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Nucleic Acids Research, 1987, Vol. 15, No. 16 6625-6641
© 1987

Articles

{alpha}-DNA IV: {alpha}-anomeric and ß-anomeric tetrathymidylates covalently linked to intercalating oxazolopyridocarbazole. Synthesis, physicochemical properties and poly (rA) binding

Claudie Gautier, François Morvan1, Bernard Rayner1, Tam Huynh-Dinh2, Jean Igolen2, Jean-Louis Imbach1, Claude Paoletti and Jacques Paoletti*

Laboratoire de Biochimie, INSERM U 140, CNRS LA 147, Institut Gustave Roussy 94800 Villejuif 1Laboratoire de Chimie Bio-organique, UA 488 du CNRS, Université des Sciences et Techniques du Languedoc 34060 Montpellier Cédex 2Unité de Chimie Organique, ERA/CNRS 927, Institut Pasteur, 28 rue du Docteur Roux 75015 Paris, France

*To whom correspondence should be addressed

Received May 18, 1987. Revised July 25, 1987. Accepted July 25, 1987.

A nesw set of molecules made of an intercalating agent (oxazolopyridocarbazole, OPC) covalently linked through a polymethylene chain of various length to the 3' end of {alpha}-anomeric or ß-anomeric tetradeoxynucleotides ({alpha}-or ß-T4) have been synthesized. The ß-thymidylate modified compound (p-T4C5OPC) is able to interact with the complementary sequence, ß-poly (rA); this interaction is strongly stabilized compared to the parent compound, p-oligo(dT)4 and is specific for poly (rA). The molecule synthesized from the unnatural {alpha}-anomer, {alpha}-T4C5OPC, is also able to interact with poly (rA) leading to the formation of an {alpha}-ß hybrid stabilized by the energy provided by the OPC moiety. The stoechiometry of the Dinding reaction shows that an A-T pairing occurs in the {alpha}-ß heterohybrids. Tm studies reveal that the {alpha}-ß heterohybrids are more stable than their ß-ß counterparts.


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