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Reactions of Exocyclic Substituents of Nucleic Acid Bases and their Derivatives

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Organic Chemistry of Nucleic Acids

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Abstract

Considerable light is shed on the problems of reactivity and chemical modification of nucleic acids by reactions involving exocyclic substituents of the purine and pyrimidine bases, i. e., the amino groups of cytosine, adenine, or guanine, and the carbonyl groups of uracil, guanine, xanthine, and their derivatives, and also reactions of the sulphur atom of thio derivatives (minor components of RNA). As was mentioned previously (see Chapter 3), n electrons of the nitrogen atoms of amino groups and of the oxygen atom of carbonyl groups of the nucleic acid bases (and their derivatives) react strongly with the π electron system of the heterocyclic ring, and consequently the properties of the corresponding components of the nucleic acids differ greatly from the properties of simple amines, amides, or thioamides.

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Bibliography

  1. A. M. Michelson, J. Chem. Soc., 3655 (1959).

    Google Scholar 

  2. T. Sasaki and Y. Mizuno, Chem. Pharm. Bull., 15:894 (1967).

    Article  CAS  Google Scholar 

  3. M. Van Montagu and J. Stockx, Arch. Int. Physiol. Biochim., 73:158 (1965).

    Google Scholar 

  4. Y. Mizuno, T. Itoh, and H. Tagawa, Chem. Ind., 1498 (1965).

    Google Scholar 

  5. F. Cramer, W. Saenger, K. H. Scheit, and J. Tennigkeit, Ann., 679:156 (1964).

    CAS  Google Scholar 

  6. L. N. Nikolenko, V. N. Nezavibat’ko, and N. S. Tolmacheva, Khimiya Prirod. Soedin, 539 (1967).

    Google Scholar 

  7. L. N. Nikolenko, V. N. Nezavibat’ko, and M. I. Semenova, Zh. Org. Khimii, 49:223 (1969).

    Google Scholar 

  8. K. A. Watanabe and J. J. Fox, Angew. Chem., 78:589 (1966).

    Article  CAS  Google Scholar 

  9. B. A. Otter and J. J. Fox, in: Synthetic Procedures in Nucleic Acid Chemistry, Vol. 1, W. W. Zorbach and R. S. Tipson (editors), Interscience Publ., New York-London-Sydney-Toronto (1968), p. 285.

    Google Scholar 

  10. M. Anteonis and M. Van Montagu, Bull. Soc. Chim. Belg., 74:481 (1965).

    Article  Google Scholar 

  11. M. Van Montagu, F. Molemans, and J. Stockx, Bull. Soc. Chim. Belg., 77:471 (1968).

    Google Scholar 

  12. D. M. Brown, A. Todd, and S. Varadarajan. J. Chem. Soc., 2384 (1956).

    Google Scholar 

  13. D. H. Rammler and H. G. Khorana, J. Am. Chem. Soc., 84:3112 (1962).

    Article  CAS  Google Scholar 

  14. H. Schaller, G. Weimann, B. Lerch, and H. G. Khorana, J. Am. Chem. Soc., 85:3821 (1963).

    Article  CAS  Google Scholar 

  15. H. R. Bentley, K. G. Cunningham, and F. S. Spring, J. Chem. Soc., 2301 (1951).

    Google Scholar 

  16. F. Weygand and F. Wirth, Chem. Ber., 85:1000 (1952).

    Article  CAS  Google Scholar 

  17. M. Smith, D. H. Rammler, I. H. Goldberg, and H. G. Khorana, J. Am. Chem. Soc., 84:430 (1962).

    Article  CAS  Google Scholar 

  18. R. H. Hall, Biochemistry, 3:769 (1964).

    Article  CAS  Google Scholar 

  19. R. Lohrmann and H. G. Khorana, J. Am. Chem. Soc., 86:4188 (1964).

    Article  CAS  Google Scholar 

  20. H. P. M. Fromageot, C.B. Reese, and J. B. Suiston, Tetrahedron, 24:3533 (1968).

    Article  CAS  Google Scholar 

  21. N. I. Sokolova, V. A. Bakanova, Z. A. Shabarova, and M. A. Prokof’ev, Zh. Org. Khimii, 33:2480 (1963).

    CAS  Google Scholar 

  22. R. L. Letsinger, P. S. Miller, and G. W. Grams, Tetrahedron Letters, 2621 (1968).

    Google Scholar 

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

    Article  CAS  Google Scholar 

  24. Z. A. Shabarova, N. I. Sokolova, L. A. Boikova, and M. A. Prokof’ev, Zh. Org. Khimii, 29:2917 (1959).

    CAS  Google Scholar 

  25. Z. A. Shabarova, N. I. Sokolova, and M. A. Prokof’ev, Zh. Org. Khimii, 27:2891, 3028 (1957); 29:539 (1959).

    CAS  Google Scholar 

  26. N. I. Sokolova, V. A. Bakanova, Z. A. Shabarova, and M. A. Prokof’ev, Biokhimiya, 27:1079 (1962).

    CAS  Google Scholar 

  27. Z. A. Shabarova, Z. P. Polyakova, and M. A. Prokof’ev, Zh. Org. Khimii, 29:215 (1959).

    CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  29. G. M. Tener, J. Am. Chem. Soc., 83:159 (1961).

    Article  CAS  Google Scholar 

  30. R. K. Ralph and H. G. Khorana, J. Am. Chem. Soc., 83:2926 (1961).

    Article  CAS  Google Scholar 

  31. R. K. Ralph, W. J. Connors, H. Schaller, and H. G. Khorana, J. Am. Chem. Soc., 85:1983 (1963).

    Article  Google Scholar 

  32. Y. Lapidot and H. G. Khorana, J. Am. Chem. Soc., 85:3857 (1963).

    Article  CAS  Google Scholar 

  33. S. Chladek and J. Smrt, Coll. Czech. Chem. Comm., 29:214 (1964).

    CAS  Google Scholar 

  34. S. Chladek and J. Žemlička, Coll. Czech. Chem. Comm., 31:1785 (1966).

    Google Scholar 

  35. A. M. Michelson and M. Grunberg-Manago, Biochim. Biophys. Acta, 91:92 (1964).

    CAS  Google Scholar 

  36. H. Fraenkel-Conrat, Biochim. Biophys. Acta, 15:307 (1954).

    Article  CAS  Google Scholar 

  37. D. E. Hoard, Biochim. Biophys. Acta, 40:62 (1960).

    Article  CAS  Google Scholar 

  38. S. Lewin and D. A. Humphreys, J. Chem. Soc., (B), 562 (1967).

    Google Scholar 

  39. R. Haselkorn and P. Doty, J. Biol. Chem., 236:2738 (1961).

    CAS  Google Scholar 

  40. L. Grossman, S. S. Levine, and W. S. Allison, J. Mol. Biol., 3:47 (1961).

    Article  CAS  Google Scholar 

  41. M. Ya. Fel’dman, Biokhimiya, 27:378 (1962).

    Google Scholar 

  42. M. Ya. Fel’dman and M. R. Shubina, Dokl. Akad. Nauk SSSR, 174:236 (1967).

    Google Scholar 

  43. M. Ya. Feldman, Biochim. Biophys. Acta, 149:20 (1967).

    CAS  Google Scholar 

  44. M. Ya. Fel’dman, Biokhimiya, 30:203 (1965).

    Google Scholar 

  45. M. Ya. Fel’dman, Biokhimiya, 29:720 (1964).

    Google Scholar 

  46. M. Staehelin, Biochim. Biophys. Acta, 29:410 (1958).

    Article  CAS  Google Scholar 

  47. C. L. Stevens and A. Rosenfeld, Biochemistry, 5:2714 (1966).

    Article  CAS  Google Scholar 

  48. G. D. Fasman, C. Lindblow, and L. Grossman, Biochemistry, 3:1015 (1964).

    Article  CAS  Google Scholar 

  49. J. T. Penniston and P. Doty, Biopolymers, 1:145 (1963).

    Article  CAS  Google Scholar 

  50. W. M. Stanley and R. M. Bock, Biochemistry, 4:1302 (1965).

    Article  CAS  Google Scholar 

  51. R. Marciello and G. Zubay, Biochem. Biophys. Res. Comm., 14:272 (1964).

    Article  CAS  Google Scholar 

  52. G. D. Fasman, C. Lindblow, and E. Seaman, J. Mol. Biol., 12:630 (1965).

    Article  CAS  Google Scholar 

  53. H. Boedtker, Biochemistry, 6:2718 (1967).

    Article  CAS  Google Scholar 

  54. D. Stollar and L. Grossman, J. Mol. Biol., 4:31 (1962).

    Article  CAS  Google Scholar 

  55. S. Lewin, Arch. Biochem. Biophys., 113:584 (1966);

    Article  CAS  Google Scholar 

  56. K. I. Berns and C. A. Thomas, J. Mol. Biol., 3:289 (1961).

    Article  CAS  Google Scholar 

  57. É. N. Trifonov, Yu. S. Lazurkin, and M. D. Frank-Kamenetskii, Molekul. Biol., 1:164 (1967).

    CAS  Google Scholar 

  58. É. N. Trifonov, N. N. Shafranovskaya, M. D. Frank-Kamenetskii, and Yu. S. Lazurkin, Molekul. Biol., 2:887 (1968).

    CAS  Google Scholar 

  59. J. T. Penniston and P. Doty, Biopolymers, 1:209 (1963).

    Article  CAS  Google Scholar 

  60. M. K. Kukhanova, L. L. Kiselev, and L. Yu. Frolova, Biokhimiya, 28:1053 (1963).

    CAS  Google Scholar 

  61. B. M. Goldschmidt, T. P. Blazei, and V. L. Van Duuren, Tetrahedron Letters, 1583 (1968).

    Google Scholar 

  62. M. Staehelin, Biochim. Biophys. Acta, 31:488 (1959).

    Article  Google Scholar 

  63. R. Shapiro and J. Hachmann, Biochemistry, 5:2799 (1966).

    Article  CAS  Google Scholar 

  64. N. K. Kochetkov, É. I. Budowsky, N. E. Broude, and L. M. Klebanova, Biochim. Biophys. Acta, 134:492 (1967).

    CAS  Google Scholar 

  65. N. K. Kochetkov, É. I. Budovskii, and N. E. Broude, Molekul. Biol., 1:214 (1967).

    Google Scholar 

  66. K. Nakaya, O. Takenaka, H. Horinishi, and K. Shibata, Biochim. Biophys. Acta, 161:23 (1968).

    CAS  Google Scholar 

  67. M. Litt and V. Hancock, Biochemistry, 6:1848 (1967).

    Article  CAS  Google Scholar 

  68. R. Shapiro, S. C. Agarwal, and B. I. Cohen, Abstr. Papers XXIst Congr. IUPAC, Nucleic Acid Chem., Prague, N 7 (1967).

    Google Scholar 

  69. P. Whitfeld and H. Witzel, Biochim. Biophys. Acta, 72:338 (1963).

    Article  CAS  Google Scholar 

  70. N. E. Broude, I. A. Bass, and É. I. Budovskii, Biochim. Biophys. Acta (in press).

    Google Scholar 

  71. R. Shapiro and S. C. Agarwal, J. Am. Chem. Soc., 90:474 (1968).

    Article  CAS  Google Scholar 

  72. A. Strecker, Ann., 118:166 (1861).

    Google Scholar 

  73. A. Kossel, Ber., 18:1928 (1885).

    Google Scholar 

  74. A. Kossel and H. Steudel, Z. Physiol. Chem., 37:377 (1903).

    Article  CAS  Google Scholar 

  75. P. A. Levene and W. A. Jacobs, Ber., 43:3150 (1910).

    Google Scholar 

  76. K. Lohman, Biochem. Z., 254:381 (1932).

    Google Scholar 

  77. R. Shapiro and S. H. Pohl, Biochemistry, 7:448 (1968).

    Article  CAS  Google Scholar 

  78. R. Shapiro, J. Am. Chem. Soc., 86:2948 (1964).

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  80. M. Matsuda and H. Ogoshi, Biochim. Biophys. Acta, 119:210 (1966).

    CAS  Google Scholar 

  81. É. P. Geiduschek, Proc. Nat. Acad. Sci. USA, 47:950 (1961).

    Article  CAS  Google Scholar 

  82. E. F. Becher, B. K. Zimmerman, and E. P. Geiduschek, J. Mol. Biol., 8:377 (1964).

    Article  Google Scholar 

  83. E. E. Horn and R. M. Herriot, Proc. Nat. Acad. Sci. USA, 48:1409 (1962).

    Article  CAS  Google Scholar 

  84. T. Ushida and F. Egami, J. Biochem., 57:742 (1965).

    Google Scholar 

  85. J. A. Carbon, Biochim. Biophys. Acta, 95:550 (1965).

    CAS  Google Scholar 

  86. H. Schuster and G. Schramm, Z. Naturforsch., 13b:697 (1958).

    CAS  Google Scholar 

  87. H. Schuster and R. C. Wilhelm, Biochim. Biophys!. Acta, 68:554 (1963).

    Article  CAS  Google Scholar 

  88. H. Schuster, Z. Naturforsch., 15b:304 (1960).

    Google Scholar 

  89. T. I. Tikhonenko, E. N. Dobrov, G. A. Velikodvorskaya, and N. P. Kiseleva, J. Mol. Biol., 18:58 (1966).

    Article  CAS  Google Scholar 

  90. J. A. Nelson, S. C. Ristow, and R. W. Holley, Biochim. Biophys. Acta, 149:590 (1967).

    CAS  Google Scholar 

  91. J. Carbon and J. B. Gurry, Proc. Nat. Acad. Sci. USA, 59:467 (1968).

    Article  CAS  Google Scholar 

  92. T. Kotaka and R. L. Baldwin, J. Mol. Biol., 9:323 (1964).

    Article  CAS  Google Scholar 

  93. C. Basilio, A. J. Wahba, P. Lerigyel, J. F. Speyer, and S. Ochoa, Proc. Nat. Acad. Sci. USA, 48:613 (1962).

    Article  CAS  Google Scholar 

  94. R. C. Orgel, Adv. Enzymology, 27:289 (1965).

    Google Scholar 

  95. J. Zemlicka, Coll. Czech. Chem. Comm., 28:1060 (1963).

    CAS  Google Scholar 

  96. J. Zemlicka, S. Chladek, A. Holy, and J. Smrt, Coll. Czech. Chem. Comm., 31:3198 (1966).

    CAS  Google Scholar 

  97. J. Zemlicka, Coll. Czech. Chem. Comm., 32:3159 (1967).

    CAS  Google Scholar 

  98. A. Holy and J. Smrt, Coll. Czech. Chem. Comm., 31:3800 (1966).

    CAS  Google Scholar 

  99. J. Smrt, Coll. Czech, Chem. Comm., 33:1462 (1968).

    CAS  Google Scholar 

  100. A. M. Michelson and A. R. Todd, J. Chem. Soc., 2476 (1949).

    Google Scholar 

  101. R. Brimacombe, W. Kemper, T. Jaonini, and J. Smrt, Coll. Czech. Chem. Comm., 33:2074 (1968).

    CAS  Google Scholar 

  102. M. Azegawi and K. Iwai, J. Biochem., 55:346 (1964).

    Google Scholar 

  103. H. Kössel, Z. Physiol. Chem., 340:210 (1965).

    Article  Google Scholar 

  104. E. N. Moundrianakis and M. Beer, Biochim. Biophys. Acta, 95:23 (1965).

    Google Scholar 

  105. H. D. Hoffmann and W. Müller, Biochim. Biophys. Acta, 123:421 (1966).

    CAS  Google Scholar 

  106. H. Fischer, Z. Physiol. Chem., 69:69 (1909).

    Google Scholar 

  107. A. Albert and D. J. Brown, J. Chem. Soc., 2060 (1954).

    Google Scholar 

  108. H. Kössel and S. Doehring, Z. Physiol. Chem., 340:221 (1965).

    Article  Google Scholar 

  109. M. Beer and E. N. Moundrianakis, Proc. Nat. Acad. Sci. USA, 48:409 (1962).

    Article  CAS  Google Scholar 

  110. E. N. Moundrianakis and M. Beer, Proc. Nat. Acad. Sci. USA, 53:564 (1965).

    Article  Google Scholar 

  111. H. Erikson and M. Beer, Biochemistry, 6:2694 (1967).

    Article  Google Scholar 

  112. J. J. Roberts and G. P. Warwick, Nature, 197:88 (1963);

    Article  Google Scholar 

  113. J. J. Roberts and G. P. Warwick, Int. J. Cancer, 1:107, 179 (1966).

    Article  Google Scholar 

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

    Google Scholar 

  115. O. M. Friedman, G. N. Nahapatra, B. Dash, and R. Stevenson, Biochim. Biophys. Acta, 103:286 (1965).

    CAS  Google Scholar 

  116. H. T. Miles, J. Org. Chem., 26:4761 (1961).

    Article  CAS  Google Scholar 

  117. K. H. Scheit and A. Holy, Biochim. Biophys. Acta, 149:344 (1967).

    CAS  Google Scholar 

  118. Y. Furukawa, K. Kobayashi, Y. Kanai, and M. Honjo, Chem. Pharm. Bull., 13:1273 (1965).

    Article  CAS  Google Scholar 

  119. J. J. Fox and I. Wempen, Adv. Carboh. Chem., 14:283 (1959).

    CAS  Google Scholar 

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

    Google Scholar 

  121. H. G. Garg, J. Sci. Ind. Res., 25:404 (1966).

    CAS  Google Scholar 

  122. K. H. Scheit, Tetrahedron Letters, 113 (1967).

    Google Scholar 

  123. M. Ikehara, T. Ueda, and K. Ikeda, Chem. Pharm. Bull., 10:767 (1962).

    Article  CAS  Google Scholar 

  124. K. Kikugawa, F. Sato, T. Tsuruo, M. Imura, and T. Ukita, Chem. Pharm. Bull., 16:1110 (1968).

    Article  CAS  Google Scholar 

  125. H. J. Thomas and J. A. Montgomery, J. Med. Chem., 11:44 (1968).

    Article  CAS  Google Scholar 

  126. J. Ofengand, J. Biol. Chem., 242:5034 (1967).

    CAS  Google Scholar 

  127. J. Carbon and H. David, Biochemistry, 7:3851 (1968).

    Article  CAS  Google Scholar 

  128. B. R. Reid, Biochem. Biophys. Res. Comm., 33:627 (1968).

    Article  CAS  Google Scholar 

  129. M. Saneyoshi and S. Nishimura, Biochim. Biophys. Acta, 145:208 (1967).

    CAS  Google Scholar 

  130. M. Saneyoshi and G. Chihara, Chem. Pharm. Bull., 15:909 (1967).

    Article  CAS  Google Scholar 

  131. J. J. Fox, D. Van Praag, I. Wempen, I. L. Doerr, L. Cheong, J. E. Knoll, M. L. Eidinoff, A. Bendich, and G. B. Brown, J. Am. Chem, Soc., 81:178 (1959).

    Article  CAS  Google Scholar 

  132. M. N. Lipsett, J. Biol. Chem., 240:3975 (1965).

    CAS  Google Scholar 

  133. M. N. Lipsett and B. P. Doctor, J. Biol. Chem., 242:4072 (1967).

    CAS  Google Scholar 

  134. M. N. Lipsett, J. Biol. Chem., 242:4067 (1967).

    CAS  Google Scholar 

  135. M. Uziel, Biochem. Biophys. Res. Comm., 25:106 (1966).

    Article  Google Scholar 

  136. I. L. Doerr, I. Wempen, D. A. Clarke, and J. J. Fox, J. Org. Chem., 26:3401 (1961).

    Article  CAS  Google Scholar 

  137. J. A. Carbon, L. Hung. and D. S. Jones, Proc. Nat. Acad. Sci. USA, 53:979 (1965).

    Article  CAS  Google Scholar 

  138. B. Goehler and P. H. Doi, Proc. Nat. Acad. Sci. USA, 56:1047 (1967).

    Article  Google Scholar 

  139. R. Shapiro, B. J. Cohen, S. J. Shuey, and H. Maurer, Biochemistry, 8:238 (1969).

    Article  CAS  Google Scholar 

  140. F. N. Hayes, E. Hansbury, V. E. Mitchell, R. L. Ratlieff, and D. L. Williams, Europ. J. Biochem., 6:485 (1968).

    Article  CAS  Google Scholar 

  141. G. Keith and J. P. Ebel, Biochim. Biophys. Acta, 166:16 (1968).

    CAS  Google Scholar 

  142. V. D. Axelrod, M. Ya. Feldman, I. I. Chuguev, and A. A. Bayev, Biochim. Biophys. Acta, 186:33 (1969).

    CAS  Google Scholar 

  143. R. A. Cox and K. Kanagalingam, Biochem. J., 103:749 (1967);

    CAS  Google Scholar 

  144. R. A. Cox and K. Kanagalingam, Biochem. J., 108:599 (1968).

    CAS  Google Scholar 

  145. M. L. Fenwick, Biochem. J., 107:851 (1968).

    CAS  Google Scholar 

  146. M. F. Bourguignon, Biochim. Biophys. Acta, 166:242 (1968).

    CAS  Google Scholar 

  147. N. E. Broude and E. I. Budovskii, Biochim. Biophys. Acta (in press).

    Google Scholar 

  148. M. Litt, Biochemistry, 8:3249 (1969).

    Article  CAS  Google Scholar 

  149. A. Holý, Coll. Czech. Chem. Comm., 33:2245 (1968).

    Google Scholar 

  150. R. Shapiro and S. J. Shuey, Biochim. Biophys. Acta, 174:403 (1969).

    CAS  Google Scholar 

  151. A. Holý and J. Žemlička, Coll. Czech. Chem. Comm., 34:2449 (1969).

    Google Scholar 

  152. B. C. Pal, M. Uziel, D. G. Doherty, and W. E. Conn, J. Am. Chem. Soc., 91:3634 (1969).

    Article  CAS  Google Scholar 

  153. H. Yayatsu and M. Yano, Tetrahedron Letters, 755 (1969).

    Google Scholar 

  154. E. B. Ziff and J. R. Fresco, J. Am. Chem. Soc., 90:7338 (1968).

    Article  CAS  Google Scholar 

  155. E. B. Ziff and J. R. Fresco, Biochemistry, 8:3242 (1969).

    Article  CAS  Google Scholar 

  156. M. Pleiss, H. Ochiai, and P. A. Cerutti, Biochem. Biophys. Res. Comm., 34:70 (1969).

    Article  CAS  Google Scholar 

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  1. N. K. Kochetkov
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N. K. Kochetkov E. I. Budovskii

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Kochetkov, N.K., Budovskii, E.I. (1972). Reactions of Exocyclic Substituents 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_2

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