Oligonucleotides functionalized by fluorescein and rhodamine dyes: Michael addition of methyl acrylate to 2'-deoxypseudouridine

Helvetica Chimica Acta

Volumn 83, Issue 6, 2000, Pages 1108-1126

  Ramzaeva, Natalya ^a   Rosemeyer, Helmut ^a   Leonard, Peter ^a   Mühlegger, Klaus ^b   Bergmann, Frank ^b   Von Der Eltz, Herbert ^b   Seela, Frank ^a  

^a UNIVERSITY OF OSNABRÜCK   (Germany)

^b ROCHE DIAGNOSTICS GMBH   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ACRYLIC ACID METHYL ESTER; DEOXYURIDINE DERIVATIVE; PSEUDOURIDINE;

ARTICLE; FLUORESCENCE ANALYSIS; PEPTIDE SYNTHESIS; REACTION ANALYSIS; STRUCTURE ANALYSIS;

EID: 0034085537     PISSN: 0018019X     EISSN: None     Source Type: Journal    
DOI: 10.1002/1522-2675(20000607)83:6<1108::AID-HLCA1108>3.0.CO;2-9     Document Type: Article

References (44)

1. F. F. Davis, F. W. Allen, J. Biol. Chem. 1957, 227, 907; W. E. Cohn, Fed. Proc. 1957, 16, 166.
2. F. F. Davis, F. W. Allen, J. Biol. Chem. 1957, 227, 907; W. E. Cohn, Fed. Proc. 1957, 16, 166.
3. R. Shapiro, R. W. Chambers, J. Am. Chem. Soc. 1961, 83, 3920.
4. A. M. Michelson, W. E. Cohn, Biochemistry 1962, 1, 490; R. W. Chambers, Prog. Nucleic Acid Res. Mol. Biol. 1966, 5, 349.
5. A. M. Michelson, W. E. Cohn, Biochemistry 1962, 1, 490; R. W. Chambers, Prog. Nucleic Acid Res. Mol. Biol. 1966, 5, 349.
6. R. Cortese, H. O. Kammen, S. J. Spengler, B. N. Ames, J. Biol. Chem. 1974, 249, 1103.
7. K. A. Watanabe, in 'Chemistry of Nucleosides and Nucleotides', Ed. L. B. Townsend, Plenum Press, New York, London, 1994, p. 421.
8. C. K. Chu, U. Reichman, K. A. Watanabe, J. J. Fox, J. Heterocycl. Chem. 1977, 14, 1119.
9. K. Pankiewicz, A. Matsuda, K. A. Watanabe, J. Org. Chem. 1982, 47, 485.
10. J. A. Piceirilli, S. E. Moroney, S. A. Benner, Biochemistry 1991, 30, 10350.
11. B. K. Bhattacharya, R. V. Devivar, G. R. Revankar, Nucleosides Nucleotides 1995, 14, 1269.
12. I. Rosenberg, J. F. Soler, Z. Tocik, W.-Y. Ren, L. A. Ciszewski, P. Kois, K. H. Pankiewicz, M. Spassova, K. A. Watanabe, Nucleosides Nucleotides 1993, 12, 381.
13. J. Haralambidis, M. Chai, G. W. Tregear, Nucleic Acids Res. 1987, 15, 4857.
14. P. Hagmar, M. Bailey, G. Tong, J. Haralambidis, W. H. Sawyer, B. E. Davidson, Biochim. Biophys. Acta 1995, 1244, 259.
15. J. A. Brumbaugh, L. R. Middendorf, D. L. Grone, J. L. Ruth, Proc. Natl. Acad. Sci. U.S.A. 1988, 85, 5610.
16. R. W. Chambers, Biochemistry 1965, 4, 219; A. Wilk, A. Grajkowski, L. R. Phillips, S. A. Beaucage, J. Org. Chem. 1999, 64, 7515; M. Mag, J. W. Engels, Nucleic Acids Res. 1988, 16, 3525.
17. R. W. Chambers, Biochemistry 1965, 4, 219; A. Wilk, A. Grajkowski, L. R. Phillips, S. A. Beaucage, J. Org. Chem. 1999, 64, 7515; M. Mag, J. W. Engels, Nucleic Acids Res. 1988, 16, 3525.
18. R. W. Chambers, Biochemistry 1965, 4, 219; A. Wilk, A. Grajkowski, L. R. Phillips, S. A. Beaucage, J. Org. Chem. 1999, 64, 7515; M. Mag, J. W. Engels, Nucleic Acids Res. 1988, 16, 3525.
19. M. Yoshida, T. Ukita, Biochim. Biophys. Acta 1968, 157, 455.
20. A. V. Rake, G. M. Tener, Biochemistry 1966, 5, 3992.
21. I. Luyten, K. W. Pankiewicz, K. A. Watanabe, J. Chattopadhyaya, J. Org. Chem. 1998, 63, 1033.
22. R. A. Earl, L. B. Townsend, J. Heterocycl. Chem. 1977, 14, 699.
23. A. Matsuda, C. K. Chu, U. Reichman, K. Pankiewicz, K. A. Watanabe, J. J. Fox, J. Org. Chem. 1981, 46, 3603.
24. A. D. Argoudelis, S. A. Mizsak, J. Antibiotics 1976, 29, 818.
25. H. Schaller, G. Weimann, B. Lerch, H. G. Khorana, J. Am. Chem. Soc. 1963, 85, 3821.
26. S. L. Beaucage, M. Caruthers, Tetrahedron Lett. 1981, 22, 1859.
27. B. C. Froehler, 'Protocols for Oligonucleotides and Analogs', in 'Methods in Molecular Biology', Ed. E. S. Agrawal, Humana Press, Totowa, N.J., 1993, Vol. 20, p. 63.
28. J. C. Schulhof, D. Molko, R. Teoule, Nucl. Acids Res. 1987, 15, 397 (manufactures information: http:// www.glenres.com).
29. S. Kohgo, K. Shinozuka, H. Ozaki, H. Sawai, Tetrahedron Lett. 1998, 39, 4067.
30. J. Hovinen, A. Guzaev, E. Azhayeva, A. Azhayev, H. Lönnberg, J. Org. Chem. 1995, 60, 2205.
31. J. B. Randolph, A. S. Waggoner, Nucleic Acids Res. 1997, 25, 2923.
32. T. L. Trapane, M. S. Christopherson, C. D. Roby, P. O. P. Ts'o, D. Wang, J. Am. Chem. Soc. 1994, 116, 8412.
33. N. Branda, G. Kurz, J.-M. Lehn, J. Chem. Soc., Chem. Commun. 1996, 2443.
34. H. Rosemeyer, G. Toth, B. Golankiewicz, Z. Kazimierczuk, W. Bourgeois, U. Kretschmer, H.-P. Muth, F. Seela, J. Org. Chem. 1990, 55, 5784.
35. J. van Wijk, C. Altona, 'PSEUROT 6.2 - A Program for the Conformational Analysis of the Five-Membered Rings', University of Leiden, July, 1993.
36. C. Thibaudeau, J. Plavec, K. A. Watanabe, J. Chattopadhyaya, J. Chem. Soc., Chem. Commun. 1994, 537.
37. H. Rosemeyer, M. Zulauf, N. Ramzaeva, G. Becher, E. Feiling, K. Mühlegger, I. Münster, A. Lohmann, F. Seela. Nucleosides Nucleotides 1997, 16, 821.
38. F. Seela, Y. He, unpublished results.
39. Dr. Frank Bergmann (Roche Diagnostics GmbH, Penzberg), personal communication.
40. G. T. Hermanson, 'Bioconjugate Techniques', Academic Press, New York, 1996, p. 670.
41. R. Hermann, H.-P. Josel, K.-H. Drexhage, J. Arden-Jacob, European Patent EP 0 567 622 B1, 24.04. 1996.
42. F. Seela, S. Lampe, Helv. Chim. Acta 1991, 74, 1790.
43. J. A. McDowell, D. H. Turner, Biochemistry 1996, 35, 14077.
44. F. M. Rossi, J. P. Y. Kao, Bioconjugate Chem. 1997, 8, 495.