Novel uridin-2′-yl carbamates: Synthesis, incorporation into oligodeoxyribonucleotides, and remarkable fluorescence properties of 2′-pyren-1-ylmethylcarbamate

Journal of the Chemical Society. Perkin Transactions 1

Volumn 2, Issue 8, 2002, Pages 1092-1104

  Korshun, Vladimir A ^a,b   Stetsenko, Dmitry A ^a   Gait, Michael J ^a  

^a MRC LABORATORY OF MOLECULAR BIOLOGY   (United Kingdom)

^b SHEMYAKIN OVCHINNIKOV INSTITUTE OF BIOORGANIC CHEMISTRY   (Russian Federation)

Author keywords

[No Author keywords available]

Indexed keywords

DNA; FLUORESCENCE; RNA; SYNTHESIS (CHEMICAL);

OLIGONUCLEOTIDE DUPLEXES;

DERIVATIVES;

EID: 0036010004     PISSN: 14727781     EISSN: 13645463     Source Type: Journal    
DOI: 10.1039/b111434b     Document Type: Article

References (42)

1. D.J. Earnshaw, M.J. Gait Nucl. Acids Res. 1998, 26, 5551.
2. D.M.J. Lilley Curr. Opin. Struct. Biol. 1999, 9, 330.
3. R.B. Rupert, R. Ferré-D’Amaré Nature 2001, 410, 780.
4. S.K. Silverman, T.R. Cech Biochemistry 1999, 38, 14224.
5. H. Inoue, Y. Hayase, A. Imura, S. Iwai, K. Miura, E. Ohtsuka Nucl. Acids Res. 1987, 15, 6131.
6. T.H. Keller, R. Häner Helv. Chim. Acta 1993, 76, 884.
7. M. Grøtli, M. Douglas, B. Beijer, R.G. García, R. Eritja, B. Sproat J. Chem. Soc., Perkin Trans. 1 1997, 2779.
8. M. Grøtli, M. Douglas, R. Eritja, B. Sproat Tetrahedron 1998, 54, 5899.
9. A.M. Kawasaki, M.D. Casper, T.P. Prakash, S. Manalili, H. Sasmor, M. Manoharan, P.D. Cook Tetrahedron Lett. 1999, 40, 661.
10. X. Wu, S. Pitsch Helv. Chim. Acta 2000, 83, 1127.
11. B. Guenoud, F. Casset, D. Hüsken, F. Natt, R.M. Wolf, K.-H. Altmann, P. Martin, H.E. Moser Angew. Chem., Int. Ed. 1998, 37, 1288.
12. D. Ly, L. Sanii, G.B. Schuster J. Am. Chem. Soc. 1999, 121, 9400.
13. K. Yamana, R. Aota, H. Nakano Tetrahedron Lett. 1995, 36, 8427.
14. H. Asanuma, T. Yoshida, T. Ito, M. Komiyama Tetrahedron Lett. 1999, 40, 7995.
15. A. Wachter, J.-A. Jablonski, K.L. Ramachandran Nucl. Acids Res. 1986, 14, 7985.
16. B.S. Sproat, D.M. Brown Nucl. Acids Res. 1983, 13, 2979.
17. K. Seio, T. Wada, K. Sakamoto, S. Yokoyama, M. Sekine J. Org. Chem. 1998, 63, 1429.
18. I. Dubey, G. Pratviel, B. Meunier J. Chem. Soc., Perkin Trans. 1 2000, 3088.
19. S.M. Freier, K.-H. Altmann Nucl. Acids Res. 1997, 25, 4429.
20. P.D. Cook and M. Manoharan, US Pat. 2000, 6,111,085.
21. P.D. Cook and M. Manoharan, US Pat., 2000, 6,166,188.
22. M. Prhavc, E.A. Lesnik, V. Mohan, M. Manoharan Tetrahedron Lett. 2001, 42, 8777.
23. W.T. Markiewicz J. Chem. Res. (S) 1979, 24.
24. B. Beijer, M. Grøtli, M.E. Douglas, B.S. Sproat Nucleosides Nucleotides 1994, 13, 1905.
25. S.P. Rannard, N.P. Davis Org. Lett. 2000, 2, 2117.
26. W.T. Markiewicz, P. Godzina, M. Markiewicz, A. Astriab Nucleosides Nucleotides 1998, 17, 1871.
27. K. Shinozuka, M. Matsukura, T. Okamoto, H. Sawai Nucleosides Nucleotides 1998, 17, 2081.
28. P. Potier, A. Abdennaji, J.-P. Behr Chem. Eur. J. 2000, 6, 4188.
29. D.M. Jameson, J.F. Eccleston Methods Enzymol. 1997, 278, 363.
30. K. Oiwa, J.F. Eccleston, M. Anson, M. Kikumoto, C.T. Davis, G.P. Reid, M.A. Ferenczi, J.E.T. Corrie, A. Yamada, H. Nakayama, D.R. Trentham Biophys. J. 2000, 78, 3048.
31. M. Smith, D.H. Rammler, I.H. Goldberg, H.G. Khorana J. Am. Chem. Soc. 1962, 84, 430.
32. H. Lutz, W. Pfleiderer Carbohydr. Res. 1984, 130, 179.
33. N.E. Geacintov, T. Prusik, J.M. Khosrofian J. Am. Chem. Soc. 1976, 98, 6444.
34. A. Wolfe, G.H. Shimer, Jr., T. Meehan Biochemistry 1987, 26, 6392.
35. N. Cho, S.A. Asher J. Am. Chem. Soc. 1993, 115, 6349.
36. K. Yamana, T. Gokota, H. Ozaki, H. Nakano, O. Sangen, T. Shimidzu Nucleosides Nucleotides 1992, 11, 383.
37. K. Yamana, R. Iwase, S. Furutani, H. Tsuchida, H. Zako, T. Yamaoka, A. Murakami Nucleic Acids Res. 1999, 27, 2387.
38. R. Iwase, A. Mahara, K. Yamana, T. Yamaoka, A. Murakami Nucleic Acids Symp. Ser. 1999, 42, 115.
39. K. Yamana, K. Asazuma, H. Nakano Nucleic Acids Symp. Ser. 1999, 42, 113.
40. K. Yamana, H. Zako, K. Asazuma, R. Iwase, H. Nakano, A. Murakami Angew. Chem., Int. Ed. 2001, 40, 1104.
41. M.H. Caruthers, A.D. Barone, S.L. Beaucage, D.R. Dodds, E.F. Fisher, L.J. McBride, M. Matteucci, Z. Stabinsky, J.-Y. Tang Methods Enzymol. 1987, 154, 287.
42. T. Brown and D.J.S. Brown. Modern machine-aided methods of oligodeoxyribonucleotide synthesis. Oligonucleotides and Analogues: A Practical Approach, ed. F. Eckstein, 1991, 1.