Biomimetic oxidation studies of monensin A catalyzed by metalloporphyrins: Identification of hydroxyl derivative product by electrospray tandem mass spectrometry

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Abstract

Monensin A is an important commercially available natural product isolated from Streptomyces cinnamonensins that shows antibiotic and anti-parasitic activities. This molecule has a signifi cant infl uence in the antibiotic market, but until now there are no studies on putative metabolite formations. Bioorganic catalysts applying metalloporphyrins and mono-oxygen donors are able to mimic the cytochrome P450 reactions. This model has been employed for natural product metabolism studies affording several new putative metabolites and in vivo experiments confi rming the relevance of this procedure. In this work we evaluated the potential of 10,15,20-tetrakis (pentafl uorophenyl) porphyrin metal(III) chloride [Fe(TFPP)Cl] catalyst models to afford a putative monensin A metabolite. Oxidation agents such as meta-chloroperoxy benzoic acid, iodosylbenzene, hydrogen peroxide 30 wt.% and tert-butyl hydroperoxide 70 wt.%, were used to investigate different reaction conditions, in addition to the analysis of the infl uence of the solvent. The quantifi cation of total monensin A conversion and the structure of the new hydroxylated putative metabolite were proposed based on electrospray ionization tandem mass spectrometry analysis. The porphyrin tested, afforded moderate conversions of monensin A in all reaction conditions and the selectivity was found to be dependent on the oxidation/medium employed.

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Sousa-Junior, J. N., Rocha, B. A., Assis, M. D., Peti, A. P. F., Moraes, L. A. B., Iamamoto, Y., … Lopes, N. P. (2013). Biomimetic oxidation studies of monensin A catalyzed by metalloporphyrins: Identification of hydroxyl derivative product by electrospray tandem mass spectrometry. Revista Brasileira de Farmacognosia, 23(4), 621–629. https://doi.org/10.1590/S0102-695X2013005000053

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