Replacement of the phosphodiester linkage in oligonucleotides by an acetylenic bond: Comparison between carbon-, sulfur-, and oxygen-containing analogs

Tetrahedron Letters

Volumn 37, Issue 31, 1996, Pages 5511-5514

  Wendeborn, Sebastian ^a   Jouanno, Chantal ^a   Wolf, Romain M ^a   De Mesmaeker, Alain ^a  

^a CIBA GEIGY LTD   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

OLIGONUCLEOTIDE;

ARTICLE; DRUG SYNTHESIS; RNA HYBRIDIZATION;

EID: 0030605864     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01164-1     Document Type: Article

References (19)

1. 1. a) Lebreton, J.; Waldner, A.; Lesueur, C.; De Mesmaeker, A. Synlett 1994, 137-140.
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, 226-229.
3. c) Lebreton, J.; Waldner, A.; Fritsch, V.; Wolf, R.M.; De Mesmaeker, A. Tetrahedron Lett. 1994, 35, 5225-5228.
4. 2. For the synthesis of an allyl-ether and -thioether containing backbone see: Cao, X.; Matteucci, M.D. Tetrahedron Lett. 1994, 35, 2325-2328.
5. 3. Lebreton, J.; De Mesmaeker, A.; Waldner, A. Synlett 1994, 54-56.
6. 4. a) Brill, W. K.-D. Tetrahedron Lett. 1995, 36, 703-706.
7. b) Brill, W. K.-D. (Ciba AG) Eur. Pat. Appl. No. 94810522.6.
8. 5. Cosstick, R.; Vyle, J.S. J. Chem. Soc., Chem. Commun. 1988, 992-993.
9. 6. Takai, K.; Kuroda, T.; Nakatsukasa, S.; Oshioma, K.; Nozaki, H. Tetrahedron Lett. 1985, 26, 5585-5588.
10. 7. Trost, B.M.; Belletire, J.L.; Godleski, S.; McDougal, P.G.; Balkovec, J.M.; Baldwin, J.J.; Christy, M.E.; Ponticello, G.S.; Varga, S.L.; Springer, J.P. J. Org. Chem. 1986, 51, 2370-2374. The differences in the chemical shifts of relevant protons in the two diastereomers were minimal (sometimes <0.1 ppm), but in agreement with the predictions. No crystals for X-ray crystallography could be obtained. The assignment of the absolute stereochemistry should be taken with precaution.
11. 3CN. Gradient: 15-45% B in 55 min.. Oligonucleotides were obtained in ca. 40% overall yield. Molecular weight of oligonucleotides was checked by mass spectroscopy (MALDI-TOF MS: Pieles, U.; Zürcher, W.; Schär, M.; Moser, H. Nucl. Acid Res. 1993, 21, 3191-3196).
12. 3CN. Gradient: 15-45% B in 55 min.. Oligonucleotides were obtained in ca. 40% overall yield. Molecular weight of oligonucleotides was checked by mass spectroscopy (MALDI-TOF MS: Pieles, U.; Zürcher, W.; Schär, M.; Moser, H. Nucl. Acid Res. 1993, 21, 3191-3196).
13. 9. a) Fritsch, V.; De Mesmaeker, A.; Waldner, A.; Lebreton, J.; Blommers, M.J.J., Wolf, R.M. Bioorg.Med.Chem. 1995, 3, 321-335.
14. b) De Mesmaeker, A.; Waldner, A.; Fritsch, V.; Lebreton J.; Wolf, R.M. Bull.Soc.Chim.Belg. 1994, 103, 705-717.
15. c) Wolf, R.M.; Fritsch, V.; De Mesmaeker, A.; Lebreton, J.; Waldner, A. in Computer-Aided Molecular Design, Applications in Agrochemicals, Materials, and Pharmaceuticals, Reynolds, C.H.; Holloway, M.K.; Cox, H.K. eds., ACS Symposium Series 589, ACS, Washington DC, 1995, p. 114-126.
16. 10. a) As incorporated in the InsightII/DISCOVER package of BIOSYM/MSI, San Diego, USA.
17. b) Weiner, S.J., Kollman, P.A.; Nguyen, D.T.; Case, D.A. J.Comp.Chem. 1986, 7, 230-252
18. c) Howard, A.E.; Cieplak, P.; Kollman, P.A. J.Comp.Chem. 1995, 16, 243-261.
19. 11. Fritsch, V.; Wolf, R.M. J.Biomol.Struct.Dyn. 1994, 11, 1161-1174 and references therein.