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Conformational states of antamanide and its analogs in solutions

Summary

1. A preferred conformation of antamanide in nonpolar solvents has been proposed with the aid of a wide group of physicochemical methods and theoretical analyses.

2. On the basis of spectroscopic results, the hypothesis has been put forward of the existence of two other forms of antamanide (B and C) which form on passing from nonpolar to polar media.

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Literature cited

  1. 1.

    M. M. Shemyakin, Yu. A. Ovchinnikov, V. T. Ivanov, V. K. Antonov, E. I. Vinogradova, A. M. Shkrob, G. G. Malenkov, A. V. Evstratov, I. A. Laine, E. I. Melnik, and I. D. Ryabova, J. Membr. Biol.,1, 402 (1969).

  2. 2.

    C. Moore and B. C. Pressman, Biochem. Biophys. Res. Commun.,15, 562 (1964).

  3. 3.

    T. Wieland, H. Faulstich, W. Burgermeister, W. Möhle, M. M. Shemyakin, Yu. A. Ovchinnikov, V. T. Ivanov, and G. G. Malenkov, FEBS Letters,9, 89 (1970); I. M. Andreev, G. G. Malenkov, A. M. Shkrob, and M. M. Shemyakin, Molekul. Biol.,4, 614 (1971).

  4. 4.

    V. T. Ivanov, A. I. Miroshnikov, N. D. Abdullaev, L. B. Senyavina, S. F. Arkhipova, N. N. Uvarova, K. Kh. Khalilulina, V. F. Bystrov, and Yu. A. Ovchinnikov, Biochem. Biophys. Res. Commun.,42, 654 (1971).

  5. 5.

    Yu. A. Ovchinnikov, V. T. Ivanov, and A. M. Shkrob, Proceedings of an International Symposium on Molecular Mechanisms of Antibiotic Action on Protein Biosynthesis and Membranes, Elsevier, Amsterdam (1972); Yu. A. Ovchinnikov, V. T. Ivanov, V. F. Bystrov, N. D. Abdullaev, and A. I. Miroshnikov, Proceedings of the 10th European Peptide Symposium, Vienna (1971).

  6. 6.

    B. C. Pressman, E. J. Harris, W. S. Jagger, and J. H. Johnson, Proc. Nat. Acad. Sci. USA,58, 1949 (1956).

  7. 7.

    Yu. A. Ovchinnikov, V. T. Ivanov, L. I. Barsukov, E. I. Melnik, N. I. Oreshnikova, N. D. Bogolyubova, I. D. Ryabova, A. I. Miroshnikov, and V. A. Rimskaya, Exper.,28, 399 (1972); Yu. A. Ovchinnikov, V. T. Ivanov, A. I. Miroshnikov, K. Kh. Khalilulina, and N. N. Uvarova, Khim. Prirodn. Soedin., 469 (1971).

  8. 8.

    A. I. Miroshnikov, K. Kh. Khalilulina, N. N. Uvarova, V. T. Ivanov, and Yu. A. Ovchinnikov, Khim. Prirodn. Soedin., 214 (1973).

  9. 9.

    M. Ohnishi and D. W. Urry, Biochem. Biophys. Res. Commun.,36, 194 (1969); D. W. Urry, Spectroscopic Approaches to Biomolecular Conformation, Amer. Med. Association, Chicago (1970); S. L. Portnova, T. A. Balashova, V. F. Bystrov, V. V. Shilin, J. Biernat, V. T. Ivanov, and Yu. A. Ovchinnikov, Khim. Prirodn. Soedin., 323 (1971).

  10. 10.

    S. L. Portnova, V. V. Shilin, T. A. Balashova, J. Biernat, V. F. Bystrov, V. T. Ivanov, and Yu. A. Ovchinnikov, Tetrahedron Lett., 3085 (1971).

  11. 11.

    V. T. Ivanov, I. A. Laine, N. D. Abdullaev, V. Z. Pletnev, G. M. Lipkind, S. F. Arkhipova, L. B. Senyavina, E. N. Meshcheryakova, E. M. Popov, V. F. Bystrov, and Yu. A. Ovchinnikov, Khim. Prirodn. Soedin., 221 (1971).

  12. 12.

    Yu. A. Ovchinnikov, V. T. Ivanov, V. F. Bystrov, A. I. Miroshnikov, E. N. Shepel, N. D. Abdullaev, E. S. Efremov, and L. B. Senyavina, Biochem. Biophys. Res. Commun.,39, 217 (1970).

  13. 13.

    V. F. Bystrov, S. L. Portnova, V. I. Tsetlin, V. T. Ivanov, and Yu. A. Ovchinnikov, Tetrahedron,25, 493 (1969).

  14. 14.

    R. Garner and W. B. Watkins, J. Chem. Soc., 386 (1969); V. Madison and J. Schellman, Biopolymers,9, 511 (1970).

  15. 15.

    V. Madison and J. Schellman, Biopolymers,9, 65 (1970); C. M. Deber, F. A. Bovey, J. P. Carver, and E. R. Blout, J. Amer. Chem. Soc.,92, 6191 (1970); V. J. Hruby, A. I. Brewster, and J. A. Glasel, Proc. Nat. Acad. Sci. USA,68, 450 (1971).

  16. 16.

    G. H. Cooper, Chem. Ind. (London), 1304 (1969); H. L. Maja, K. G. Orrell, and H. N. Ryden, J. Chem. Soc., 1209 (1971); V. T. Ivanov, P. V. Kostetskii, T. A. Balashova, S. L. Portnova, E. S. Efremov, and Yu. A. Ovchinnikov, Khim. Prirodn. Soedin., 339 (1973).

  17. 17.

    D. A. Torchia, A. di Corato, S. C. K. Wong, C. M. Deber, and E. R. Blout, J. Amer. Chem. Soc.,93, 609 (1971); D. A. Torchia, S. C. K. Wong, C. M. Deber, and E. R. Blout, J. Amer. Chem. Soc.,93, 616 (1971).

  18. 18.

    J. C. Kendrew, W. Klyne, S. Lifson, T. Miyazawa, G. Nemethy, D. C. Phillips, G. N. Ramachandran, and H. A. Scheraga, J. Mol. Biol.,52, 1 (1970); Biochemistry,9, 3471 (1970); Arch. Biochem. Biophys.,145, 405 (1971).

  19. 19.

    P. R. Schimmel and P. J. Flory, J. Mol. Biol.,34, 105 (1968).

  20. 20.

    S. J. Leach, G. Nemethy, and H. A. Scheraga, Biopolymers,4, 369 (1966); N. Go, P. N. Lewis, and H. A. Scheraga, Macromolecules,3, 628 (1970).

  21. 21.

    E. M. Popov, G. M. Lipkind, S. F. Arkhipova, and V. G. Dashevskii, Molekul. Biol.,2, 622 (1968).

  22. 22.

    A. Damiani, P. de Santis, and A. Pizzi, Nature,226, 542 (1970); M. Maigret, B. Pullman, and J. Caillet, Biochem. Biophys. Res. Commun.,40, 808 (1970).

  23. 23.

    M. Maigret, B. Pullman, and D. Perahia, J. Theor. Biol.,31, 269 (1971); M. Venkatachalam, Biopolymers,6, 1425 (1968).

  24. 24.

    S. L. Portnova, V. F. Bystrov, T. A. Balashova, V. I. Tsetlin, P. V. Kostetskii, V. T. Ivanov, and Yu. A. Ovchinnikov, Tetrahedron Lett., 5225 (1969); S. L. Portnova, V. F. Bystrov, T. A. Balashova, V. I. Tsetlin, P. V. Kostetskii, V. T. Ivanov, and Yu. A. Ovchinnikov, Zh. Obshch. Khim.,41, 407 (1971).

  25. 25.

    B. Pullman, Aspects de la Chimie Quantique Contemporaine, ed. R. Daudel and A. Pullman, Colloque International du CNRS, Paris (1971); p. 261; E. M. Popov and G. M. Lipkind, Molekul. Biol.,5, 624 (1971).

  26. 26.

    V. T. Ivanov, S. L. Portnova, T. A. Balashova, V. F. Bystrov, V. V. Shilin, J. Biernat, and Yu. A. Ovchinnikov, Khim. Prirodn. Soedin., 339 (1971); V. T. Ivanov, L. B. Senyavina, E. S. Efremov, V. V. Shilin, and Yu. A. Ovchinnikov, Khim. Prirodn. Soedin., 347 (1971); V. T. Ivanov, V. V. Shilin, G. A. Kogan, E. N. Meshcheryakova (Mesheryakova), L.B. Senyavina, E. S. Efremov, and Yu. A. Ovchinnikov, Tetrahedron Lett., 2841 (1971); V. T. Ivanov, P. V. Kostetskii, E. N. Meshcheryakova, E. S. Efremov, E. M. Popov, and Yu. A. Ovchinnikov, Khim. Prirodn. Soedin., 363 (1973); A. D. Rudko, F. M. Lovell, and B. W. Low, Nature (New Biology),232, 18 (1971); T. Ueki, T. Ashida, M. Kakudo, Y. Sasada, and Y. Katsube, Acta Cryst., B,25, 1840 (1969); I. L. Karle and J. Karle, Acta Cryst.,16, 969 (1963); I. L. Karle, J. W. Gibson, and J. Karle, J. Amer. Chem. Soc.,92, 3755 (1970).

  27. 27.

    E. M. Popov, V. Z. Pletnev, A. V. Evstratov, V. T. Ivanov, and Yu. A. Ovchinnikov, Khim. Prirodn. Soedin., 616 (1970).

  28. 28.

    A. E. Tonelli, D. J. Patel, M. Goodman, F. Naider, H. Faulstich, and T. Wieland, Biochemistry,10, 3211 (1971).

  29. 29.

    V. J. Kowalevsky, Progress in NMR Spectroscopy,5, 1 (1969).

  30. 30.

    G. Hedestrand, Z. Phys. Chem., B,2, 428 (1929).

  31. 31.

    E. S. Efremov, P. V. Kostetskii, V. T. Ivanov, E. M. Popov, and Yu. A. Ovchinnikov, Khim. Prirodn. Soedin., 354 (1973).

  32. 32.

    H. Strassmair, J. Engel, and G. Zundel, Biopolymers,8, 237 (1969).

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Additional information

M. M. Shemyakin Institute of the Chemistry of Natural Compounds, Academy of Sciences of the USSR. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 378–394, May–June, 1973.

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Ivanov, V.T., Miroshnikov, A.I., Koz'min, S.A. et al. Conformational states of antamanide and its analogs in solutions. Chem Nat Compd 9, 353–365 (1973). https://doi.org/10.1007/BF00565693

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Keywords

  • Conformational State
  • Valinomycin
  • Deuterium Exchange
  • Conformational Equilibrium
  • Nonpolar Medium