Synthesis and structure of dinucleotides with S-type sugar puckering and noncanonical ε and ζ torsion angle combination (ν2, ε,ζ-D-CNA)

European Journal of Organic Chemistry

Volumn , Issue 7, 2008, Pages 1285-1294

  Dupouy, Christelle ^a   Lavedan, Pierre ^a   Escudier, Jean Marc ^b  

^a CNRS   (France)

^b UNIVERSITÉ PAUL SABATIER   (France)

Author keywords

Conformation analysis; DNA structure; Nucleotides; Phosphorus heterocycles; Strained molecules

Indexed keywords

EID: 49149109089     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200701022     Document Type: Article

References (50)

1. C. J. Leumann, Bioorg. Med. Chem. 2002, 10, 841-854.
2. J. Wengel, Acc. Chem. Res. 1999, 32, 301-310.
3. P. Herdewijn, Biochim. Biophys. Acta 1999, 1489, 167-179.
4. S. Obika, D. Nanbu, Y. Hari, K.-I. Morio, Y. In, T. Ishida, T. Imanishi, Tetrahedron Lett. 1997, 38, 8735-8738.
5. S. Obika, D. Nanbu, Y. Hari, J.-I. Andoh, K.-I. Morio, T. Doi, T. Imanishi, Tetrahedron Lett. 1998, 39, 5401-5404.
6. S. K. Singh, P. Nielsen, A. A. Koshkin, J. Wengel, Chem. Commun. 1998, 455-456.
7. M. Maderia, S. Shenoy, Q. N. Van, V. E. Marquez, J. J. Barchi Jr, Nucleic Acids Res. 2007, 35, 1978-1991.
8. D. Renneberg, C. J. Leumann, J. Am. Chem. Soc. 2002, 124, 5993-6002.
9. E. T. Kool, Chem. Rev. 1997, 97, 1473-1487.
10. a) K. Seio, T. Wada, K. Sakamoto, S. Yokoyama, M. Sekine, J. Org. Chem. 1998, 63, 1429-1443;
11. b) K. Seio, T. Wada, M. Sekine, Helv. Chim. Acta 2000, 83, 162-180;
12. c) M. Sekine, O. Kurasawa, K. Shohda, K. Seio, T. Wada, J. Org. Chem. 2000, 65, 3571-3578;
13. d) M. Sekine, O. Kurasawa, K. Shohda, K. Seio, T. Wada, J. Org. Chem. 2000, 65, 6515-6524;
14. e) M. Sekine, O. Kurasawa, K. Shohda, K. Seio, T. Wada, Eur. J. Org. Chem. 2001, 1989-1999.
15. a) A. M. Sørensen, P. Nielsen, Org. Lett. 2000, 2, 4217-4219;
16. b) A. M. Sørensen, K. E. Nielsen, B. Vogg, J. P. Jacobsen, P. Nielsen, Tetrahedron 2001, 57, 10191-10201;
17. c) P. Børsting, P. Nielsen, Chem. Commun. 2002, 2140-2141;
18. d) C. Kirchhoff, P. Nielsen, Tetrahedron Lett. 2003, 44, 6475-6478;
19. e) P. Børsting, M. Freitag, P. Nielsen, Tetrahedron 2004, 60, 10955-10966;
20. f) P. Børsting, K. E. Nielsen, P. Nielsen, Org. Biomol. Chem. 2005, 3, 2183-2190;
21. g) P. K. Sharma, B. H. Mikkelsen, M. S. Christensen, K. E. Nielsen, C. Kirchhoff, S. L. Pedersen, A. M. Sørensen, K. Østergaard, M. Petersen, P. Nielsen, Org. Biomol. Chem. 2006, 4, 2433-2445.
22. P. Belmont, J.-F. Constant, M. Demeunynck, Chem. Soc. Rev. 2001, 30, 70-81.
23. P. Várnai, D. Djuranovic, R. Lavery, B. Hartmann, Nucleic Acids Res. 2002, 30, 5398-5406.
24. a) D. Djuranovic, B. Hartmann, Biopolymers 2004, 73, 356-368;
25. b) B. Heddi, N. Foloppe, N. Bouchemal, E. Hantz, B. Hartmann, J. Am. Chem. Soc. 2006, 128, 9170-9177.
26. C. M. Duarte, A. M. Pyle, J. Mol. Biol. 1998, 284, 1465-1478.
27. I. Le Clezio, J.-M. Escudier, A. Vigroux, Org. Lett. 2003, 5, 161-164.
28. C. Dupouy, I. Le Clezio, P. Lavedan, H. Gornitzka, J.-M. Escudier, A. Vigroux, Eur. J. Org. Chem. 2006, 5515-5525.
29. C. Dupouy, N. Iché-Tarrat, M.-P. Durrieu, F. Rodriguez, J.-M. Escudier, A. Vigroux, Angew. Chem. 2006, 118, 3705-3709;
30. Angew. Chem. Int. Ed. 2006, 45, 3623-3627.
31. I. Le Clezio, C. Dupouy, P. Lavedan, J.-M. Escudier, Eur. J. Org. Chem. 2007, 3894-3900.
32. I. Le Clezio, A. Vigroux, J.-M. Escudier, Eur. J. Org. Chem. 2007, 1935-1941.
33. C. Dupouy, P. Lavedan, J.-M. Escudier, Eur. J. Org. Chem. 2007, 5256-5264.
34. I. Le Clezio, H. Gornitzka, J.-M. Escudier, A. Vigroux, J. Org. Chem. 2005, 70, 1620-1629.
35. C. Dupouy, P. Lavedan, J.-M. Escudier, Tetrahedron 2007, 63, 11235-11243.
36. M. H. Caruthers, Acc. Chem. Res. 1991, 24, 278-284.
37. H. Vorbrüggen, K. Krolikiewiecz, B. Bennua, Chem. Ber. 1981, 114, 1234-1255.
38. C. K. H. Tseng, V. E. Marquez, G. W. A. Milne, R. J. Wysocki, H. Mitsuya, T. Shirasaki, J. S. Driscoll, J. Med. Chem. 1991, 34, 343-349.
39. N.-S. Li, J. A. Piccirilli, J. Org. Chem. 2004, 69, 4751-4759.
40. A. Matsuda, K. Takenuki, M. Tanaka, T. Sasaki, T. Ueda, J. Med. Chem. 1991, 34, 812-819.
41. J. B. J. Pavey, A. J. Lawrence, A. J. Potter, R. Cosstick, I. A. O'Neil, Tetrahedron Lett. 1998, 39, 6967-6970.
42. a) S. S. Jones, B. Rayner, C. B. Reese, A. Ubazawa, M. Ubasawa, Tetrahedron 1980, 36, 3075-3085;
43. b) C. B. Reese, R. C. Titmas, L. Yau, Tetrahedron Lett. 1978, 19, 2727-2730.
44. D. J. Wood, F. E. Hruska, K. K. Ogilvie, Can. J. Chem. 1974, 52, 3353-3366.
45. D. J. Wood, K. K. Ogilvie, F. E. Hruska, Can. J. Chem. 1975, 53, 2781-2790.
46. D. G. Gorenstein, R. Rowell, J. Findlay, J. Am. Chem. Soc. 1980, 102, 5077-5081.
47. W. C. Johnson in Circular Dichroism: Principles and Applications (Eds.: N. Berova, K. Nakanishi, R. W. Woody), John Wiley & Sons, New York, 2000, pp. 703-718.
48. C. Altona, M. Sundaralingam, J. Am. Chem. Soc. 1973, 95, 2333-2344.
49. N. Camerman, J. K. Fawcett, A. Camerman, J. Mol. Biol. 1976, 107, 601-621.
50. B. Schneider, S. Neidle, H. M. Berman, Biopoly. 1997, 42, 113-124.