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Synthesis 2005(14): 2327-2334  
DOI: 10.1055/s-2005-870024
PAPER
© Georg Thieme Verlag Stuttgart · New York

Linker-Free Fluorophore-Labeled Oligonucleotides: Synthesis of 3′-Fluoresceinylthymidine Building Blocks and their Coupling Reactions

Niels Griesang, Eric Kervio, Clemens Richert*
Institut für Organische Chemie, Universität Karlsruhe (TH), 76131 Karlsruhe, Germany
Fax: +49(721)6084825; e-Mail: cr@rrg.uka.de;
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Publication History

Received 2 February 2005
Publication Date:
14 July 2005 (online)

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Abstract

Reported here are the syntheses of two thymidine derivatives with an amide-linked 6-carboxyfluorescein residue at their 3′-position that are suitable for the synthesis of fluorophore-labeled oligonucleotides. The first is a 5′-phosphoramidite with a pivaloyl-protected carboxyfluorescein residue in the lactone form. It was prepared from 3′-azido-3′-deoxythymidine (AZT) in three steps and 73% overall yield and coupled on solid support. The second is an imidazolide of thymidine 5′-monophosphate that was obtained from AZT in five steps and 48% overall yield. The imidazolide can be coupled to amino-terminated nucleic acids in aqueous solution.

Key words

DNA - nucleosides - oligomerization - oligonucleotides - solid-phase synthesis