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Nucleic Acids Research, 1992, Vol. 20, No. 6 1193-1200
© 1992

CHEMISTRY

Synthesis and base-pairing properties of the nuclease-resistant {alpha}-anomeric dodecaribonucleotide {alpha}-[r(UCUUAACCCACA)]

Francoise Debart, Bernard Rayner*, Genevieve Degols1 and Jean-Louis Imbach

Laboratoire de Chimie Bioorganique, UA 488 CNRS, Universiteé Montpellier II, Place Eugeéne-Bataillon 34095 Montpellier Cedex 5, France 1Laboratoire de Biochimie des Proteéines, UA 1191 CNRS, Universiteé Montpellier II, Place Eugeéne-Bataillon 34095 Montpellier Cedex 5, France

*To whom correspondence should be addressed

Received February 12, 1992. Accepted February 21, 1992.

The non natural oligoribonucleotide {alpha}-[r(UCUUAACCC-ACA)] consisting exclusively of {alpha}-anomeric ribonucleoside units was synthesized according to the phosphoramidite methodology and the solid support technology. For this purpose, the base-protected {alpha}-rlbonucleosides were synthesized and converted into their O-methylphosphoramidites. Assembling was carried out on a DNA synthesizer with an average efficiency of 97% per step. Base composition of this nuclease-resistant {alpha}-RNA strand was ascertained after chemical and enzymatic hydrolysis and HPLC analysis of the hydrolysate. Whereas no spectroscopic evidence of base pairing was found above 0°C between {alpha}-[r(UCUUAACCCACA)] and ,ß-[d(TGTGGGTTAAGA)], a clear UV absorbance transition (Tm 25.5°C) was observed during the hybridization of the same {alpha}-RNA strand with ß-[d(AGAATTGGGTGT)]. In this latter case, the mixing curve titration suggests formation at low temperature of a triplex involving two {alpha}-RNA and one ß-DNA strands. Moreover, this {alpha}-decaribonucleotide complementary in parallel orientation of the splice receptor of HIV-1 tat mRNA was found to inhibit (10 µW <ED50<20 µM), with apparent lack of sequence specificity, the de novo HIV-1 infection in cultured cells.


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