Amide-Modified Oligonucleotides with Preorganized Backbone and Furanose Rings: Highly Increased Thermodynamic Stability of the Duplexes Formed with their RNA and DNA Complements

Synlett

Volumn 1997, Issue 11, 1997, Pages 1287-1290

  De Mesmaeker, Alain ^a   Lebreton, Jacques ^a   Jouanno, Chantal ^a   Fritsch, Valérie ^a   Wolf, Romain M ^a   Wendeborn, Sebastian ^a  

^a NOVARTIS PHARMA AG   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 2342476659     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-1003     Document Type: Article

References (12)

1. a) Lebreton, J.; De Mesmaeker, A.; Waldner, A.; Fritsch, V.; Wolf, R.M.; Freier, S.M. Tetrahedron Left. 1993, 34, 6383.
2. b) De Mesmaeker, A.; Waldner, A.; Lebreton, J.; Hoffmann, P.; Fritsch, V.; Wolf, R.M.; Freier, S.M. Angew. Chem. Int. Ed. Engl. 1994, 33, 226.
3. c) Idziak, I.; Just, G.; Damha, M.J.; Giannaris, P.A. Tetrahedron Lett. 1993, 34, 5417.
4. d) Wendeborn, S.; Wolf, R.M.; De Mesmaeker, A. Tetrahedron Lett. 1995, 36, 6879.
5. De Mesmaeker, A.; Lesueur, C.; Bévièrre, M.O.; Waldner, A.; Fritsch, V.; Wolf, R.M. Angew. Chem. Int. Ed. Engl. 1996, 35, 2790.
6. Fritsch, V.; De Mesmaeker, A.; Waldner, A.; Lebreton, J.; Blommers, M.J.J.; Wolf, R.M. Bioorg. Med. Chem. 1995, 3, 321.
7. The non stereoselective incorporation of a 5′-Me substituent into a DNA strand (as a 1:1 mixture of 5′-(R) and 5′-(5) epimers) was shown to have no major impact on the hybridization with a DNA complement. Saha, A.K.; Caulfield, T.J.; Hobbs, C.; Upson, D.A.; Waychunas, C.; Yawman, A.M. J. Org. Chem. 1995, 60, 788. In contrast to our hypothesis for amide backbones, these authors postulated that the configuration at the 5′-methine stereocenter in a DNA backbone may not severely impact the hybridization.
8. Niedballa, U.; Vorbrüggen, H. J. Org. Chem. 1974, 39, 3654.
9. For preparation of modified oligonucleotides see ref. 13 in 1b.
10. Thermal denaturation of duplexes was performed as in ref. 1.
11. Wolf, R.M.; De Mesmaeker, A.; Waldner, A.; Wendeborn, S.; Fritsch, V.; Lebreton J. New J. Chem. 1997, 21, 61.
12. Weiner, S. J.; Kollman, P. A.; Nguyen, D. T.; Case, D. A. J. Comp. Chem. 1986, 7, 230.