In an effort to evaluate the reactivity of nucleobases with halogenated metalloporphyrins, adenine and adenosine derivatives were oxidized by dimethyldioxirane (DMDO) as oxygen atom donor using Mn[(Cl16)TDMPP]Cl and Mn[(Cl8)TDCPP]Cl porphyrins as catalysts. The role of hydrogen bonding interactions in the selectivity of the reaction was investigated through the oxidation of adenine and adenosine derivatives bearing hydrogen bond donors on the sugar moiety or on the N-9 side chain. This procedure is a useful synthetic tool for the selective C-8 versus N-1 oxidation of purine derivatives. © 2004 Elsevier B.V. All rights reserved.
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