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

Cesare Giordano; Cristina Del Bianco; Sara Faini; Anna Napoli; Giovanni Sindona; Luciano Cellai

doi:10.1055/s-2004-829143

PAPER

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

Cesare Giordano*^a, Cristina Del Bianco^b, Sara Faini^b, Anna Napoli^c, Giovanni Sindona^c, Luciano Cellai^b
^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

Abstract

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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

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