Synthesis 2003(15): 2335-2340  
DOI: 10.1055/s-2003-41069
PAPER
© Georg Thieme Verlag Stuttgart · New York

Preparation of Pyrene-Modified Purine and Pyrimidine Nucleosides via Suzuki-Miyaura Cross-Couplings and Characterization of their Fluorescent Properties

Elke Mayer, Linda Valis, Robert Huber, Nicole Amann, Hans-Achim Wagenknecht*
Technical University of Munich, Institute for Organic Chemistry and Biochemistry, Lichtenbergstr. 4, 85747 Garching, Germany
Fax: +49(89)28913210; e-Mail: Wagenknecht@ch.tum.de;
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Publikationsverlauf

Received 6 June 2003
Publikationsdatum:
23. September 2003 (online)

Abstract

A set of pyrene-modified pyrimidine and purine nucleosides, consisting of 5-(1-pyrenyl)-2′-deoxyuridine (1), 5-(1-pyrenyl)-2′-deoxycytidine (2), 8-(1-pyrenyl)-2′-deoxyguanosine (3), and 8-(1-pyrenyl)-2′-deoxyadenosine (4), was prepared via palladium-catalyzed Suzuki-Miyaura-type cross-coupling reactions. The syntheses started from 1-pyrenylboronic acid (5) and the corresponding halogenated nucleoside precursors. They were performed without protection of the hydroxy functions of the 2′-deoxyribose moiety and the exocyclic amino functions of the nucleoside bases. Good yields could be obtained for the preparation of 1 and 3, but not in case of 2 and 4. Obviously, the latter compounds require a protecting group strategy. The absorption and steady-state fluorescence properties of the pyrene-modified nucleosides 1-4 were characterized in MeCN and MeOH.

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Pandurski, E.; Wagenknecht, H.-A.; Fiebig, T., unpublished results.