Abstract
From the pH–rate profile of autoxidation of the Cypridina luciferin analogue {2-methyl-6-phenylimidazo[1,2-a]pyrazin-3(7H)-one, CLA}, CLA was found not to react with ground-state molecular oxygen at a measurable rate, while the conjugate base of CLA was found to react with molecular oxygen with a second-order rate constant of 0.434 ± 0.001 dm3 mol–1 s–1 at 25 °C. No chain reaction process contributed in the autoxidation of CLA. Superoxide dismutase (SOD) was observed to reduce the rate of the autoxidation to a small extent in the reaction with low-pH buffers, while SOD did not affect the reaction in buffers of pH higher than 7. The intimate radical pair (CLA˙O2˙–) is proposed to be the primary product of the reaction.
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