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Nucleic Acids Research, 1987, Vol. 15, No. 8 3421-3437
© 1987

Articles

{alpha}-DNA II. Synthesis of unnatural {alpha}-anomeric oligodeoxyribonucleotides containing the four usual bases and study of their substrate activities for nucleases

Francois Morvan, Bernard Rayner, Jean-Louis Imbach, Sophie Thenet*, Jean-Remy Bertrand*, Jacques Paoletti*, Claude Malvy* and Claude Paoletti*

Laboratoire de Chimie Bio-Organique, UA 488 CNRS, Université des Sciences et Techniques du Languedoc Place E. Bataillon, 34060 Montpevier Cédex *LA 147 CNRS, U-140 INSERM, institut Gustave-Roussy 53 rue Camille-Desmoulins, 94800 Villejuivgf, France

Received February 17, 1987. Accepted March 3, 1987.

This paper describes for the first time the synthesis of {alpha}-oligonucleotides containing the four usual bases. Two unnatural hexadeoxyribonucleotidesi {alpha}-[d(CPAPTPGPCPG)] and {alpha}-[d(CPGPCPHPTPG)], consisting only of a-anomeric nucleotide units, were obtained by an improved phosphotriester method, in solution. Starting material was the four base-protected {alpha}-deoxyribo-nucleosides 3-d. Pyrimidine a-deoxynucleosides 3a and 3b were prepared by self-anomerization reactions followed by selective deprotection of sugar hydroxyles, while the two purine {alpha}-deoxynucleosides 3c and 3d were prepared by glycosylation reactions. In the case of guanine {alpha}-nucleoside derivative a supplementary base-protecting group: N, N-diphenylcarbamoyl was introduced on O6-position in order to avoid side-reactions during oligonucleotide assembling. The hexadeorynucleotide {alpha}-[d(CPAPTPGPCPG)] was tested as substrate of selected endo- and exonucleases. In conditions where the natural corresponding ß-hexamer was completely degradated by nuclease s1 and calf spleen phosphodiesterase, the {alpha}-oligonucleotide remained almost intact.


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