3-4X106s-1.These radicals decayed with a second-order rate, suggesting a radical-radical recombination.D-Serine was detected as the major product.
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