Skip to main content

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

  • Chapter

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.

This is a preview of subscription content, log in via an institution.

Buying options

Chapter
USD   29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD   39.99
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD   54.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Learn about institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Bibliography

  1. A. Kossel, Arch. Anat. Physiol., Physiol. Abt., 181 (1891).

    Google Scholar 

  2. A. Kossel and A. Neumann, Ber., 26:2753 (1863);

    Google Scholar 

  3. A. Kossel and A. Neumann, Z. Phys. Chem., 22:74 (1897).

    Article  Google Scholar 

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

    Google Scholar 

  5. C. Tamm, M. E. Hodes, and E. Chargaff, J. Biol. Chem., 195:49 (1952).

    CAS  Google Scholar 

  6. H. S. Shapiro and E. Chargaff, Biochim. Biophys. Acta, 23:451 (1957).

    Article  CAS  Google Scholar 

  7. P. A. Levene and W. A. Jacobs, Ber., 42:2469, 2703 (1909).

    CAS  Google Scholar 

  8. P. A. Levene and W. A. Jacobs, Ber., 44:1027 (1911).

    CAS  Google Scholar 

  9. E. R. Garrett, J. K. Seydel, and A. J. Sharper, J. Org. Chem., 31:2219 (1966).

    Article  CAS  Google Scholar 

  10. H. Venner, Hoppe-Sayler’s Z. Physiol. Chem., 339:14 (1964);

    Article  CAS  Google Scholar 

  11. H. Venner, Hoppe-Sayler’s Z. Physiol. Chem., 344:189 (1966).

    Article  CAS  Google Scholar 

  12. G. W. Kenner, in: Ciba Foundation Symposium on Chemistry and Biology of Purines, J. and A. Churchill, London (1957).

    Google Scholar 

  13. H. S. Isabelle and H. I. Frush, J. Org. Chem., 23:1309 (1958).

    Article  Google Scholar 

  14. R. Shapiro and S. King, Biochemistry, 8:1806 (1969).

    Article  CAS  Google Scholar 

  15. C. A. Dekker, Ann. Rev. Biochem., 29:453 (1960).

    Article  CAS  Google Scholar 

  16. F. Micheel and A. Heesing, Chem. Ber., 94:1814 (1961).

    Article  CAS  Google Scholar 

  17. B. Capon and B. E. Connett, Tetrahedron Letters, 1395 (1964).

    Google Scholar 

  18. B. Capon and B. E. Connett, J. Chem. Soc., 4497 (1965).

    Google Scholar 

  19. H. Simon and D. Palm, Chem. Ber., 98:433 (1965).

    Article  CAS  Google Scholar 

  20. M. N. Preobrazhenskaya, N. N. Vigdorchik, and N. N. Suvorov, Tetrahedron, 23:4653 (1967).

    Article  CAS  Google Scholar 

  21. D. M. Brown, G. D. Fasman, D. I. Magrath, and A. R. Todd, J. Chem, Soc., 1448 (1954).

    Google Scholar 

  22. I. Wempen, I. L. Doerr, L. Kaplan, and J. J. Fox, J. Am. Chem. Soc., 82:1624 (1960).

    Article  CAS  Google Scholar 

  23. K. E. Pfitzer and J. G. Moffatt, J. Org. Chem., 29:1508 (1964).

    Article  Google Scholar 

  24. A. Wacker and L. Träger, Z. Naturforsch., 18b:13 (1963).

    CAS  Google Scholar 

  25. S. Greer and S. Zamenhof, J. Mol. Biol., 4:123 (1962).

    Article  CAS  Google Scholar 

  26. H. S. Shapiro and E. Chargaff, Biochim. Biophys. Acta, 39:62 (1960).

    Article  CAS  Google Scholar 

  27. H. S. Shapiro and E. Chargaff, Biochim. Biophys. Acta, 26:596 (1957).

    Article  CAS  Google Scholar 

  28. A. M. Michelson and A. R. Todd, J. Chem. Soc., 34 (1954).

    Google Scholar 

  29. H. G. Khorana, A. F. Turner, and J. P. Vissolyi, J. Am. Chem. Soc., 83:686 (1961).

    Article  CAS  Google Scholar 

  30. N. K. Kochetkov, É. I. Budovskii, and V. N. Shibaev, Khimiya Prirodn. Soedin., 328 (1965).

    Google Scholar 

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

    Article  CAS  Google Scholar 

  32. P. A. Levene and F. B. La Forge, Ber., 45:608 (1912);

    CAS  Google Scholar 

  33. P. A. Levene and F. B. La Forge, J. Biol. Chem., 13:508 (1912).

    Google Scholar 

  34. G. E. Hilbert and T. B. Johnson, J. Am. Chem. Soc., 52:5489 (1930).

    Google Scholar 

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

    Article  Google Scholar 

  36. D. C. Burke, Chem. and Ind., 1393 (1954).

    Google Scholar 

  37. S. G. Laland and E. Rothe, Acta Chem. Scand., 10:1058 (1956).

    Article  CAS  Google Scholar 

  38. L. Haaveldsen, S. G. Laaland, J. M. McKee, and E. Roth, Biochim. Biophys. Acta, 33:201 (1959).

    Article  Google Scholar 

  39. L. Massart and J. Hoste, Biochim. Biophys. Acta, 1:83 (1947).

    Article  CAS  Google Scholar 

  40. T. G. Brady and F. McEvoy-Bowe, Nature, 168:299 (1951).

    Article  CAS  Google Scholar 

  41. W. E. Conn, Biochem. J., 64:28P (1956).

    Google Scholar 

  42. M. Smith, G. I. Drummond, and H. G. Khorana, J. Am. Chem. Soc., 83:698 (1961).

    Article  CAS  Google Scholar 

  43. G. M. Tener, H. G. Khorana, R. Markham, and E. H. Pol, J. Am. Chem. Soc., 80:6223 (1958).

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  45. 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. B. Reiner and S. Zamenhof, J. Biol. Chem., 228:475 (1957).

    CAS  Google Scholar 

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

    Google Scholar 

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

    Google Scholar 

  49. P. D. Lawley and P. Brookes, Nature, 192:1081 (1961).

    Article  CAS  Google Scholar 

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

    CAS  Google Scholar 

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

    CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  53. H. G. Windmuller and N. O. Kaplan, Biochim. Biophys. Acta, 61:307 (1962).

    Google Scholar 

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

    Google Scholar 

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

    Google Scholar 

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

    Google Scholar 

  57. H. M. Kissman, C. Pidacks, and B. R. Baker, J. Am. Chem. Soc., 77:18(1955).

    Google Scholar 

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

    CAS  Google Scholar 

  59. R. A. Zakharyan, T. V. Venkstern, and A. A. Baev, Biokhimiya, 32:1068 (1967).

    CAS  Google Scholar 

  60. P. D. Lawley and P. Brookes, Biochem. J., 92:19C (1964).

    CAS  Google Scholar 

  61. 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. W. Pollman and G. Schramm, Z. Naturforsch., 16b:673 (1961).

    CAS  Google Scholar 

  63. S. Greer and S. Zamenhof, Fed. Proc., 18:238 (1959).

    Google Scholar 

  64. A. S. Jones, J. R. Tittensor, and R. T. Walker, Nature, 209:296 (1966).

    Article  CAS  Google Scholar 

  65. G. B. Petersen and K. Burton, Biochem. J., 75:17 (1960).

    Google Scholar 

  66. K. Burton and G. B. Petersen, Biochem. J., 92:666 (1964).

    Google Scholar 

  67. S. G. Laland, Acta Chem. Scand., 8:449 (1954).

    Article  CAS  Google Scholar 

  68. J. A. Lucy and P. W. Kent, Research, 6:495 (1953).

    Google Scholar 

  69. P. W. Kent, J. A. Lucy, and P. F. V. Ward, Biochem. J., 61:529 (1955).

    CAS  Google Scholar 

  70. A. S. Jones and D. S. Letham, J. Chem. Soc., 2573 (1956).

    Google Scholar 

  71. E. Hurlen, S. G. Laland, R. A. Cox, and A. R. Peacock, Acta Chem. Scand., 10:793 (1956).

    Article  CAS  Google Scholar 

  72. C. Tamm and E. Chargaff, J. Biol. Chem., 203:689 (1953).

    CAS  Google Scholar 

  73. H. Witzel, Ann., 620:126 (1959).

    CAS  Google Scholar 

  74. 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).

    Article  Google Scholar 

  75. R. Thilbe and H. G. Zachau, Europ. J. Biochem., 5:546 (1968).

    Article  Google Scholar 

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

    Google Scholar 

  77. E. W. Sutherland and T. W. Rall, Biol. Chem., 232:1077 (1958).

    CAS  Google Scholar 

  78. D. Lipkin, W. H. Cook, and R. Markham, J. Am. Chem. Soc., 81:6196 (1959).

    Google Scholar 

  79. E. R. Garrett, J. Am. Chem. Soc., 82:827 (1960).

    Article  CAS  Google Scholar 

  80. L. W. Parks and F. Schlenk, J. Biol. Chem., 230:295 (1958).

    CAS  Google Scholar 

  81. W. Frank, J. Weiczotkowski, N. A. Hughe, and J. Baddiley, Proc. Chem. Soc. London, 449 (1961).

    Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  84. 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. S. Takemura and M. Miyazaki, Bull. Chem. Soc Japan, 32:9261 (1959).

    Google Scholar 

  86. S. Takemura, J. Biochem. Japan, 44:321 (1957);

    CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    CAS  Google Scholar 

  90. A. Temperli, H. Turler, P. Rüst, A. Danon, and E. Chargaff, Biochim. Biophys. Acta, 91:462 (1964).

    CAS  Google Scholar 

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

    CAS  Google Scholar 

  92. E. Freese, E. Bautz-Freese, and E. Bautz, J. Mol. Biol., 3:133 (1961).

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  94. D. W. Verwoerd, H. Kohlage, and W. Zillig, Nature, 192:1038 (1961).

    Article  CAS  Google Scholar 

  95. N. K. Kochetkov, E. I. Budowsky, and N. A. Simukova, Biochim. Biophys. Acta, 55:255 (1962).

    Article  CAS  Google Scholar 

  96. 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 

  97. M. F. Turchinskii, L. I. Gus’kova, and É. I. Budovskii, Molekul. Biol., 1:793 (1967).

    Google Scholar 

  98. H. Priess and W. Zillig, Hoppe-Seyler’s Z. Physiol. Chem., 342:73 (1965).

    Article  CAS  Google Scholar 

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

    Google Scholar 

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

    Google Scholar 

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

    CAS  Google Scholar 

  102. H. Seidel, Biochim. Biophys. Acta, 138:98 (1967).

    CAS  Google Scholar 

  103. M. I. Simon and H. Van Vunakis, J. Mol. Biol., 4:488 (1962);

    Article  CAS  Google Scholar 

  104. M. I. Simon and H. Van Vunakis, Arch. Biochem. Biophys., 105:197 (1964).

    Article  CAS  Google Scholar 

  105. J. S. Sussenbach and W. Berends, Biochim. Biophys. Acta, 76:154 (1963).

    Article  CAS  Google Scholar 

  106. K. S. Sastry and M. P. Gordon, Biochim. Biophys. Acta, 129:42 (1966).

    CAS  Google Scholar 

  107. P. A. Friedman, Biochim. Biophys. Acta, 166:1 (1968).

    CAS  Google Scholar 

  108. J. X. Khym and W. E. Cohn, J. Am. Chem. Soc., 82:638 (1960).

    Article  Google Scholar 

  109. M. Tomasz, Y. Sano, and R. W. Chambers, Biochemistry, 4:1710 (1965).

    Article  CAS  Google Scholar 

  110. A. F. Cook and J. G. Moffatt, J. Am. Chem. Soc., 89:2697 (1967).

    Article  CAS  Google Scholar 

  111. T. Gabriel, W. Y. Chen, and A. L. Nussbaum, J. Am. Chem. Soc., 90:6833 (1968).

    Article  CAS  Google Scholar 

  112. H.-J. Raese and E. Freese, Biochim. Biophys. Acta, 155:476 (1968).

    Google Scholar 

  113. H.-J. Raese, E. Freese, and M. S. Melzer, Biochim. Biophys. Acta, 155:491 (1968).

    Google Scholar 

  114. B. Singer and H. Fraenkel-Conrat, Biochemistry, 4:227 (1965).

    Google Scholar 

Download references

Authors

Editor information

N. K. Kochetkov E. I. Budovskii

Rights and permissions

Reprints and permissions

Copyright information

© 1972 Plenum Publishing Company Ltd.

About this chapter

Cite this chapter

Kochetkov, N.K., Budovskii, E.I. (1972). Hydrolysis of N-glycosidic Bonds in Nucleosides, Nucleotides, 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_4

Download citation

  • DOI: https://doi.org/10.1007/978-1-4684-2973-2_4

  • Publisher Name: Springer, Boston, MA

  • Print ISBN: 978-1-4684-2975-6

  • Online ISBN: 978-1-4684-2973-2

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics