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Synthesis 2004(11): 1835-1843  
DOI: 10.1055/s-2004-829143
PAPER
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Metal-Chelating Deoxycytidine-Analogue Phosphoramidites for the Automatic Synthesis of Labelled Oligonucleotides

Cesare Giordano*a, Cristina Del Biancob, Sara Fainib, Anna Napolic, Giovanni Sindonac, Luciano Cellaib
a Istituto di Chimica Biomolecolare del CNR, Sezione di Roma, Dipartimento di Studi Farmaceutici, Università ‘La Sapienza’, P. le A. Moro 5, 00185 Rome, Italy
Fax: +39(6)491491; e-Mail: cesare.giordano@uniroma1.it;
b Istituto di Cristallografia del CNR, Sezione di Monterotondo, CP 10, 00016 Monterotondo Stazione, Rome, Italy
c Dipartimento di Chimica, Università degli Studi della Calabria, 87036, Arcavacata di Rende, Cosenza, Italy
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Publication History

Received 30 July 2003
Publication Date:
13 July 2004 (online)

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Abstract

The new deoxycytidine (dC) analogue phosphoramidites 1-3 were synthesized, which bear an ethylenediaminetetraacetic acid triethyl ester [EDTA(OEt)3] attached to the exocyclic amino group through either a cyclic-C6, a C2, or a linear-C6 tether. By this way, the chelating base dC-EDTA can be inserted, by automatic synthesis, in a site-specific manner into oligodeoxynucleotides (ODNs), in place of any dC along the sequence, and can be thus exploited, for example, for footprinting experiments. Furthermore, the analogue phosphoramidite 4, bearing a diethylenetriaminepentaacetic acid tetraethyl ester [DTPA(OEt)4] attached through the cyclic-C6 tether was also prepared. The possibility of insertion of 1-4 into ODNs was verified.

Key words

DNA - chelates - nucleosides - oligonucleotides - footprinting