Advertisement

Hydrolysis of N-glycosidic Bonds in Nucleosides, Nucleotides, and their Derivatives

  • N. K. Kochetkov
  • E. I. Budovskii

Abstract

Reactions of hydrolysis of glycosidic bonds in nucleosides, nucleotides, and nucleic acids have in the past played an important role in determination of the structure of these compounds. They are widely used nowadays to analyse the nucleotide composition of nucleic acids and to study their primary structure.

Keywords

Acid Hydrolysis Glycosidic Bond Pyrimidine Ring Purine Nucleoside Pyrimidine Derivative 
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.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Bibliography

  1. 1.
    A. Kossel, Arch. Anat. Physiol., Physiol. Abt., 181 (1891).Google Scholar
  2. 2.
    A. Kossel and A. Neumann, Ber., 26:2753 (1863);Google Scholar
  3. 2a.
    A. Kossel and A. Neumann, Z. Phys. Chem., 22:74 (1897).CrossRefGoogle Scholar
  4. 3.
    F. Baron and D. M. Brown, J. Chem. Soc., 2855 (1955).Google Scholar
  5. 4.
    C. Tamm, M. E. Hodes, and E. Chargaff, J. Biol. Chem., 195:49 (1952).Google Scholar
  6. 5.
    H. S. Shapiro and E. Chargaff, Biochim. Biophys. Acta, 23:451 (1957).CrossRefGoogle Scholar
  7. 6.
    P. A. Levene and W. A. Jacobs, Ber., 42:2469, 2703 (1909).Google Scholar
  8. 7.
    P. A. Levene and W. A. Jacobs, Ber., 44:1027 (1911).Google Scholar
  9. 8.
    E. R. Garrett, J. K. Seydel, and A. J. Sharper, J. Org. Chem., 31:2219 (1966).CrossRefGoogle Scholar
  10. 9.
    H. Venner, Hoppe-Sayler’s Z. Physiol. Chem., 339:14 (1964);CrossRefGoogle Scholar
  11. 9a.
    H. Venner, Hoppe-Sayler’s Z. Physiol. Chem., 344:189 (1966).CrossRefGoogle Scholar
  12. 10.
    G. W. Kenner, in: Ciba Foundation Symposium on Chemistry and Biology of Purines, J. and A. Churchill, London (1957).Google Scholar
  13. 11.
    H. S. Isabelle and H. I. Frush, J. Org. Chem., 23:1309 (1958).CrossRefGoogle Scholar
  14. 11a.
    R. Shapiro and S. King, Biochemistry, 8:1806 (1969).CrossRefGoogle Scholar
  15. 12.
    C. A. Dekker, Ann. Rev. Biochem., 29:453 (1960).CrossRefGoogle Scholar
  16. 13.
    F. Micheel and A. Heesing, Chem. Ber., 94:1814 (1961).CrossRefGoogle Scholar
  17. 14.
    B. Capon and B. E. Connett, Tetrahedron Letters, 1395 (1964).Google Scholar
  18. 15.
    B. Capon and B. E. Connett, J. Chem. Soc., 4497 (1965).Google Scholar
  19. 16.
    H. Simon and D. Palm, Chem. Ber., 98:433 (1965).CrossRefGoogle Scholar
  20. 17.
    M. N. Preobrazhenskaya, N. N. Vigdorchik, and N. N. Suvorov, Tetrahedron, 23:4653 (1967).CrossRefGoogle Scholar
  21. 18.
    D. M. Brown, G. D. Fasman, D. I. Magrath, and A. R. Todd, J. Chem, Soc., 1448 (1954).Google Scholar
  22. 19.
    I. Wempen, I. L. Doerr, L. Kaplan, and J. J. Fox, J. Am. Chem. Soc., 82:1624 (1960).CrossRefGoogle Scholar
  23. 20.
    K. E. Pfitzer and J. G. Moffatt, J. Org. Chem., 29:1508 (1964).CrossRefGoogle Scholar
  24. 21.
    A. Wacker and L. Träger, Z. Naturforsch., 18b:13 (1963).Google Scholar
  25. 22.
    S. Greer and S. Zamenhof, J. Mol. Biol., 4:123 (1962).CrossRefGoogle Scholar
  26. 23.
    H. S. Shapiro and E. Chargaff, Biochim. Biophys. Acta, 39:62 (1960).CrossRefGoogle Scholar
  27. 24.
    H. S. Shapiro and E. Chargaff, Biochim. Biophys. Acta, 26:596 (1957).CrossRefGoogle Scholar
  28. 25.
    A. M. Michelson and A. R. Todd, J. Chem. Soc., 34 (1954).Google Scholar
  29. 26.
    H. G. Khorana, A. F. Turner, and J. P. Vissolyi, J. Am. Chem. Soc., 83:686 (1961).CrossRefGoogle Scholar
  30. 27.
    N. K. Kochetkov, É. I. Budovskii, and V. N. Shibaev, Khimiya Prirodn. Soedin., 328 (1965).Google Scholar
  31. 28.
    I. L. Doerr and J. J. Fox, J. Org. Chem., 32:1462 (1967).CrossRefGoogle Scholar
  32. 29.
    P. A. Levene and F. B. La Forge, Ber., 45:608 (1912);Google Scholar
  33. 29a.
    P. A. Levene and F. B. La Forge, J. Biol. Chem., 13:508 (1912).Google Scholar
  34. 30.
    G. E. Hilbert and T. B. Johnson, J. Am. Chem. Soc., 52:5489 (1930).Google Scholar
  35. 31.
    W. E. Conn and D. G. Doherty, J. Am. Chem. Soc., 78:2863 (1956).CrossRefGoogle Scholar
  36. 32.
    D. C. Burke, Chem. and Ind., 1393 (1954).Google Scholar
  37. 33.
    S. G. Laland and E. Rothe, Acta Chem. Scand., 10:1058 (1956).CrossRefGoogle Scholar
  38. 34.
    L. Haaveldsen, S. G. Laaland, J. M. McKee, and E. Roth, Biochim. Biophys. Acta, 33:201 (1959).CrossRefGoogle Scholar
  39. 35.
    L. Massart and J. Hoste, Biochim. Biophys. Acta, 1:83 (1947).CrossRefGoogle Scholar
  40. 36.
    T. G. Brady and F. McEvoy-Bowe, Nature, 168:299 (1951).CrossRefGoogle Scholar
  41. 37.
    W. E. Conn, Biochem. J., 64:28P (1956).Google Scholar
  42. 38.
    M. Smith, G. I. Drummond, and H. G. Khorana, J. Am. Chem. Soc., 83:698 (1961).CrossRefGoogle Scholar
  43. 39.
    G. M. Tener, H. G. Khorana, R. Markham, and E. H. Pol, J. Am. Chem. Soc., 80:6223 (1958).CrossRefGoogle Scholar
  44. 40.
    H. S. Shapiro and E. Chargaff, Biochemistry, 5:3012 (1966).CrossRefGoogle Scholar
  45. 41.
    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. 290.Google Scholar
  46. 42.
    B. Reiner and S. Zamenhof, J. Biol. Chem., 228:475 (1957).Google Scholar
  47. 43.
    P. D. Lawley, Proc. Chem. Soc. London, 290 (1957).Google Scholar
  48. 44.
    P. Brookes and P. D. Lawley, J. Chem. Soc., 3923 (1961).Google Scholar
  49. 45.
    P. D. Lawley and P. Brookes, Nature, 192:1081 (1961).CrossRefGoogle Scholar
  50. 46.
    P. Brookes and P. D. Lawley, Biochem. J., 80:496 (1961).Google Scholar
  51. 47.
    P. D. Lawley and P. Brookes, Biochem. J., 89:127 (1963).Google Scholar
  52. 48.
    J. W. Jones and R. K. Robins, J. Am. Chem. Soc., 85:193 (1963).CrossRefGoogle Scholar
  53. 49.
    H. G. Windmuller and N. O. Kaplan, Biochim. Biophys. Acta, 61:307 (1962).Google Scholar
  54. 50.
    P. Brookes, A. Dipple, and P. D. Lawley, J. Chem. Soc., (C), 2026 (1968).Google Scholar
  55. 51.
    J. A. Haines, C. B. Reese, and A. R. Todd, J. Chem. Soc., 5281 (1962).Google Scholar
  56. 52.
    D. M. Martin and C. B. Reese, J. Chem. Soc., (C), 1731 (1968).Google Scholar
  57. 53.
    H. M. Kissman, C. Pidacks, and B. R. Baker, J. Am. Chem. Soc., 77:18(1955).Google Scholar
  58. 54.
    E. Kriek and P. Emelot, Biochim. Biophys. Acta, 91:59 (1964).Google Scholar
  59. 55.
    R. A. Zakharyan, T. V. Venkstern, and A. A. Baev, Biokhimiya, 32:1068 (1967).Google Scholar
  60. 56.
    P. D. Lawley and P. Brookes, Biochem. J., 92:19C (1964).Google Scholar
  61. 57.
    G. R. Wyatt, in: The Nucleic Acids, Vol. 1, E. Chargaff and J. N. Davidson (editors), Academic Press, New York-London (1955).Google Scholar
  62. 58.
    W. Pollman and G. Schramm, Z. Naturforsch., 16b:673 (1961).Google Scholar
  63. 59.
    S. Greer and S. Zamenhof, Fed. Proc., 18:238 (1959).Google Scholar
  64. 60.
    A. S. Jones, J. R. Tittensor, and R. T. Walker, Nature, 209:296 (1966).CrossRefGoogle Scholar
  65. 61.
    G. B. Petersen and K. Burton, Biochem. J., 75:17 (1960).Google Scholar
  66. 62.
    K. Burton and G. B. Petersen, Biochem. J., 92:666 (1964).Google Scholar
  67. 63.
    S. G. Laland, Acta Chem. Scand., 8:449 (1954).CrossRefGoogle Scholar
  68. 64.
    J. A. Lucy and P. W. Kent, Research, 6:495 (1953).Google Scholar
  69. 65.
    P. W. Kent, J. A. Lucy, and P. F. V. Ward, Biochem. J., 61:529 (1955).Google Scholar
  70. 66.
    A. S. Jones and D. S. Letham, J. Chem. Soc., 2573 (1956).Google Scholar
  71. 67.
    E. Hurlen, S. G. Laland, R. A. Cox, and A. R. Peacock, Acta Chem. Scand., 10:793 (1956).CrossRefGoogle Scholar
  72. 68.
    C. Tamm and E. Chargaff, J. Biol. Chem., 203:689 (1953).Google Scholar
  73. 69.
    H. Witzel, Ann., 620:126 (1959).Google Scholar
  74. 70.
    U. L. Raj Bhandary, S. H. Chang, A. Stuart, R. D. Faulkner, R. M. Hoskonson, and H. G. Khorana, Proc. Nat. Acad. Sci. USA, 57:751 (1967).CrossRefGoogle Scholar
  75. 71.
    R. Thilbe and H. G. Zachau, Europ. J. Biochem., 5:546 (1968).CrossRefGoogle Scholar
  76. 72.
    A. S. Jones, A. M. Mian, and R. T. Walker, J. Chem. Soc., (C), 692 (1966).Google Scholar
  77. 73.
    E. W. Sutherland and T. W. Rall, Biol. Chem., 232:1077 (1958).Google Scholar
  78. 74.
    D. Lipkin, W. H. Cook, and R. Markham, J. Am. Chem. Soc., 81:6196 (1959).Google Scholar
  79. 75.
    E. R. Garrett, J. Am. Chem. Soc., 82:827 (1960).CrossRefGoogle Scholar
  80. 76.
    L. W. Parks and F. Schlenk, J. Biol. Chem., 230:295 (1958).Google Scholar
  81. 77.
    W. Frank, J. Weiczotkowski, N. A. Hughe, and J. Baddiley, Proc. Chem. Soc. London, 449 (1961).Google Scholar
  82. 78.
    M. P. Gordon, V. S. Weliky, and G. B. Brown, J. Am. Chem. Soc., 79:3245 (1957).CrossRefGoogle Scholar
  83. 79.
    D. I. Magrath and G. B. Brown, J. Am. Chem. Soc., 79:3252 (1957).CrossRefGoogle Scholar
  84. 80.
    G. B. Brown, M. P. Gordon, D.I. Magrath, and A. Hampton, in: Ciba Foundation Simposium on Chemistry and Biology of Purines, J. and A. Churchill, London (1957).Google Scholar
  85. 81.
    S. Takemura and M. Miyazaki, Bull. Chem. Soc Japan, 32:9261 (1959).Google Scholar
  86. 82.
    S. Takemura, J. Biochem. Japan, 44:321 (1957);Google Scholar
  87. 82a.
    S. Takemura, Biochim. Biophys. Acta, 29:447 (1958);CrossRefGoogle Scholar
  88. 82b.
    S. Takemura, Bull. Chem. Soc. Japan, 32:920 (1959).CrossRefGoogle Scholar
  89. 83.
    V. Habermann, Coll. Czech. Chem. Comm., 28:510 (1963).Google Scholar
  90. 84.
    A. Temperli, H. Turler, P. Rüst, A. Danon, and E. Chargaff, Biochim. Biophys. Acta, 91:462 (1964).Google Scholar
  91. 85.
    E. I. Budovskii, J. A. Haines, and N. K. Kochetkov, Dokl. Akad. Nauk SSSR, 158:379 (1964).Google Scholar
  92. 86.
    E. Freese, E. Bautz-Freese, and E. Bautz, J. Mol. Biol., 3:133 (1961).CrossRefGoogle Scholar
  93. 87.
    H. Schuster, J. Mol. Biol., 3:447 (1961).CrossRefGoogle Scholar
  94. 88.
    D. W. Verwoerd, H. Kohlage, and W. Zillig, Nature, 192:1038 (1961).CrossRefGoogle Scholar
  95. 89.
    N. K. Kochetkov, E. I. Budowsky, and N. A. Simukova, Biochim. Biophys. Acta, 55:255 (1962).CrossRefGoogle Scholar
  96. 90.
    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).Google Scholar
  97. 91.
    M. F. Turchinskii, L. I. Gus’kova, and É. I. Budovskii, Molekul. Biol., 1:793 (1967).Google Scholar
  98. 92.
    H. Priess and W. Zillig, Hoppe-Seyler’s Z. Physiol. Chem., 342:73 (1965).CrossRefGoogle Scholar
  99. 93.
    P. Howgate, A. S. Jones, and J. R. Tittensor, J. Chem. Soc., (C), 275 (1968).Google Scholar
  100. 94.
    A. S. Jones, G. W. Ross, S. Takemura, T. W. Tompson, and R. T. Walker, J. Chem. Soc., 373 (1964).Google Scholar
  101. 95.
    K. Burton and W. T. Riley, Biochem. J., 98:70 (1966).Google Scholar
  102. 96.
    H. Seidel, Biochim. Biophys. Acta, 138:98 (1967).Google Scholar
  103. 97.
    M. I. Simon and H. Van Vunakis, J. Mol. Biol., 4:488 (1962);CrossRefGoogle Scholar
  104. 97a.
    M. I. Simon and H. Van Vunakis, Arch. Biochem. Biophys., 105:197 (1964).CrossRefGoogle Scholar
  105. 98.
    J. S. Sussenbach and W. Berends, Biochim. Biophys. Acta, 76:154 (1963).CrossRefGoogle Scholar
  106. 99.
    K. S. Sastry and M. P. Gordon, Biochim. Biophys. Acta, 129:42 (1966).Google Scholar
  107. 100.
    P. A. Friedman, Biochim. Biophys. Acta, 166:1 (1968).Google Scholar
  108. 101.
    J. X. Khym and W. E. Cohn, J. Am. Chem. Soc., 82:638 (1960).CrossRefGoogle Scholar
  109. 102.
    M. Tomasz, Y. Sano, and R. W. Chambers, Biochemistry, 4:1710 (1965).CrossRefGoogle Scholar
  110. 103.
    A. F. Cook and J. G. Moffatt, J. Am. Chem. Soc., 89:2697 (1967).CrossRefGoogle Scholar
  111. 104.
    T. Gabriel, W. Y. Chen, and A. L. Nussbaum, J. Am. Chem. Soc., 90:6833 (1968).CrossRefGoogle Scholar
  112. 105.
    H.-J. Raese and E. Freese, Biochim. Biophys. Acta, 155:476 (1968).Google Scholar
  113. 106.
    H.-J. Raese, E. Freese, and M. S. Melzer, Biochim. Biophys. Acta, 155:491 (1968).Google Scholar
  114. 107.
    B. Singer and H. Fraenkel-Conrat, Biochemistry, 4:227 (1965).Google Scholar

Copyright information

© Plenum Publishing Company Ltd. 1972

Authors and Affiliations

  • N. K. Kochetkov
  • E. I. Budovskii

There are no affiliations available

Personalised recommendations