Oxidation of caffeine with hydrogen peroxide catalyzed by metalloporphyrins

resumo

The biomimetic oxidation of caffeine with hydrogen peroxide using metalloporphyrins as catalysts, which are known to be good biomimetic models of cytochrome P450 enzymes, is investigated. The two manganese porphyrins tested, chloro[5,10,15,20-tetrakis(2,6-dichlorophenyl)porphyrinato]manganese(III), [Mn(TDCPP)Cl], and chloro [5,10,15,20-tetrakis(pentafluorophenyl)porphyrinato]manganese(III), [Mn(TPEPP)Cl], afford high conversions of caffeine for all substrate/catalyst molar ratios. Selectivity was found to be dependent on the catalyst employed, and a new spiro racemic compound is described and fully characterized in the solid state from X-ray diffraction studies. (C) 2011 Elsevier Ltd. All rights reserved.

palavras-chave

EPOXIDATION REACTIONS; PORPHYRIN COMPLEXES; MN(III) PORPHYRINS; MASS-SPECTROMETRY; METABOLISM; HISTORY

categoria

Chemistry

autores

Neves, CMB; Simoes, MMQ; Santos, ICMS; Domingues, FMJ; Neves, MGPMS; Paz, FAA; Silva, AMS; Cavaleiro, JAS

nossos autores

agradecimentos

Thanks are due to Fundacao para a Ciencia e a Tecnologia (FCT/FEDER) for funding QOPNA and CICECO and for specific funding towards the purchase of the single-crystal X-ray diffractometer. Authors acknowledge the Portuguese National NMR Network (RNRMN), supported with funds from FCT.

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