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Synlett 2004(9): 1579-1583  
DOI: 10.1055/s-2004-829541
LETTER
© Georg Thieme Verlag Stuttgart · New York

Synthesis and Spectroscopic Properties of Porphyrin-Substituted Uridine and Deoxyuridine

Imenne Bouamaied, Eugen Stulz*
Department of Chemistry, University of Basel, St. Johanns Ring 19, 4056 Basel, Switzerland
Fax: +41(61)2670976; e-Mail: eugen.stulz@unibas.ch;
Further Information

Publication History

Received 5 April 2004
Publication Date:
01 July 2004 (online)

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Abstract

A general synthetic route to porphyrin-substituted uridine and 2′-deoxyuridine using Sonogashira coupling with acetylene porphyrins is presented. Both diphenyl and tetraphenyl porphyrins, as free base or zinc metallated, can be attached to the nucleobase. Selective TBDMS protection of the deoxyribose does not affect the coupling reaction. The substituents on the porphyrins render the conjugates soluble either in organic solvents (carboxy ­esters) or in water (carboxylates). No electronic communication ­between the chromophore and the nucleobase occurs, as indicated by UV/Vis spectroscopy. In aqueous solution, the absorption of the porphyrins is substantially lower than in organic solvents.

Key words

porphyrins - nucleosides - cross-coupling - spectros­copy - protecting groups

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