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Nucleic Acids Research, 1993, Vol. 21, No. 7 1587-1593
© 1993

CHEMISTRY

4'-Thio-oligo-ß-D-ribonucleotides: synthesis of ß-4'-thio-oligouridylates, nuclease resistance, base pairing properties, and interaction with HIV-1 reverse transcriptase

Laurent Bellon, Jean-Louis Barascut, Georges Maury, Gilles Divita1, Roger Goody1 and Jean-Louis Imbach*

Laboratoire de Chimie Bio-organique, UA 488 CNRS, Université Montpellier II, Place Eugène Bataillon 34095 Montpellier Cedex 5, France 1Abteilung Biophysik, Max-Planck Institut für Medizinische Forschung Jahnstrasse 29, 6900 Heidelberg, Germany

* To whom correspondence should be addressed

Received January 15, 1993. Revised February 26, 1993. Accepted February 26, 1993.

We present the synthesis and the study of properties of a new series of modified oligonucleotides, namely 4'-thio-oligo-ß-D-ribonucleotides (4'-S-RNA). Homo-oligonucleotides of this class (4'-SU6 and 4'-SU12) were prepared from the previously known thionucleosides using the phosphoramidite methodology. The comparison of the substrate properties of 4'-SU6 and its natural analog U6 with respect to four nucleases indicates that the former is much more resistant than the latter. Such resistance to nucleases in addition to relatively high Tm values for 4'-SU6 hybridized with Poly(A) show that these new 4'-S-RNA are good candidates for potential antisense effects. The oligonucleotides 4'-SU6 and 4'-SU12 have been also evaluated as non sequence specific inhibitors of HIV-1 reverse transcriptase. All available evidences, based primarily on fluorescence measurements, are consistent with the binding of 4'-SU6 and 4'-SU12 to RT at a site which is different from the polymerase site of the enzyme.


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