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Reactions Involving the Cleavage or Rearrangement of Heterocyclic Rings of Nucleic Acid Bases and their Derivatives

  • Chapter
Organic Chemistry of Nucleic Acids

Abstract

Cleavage of the heterocyclic rings of the bases of nucleic acids (and their derivatives) can occur through the action of a number of reagents. Sometimes this opening of the ring is an intermediate stage of the reaction and is followed by its closure by groups of atoms which differ from those in the original ring, or in other words, rearrangement takes place.

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Bibliography

  1. P. Brookes and P. D. Lawley, Biochem. J., 89:127 (1963).

    Google Scholar 

  2. A. M. Mian and R. T. Walker, J. Chem. Soc., (C), 2577 (1968).

    Google Scholar 

  3. A. S. Jones, A. M. Mian, and R. T. Walker, J. Chem. Soc. (C), 692 (1966).

    Google Scholar 

  4. D. I. Magrath and G. B. Brown, J. Am. Chem. Soc., 79:3252 (1957).

    CAS  Google Scholar 

  5. M. P. Gordon, V. S. Weliky, and G. B. Brown, J. Am. Chem. Soc., 79:3245 (1957).

    CAS  Google Scholar 

  6. C. C. Price, G. M. Gache, P. Koneru, R. Shibakawa, J. R. Sowa, and M. Yamaguchi, Biochim. Biophys. Acta, 166, 327 (1968).

    CAS  Google Scholar 

  7. E. Kriek and P. Emelot, Biochemistry, 2:733 (1963).

    CAS  Google Scholar 

  8. P. Brookes, A. Dipple, and P. D. Lawley, J. Chem. Soc. (C), 2026 (1968).

    Google Scholar 

  9. J. A. Haines, C. B. Reese, and A. Todd, J. Chem. Soc., 5281 (1962).

    Google Scholar 

  10. G. B. Brown, M. P. Gordon, D. F. Magrath, and A. Hampton, in: Ciba Foundation Symposium on the Chemistry and Biology of Purines, J. and A. Churchill, London (1957), p. 57.

    Google Scholar 

  11. E. Kriek and P. Emelot, Biochim. Biophys. Acta, 91:59 (1964).

    CAS  Google Scholar 

  12. P. D. Lawley and P. Brookes, J. Mol. Biol., 25:143 (1967).

    CAS  Google Scholar 

  13. P. D. Lawley, in: Progress in Nucleic Acid Research and Molecular Biology, Vol. 5, J. N. Davidson and W. E. Cohn (editors), Academic Press, New York -London (1966), p. 91.

    Google Scholar 

  14. R. O. Hurst and A. Kurkiss, Canad. J. Biochem. Physiol., 36:919, 931 (1958).

    CAS  Google Scholar 

  15. P. D. Lawley and C. A. Wallik, Chem. and Ind., 633 (1957).

    Google Scholar 

  16. P. D. Lawley, Proc. Chem. Soc., 290 (1957).

    Google Scholar 

  17. P. Brookes and P. D. Lawley, J. Chem. Soc., 3923 (1961).

    Google Scholar 

  18. P. Brookes and P. D. Lawley, Biochem. J., 80:496 (1961).

    CAS  Google Scholar 

  19. J. W. Jones and R. K. Robins, J. Am. Chem. Soc., 85:193 (1963).

    CAS  Google Scholar 

  20. L. B. Townsend and R. K. Robins, J. Am. Chem. Soc., 85:243 (1963);

    Google Scholar 

  21. L. B. Townsend and R. K. Robins, in: Synthetic Procedures in Nucleic Acid Chemistry, Vol. 1, W. W. Zorbach and R. S. Tipson (editors), Wiley, New York-London (1968), p. 315.

    Google Scholar 

  22. L. B. Townsend, Chem. Revs., 67:533 (1967).

    CAS  Google Scholar 

  23. E. Shaw, J. Am. Chem. Soc., 80:3890 (1958).

    Google Scholar 

  24. E. Shaw, J. Am. Chem. Soc., 81:6021 (1959).

    CAS  Google Scholar 

  25. E. Shaw, J. Am. Chem. Soc., 83:4770 (1961).

    CAS  Google Scholar 

  26. C. M. Baugh and E. Shaw, Biochim. Biophys. Acta, 114:213 (1966).

    CAS  Google Scholar 

  27. J. F. Cavalieri, J. F. Tinker, and G. B. Brown, J. Am. Chem. Soc., 70:3875 (1948).

    CAS  Google Scholar 

  28. P. Brookes and P. D. Lawley, J. Chem. Soc., 539 (1960).

    Google Scholar 

  29. C. E. Carter, J. Biol. Chem., 223:139 (1956).

    CAS  Google Scholar 

  30. B. C. Pal and C. A. Horton, J. Chem. Soc., 401 (1964).

    Google Scholar 

  31. M. A. Stevens and G. B. Brown, J. Am. Chem. Soc., 80:2759 (1958).

    CAS  Google Scholar 

  32. M. A. Stevens, A. Giner-Sorolla, H. W. Smith, and G. B. Brown, J. Org. Chem., 27:567 (1962).

    CAS  Google Scholar 

  33. M. A. Stevens, H. W. Smith, and G. B. Brown, J. Am. Chem. Soc., 81:1734 (1959).

    CAS  Google Scholar 

  34. M. A. Stevens, H. W. Smith, and G. B. Brown, J. Am. Chem. Soc., 82:1148 (1960).

    CAS  Google Scholar 

  35. H. Klenow and S. Frederiksen, Biochim. Biophys. Acta, 52:384 (1961).

    CAS  Google Scholar 

  36. J. A. Montgomery, K. Newson, S. J. Clayton, and H. J. Thomas, J. Org. Chem., 31:2202 (1966).

    CAS  Google Scholar 

  37. M. Ikehara and K. Muneyama, Chem. Pharm. Bull. Tokyo, 14:46 (1966).

    CAS  Google Scholar 

  38. G. B. Elion, J. Org. Chem., 27:2478 (1962).

    CAS  Google Scholar 

  39. J. A. Montgomery and H. J. Thomas, J. Org. Chem., 28:2304 (1963).

    CAS  Google Scholar 

  40. B. R. Baker and J. P. Joseph, Am. Chem. Soc., 77:15 (1955).

    CAS  Google Scholar 

  41. A. M. Michelson, The Chemistry of Nucleosides and Nucleotides, Academic Press, London-New York (1963).

    Google Scholar 

  42. M. E. King and C. E. Carter, Biochim. Biophys. Acta, 44:232 (1960).

    CAS  Google Scholar 

  43. O. Dimroth, Ann., 373:336 (1910).

    CAS  Google Scholar 

  44. E. C. Taylor and P. K. Leoffler, J. Am. Chem. Soc., 82:3147 (1960).

    CAS  Google Scholar 

  45. N. J. Leonard and T. Fujii, Proc. Nat. Acad. Sci. USA, 51:73 (1964).

    CAS  Google Scholar 

  46. N. J. Leonard, S. Achmatowicz, R. N. Loeppky, K. L. Carraway, W. A. H. Grimm, A. Szweykowska, H. Q. Hamzi, and F. Skoog, Proc. Nat. Acad. Sci. USA, 56:709 (1966).

    CAS  Google Scholar 

  47. D. M. G. Martin and C. B. Reese, J. Chem. Soc., (C), 1731 (1968).

    Google Scholar 

  48. W. A. H. Grimm and N. J. Leonard, Biochemistry, 6:3625 (1967).

    CAS  Google Scholar 

  49. E. C. Taylor, in: Ciba Foundation Symposium on the Chemistry and Biology of Purines, J. and A. Churchill, London (1957), p. 57.

    Google Scholar 

  50. D. J. Brown, Nature, 189:828 (1961).

    CAS  Google Scholar 

  51. J. B. Macon and R. Wolfenden, Biochemistry, 7:3453 (1968).

    CAS  Google Scholar 

  52. G. B. Chheda and R. H. Hall, Biochemistry, 5:2082 (1966).

    CAS  Google Scholar 

  53. N. J. Leonard, K. L. Carraway, and J. P. Helgeson, J. Heterocyclic Chem., 2:291 (1965).

    CAS  Google Scholar 

  54. A. Coddington, Biochim. Biophys. Acta, 59:472 (1962).

    CAS  Google Scholar 

  55. A. M. Michelson, The Chemistry of Nucleosides and Nucleotides, Academic Press, London-New York (1963).

    Google Scholar 

  56. A. S. Jones, A. M. Mian, and R. T. Walker, J. Chem. Soc., (C), 1784 (1968).

    Google Scholar 

  57. C. Janion and D. Shugar, Acta Biochim. Polon., 7:309 (1960).

    CAS  Google Scholar 

  58. W. Szer and D. Shugar, Acta Biochim. Polon., 7:491 (1960).

    CAS  Google Scholar 

  59. W. Szer and D. Shugar,Acta Biochim. Polon., ibid., 7:491 (1960).

    CAS  Google Scholar 

  60. J. J. Fox and D. Shugar, Bull. Soc. Chim. Belge, 61:44 (1952).

    CAS  Google Scholar 

  61. D. Shugar and J. J. Fox, Biochim. Biophys. Acta, 9:199 (1952).

    CAS  Google Scholar 

  62. D. Shugar and J. J. Fox, Bull. Soc. Chim., Belge, 61:293 (1952).

    CAS  Google Scholar 

  63. P. Brookes and P. D. Lawley, J. Chem. Soc., 1349 (1962).

    Google Scholar 

  64. H. Siedel, Biochim. Biophys. Acta, 138:98 (1967).

    Google Scholar 

  65. W. E. Conn and D. G. Doherty, J. Am. Chem. Soc., 78:2863 (1956).

    Google Scholar 

  66. M. Green and S. S. Cohen, J. Biol. Chem., 225:397 (1957).

    CAS  Google Scholar 

  67. M. Green and S. S. Cohen, J. Biol. Chem., 228:601 (1957).

    CAS  Google Scholar 

  68. R. D. Batt, J. K. Martin, J. M. Poeser, J. J. Murray, J. Am. Chem. Soc., 76:3663 (1954).

    CAS  Google Scholar 

  69. P. Cerutti, Y. Kondo, W. R. Landis, and B. Witkop, J. Am. Chem. Soc., 90:771 (1968).

    CAS  Google Scholar 

  70. P. A. Levene and F. B. La Forge, Chem. Ber., 45:615 (1912).

    Google Scholar 

  71. W. E. Cohn, Biochem. J., 64:28P (1956).

    Google Scholar 

  72. A. S. Jones, J. R. Tittensor, and R. T. Walker, J. Chem. Soc., (C), 1635 (1966).

    Google Scholar 

  73. J. J. Fox, N. C. Miller, and R. J. Cushley, Tetrahedron Letters, 4927 (1966).

    Google Scholar 

  74. B. A. Otter and J. J. Fox, J. Am. Chem. Soc., 89:3663 (1967).

    Google Scholar 

  75. I. L. Doerr and J. J. Fox, J. Org. Chem., 32:1462 (1967).

    CAS  Google Scholar 

  76. B. A. Otter, E. A. Falco, and J. J. Fox, Tetrahedron Letters, 2964 (1968).

    Google Scholar 

  77. B. A. Otter, E. A. Falco, and J. J. Fox, J. Org. Chem., 33:3593 (1968).

    CAS  Google Scholar 

  78. D. J. Brown and J. S. Harper, J. Chem. Soc., 5543 (1965).

    Google Scholar 

  79. D. J. Brown and M. N. Paddon-Row, J. Chem. Soc., (C), 1928 (1967).

    Google Scholar 

  80. D. J. Brown and B. T. England, J. Chem. Soc., (C), 1922 (1967).

    Google Scholar 

  81. I. Wempen, G. B. Brown, T. Ueda, and J. J. Fox, Biochemistry, 4:54 (1965).

    CAS  Google Scholar 

  82. T. Ueda and J. J. Fox, J. Org. Chem., 29:1770 (1964).

    Google Scholar 

  83. H. Mizuno, H. Okuyama, H. Hayatsu, and T. Ukita, Chem. Pharm. Bull. Tokyo, 12:1240 (1964).

    CAS  Google Scholar 

  84. P. A. Levene and L. W. Bass, J. Biol. Chem., 71:126 (1926).

    Google Scholar 

  85. F. Baron and D. M. Brown, J. Chem. Soc., 2855 (1955).

    Google Scholar 

  86. F. F. Davis and F. W. Allen, J. Biol. Chem., 227, 907 (1957).

    CAS  Google Scholar 

  87. A. Temperli, H. Türler, P. Rust, A. Danon, and E. Chargaff, Biochim. Biophys. Acta, 91:462 (1964).

    CAS  Google Scholar 

  88. E. I. Budovskii, J. A. Haines, and N. K. Kochetkov, Dokl. Akad. Nauk SSSR, 158:379 (1964).

    CAS  Google Scholar 

  89. F. Lingens and H. Schneider-Bernlöhr, Biochim. Biophys. Acta, 123:611 (1966).

    CAS  Google Scholar 

  90. D. W. Werwoerd and W. Zillig, Biochim. Biophys. Acta, 68:484 (1963).

    Google Scholar 

  91. V. Habermann, Coll. Czech. Chem. Comm., 26:3147 (1961).

    CAS  Google Scholar 

  92. F. Lingens and H. Schneider-Bernlohr, Angew. Chem., 76:378 (1964).

    CAS  Google Scholar 

  93. F. Lingens and H. Schneider-Bernlöhr, Ann., 686:134 (1967).

    Google Scholar 

  94. B. W. Ellery and R. H. Simmons, Nature, 210:1159 (1966).

    CAS  Google Scholar 

  95. R. L. Sinsheimer and J. Sedat, J. Mol. Biol., 9:489 (1964).

    Google Scholar 

  96. R. Cape and J. Spencer, Canad. J. Biochem., 46:1063 (1968).

    CAS  Google Scholar 

  97. A. R. Cashmore and G. B. Petersen, Biochim. Biophys. Acta, 174:591 (1969).

    CAS  Google Scholar 

  98. S. Takemura, Biochim. Biophys. Acta, 29:447 (1958).

    CAS  Google Scholar 

  99. S. Takemura, Bull. Chem. Soc. Japan, 32:926 (1959).

    CAS  Google Scholar 

  100. S. Takemura, Bull. Chem. Soc. Japan, 32:920 (1959).

    CAS  Google Scholar 

  101. E. Chargaff, P. Rüst, A. Temperli, S. Morisawa, and A. Danon, Biochim. Biophys. Acta, 76:149 (1963).

    CAS  Google Scholar 

  102. V. Habermann, Biochim. Biophys. Acta, 55:999 (1962).

    CAS  Google Scholar 

  103. V. Habermann and E. Maidlova, Coll. Czech. Chem. Comm., 28:2537 (1963).

    CAS  Google Scholar 

  104. V. Habermann, Coll. Czech. Chem. Comm., 28:510 (1963).

    CAS  Google Scholar 

  105. E. Chargaff, J. Buchowicz, H. Türler, and H. S. Shapiro, Nature, 206:145 (1965).

    CAS  Google Scholar 

  106. N. K. Kochetkov, A. F. Bochkov, B. A. Dmitriev, A. I. Usov, A. S. Chizhov, and V. N. Shibaev, in: The Chemistry of Carbohydrates [in Russian], Khimiya (1967), p. 113.

    Google Scholar 

  107. D. H. Hayes and F. Hayes-Baron, J. Chem. Soc., (C), 1528 (1967).

    Google Scholar 

  108. D. W. Verwoerd, W. Zillig, and H. Kohlhage, Z. Physiol. Chem., 332:184 (1963).

    CAS  Google Scholar 

  109. D. W. Verwoerd, H. Kohlhage, and W. Zillig, Nature, 192:1038 (1961).

    CAS  Google Scholar 

  110. H. Schuster, J. Mol. Biol., 3:447 (1961).

    CAS  Google Scholar 

  111. N. K. Kochetkov, É. I. Budovskii, and N. A. Simukova, Biokhimiya, 27:519 (1962);

    CAS  Google Scholar 

  112. N. K. Kochetkov, É. I. Budovskii, and N. A. Simukova, Biochim. Biophys. Acta, 55:255 (1962).

    CAS  Google Scholar 

  113. N. K. Kochetkov, E. I. Budowsky, V. P. Demushkin, M. F. Turchinsky, N. A. Simukova, and E. D. Sverdlov, Biochim. Biophys. Acta, 142:35 (1967).

    CAS  Google Scholar 

  114. N. K. Kochetkov, É. I. Budovskii, V. N. Shibaev, and G. I. Eliseeva, Dokl. Akad. Nauk SSSR, 172:603 (1967).

    CAS  Google Scholar 

  115. N. K. Kochetkov, É. I. Budovskii, and V. N. Shibaev, Biokhimiya, 28:741 (1963).

    CAS  Google Scholar 

  116. G. Nemethy and H. A. Scheraga, J. Phys. Chem., 66:1773 (1962).

    CAS  Google Scholar 

  117. N. K. Kochetkov, É. I. Budovskii, M. F. Turchinskii, and V. P. Demushkin, Dokl. Akad. Nauk SSSR, 152:1005 (1963).

    CAS  Google Scholar 

  118. N. K. Kochetkov, E. I. Budowsky, M. F. Turchinsky, and N. A. Simukova, Biochem. Biophys. Res. Comm., 19:49 (1965).

    CAS  Google Scholar 

  119. M. F. Turchinskii, L. I. Gus’kova, and É. I. Budovskii, Molekul. Biol., 1:792 (1967).

    CAS  Google Scholar 

  120. E. I. Budowsky, N. A. Simukova, and L. I. Guskova, Biochim. Biophys. Acta, 166:755 (1968).

    Google Scholar 

  121. N. K. Kochetkov, É. I. Budovskii, and V. P. Demushkin, Dokl. Akad. Nauk SSSR, 168:102 (1966).

    CAS  Google Scholar 

  122. N. K. Kochetkov, É. I. Budovskii, and V. P. Demushkin, Molekul. Biol., 1:583 (1967).

    CAS  Google Scholar 

  123. H. S. Shapiro and E. Chargaff, Biochemistry, 5:3012 (1966).

    CAS  Google Scholar 

  124. E. Freese, E. Bautz-Freese, and S. Graham, Biochim. Biophys. Acta, 123:17 (1966).

    CAS  Google Scholar 

  125. H. J. Rhaese and E. Freese, Biochim. Biophys. Acta, 155:476 (1968).

    CAS  Google Scholar 

  126. H. J. Rhaese, E. Freese, and M. S. Melzer, Biochim. Biophys. Acta, 155:491 (1968).

    CAS  Google Scholar 

  127. E. Freese and E. Bautz-Freese, Biochemistry, 4:2419 (1965).

    CAS  Google Scholar 

  128. M. H. Benn, B. Chatamra, and A. S. Jones, J. Chem. Soc., 1014 (1960).

    Google Scholar 

  129. P. Howgate, A. S. Jones, and J. R. Tittensor, J. Chem. Soc., (C), 275 (1968).

    Google Scholar 

  130. A. S. Jones and R. T. Walker, J. Chem. Soc., 3554 (1963).

    Google Scholar 

  131. B. Chatamra and A. S. Jones, J. Chem. Soc., 811 (1963).

    Google Scholar 

  132. H. Hayatsu and T. Ukita, Biochem. Biophys. Res. Comm., 29:556 (1967).

    CAS  Google Scholar 

  133. K. Burton and W. T. Riley, Biochem. J., 98:70 (1966).

    CAS  Google Scholar 

  134. K. Burton, N. F. Varney, and P. C. Zamecnik, Biochem. J., 99:29c (1966).

    Google Scholar 

  135. A. S. Jones and C. R. Bayley, Trans. Farad. Soc., 55:492 (1959).

    Google Scholar 

  136. A. S. Jones and R. T. Walker, Nature, 202:1108 (1964).

    CAS  Google Scholar 

  137. A. S. Jones and R. T. Walker, Nature, 202:24 (1964).

    CAS  Google Scholar 

  138. A. S. Jones, G. W. Ross, S. Takemura, T. W. Thompson, and R. T. Walker, J. Chem. Soc., 373 (1964).

    Google Scholar 

  139. G. K. Darby, A. S. Jones, J. K. Tittensor, and R. T. Walker, Nature, 216:793 (1967).

    CAS  Google Scholar 

  140. J. J. Holbrook, A. S. Jones, and M. J. Welch, J. Chem. Soc., 3998 (1965).

    Google Scholar 

  141. H. Priess and W. Zillig, Physiol. Chem., 342:73 (1965).

    CAS  Google Scholar 

  142. M. S. Melzer and R. V. Tomlinson, Arch. Biochem. Biophys., 115:226 (1966).

    CAS  Google Scholar 

  143. H. Schweitz and D. Luzzati, J. Chim. Phys., 60:1173 (1963).

    CAS  Google Scholar 

  144. G. Scholes and J. Weiss, Nature, 185:305 (1960).

    CAS  Google Scholar 

  145. B. Ekert and K. Monier, Nature, 184:58 (1959).

    CAS  Google Scholar 

  146. G. Scholes, J. F. Ward, and J. Weiss, J. Mol. Biol., 2:379 (1960).

    CAS  Google Scholar 

  147. H. Schweitz, C. r., D264:1335 (1967).

    Google Scholar 

  148. E. C. Pollard and P. K. Weller, Rad. Res., 32:417 (1967).

    CAS  Google Scholar 

  149. D. Luzzati, H. Schweitz, M. L. Bach, and M. R. Chevallier, J. Chim. Phys., 58:1021 (1961).

    CAS  Google Scholar 

  150. L. R. Subbraman, J. Subbraman, and E. J. Behrman, Chem. Comm., 1024 (1968).

    Google Scholar 

  151. R. E. Harmon, C. V. Zmarova, and S. K. Gupta, Chem. and Ind., 1141 (1969).

    Google Scholar 

  152. G. B. Shheda, R. H. Hall, and P. M. Tauna, J. Org. Chem., 34:3498 (1969).

    Google Scholar 

  153. E. G. Sander, J. Am. Chem. Soc., 91:3629 (1969).

    CAS  Google Scholar 

  154. B. A. Otter, E. A. Falco and J. J. Fox, J. Org. Chem., 34:2636 (1969).

    CAS  Google Scholar 

  155. É. I. Budovskii, V. D. Domkin, and N. K. Kochetkov, Dokl. Akad. Nauk SSSR (1970) (in press).

    Google Scholar 

  156. H. J. Rhaese, Biochim. Biophys. Acta, 166:311 (1968).

    CAS  Google Scholar 

  157. J. J. Weiss, Progr. Nucl. Acid Res., 3:103 (1964).

    CAS  Google Scholar 

  158. G. Schules, Progr. Biophys., 13:59 (1963).

    Google Scholar 

  159. E. Freese and E. Bautz-Freese, Radiation Res. Suppl. 6, 97 (1966).

    Google Scholar 

  160. R. Latarjet, B. Ekert, and P. Demeresman, Radiation Res. Suppl. 3, 247 (1963).

    CAS  Google Scholar 

  161. L. R. Subbaraman, J. Subbaraman, and E. J. Behrman, Biochemistry, 8:3059 (1969).

    CAS  Google Scholar 

  162. J. P. Ebel and J. Gangloff, Bull. Soc. Chim. Biol., 50:2335 (1968).

    Google Scholar 

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Kochetkov, N.K., Budovskii, E.I. (1972). Reactions Involving the Cleavage or Rearrangement of Heterocyclic Rings of Nucleic Acid Bases and their Derivatives. In: Kochetkov, N.K., Budovskii, E.I. (eds) Organic Chemistry of Nucleic Acids. Springer, Boston, MA. https://doi.org/10.1007/978-1-4684-2973-2_3

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