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Ion-Binding Polyesters and Polyamides Containing THF Rings

  • J. A. Moore
  • E. M. PartainIII
Part of the Polymer Science and Technology book series (POLS)

Abstract

In 1955, Corbaz and coworkers1 isolated an antibiotic from Streptomyces viridochromogenes and Streptomyces olivochromogenes which was named nonactin. The antibiotic was unusual because it was a neutral, optically inactive solid. In addition to nonactin, three homologs named monactin, dinactin, and triactin were subsequently isolated.2 This class of antibiotics is called the actins (Fig. 1).

Keywords

Crown Ether Alkali Metal Cation Alkali Metal Hydroxide Picrate Anion Potassium Picrate 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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References

  1. 1.
    R. Corbaz, L. Ettlinger, E. Gaumann, W. Keller-Schierlein, F. Krandolfer, L. Neipp, V. Prelog, and H. Zahner, Helv. Chim. Acta, 38, 1445 (1955).CrossRefGoogle Scholar
  2. 2a.
    H. Gerlach, K. Oertle, A. Thalmann, and S. Servi, Helv. Chim. Acta, 58, 2036 (1975). b. J. Beck, H. Gerlach, V. Prelog, and W. Voser, Ibid., 45, 620 (1962).CrossRefGoogle Scholar
  3. 3a.
    J. Dominguez, J. D. Dunitz, H. Gerlach, and V. Prelog, Helv. Chim. Acta, 45, 129 (1962). b. H. Gerlach and V. Prelog, Ann., 669, 121 (1963).CrossRefGoogle Scholar
  4. 4a.
    J. Gombas, E. Haslinger, H. Azk, and U. Schmidt, Tetrahedron Letters, 3391 (1975).Google Scholar
  5. 4b.
    J. Gombas, E. Haslinger, A. Nikiforov, H. Zak, and U. Schmidt Monatsh. Chem., 106, 1043 (1975). c. U. Schmidt, J. Gombas, E. Haslinger, and H. Zak, Chem. Ber., 109, 2628 (1976).Google Scholar
  6. 5a.
    B. C. Pressman, E. J. Harris, W. S. Jagger, and J. H. Johnson Proc. Natl. Acad. Sci., 58, 1949 (1967). b. B. C. Pressman, ibid., 53, 1076 (1965).CrossRefGoogle Scholar
  7. 6a.
    S. N. Graven, H. A. Lardy, and S. Estrada-O, Biochemistry, 6 365 (1967). b. S. N. Graven, H. A. Lardy, D. Johnson, and A. Rutter, ibid., 5, 1729 (1966).Google Scholar
  8. 7.
    G. Szabo, G. Eisenman, and S. Ciani, J. Membrane Biol., 3, 346 (1969).CrossRefGoogle Scholar
  9. 8.
    B. C. Pressman, Fed. Proced., 27, 1283 (1968).Google Scholar
  10. 9a.
    A. Agtarap, J. W. Chamberlin, M. Pinkerton, and I. Steinrauf, J. Am. Chem. Soc., 89, 5737 (1967). b. L. A. R. Pioda, H. A. Wachter, R. E. Dohner, and W. Simon, Helv. Chim. Acta, 50, 1373 (1967).CrossRefGoogle Scholar
  11. 10.
    B. T. Kilbourn, J. D. Dunitz, L. A. R. Pioda, and W. Simon, J. Mol. Biol., 30, 559 (1967).CrossRefGoogle Scholar
  12. 11a.
    C. J. Pedersen, J. Am. Chem. Soc., 89, 7017 (1967). b. idem., ibid., 92, 391 (1970).CrossRefGoogle Scholar
  13. 12a.
    idem., Fed. Proced., 27, 1305 (1968). b. C. J. Pedersen and H. K. Frensdorff, Angew. Chem., Int. Ed., 11, 16 (1972).Google Scholar
  14. 13.
    J. S. Bradshaw, S. L. Baxter, J. D. Lamb, R. M. Izatt, and J. J. Christensen, J. Am. Chem. Soc., 103, 1821 (1981).CrossRefGoogle Scholar
  15. 14.
    J. M. Timko, S. S. Moore, D. M. Walba, P. C. Hiberty, and D. J. Cram, ibid., 99, 4207 (1977).Google Scholar
  16. 15.
    R. T. Gray, D. N. Reinhoudt, C. J. Smit, I. Veenstra, Rec. trav. Chim. Pays-Bas, 95, 258 (1976).CrossRefGoogle Scholar
  17. 16.
    J. D. Lamb, R. M. Izatt, J. J. Christensen, and D. J. Eatough in “Coordination Chemistry of Macrocyclic Compounds”, G. A. Melson, ed., Chap. 3, Plenum Press, New York, 1979.Google Scholar
  18. 17a.
    J. J. Christensen, D. J. Eatough, and R. M. Izatt, Chem. Rev. 74, 351 (1974). b. J. J. Christensen, J. O. Hill, and R. M. Izatt, Science, 174, 459 (1971). c. R. M. Izatt, D. J. Eatough, and J. J. Christensen, Structure and Bonding, 16, 161 (1973). d. P. N. Kapoor and R. C. Mehrotra, Coord. Chem. Rev., 14, 1 (1974). e. J.-M. Lehn, J. Simon, and J. Wagner, Angew. Chem., Int. Ed., 12, 578 (1973). f. D. J. Cram and J. M. Cram, Science, 183, 803 (1974). g. J. S. Bradshaw, J. Y. Hui, B. I. Haymore, J. J. Christensen, and R. M. Izatt, J. Heterocycl. Chem., 10, 1 (1973). h. G. R. Newkome, J. D. Sauer, J. M. Roper, and D. C. Hager, Chem. Rev., 77, 513 (1977).Google Scholar
  19. 17i.
    R. M. Izatt and J. J. Christensen, “Synthetic Multidentate Macrocycle Compounds”, Academic Press, New York, 1978. j. R. M. Izatt and J. J. Christensen, “Progress in Macrocyclic Chemistry”, Volumes 1 and 2, J. Wiley, New York, 1980 and 1981. k. D. A. Laidler and J. F. Stoddart (Chapter 1), and F. Vogtle and E. Weber (Chapter 2), in “The Chemistry of Ethers, Crown Ethers, Hydroxyl Groups, and their Sulfur Analogs”, Supplement E, Part 1, S. Patai, ed., J. Wiley, New York, 1980.Google Scholar
  20. 18a.
    D. Bright and M. R. Truter, J. Chem. Soc., B, 1544 (1970). b. M. A. Bush and M. R. Truter, ibid., 1440 (1971).Google Scholar
  21. 19.
    M. R. Truter, Struct, and Bonding, 16, 71 (1973).CrossRefGoogle Scholar
  22. 20a.
    H. K. Frensdorff, J. Am. Chem. Soc., 93, 600 (1971). b. idem., ibid., 93, 4684 (1971).CrossRefGoogle Scholar
  23. 21a.
    J. H. Prestegard and S. I. Chan, Biochemistry, 8, 3921 (1969). b. idem., J. Am. Chem. Soc., 92, 4440 (1970).CrossRefGoogle Scholar
  24. 22a.
    J. S. Bradshaw, L. D. Hansen, S. F. Nielsen, M. D. Thompson, R. A. Reeder, R. M. Izatt, and J. J. Christensen, J. Chem. Soc., Chem. Comm., 874 (1975). b. J. S. Bradshaw, G. E. Maas, R. M. Izatt, and J. J. Christensen, Chem. Rev., 79, 37 (1979).Google Scholar
  25. 23a.
    J. S. Bradshaw and M. D. Thompson, J. Org. Chem., 43, 2456 (1978). b. R. M. Izatt, J. D. Lamb, G. E. Maas, R. E. Asay, J. S. Bradshaw, and J. J. Christensen, J. Am. Chem. Soc., 99, 2365 (1977).CrossRefGoogle Scholar
  26. 24.
    A. Samat, J. Elgnero, and J. Metzger, J. Chem. Soc., Chem. Comm., 1182 (1979).Google Scholar
  27. 25a.
    G. R. Newkome, G. L. McClure, J. B. Broussard, and F. Danesh-Khoshboo, ibid., 97, 3232 (1975). b. M. Newcomb, G. W. Gokel, and D. J. Cram, ibid., 96, 6810 (1974). c. G. W. Gokel, J. M. Timko, and D. J. Cram, J. Chem. Soc., Chem. Comm., 444 (1975).Google Scholar
  28. 26a.
    J. S. Bradshaw, G. E. Maas, J. D. Lamb, R. M. Izatt, and J. J. Christensen, ibid., 102, 467 (1980). b. R. M. Izatt, J. D. Lamb, R. E. Asay, G. E. Maas, J. S. Bradshaw, and J. J. Christensen, ibid., 99, 6134 (1977).Google Scholar
  29. 27.
    D. N. Reinhoudt and R. T. Gray, Tetrahedron Letters, 2105, 2109 (1975).Google Scholar
  30. 28.
    G. R. Newkome, J. D. Sauer, J. M. Roper, and D. C. Hager, Chem. Rev., 77, 513 (1977).CrossRefGoogle Scholar
  31. 29.
    Y. Kobuke, K. Hanji, Kl Horiguchi, M. Asada, Y. Nakayama, and J. Furukawa, J. Am. Chem. Soc., 98, 7414 (1976).CrossRefGoogle Scholar
  32. 30a.
    L. L. Chan and J. Smid, J. Am. Chem. Soc., 89, 4547 (1967). b. L. L. Chan, K. H. Wong, and J. Smid, ibid., 92, 1955 (1970).CrossRefGoogle Scholar
  33. 31.
    B. Tümmler, G. Maass, F. Vogtle, H. Sieger, U. Heimann, and E. Weber, J. Am. Chem. Soc., 101, 2588 (1979).CrossRefGoogle Scholar
  34. 32.
    S. Yanagida, K. Takahashi, and M. Okahara, Bull. Chem. Soc. Jap., 51, 3111 (1978).CrossRefGoogle Scholar
  35. 33.
    W. Saenger, I. H. Suh, and G. Weber, Israel J. Chem., 18, 253 (1979).Google Scholar
  36. 34a.
    E. Weber and F. Vogtle, Tetrahedron Letters, 2415 (1975). b. B. Tummler, G. Maass, E. Weber, W. Wehner, and F. Vogtle, J. Am. Chem. Soc., 99, 4683 (1977).Google Scholar
  37. 35a.
    F. Vogtle and H. Sieger, Angew. Chem., Int. Ed., 16, 396 (1977). b. idem., ibid., 17, 198 (1978). c. W. Rasshofer, G. Oepen, and F. Vogtle, Chem. Ber., 111, 419 (1978).Google Scholar
  38. 36.
    W. Wiereng, B. R. Evans, and J. A. Woltersom, J. Am. Chem. Soc., 101, 1334 (1979).CrossRefGoogle Scholar
  39. 37.
    see also J. O. Gardner and C. C. Beard, J. Med. Chem., 21 357 (1978).Google Scholar
  40. 38.
    N. N. L. Kirsch and W. Simon, Helv. Chim. Acta, 59, 356 (1976).Google Scholar
  41. 39a.
    E. Blasius and P. G. Maurer, Makromol. Chem., 178, 649 (1977). b. G. Dotsevi, Y. Sogah, and D. J. Cram, J. Am. Chem. Soc., 98, 3038 (1976). c. W. M. Feigenbaum and R. H. Michel, J. Polym. Sci., A-l, 9, 817 (1971). d. E. Shchori and J. Jagur-Grodzinski, J. Appl. Polym. Sci., 20, 773 (1976).CrossRefGoogle Scholar
  42. 40.
    J. S. Bradshaw and P. E. Stott, Tetrahedron, 36, 461 (1980).CrossRefGoogle Scholar
  43. 41.
    W. M. Feigenbaum and R. H. Michel, J. Polym. Sci., A-l, 9, 817 (1971).CrossRefGoogle Scholar
  44. 42.
    E. Shchori and J. Jagur-Grodzinski, J. Appl. Polym. Sci., 20, 773, 1665 (1976).CrossRefGoogle Scholar
  45. 43a.
    E. Blasius, K. P. Jangen, W. Adrian, G. Klantke, R. Lorscheider, P. G. Maurer, V. G. Nguyen, T. Nguyen Tien, G. Schölten, and J. Stockerer, Z. Anal. Chem., 284, 337 (1977). b. E. Blasius, K. P. Jangen, and W. Neumann, Mikrochim. Acta, 2, 279 (1977). c. E. Blasius and P. G. Maurer, Makromol. Chem., 178, 649 (1977). d. E. Blasius, W. Adrian, K. P. Jangen, and G. Klautke.Google Scholar
  46. 44a.
    P. Gramain and Y. Frere, Mactomolecules, 12, 1038 (1979). b. S. Bormann, J. Brossas, E. Franta, P. Gramain, M. Kirsch, and J. M. Lehn, Tetrahedron, 31, 2791 (1975).CrossRefGoogle Scholar
  47. 45.
    P. Gramain and Y. Frere, Makromol. Chem., Rapid Comm., 2, 161 (1981).CrossRefGoogle Scholar
  48. 46.
    I. Cho and S. K. Chang, ibid., 2, 155 (1981).Google Scholar
  49. 47a.
    K. H. Wong, G. Konizer, and J. Smid, J. Am. Chem. Soc., 92, 666 (1970). b. S. Kopolow, T. E. Hogen-Esch, and J. Smid, Macromolecules, 6, 133 (1973). c. S. Kopolow, Z. Machacek, U. Takaki, and J. Smid, J. Macromol. Sci., Chem., A7, 1015 (1973). d. S. C. Shah, S. Kopolow, and J. Smid, J. Polym. Sci., Polym. Chem., 14, 2023 (1976).Google Scholar
  50. 48.
    K. H. Wong, K. Yagi, and J. Smid, J. Membrane Biol., 18, 379 (1974).CrossRefGoogle Scholar
  51. 49a.
    K. Yagi, J. A. Ruiz, and M. C. Sanchez, Makromol. Chem., Rapid Comm., 1, 263 (1980). b. K. Yagi and M. C. Sanchez, ibid., 2, 311 (1981).CrossRefGoogle Scholar
  52. 50.
    I. M. Panayotov, C. B. Tsvetanov, I. V. Berlinova, and R. S. Velichkova, Makromol. Chem., 134, 313 (1970).CrossRefGoogle Scholar
  53. 51.
    I. M. Panayotov, C. B. Tsvetanov, and D. K. Dimov, ibid., 177, 279 (1976).Google Scholar
  54. 52.
    A. Hirao, S. Nakahama, M. Takahashi, and N. Yamazaki, ibid., 179, 1735 (1978), and 179, 915 (1978).Google Scholar
  55. 53.
    S. Yanagida, K. Takahashi, and M. Okahara, Bull. Chem. Soc. Jap., 50, 1386 (1977).CrossRefGoogle Scholar
  56. 54a.
    Y. Takahashi and E. Tadokoro, Macromolecules, 6, 672 (1973). b. H. Tadokoro, Y. Chatani, T. Yoshihara, S. Tahara, and S. Murahasi, Makromol. Chem., 73, 109 (1964).CrossRefGoogle Scholar
  57. 55.
    S. Iwabuchi, T. Nakahira, A. Tsuchiya, K. Kojima, and V. Böhmer, Makromol. Chem., in press.Google Scholar
  58. 56a.
    W. Kern, S. Iwabuchi, H. Sato, and V. Bohmer, Makromol. Chem., 180, 2539 (1979). b. H. Sato, S. Iwabuchi, V. Bohmer, and W. Kern, ibid., 182, 755 (1981). c. W. Kern, M. M. Bhagwat, and V. Bohmer, Makromol. Chem., Rapid Comm., 2, 557 (1981).CrossRefGoogle Scholar
  59. 57.
    W. J. Schultz, M. C. Etter, A. V. Pocius, and S. Smith, J. Am. Chem. Soc., 102, 7981 (1980).CrossRefGoogle Scholar
  60. 58a.
    H. Sumitomo and K. Hasimoto, Macromolecules, 10, 1327 (1977). b. H. Sumitomo, K. Hasimoto, and T. Ghyamo, Polym. Bull., 1, 133 (1978). c. H. Sumitomo, K. Hasimoto, and M. Ando, J. Polym. Sci., Polym. Lett., 11, 635 (1973).CrossRefGoogle Scholar
  61. 59.
    K. Hashimoto and H. Sumitomo, Macromolecules, 13, 786 (1980).CrossRefGoogle Scholar
  62. 60a.
    I. Tajima, M. Okada, and H. Sumitomo, Makromol. Chem., Rapid Comm., 1, 197 (1980). b. I. Tanaka, I. Tajima, Y. Hayakawa, M. Okada, M. Bitoh, T. Ashida, and H. Sumitomo, J. Am. Chem. Soc., 102, 7873 (1980).CrossRefGoogle Scholar
  63. 61.
    J. E. Kelly, Ph.D. Dissertation, Rensselaer Polytechnic Institute, 1975.Google Scholar
  64. 62.
    J. A. Moore and J. E. Kelly, J. Polym. Sci., Polym. Lett. Ed., 13, 333 (1975).Google Scholar
  65. 63.
    J. A. Moore and E. M. Partain, III, ibid., submitted for publication.Google Scholar
  66. 64a.
    T. Saegusa, H. Imai, and J. Furukawa, Makromol. Chem., 65, 60 (1963). b. K. Weissermel and E. Nolken, ibid., 68, 140 (1963). c. I. Penczek, and S. Penczek, ibid., 94, 228 (1966). c. V. A. Kropachev, L. V. Alferova, and B. A. Dolgoplosk, Polym. Sci., USSR, 5, 46 (1964).CrossRefGoogle Scholar
  67. 65.
    E. L. Wittbecker, H. K. Hall, and T. W. Campbell, J. Am. Chem. Soc., 82, 1218 (1960).CrossRefGoogle Scholar
  68. 66a.
    N. Ogata, T. Asahara, and S. Tohyama, J. Polym. Sci. A-l, 4, 1359 (1966). b. N. Ogata and S. Tohyama, Bull. Chem. Soc. Jpn., 39, 1556 (1966).Google Scholar
  69. 67.
    H. Wexler, Makromol. Chem., 115, 262 (1968).CrossRefGoogle Scholar
  70. 68.
    C. Tanford, “Physical Chemistry of Macromolecules”, Chap. 8, J. Wiley, New York, 1961.Google Scholar
  71. 69.
    R. Sinta and J. Smid, Macromolecules, 13, 339 (1980).CrossRefGoogle Scholar
  72. 70.
    O. Silberrad and H. A. Phillips, J. Chem. Soc., 93, 474 (1908).CrossRefGoogle Scholar
  73. 71.
    D. Balasubramanian and B. C. Misra, “Metal-Ligand Interactions in Organic Chemistry and Biochemistry, Part 1”, B. Pullman and N. Goldblum, eds., D. Reidel Comp., New York, 1977, pg. 159.CrossRefGoogle Scholar
  74. 72.
    N. Lotan, J. Phys. Chem., 77, 242 (1973).CrossRefGoogle Scholar
  75. 73.
    M. L. Tiffany and S. Krimm, Biopolymers, 8, 347 (1969).CrossRefGoogle Scholar
  76. 74.
    F. Quadrifoglio and D. W. Urry, J. Am. Chem. Soc., 90, 2760 (1968).CrossRefGoogle Scholar
  77. 75.
    W. L. Mattice and L. Mandelkern, Biochemistry, 8, 1049 (1969).Google Scholar
  78. 76a.
    D. Balasubramanian, A. Goel, and C. N. R. Rao, Chem. Phys. Lett., 17, 482 (1972). b. M. E. Noelken and S. N. Timasheff, J. Biol. Chem., 242, 5080 (1969). c. B. Rode and R. Fussenegger, J. Chem. Soc., Faraday Trans. II, 71, 1958 (1975).CrossRefGoogle Scholar
  79. 77a.
    K. Dachs and E. Schwartz, Angew. Chem., Int. Ed., 1, 430 (1962). b. G. B. Gechele and L. Crescentini, J. Appl. Polym. Sci., 7, 1349 (1963).Google Scholar
  80. 78a.
    F. J. Van Natta, J. W. Hill, and W. H. Carrothers, J. Am. Chem. Soc., 56, 455 (1934). b. V. Crescenzi, G. Manzini, G. Calzolari, and C. Borri, Eur. Polym. J., 8, 449 (1972).CrossRefGoogle Scholar
  81. 79.
    J. A. Moore and E. M. Partain, III, Macromolecules, submitted for publication.Google Scholar
  82. 80.
    It should be noted that repulsion cannot be invoked in the instance of polyaminde 41 at the concentration we have investigated so far. At a repeat unit concentration of 10-4M we have, on the average, only one ion pair per hundred repeat units, an ion concentration which is probably not sufficient to cause repulsion effects.Google Scholar

Copyright information

© Plenum Press, New York 1984

Authors and Affiliations

  • J. A. Moore
    • 1
  • E. M. PartainIII
    • 1
  1. 1.Department of ChemistryRensselaer Polytechnic InstituteTroyUSA

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