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Nucleic Acids Research, 1991, Vol. 19, No. 15 4067-4074
© 1991

CHEMISTRY

Synthesis and physicochemical properties of oligonucleotides built with either {alpha}-L or ß-L nucleotides units and covalently linked to an acridine derivative

Ulysse Asseline, Jean-François Hau1, Czernecki Stanislas1, Thierry Le Diguarher1, Marie-Claude Perlat1, Jean-Marc Valery1 and Nguyen Thanh Thuong*

Centre de Biophysique Moleculaire, CNRS 1A avenue la Recherche Scientifique, 45071 Orleans Cedex 2, France 1Laboratoire de Chimie des Glucides, Université Pierre et Marie Curie T74, E6, 4 Place Jussieu, 75252 Paris Cedex 05, France

* To whom correspondence should be addressed

Received June 10, 1991. Accepted July 5, 1991.

Modified deoxynucleosides 2'-deoxy- ß-L-uridine, ß-L-thymidine, {alpha}-L-thymidine, 2'-deoxy-ß-L-adenosine and 2'-deoxy-{alpha}-L-adenosine were synthesized and assembled as homooligomers, respectively: octa-ß-L-deoxyuridylates, octa ß-L and {alpha}-L-thymidylates and tetra ß-L and {alpha}-L-deoxyadenylates. These unnatural oligomers were then substituted with an acridine derivative. The binding studies of these modified oligonucleotides with D-ribo- and D-deoxyribopoly nucleotides were carried out by absorption spectros copy. While ß-L-d(Up)8m5Acr, ß-L-d(Tp)8m5Acr, {alpha};-L- (Tp)8m5Acr, did not interact with poly(rA) and poly(dA), ß-L-d(Up)4m5Acr, and {alpha}-L-d(Ap)4m5Acr, did form double and triple helices with poly(rU) and poly(dT), respectively. Their stability towards nuclease digestion was studied through comparison with that of octa-ß-D thymidylate and tetra ß-D-deoxyadenylate covalently linked to an acridine derivative. One endonuclease (nuclease P1 from Penicillium citrinum) and two exonucleases (a 3'-exonuclease from Crotalus durissus venom and a 5'-exonuclease extracted from calf thymus) were employed. ß-L- and {alpha}-L-oligomers demonstrate a high resistance toward nuclease digestion.


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