Homoserine derivatives for the preparation of base-stable nucleopeptide analogues

Letters in Peptide Science

Volumn 4, Issue 3, 1997, Pages 147-155

  Beltrán, Maite ^a   Maseda, Marta ^a   Robles, Jordi ^a   Pedroso, Enrique ^a   Grandas, Anna ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

Author keywords

Base stability; Homoserine; Nucleopeptides; Peptide oligonucleotide hybrids

Indexed keywords

EID: 0000981457     PISSN: 09295666     EISSN: None     Source Type: Journal    
DOI: 10.1007/BF02443527     Document Type: Article

References (32)

1. Ratajczak, M.Z. and Gewirtz, A.M., In Eckstein, F. and Lilley, D.M.J. (Eds.) Nucleic Acids and Molecular Biology, Vol. 8, Springer, Berlin, Germany, 1994, pp. 298-326.
2. Gamper, H.B., Reed, M.W., Cox, T., Virosco, J.S., Adams, A.D., Gall, A.A., Scholler, J.K. and Meyer, R.B., Nucleic Acids Res., 21 (1993) 145.
3. Jäschke, A., Fürste, J.P., Nordhoff, E., Hillenkamp, F., Cech, D. and Erdmann, V.A., Nucleic Acids Res., 22 (1994) 4810.
4. Juby, C.D., Richardson, C.D. and Brousseau, R., Tetrahedron Lett., 32 (1991) 879.
5. Ede, N.J., Tregear, G.W. and Haralambidis, J., Bioconj. Chem., 5 (1994) 373.
6. De la Torre, B.G., Aviñó, A., Tarrason, G., Piulats, J., Albericio, F. and Eritja, R., Tetrahedron Lett., 35 (1994) 2733.
7. Bongartz, J.-P., Aubertin, A.-M., Milhaud, P.G. and Lebleu, B., Nucleic Acids Res., 22 (1994) 4681.
8. Soukchareun, S., Tregear, G.W. and Haralambidis, J., Bioconj. Chem., 6 (1995) 43.
9. Basu, S. and Wickstrom, E., Tetrahedron Lett., 36 (1995) 4943.
10. Reed, M.W., Fraga, D., Schwartz, D.E., Scholler, J. and Hinrichsen, R.D., Bioconj. Chem., 6 (1995) 101.
11. Arar, K., Aubertin, A.-M., Roche, A.C., Monsigny, M. and Mayer, R., Bioconj. Chem., 6 (1995) 573.
12. Zhu, T., Wei, Z., Tung, C.-H., Dickerhof, W.A., Breslauer, K.J., Georgopoulos, D.E., Leibowitz, M.J. and Stein, S., Antisense Res. Dev., 3 (1993) 265.
13. Wei, Z., Tung, C.-H., Zhu, T. and Stein, S., Bioconj. Chem., 5 (1994) 468.
14. Corey, D.R., J. Am. Chem. Soc., 117 (1995) 9373.
15. Tung, C.-H., Breslauer, K.J. and Stein, S., Bioconj. Chem., 7 (1996) 529.
16. Truffert, J.-C., Lorthioir, O., Asseline, U., Thuong, N.T. and Brack, A., Tetrahedron Lett., 35 (1994) 2353.
17. Robles, J., Pedroso, E. and Grandas, A., J. Org. Chem., 59 (1994) 2482.
18. Robles, J., Pedroso, E. and Grandas, A., Nucleic Acids Res., 23 (1995) 4151.
19. Shabarova, Z.A., In Davidson, J.N. and Colun, W.E. (Eds.) Progress in Nucleic Acid Research and Molecular Biology, Academic Press, London, U.K., 1970, pp. 145-182.
20. Juodka, B.A., Nucleos. Nucleot., 3 (1984) 445.
21. Blackburn, G.M. and Gait, M.J., Nucleic Acids in Chemistry and Biology, Oxford University Press, Oxford, U.K., 1996, pp. 101-107.
22. McBride, L.J., Kierzek, R., Beaucage, S.L. and Caruthers, M.H., J. Am. Chem. Soc., 108 (1986) 2040.
23. Eritja, R., Robles, J., Fernández-Forner, D., Albericio, F., Giralt, E. and Pedroso, E., Tetrahedron Lett., 32 (1991) 1511.
24. Rabanal, F., Giralt, E. and Albericio, F., Tetrahedron, 51 (1995) 1449.
25. Montserrat, F.X., Grandas, A., Eritja, R. and Pedroso, E., Tetrahedron, 50 (1994) 2617.
26. Ozinskas, A.J. and Rosenthal, G.A., J. Org. Chem., 51 (1986) 5047.
27. Ramalingan, K. and Woodard, R.W., J. Org. Chem., 53 (1988) 1900.
28. Nair, S.A., Lee, B. and Hangaver, D.G., Synthesis, (1995) 810.
29. Baldwin, J.E., North, M. and Flinn, A., Tetrahedron, 44 (1988) 637.
30. Bolin, D.R., Sytwu, I.-I., Humiec, F. and Meienhofer, J., Int. J. Pept. Protein Res., 33 (1989) 353. See also Refs. 3, 4 and 5 cited therein.
31. Smith, M., Rammler, D.H., Goldberg, I.H. and Khorana, H.G., J. Am. Chem. Soc., 84 (1962) 430.
32. Stewart, J.M. and Young, J.D., Solid Phase Peptide Synthesis, Pierce Chemical Co., Rockford, IL, U.S.A., 1984, p. 63.