Synthesis of the monomeric building blocks of Z-olefinic (PNA) (Z-OPA) containing the bases Adenine and thymine

Tetrahedron Letters

Volumn 38, Issue 24, 1997, Pages 4211-4214

  Cantin, Michel ^a   Schütz, Rolf ^a   Leumann, Christian J ^a  

^a UNIVERSITY OF BERN   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

ADENINE DERIVATIVE; PEPTIDE NUCLEIC ACID; THYMINE DERIVATIVE;

ARTICLE; CHIRALITY; DRUG STRUCTURE; DRUG SYNTHESIS; IN VITRO STUDY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS;

EID: 0342711268     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00871-X     Document Type: Article

References (19)

1. Nielsen, P.E.; Egholm, M.; Berg, R.H.; Buchardt, O. Science 1991, 254, 1497-1500.
2. Egholm, M.; Buchardt, O.; Christensen, L.; Behrens, C.; Freier, S.; Driver, D.A.; Berg, R.H.; Kim, S.K.; Norden, B.; Nielsen, P.E. Nature 1993, 365, 566-568.
3. Hunziker, J.; Leumann, C. Nucleic Acid Analogues: Synthesis and Properties. In Modern Synthetic Methods, Vol. 7; Ernst, B.; Leumann, C., Eds.; Verlag Helvetica Chimica Acta, Basel, 1995, pp. 376-386.
4. Hyrup, B.; Nielsen, P.E. Bioorg. Med. Chem. 1996, 4, 5-23.
5. Brown, S.C.; Thomson, S. A.; Veal, J.M.; Davis, D.G. Science 1994, 265, 777-780.
6. Betts, L.; Josey, J.A.; Veal, J.M.; Jordan, S.R. Science 1995, 270, 1838-1841.
7. Rasmussen, H.; Kastrup, J.S.; Nielsen, J.N.; Nielsen, J.M.; Nielsen, P.E. Nature Struct. Biol. 1997, 4, 98-101.
8. Chen, S-M.; Mohan, V.; Kiely, J.S.; Griffith, M.C.; Griffey, R.H. Tetrahedron Lett. 1994, 35, 5105-5108.
9. a) Marshall, J. A.; Jenson, T. M.; DeHoff, B. S. J. Org. Chem. 1987, 52, 3860-3866;
10. b) Marshall, J. A.; Lebreton, J.; DeHoff, B. S.; Jenson, T. M. J. Org. Chem. 1987, 52, 3883-3889.
11. Fauvarque, J. F.; Jutand, A. J. Organomet. Chem. 1981, 209, 109-114.
12. Curé, J.; Gaudemar, M. Bull. Soc. Chim. Fr. 1968, 3244-3246.
13. Cruickshank, K. A.; Jiricny, J.; Reese, C. B. Tetrahedron Lett. 1984, 25, 681-684.
14. Jenny, T. F.; Previsani, N.; Benner, S. A. Tetrahedron Lett. 1991, 32, 7029-7032.
15. Viaud, M. C.; Rollin, P. Synthesis 1990, 130-132.
16. Watkins, B.E.; Kiely, J.S.; Rapoport, H. J. Am. Chem. Soc. 1982, 104, 5702-5708.
17. 6): 1.28 (s, 9H, 2.17 (t, J=7.0, 2H), 2.95-3.05 (m, 2H), 3.28 (s, 2H) 4.86 (d, J=7.0, 2H), 5.20, (s, 2H), 5.57 (t, J=7.0, 1H), 6.69 (t, J=5.5, 1H), 7.10-7.48 (m, 6H, 8.39 (s, 1H), 8.61 (s, 1H), 10.64 (s.br 1H).
18. Christensen, L.; Fitzpatrick, R.; Gildea, B.; Petersen, K.H.; Hansen, H.F.; Koch, T.; Egholm, M.; Buchhardt, O.; Nielsen, P.E.; Coull, J.; Berg, R.H. J. Pep. Sci. 1995, 3, 175-183
19. Will, D. W.; Breipohl, G.; Langner,D.; Knolle, J.; Uhlmann, E. Tetrahedron 1995, 57, 12069-12082.