Synthesis of Modified Peptides with C-Terminal α-Amino Aldehydes

Russian Journal of Bioorganic Chemistry

Volumn 27, Issue 3, 2001, Pages 141-150

  Potetinova, J V ^a   Milgotina, E I ^a   Makarov, V A ^b   Voyushina, T L ^a  

^a STATE RESEARCH INSTITUTE OF GENETICS AND SELECTION OF INDUSTRIAL MICROORGANISMS   (Russian Federation)

^b NATIONAL RESEARCH CENTER FOR HEMATOLOGY   (Russian Federation)

Author keywords

Chemical synthesis; Enzyme synthesis; Peptide aldehydes; Protease inhibitors

Indexed keywords

EID: 0035638193     PISSN: 10681620     EISSN: None     Source Type: Journal    
DOI: 10.1023/A:1011365401976     Document Type: Review

References (60)

1. Bajusz, S., Szell, E., Bagdy, D., Barabas, E., Horvath, G., Dioszegi, M., Fittler, Z., Szabo, G., Juhasz, A., Tomori, E., and Szilagy, G., J. Med. Chem., 1990, vol. 33, pp. 1729-1735.
2. Mehdy, Sh., Angelastro, M.R., Wiseman, J.S., and Bey, Ph., Biochem. Biophys. Res. Commun., 1988, vol. 157, pp. 1117-1123.
3. Livingston, D.J., J. Cell Biochem., 1997, vol. 64, pp. 19-26.
4. Thompson, R.C., Biochemistry, 1973, vol. 12, pp. 47-51.
5. Sarubbi, E., Seneci, P.F., Angelastro, M.R., Peet, N.P., Denaro, M., and Islam, K., FEBS Lett., 1993, vol. 319, pp. 253-256.
6. Fehrentz, J.A., Heitz, A., Castro, B., Cazaubon, C., and Nisato, D., FEBS Lett., 1984, vol. 167, pp. 273-276.
7. Basak, A., Jean, F., Seidah, N.G., and Lazure, C., Int. J. Peptide Protein Res., 1994, vol. 44, pp. 253-261.
8. Dobson, G. and Wlodawer, A., Trends Biochem. Sci., 1998, vol. 23, pp. 347-352.
9. Stefanelli, C., Bonavita, F., Stanic, I., Pignatt, C., Farruggia, G., Masotti, L., Guarnieri, C., and Caldarera, C.M., Biochem. J., 1998, vol. 332, pp. 661-665.
10. Hamazaki, H., FEBS Lett., 1998, vol. 424, pp. 136-138.
11. Bagdy, D., Barabas, E., Szabo, G., Bajusz, S., and Szell, E., Thrombosis and Haemostasis, 1992, vol. 67, pp. 357-365.
12. Teno, N., Wanaka, K., Okada, Y., Tsuda, Y., Okamoto, U., Hijikata-Okunomiya, A., Naito, T., and Okamoto, S., Chem. Pharm. Bull., 1991, vol. 39, pp. 2340-2346.
13. Thornberry, N.A., Bull, H.G., Calaycay, J.R., Chapman, K.T., Howard, A.D., Kostura, M.J., Miller, D.K., Molineaux, S.M., Weidner, J.R., and Aunins, J., Nature, 1992, vol. 356, pp. 768-774.
14. Odake, S., Kam, C.M., Narasimhan, L., Poe, M., Blake, J.T., Krahenbuhl, O., Tschopp, J., and Powers, J.C., Biochemistry, 1991, vol. 30, pp. 2217-2227.
15. Wellink, J. and van Kammen, A., Arch. Virol., 1988, vol. 98, pp. 1-26.
16. Scheidt, K.A., Roush, W.R., McKerrow, J.H., Selzer, P.M., Hansell, E., and Rosenthal, P.J., Bioorg. Med. Chem., 1998, vol. 6, pp. 2477-2494.
17. Albeck, A., Persky, R.K., and Kliper, S., Bioorg. Med. Chem. Lett., 1995, vol. 5, pp. 1767-1772.
18. Nishikata, M., Kasai, K., and Ishii, S., Biochim. Biophys. Acta, 1981, vol. 660, pp. 256-261.
19. Someno, T., Saino, T., Katoh, K., Miyazaki, H., and Ishii, S., J. Biochem., 1985, vol. 97, pp. 1493-1500.
20. Ito, A., Takahashi, R., and Baba, J., Chem. Pharm. Bull., 1975, vol. 23, pp. 3081-3087.
21. Ho, P.T. and Ngu, K.J., J. Org. Chem., 1993, vol. 58, pp. 2313-2316.
22. Rittle, K.E., Homnick, C.F., Ponticello, G.S., and Evans, B.E., J. Org. Chem., 1982, vol. 47, pp. 3016-3018.
23. Maeda, K. and Umezawa, H., J. Antibiotics, 1972, vol. 25, pp. 515-523.
24. McConnel, R.S., York, J.L., Frizzel, D., and Ezzell, C., J. Med. Chem., 1993, vol. 36, pp. 1084-1089.
25. Ried, W. and Pfaender, P., Liebigs Ann. Chem., 1961, vol. 640, pp. 111-126.
26. Masaki, T., Tanaka, T., Tsunasawa, S., Sakiyama, F., and Soejima, M., Biosci. Biotech. Biochem., 1992, vol. 56, pp. 1604-1607.
27. Modifitsirovannye aminokisloty i peptidy na ikh osnove (Modified Amino Acids and the Derived Peptides), Cipens, G.I., Ed., Riga: Zinante, 1987.
28. Potetinova, Zh.V., The Strategy of the Biocatalytic Synthesis of Modified Peptides, Protease Inhibitors, Cand. Sci. (Chem.) Dissertation, Moscow: Moscow State Univ., 2000, pp. 34-42.
29. Umezawa, H., Methods Enzymol., 1981, vol. 80, p. 842.
30. Yokosawa, H., Nishikata, M., and Ishii, S., J. Biochem., 1984, vol. 95, pp. 1819-1821.
31. McConnell, R.S., Barnes, G.E., Hoyng, C.F., and Gunn, J.M., J.. Med. Chem., 1990, vol. 33, pp. 86-93.
32. Ito, A., Takahashi, R., Miura, Ch., and Baba, Y., Chem. Pharm. Bull., 1973, vol. 22, pp. 3106-3113.
33. Someno, T. and Ishii, S., Chem. Pharm. Bull., 1986, vol. 34, pp. 1748-1754.
34. Chapman, K.T., Bioorg. Med. Chem. Lett., 1992, vol. 2, pp. 613-618.
35. Balasubramanian, N. and Laurent, D.R., Eur. Pat. Appl. Ep. 256877, 1993, vol. 5.
36. Shuman, P.T., Rothenberger, R.B., Campbell, C.S., Smith, G.F., Gifford-Moore, D.S., and Gesellchen, P.D., J. Med. Chem., 1993, vol. 36, pp. 314-319.
37. Fehrentz, J.A., Paris, M., Heitz, A., Velek, J., Liu, C.F., Winternitz, F., and Martinez, J., Tetrahedron Lett., 1995, vol. 36, pp. 7871-7874.
38. Fehrentz, J.A., Paris, M., Heitz, A., Velek, J., Winternitz, F., and Martinez, J., J. Org. Chem., 1997, vol. 62, pp. 6792-6796.
39. Pothion, C., Paris, M., Heitz, A., Rocheblave, L., Rouch, F., Fehrentz, J.A., and Martinez, J., Tetrahedron Lett., 1997, vol. 38, pp. 7749-7752.
40. Hall, B.J. and Sutherland, J.D., Tetrahedron Lett., 1998, vol. 39, pp. 6593-6596.
41. Murphy, A.M., Dagnino, R., Pureza, I.R., Vallar, L., Trippe, A.I., Sherman, Sh.L., Lumpkin, R.M., Tamura, S.Y, and Webb, Th.R., J. Am. Chem. Soc., 1992, vol. 114, pp. 3156-3157.
42. Galleotti, N., Plagnes, E., and Jouin, P., Tetrahedron Lett., 1997, vol. 38, pp. 2459-2462.
43. Galleotti, N., Giraud, M., and Jouin, P., Lett. Pept. Sci., 1997, vol. 4, pp. 437-440.
44. Ede, N.J. and Bray, A.M., Tetrahedron Lett., 1997, vol. 38, pp. 7119-7122.
45. Hamada, Y. and Shioiri, T., Chem. Pharm. Bull., 1982, vol. 30, pp. 1921-1924.
46. Shepherd, T.A., Cox, G.A., McKinney, E., Tang, J., Wakulchik, M., Zimmerman, R.E., and Villarreal, E.C., Bioorg. Med. Chem. Lett., 1996, vol. 6, pp. 2893-2896.
47. Yasuma, T., Oi, S., Choh, N., Nomura, T., Furuyama, N., Nishimura, A., Fujisawa, Y., and Sohda, T., J. Med. Chem., 1998, vol. 41, pp. 4301-4308.
48. Fehrentz, J.A., Heitz, A., and Castro, B., Int. J. Pept. Protein Res., 1985, vol. 26, pp. 236-241.
49. Tanami, T., Yokoo, C., and Hatayama, K., Jpn. Patent 03 258 800, 1991.
50. Kawamura, K., Kondo, S., Maeda, K., and Umezawa, H., Chem Pharm. Bull., 1969, vol. 17, pp. 1902-1907.
51. Reetz, M.T. and Griebenow, N., Liebigs Ann. Chem., 1996, vol. 3, pp. 335-348.
52. Webber, S.E., Okano, K., Little, T.L., Reich, S.H., Xin, Y., Fuhrman, S.A., Matthews, D.A., Love, R.A., Hendrickson, T.F., Patick, A.K., Meador, J.W.III, Ferre, R.A., Brown, E.L., Ford, C.E., Binford, S.L., and Worland, S.T, J. Med. Chem., 1998, vol. 41, pp. 2786-2805.
53. Malcolm, B.A., Lowe, C., Shechosky, S., McKay, R.T., Yang, C.C., Shah, V.J., Simon, R.J., Vederas, J.C., and Santi, D.V., Biochemistry, 1995, vol. 34, pp. 8172-8179.
54. Dahl, K.H. and Dunn, M.F., Biochemistry, 1984, vol. 23, pp. 4094-4100.
55. West, J.B. and Wong, C.-H., Tetrahedron Lett., 1987, vol. 28, pp. 1629-1632.
56. Barbas, C.F. and Wong, C.-H., J. Chem. Soc., Chem. Commun., 1987, vol. 8, pp. 533-534.
57. Potetinova, J.V., Voyushina, T.L., and Stepanov, V.M., Bioorg. Med. Chem. Lett., 1997, vol. 7, pp. 705-710.
58. Voyushina, T.L., Potetinova, J.V., Milgotina, E.I., and Stepanov, V.M., Bioorg. Med. Chem., 2000, vol. 7, pp. 2953-2959.
59. Potetinova, J.V., Makarov, V.A., an Voyushina, T.L., Proc. 26 European Peptide Symp., Montpellier, France, 2000 (in press).
60. Milgotina, E.I. and Voyushina, T.L., Proc. 26 European Peptide Symp., Montpellier, France, 2000 (in press).