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Synthetic nucleic acid analogs preparation and interaction

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Speciality Polymers

Part of the book series: Advances in Polymer Science ((POLYMER,volume 41))

Abstract

In order to prepare simply designed nucleic acid models with high functionality, a series of polymeric compounds containing purine and pyrimidine bases as pendant, functional side groups were prepared successfully from their corresponding monomers by either polymerization or polycondensation techniques. As for the functionality of the polymers prepared, specific base-base interactions were studied in detail by measuring UV, NMR and emission spectroscopies. The specific interaction study was particularly made on poly-L-Lysine derivatives having nucleic acid bases in relation to their molecular weight, their conformation in solutions and other properties. From photodimerization study on the model compounds containing thymine bases, intramolecular features of the reaction were elucidated. Owing to the specific properties of the polymers, the studies will find a number of application possibilities, including separation techniques and polymeric drug chemistry. Graft copolymers of nucleic acid bases on polyethyleneimine were also concerned.

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8 References

  1. Takemoto, K.: J. Macromol. Sci.-Rev. C5, 29 (1970)

    Google Scholar 

  2. Imoto, M., Takemoto, K.: Synthesis 1970, 173

    Google Scholar 

  3. Takemoto, K.: J. Polym. Sci. Symp. 55, 105 (1976)

    Google Scholar 

  4. Pitha, J.: Polymer 18, 425 (1977)

    Google Scholar 

  5. Takemoto, K.: Polymeric drugs. Donaruma, L. G., Vogl, O. (eds.), p. 103. New York: Academic Press 1978

    Google Scholar 

  6. Kondo, K. et al.: Makromol. Chem. 125, 42 (1969)

    Google Scholar 

  7. Kaye, H.: J. Polym. Sci. B7, 1 (1969)

    Google Scholar 

  8. Pitha, P. M., Pitha, J.: Biopolymers 9, 965 (1970)

    Google Scholar 

  9. Takemoto, K., Kawakubo, F., Kondo, K.: Makromol. Chem. 148, 131 (1971)

    Google Scholar 

  10. Pitha, J., Pitha, P. M., Stuart, E. Biochem. 10, 4595 (1971)

    Google Scholar 

  11. Kaye, H.: Macromolecules 4, 147 (1971)

    Google Scholar 

  12. Kaye, H., Chang, S. H.: Macromolecules 5, 397 (1972)

    Google Scholar 

  13. Pitha, J., Pitha, P. M., Tso, P. O. P.: Biochim. Biophys. Acta 204, 39 (1970)

    Google Scholar 

  14. Pitha, P. M., Michelson, A. M.: Biochim. Biophys. Acta 204, 381 (1970)

    Google Scholar 

  15. Kawakubo, F., Kondo, K., Takemoto, K.: Makromol. Chem. 169, 37 (1973)

    Google Scholar 

  16. Kaye, H. J.: Amer. Chem. Soc. 92, 5777 (1970)

    Google Scholar 

  17. Inaki, Y. et al.: Makromol. Chem. 176, 2683 (1975)

    Google Scholar 

  18. Browne, D. T., Eisinger, J., Leonard, N. J.: J. Amer. Chem. Soc. 90, 7302 (1968)

    Google Scholar 

  19. Fox, R. B. et al.: J. Chem. Phys. 57, 534 (1972)

    Google Scholar 

  20. Yokoyama, M.: Chem. Lett. 1972, 499

    Google Scholar 

  21. McDonald, J. R. et al.: J. Chem. Phys. 57, 1746 (1972)

    Google Scholar 

  22. Hirayama, F.: J. Chem. Phys. 42, 3163 (1965)

    Google Scholar 

  23. Brahms, J., Michelson, A. M., van Holde, K. E.: J. Mol. Biol. 15, 467 (1966)

    Google Scholar 

  24. Kaye, H., Chou, H. J.: J. Polym. Sci. Polym. Phys. Ed. 13, 477 (1975)

    Google Scholar 

  25. Kaye, H., Chang, S. H.: J. Macromol. Sci.-Chem. A7, 1127 (1973)

    Google Scholar 

  26. Kondo, K. et al.: Makromol. Chem. 120, 21 (1968)

    Google Scholar 

  27. Kita, Y., Inaki, Y., Takemoto, K.: J. Polym. Sci. Polym. Chem. Ed. 18, 427 (1980)

    Google Scholar 

  28. Inaki, Y. et al.: Makromol. Chem. 178, 365 (1977)

    Google Scholar 

  29. Kita, Y. et al.: Polym. Bull. 2, 195 (1980)

    Google Scholar 

  30. Inaki, Y., Futagawa, H., Takemoto, K.: J. Polym. Sci. Polym. Chem. Ed., 18, 2959 (1980)

    Google Scholar 

  31. Inaki, Y., Futagawa, H., Takemoto, K.: Org. Prep. Pros. Int., 12, 275 (1980)

    Google Scholar 

  32. Akashi, M., Inaki, Y., Takemoto, K.: Makromol. Chem. 178, 353 (1977)

    Google Scholar 

  33. Akashi, M., Inaki, Y., Takemoto, K.: J. Macromol. Sci.-Chem., A12, 619 (1978)

    Google Scholar 

  34. Takemoto, K., Akashi, M., Inaki, Y.: J. Polym. Sci. Polym. Chem. Ed. 12, 1861 (1974)

    Google Scholar 

  35. Kyogoku, Y., Lord, R. C., Rich, A.: J. Amer. Chem. Soc. 89, 496 (1967)

    Google Scholar 

  36. Pitha, J., Jones, R. N., Pithova, J.: Can. J. Chem. 44, 1044 (1966)

    Google Scholar 

  37. Akashi, M. et al.: J. Polym. Sci. Polym. Chem. Ed. 17, 301 (1979)

    Google Scholar 

  38. Akashi, M. et al.: J. Polym. Sci. Polym. Chem. Ed. 17, 905 (1979)

    Google Scholar 

  39. Tso, P. O. P.: Basic principles in nucleic acid chemistry, vol. II, p. 305. New York: Academic Press 1974

    Google Scholar 

  40. Kirste, R., Wunderlich, W.: Makromol. Chem. 73, 240 (1964)

    Google Scholar 

  41. Akashi, M. et al.: J. Polym. Sci. Polym. Chem. Ed. 17, 747 (1979)

    Google Scholar 

  42. Takemoto, K., Inaki, Y., Akashi, M.: J. Macromol. Sci.-Chem. A13, 519 (1979)

    Google Scholar 

  43. Buter, R., Tan, Y. Y., Challa, G. J.: Polym. Sci. Polym. Chem. Ed. 11, 1003, 1013, 2975 (1973)

    Google Scholar 

  44. Kita, Y., Inaki, Y., Takemoto, K.: J. Polym. Sci. Polym. Chem. Ed., in press

    Google Scholar 

  45. Kondo, K., Hisaoka, Y., Takemoto, K.: Chem. Lett. 1973, 125

    Google Scholar 

  46. Kondo, K., Tanioku, S., Takemoto, K.: Makromol. Chem. Rapid. Commun. 2, 303 (1980)

    Google Scholar 

  47. Sugita, S., Inaki, Y., Takemoto, K.: unpublished results

    Google Scholar 

  48. DeClercq, E., Merigan, T. C.: Ann. Rev. Med. (ed. DeGraff, A. C.) vol. 21. Palo Alto, Ca: Ann. Rev. Inc. 1970

    Google Scholar 

  49. Field, A. K. et al.: Proc. Nat. Acad. Sci. USA. 58, 1004 (1967); 61, 340 (1968)

    Google Scholar 

  50. Nemes, M. M. et al.: Proc. Soc. Exp. Biol. Med. 132, 776 (1969)

    Google Scholar 

  51. DeVita, V. et al.: Proc. Amer. Assoc. Cancer Res. 11, 21 (1970)

    Google Scholar 

  52. Absher, M., Stinebring, W. R.: Nature 223, 715 (1969)

    Google Scholar 

  53. Perrine, T. D.: National Institutes of Health, private commun.

    Google Scholar 

  54. Dixon, K. W.: Ph. D. thesis, The Univ. Michigan, 1974

    Google Scholar 

  55. Overberger, C. G., Inaki, Y.: J. Polym. Sci. Polym. Chem. Ed. 17, 1739 (1979)

    Google Scholar 

  56. Kondo, K., Miyata, M., Takemoto, K.: Bull. Chem. Soc. Japan 44, 2554 (1971)

    Google Scholar 

  57. Overberger, C. G., Inaki, Y., Nanbu, Y.: J. Polym. Sci. Polym. Chem. Ed. 17, 1759 (1979)

    Google Scholar 

  58. Thomas, G. J., Kyogoku, Y.: J. Amer. Chem. Soc. 89, 4170 (1967)

    Google Scholar 

  59. Pitha, P. M., Pitha, J.: Biopolymer 9, 965 (1970)

    Google Scholar 

  60. Michelson, A. M., Massoulie, J., Gushlbauer, W.: Progr. Nucleic Acid Res. Mol. Biol. 6, 83 (1967)

    Google Scholar 

  61. Morishima, Y., Overberger, C. G.: J. Macromol. Sci.-Chem. A13, 573 (1979)

    Google Scholar 

  62. Shimizu, T., Konishi, Y., Murakami, A.: Makromol. Chem. 178, 2581 (1977)

    Google Scholar 

  63. Inaki, Y., Ishikawa, T., Takemoto, K.: Modification of polymers (ACS Symposium Series, No, 121) (eds. Carraher, C. E., Tsuda, M.) Amer. Chem. Soc., p. 359, 1980

    Google Scholar 

  64. Ishikawa, T., Inaki, Y., Takemoto, K.: Polym. Bull. 1, 215 (1978)

    Google Scholar 

  65. Takemoto, K. et al.: Makromol. Chem. 169, 327 (1973)

    Google Scholar 

  66. Leuchs, H.: Chem. Ber. 39, 857 (1906)

    Google Scholar 

  67. Fields, R.: Method in enzymology, pp. 25, 464, New York: Academic Press 1972

    Google Scholar 

  68. Ishikawa, T. et al.: Nucleic Acids Res. s5, 279 (1978)

    Google Scholar 

  69. Ishikawa, T., Inaki, Y., Takemoto, K.: Polym. Bull. 1, 85 (1978)

    Google Scholar 

  70. Anand, N. et al.: Macromolecules 4, 564 (1971)

    Google Scholar 

  71. Sela, M., Arnon, R., Jacobson, I.: Biopolymers 1, 517 (1963)

    Google Scholar 

  72. Ishikawa, T., Inaki, Y., Takemoto, K.: J. Polym. Sci. Polym. Chem. Ed., 18, 1847 (1980)

    Google Scholar 

  73. Chen, Y. H., Yang, J. T.: Biochem. Biophys. Res. Commun. 44, 1285 (1971)

    Google Scholar 

  74. Fasman, G. D., Idelson, M., Blout, E. R.: J. Amer. Chem. Soc. 83, 709 (1961)

    Google Scholar 

  75. Matsuoka, M. et al.: Biopolymers 12, 1515 (1973)

    Google Scholar 

  76. Ishikawa, T., Inaki, Y., Takemoto, K.: J. Polym. Sci. Polym. Chem. Ed. 18, 949 (1980)

    Google Scholar 

  77. Shinoda, K. et al.: Polym. J. 8, 202 (1976)

    Google Scholar 

  78. Shinoda, K.: Polym. Sci. Polym. Lett. Ed., in press

    Google Scholar 

  79. Inaki, Y. et al.: J. Polym. Sci. Polym. Lett. Ed., 18, 725 (1980)

    Google Scholar 

  80. Okubo, T., Ise, N.: Adv. Polym. Sci. 25, 135 (1977)

    Google Scholar 

  81. Okubo, T., Ban, K., Ise, N.: Makromol. Chem. 175, 49 (1974)

    Google Scholar 

  82. Kondo, K., Horiike, T., Takemoto, K.: J. Macromol. Sci.-Chem., in press

    Google Scholar 

  83. Kinoshita, M., Yamauchi, K., Imoto, M.: Progr. Polym. Sci. Japan 7, 63 (1974)

    Google Scholar 

  84. Hiraoka, K., Yokoyama, T.: Int. J. Biolog. Macromolecules 1, 50 (1979)

    Google Scholar 

Citations of the figures

  1. Figs. 1–3. Inaki, Y. et al.: Makromol. Chem. 176, 2683 (1975) (Figs. 1, 2 and 15, respectively)

    Google Scholar 

  2. Fig. 4. Takemoto, K., Akashi, M., Inaki Y.: J. Polym. Sci. Polym. Chem. Ed. 12, 1861 (1974) (Fig. 1c)

    Google Scholar 

  3. Fig. 5. Akashi, M. et al.: J. Polym. Sci. Polym. Sci. Polym. Chem. Ed. 17, 301 (1979) (Fig. 1)

    Google Scholar 

  4. Akashi, M., et al.: J. Polym. Sci. Polym. Chem. Ed. 17, 905 (1979) (Figs. 2, 3 (c), 5, 6, and 10, respectively)

    Google Scholar 

  5. Akashi, M. et al.: J. Polym. Sci. Polym. Chem. Ed. 17, 747 (1979) (Figs. 2, 3 and 6, respectively)

    Google Scholar 

  6. Figs. 14, 15. no citation

    Google Scholar 

  7. Kita, Y., Inaki, Y., Takemoto, K.: J. Polym. Sci. Polym. Chem. Ed. 18, 427 (1980) (Fig. 1)

    Google Scholar 

  8. Overberger, C. G., Inaki, Y., Nanbu, Y.: J. Polym. Sci. Polym. Chem. Ed. 17, 1759 (1979). (Figs. 2, 3, 5, and 6, respectively)

    Google Scholar 

  9. Ishikawa, T., Inaki, Y., Takemoto, K.: J. Polym. Sci. Polym. Chem. Ed., 18, 1847 (1980)

    Google Scholar 

  10. (Figs. 2, 3 and 6, respectively)

    Google Scholar 

  11. Fig. 24. no citation

    Google Scholar 

  12. Ishikawa, T., Inaki, Y., Takemoto, K.: J. Polym. Sci. Polym. Chem. Ed. 18, 949 (1980) (Figs. 4 and 5, respectively)

    Google Scholar 

  13. Inaki, Y. et al.: J. Polym. Sci. Polym. Lett. Ed. 18, 725 (1980) (Figs. 1, 4 and 8, respectively)

    Google Scholar 

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© 1981 Springer-Verlag

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Takemoto, K., Inaki, Y. (1981). Synthetic nucleic acid analogs preparation and interaction. In: Speciality Polymers. Advances in Polymer Science, vol 41. Springer, Berlin, Heidelberg. https://doi.org/10.1007/3-540-10554-9_9

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  • DOI: https://doi.org/10.1007/3-540-10554-9_9

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  • Publisher Name: Springer, Berlin, Heidelberg

  • Print ISBN: 978-3-540-10554-1

  • Online ISBN: 978-3-540-38525-7

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