Skip to main content

Periodate oxidation in chemistry of nucleic acids: Dialdehyde derivatives of nucleosides, nucleotides, and oligonucleotides (Review)

Abstract

The employment of periodate oxidation in the chemistry of nucleic acids and their components is reviewed. The reaction mechanism, structural requirements to substrates, and synthesis of dialdehyde derivatives of nucleosides, nucleotides, and oligonucleotides are discussed in the first part. The second part involves chemical, physico-chemical, and biological properties of the dialdehyde derivatives, as well as their use for the affinity modifications of proteins.

This is a preview of subscription content, access via your institution.

References

  1. Malaprade, L.,Bull. Soc. Shim. France, 1928, vol. 43, pp. 683–696.

    CAS  Google Scholar 

  2. Malaprade, L.,Compt. Rend., 1928, vol. 186, pp. 382–384.

    CAS  Google Scholar 

  3. Guthrie, R.D. and Honeyman, J.,Chem. Ind. (London), 1958, vol. 13, pp. 388–389.

    Google Scholar 

  4. Colbran, R.L., Guthrie, R.D., and Parsons, M.A.,J. Chem. Soc., 1960, no. 4, pp. 3532–3539.

  5. Baddiley, J., Buchanan, J.G., and Szabo, L.,J. Chem. Soc., 1954, no. 10, pp. 3826–3831.

  6. Kochetkov, N.K., Bochkov, A.F., Dmitriev, B.A., Usov, A.I., Chizhov, O.S., and Shibaev, V.N.,Khimiya uglevodov (Chemistry of Carbohydrates), Moscow: Khimiya, 1967, pp. 88–91.

    Google Scholar 

  7. Fatiadi, A.J.,Synthesis, 1974, vol. 30, pp. 229–272.

    Article  Google Scholar 

  8. Buist, G.H. and Bunton, C.A.,J. Chem. Soc., 1954, no. 4, pp. 1406–1413.

  9. Buist, G.H., Bunton, C.A., and Miles, J.H.,J. Chem. Soc., 1959, no. 2, pp. 743–748.

  10. Dyer, J.R., Use of Periodate Oxidations in Biochemical Analysis,Methods of Biochemical Analysis, 1965, vol. 3, pp. 111–152.

    Article  Google Scholar 

  11. Cantley, M., Hough, L., and Pittet, A.O.,J. Chem. Soc., 1963, no. 8, pp. 2527–2534.

  12. Nishimura, T. and Shimizu, B.,Chem. Pharm. Bull., 1965, vol. 13, pp. 803–810.

    PubMed  CAS  Google Scholar 

  13. Beigelman, L.N., Gurskaya, G.V., Tsapkina, E.N., and Mikhailov, S.N.,Carbohydr. Res., 1988, vol. 181, pp. 77–88.

    CAS  Article  Google Scholar 

  14. Yu, R.J. and Bishop, C.T.,Can. J. Chem., 1967, vol. 45, pp. 2195–2203.

    CAS  Article  Google Scholar 

  15. Aalmo, K.M., Grasdalen, H., and Painter, T.J.,Carbohydr. Res., 1981, vol. 91, pp. 1–11.

    CAS  Article  Google Scholar 

  16. Mikhailov, S.N. and Efimtseva, E.V.,Nucl. Acids Res., Symp. Ser., 1984, no. 14, pp. 257–258.

  17. Guthrie, R.R., Periodate Oxydation. Experimental Conditions,Methods in Carbohydrate Chemistry, Whistler, R.L. and Wolfrom, M.L., Eds., New York: Academic, 1962, vol. 1, pp. 432–435. Translated under the titleMetody khimii uglevodov, Moscow: Mir, 1967, pp. 58–62.

    Google Scholar 

  18. Cantley, M., Hough, L., and Pittet, A.O.,J. Chem. Soc., 1963, no. 4, pp. 2527–2535.

  19. Khymm, J.X.,Methods in Carbohydrate Chemistry, Whistler, R.L. and Bemiller, J.N., Eds., New York: Academic, 1972, vol. 6. Translated under the titleMetody issledovaniya uglevodov, Moscow: Mir, 1975, pp. 73–77.

    Google Scholar 

  20. Dixon, J.S. and Lipkin, D.,Anal. Chem., 1954, vol. 26, pp. 1092–1093.

    CAS  Article  Google Scholar 

  21. Kennedy, J.F.,Methods in Carbohydrate Chemistry, Whistler, R.L. and Bemiller, J.N., Eds., New York: Academic, 1972, vol. 6. Translated under the titleMetody issledovaniya uglevodov, Moscow: Mir, 1975, pp. 78–83.

    Google Scholar 

  22. Guthrie, R.R.,Methods in Carbohydrate Chemistry, Whistler, R.L. and Wolfrom, M.L., Eds., New York: Academic, 1962, vol. 1, pp. 435–441. Translated under the titleMetody khimii uglevodov, Moscow: Mir, 1967, pp. 62–67.

    Google Scholar 

  23. Spek, J.K., Jr.,Methods in Carbohydrate Chemistry, Whistler, R.L. and Wolfrom, M.L., Eds., New York: Academic, 1962, vol. 1, pp. 445–447. Translated under the titleMetody khimii uglevodov, Moscow: Mir, 1967, pp. 67–70.

    Google Scholar 

  24. Zakharans, V.Ya., Lipsbergs, I.U., and Laurs, Yu.R.,Izv. Akad. Nauk Latv. SSR, 1980, vol. 9, pp. 457–462.

    Google Scholar 

  25. Busev, A.I., Zakharans, V.Ya., and Mikstais, U.Ya.,Khim-Farm. Zh., 1977, vol. 3, pp. 128–132.

    Google Scholar 

  26. Busev, A.I., Zakharans, V.Ya., and Mikstais, U.Ya.,Khim.-Farm. Zh., 1977, vol. 11, pp. 132–135.

    CAS  Google Scholar 

  27. Busev, A.I. and Zakharans, V.Ya.,Khim.-Farm. Zh., 1977, vol. 11, pp. 135–140.

    CAS  Google Scholar 

  28. Busev, A.I. and Zakharans, V.Ya.,Khim.-Farm. Zh., 1978, vol. 5, pp. 137–140.

    Google Scholar 

  29. Guthrie, R.R.,Advances in Carbohydrate Chemistry, Wolfrom, M.L., Ed., New York: Academic, 1961, vol. 16, pp. 105–158.

    Google Scholar 

  30. Lythgoe, B. and Todd, A.R.,J. Chem. Soc., 1944, no. 2, pp. 592–600.

  31. Viscontini, M., Hoch, D., and Karrer, P.,Helv. Chim. Acta, 1955, vol. 76, pp. 642–645.

    Article  Google Scholar 

  32. Lythgoe, B., Smith, H., and Todd, A.R.,J. Chem. Soc., 1947, no. 1, pp. 355–361.

  33. Davoll, J., Lythgoe, B., and Todd, A.R.,J. Chem. Soc., 1946, no. 3, pp. 833–839.

  34. Kochetkov, N.K., Budovsky, E.I., Sverdlov, E.D., Simukova, N.A., Turchinskii, M.F., and Shibaev, V.N.,Organicheskaya khimiya nukleinovykh kislot (Organic Chemistry of Nucleic Acids), Moscow: Khimiya, 1970, pp. 531–535.

    Google Scholar 

  35. Walker, R.T.,Comprehensive Organic Chemistry, Barton, D. and Ollis, B.D., Eds., New York: Pergamon, 1979, vol. 5. Translated under the titleObshchaya organicheskaya khimiya, Moscow: Khimiya, 1986, vol. 10, pp. 68–131.

    Google Scholar 

  36. Guthrie, R.R.,Methods in Carbohydrate Chemistry, Whistler, R.L. and Wolfrom, M.L., Eds., New York: Academic, 1962, vol. 1, pp. 445–447. Translated under the titleMetody khimii uglevodov, Moscow: Mir, 1967, pp. 71–73.

    Google Scholar 

  37. Knauf, A.E., Hann, R.M., and Hudson, C.S.,J. Am. Chem. Soc., 1941, vol. 63, pp. 1447–1451.

    CAS  Article  Google Scholar 

  38. Smith, M.A. and Willeford, B.R.,Anal. Chem., 1954, vol. 26, pp. 751–753.

    CAS  Article  Google Scholar 

  39. Harrison, C.R. and Hodge, P.,J. Chem. Soc., Perkin Trans. 1, 1982, vol. 2, pp. 509–511.

    Article  Google Scholar 

  40. Bessodes, M. and Antonakis, K.,Tetrahedron Lett., 1985, vol. 26, pp. 1305–1306.

    CAS  Article  Google Scholar 

  41. Lsufyeva, E.N., Brusentsov, N.A., Todorova, N., Balzarini, J., De Clercq, E., and Preobrazhenskaya, M.N.,Nucleosides Nucleotides, 1997, vol. 16, pp. 87–95.

    Article  Google Scholar 

  42. Zhong, Y.-L. and Shing, T.K.M.,J. Org. Chem., 1997, vol. 62, pp. 2622–2624.

    PubMed  CAS  Article  Google Scholar 

  43. Greenberg, H.R. and Perlin, A.S.,Carbohydr. Res., 1974, vol. 35, pp. 195–202.

    CAS  Article  Google Scholar 

  44. Perlin, A.S.,Can. J. Chem., 1966, vol. 44, pp. 1757–1764.

    CAS  Article  Google Scholar 

  45. Perlin, A.S.,Can. J. Chem., 1966, vol. 44, pp. 539–550.

    CAS  Article  Google Scholar 

  46. Hansske, F., Sprinzl, M., and Cramer, F.,Bioorg. Chem., 1974, vol. 3, pp. 367–376.

    CAS  Article  Google Scholar 

  47. Hansske, F. and Cramer, F.,Carbohydr. Res., 1977, vol. 54, pp. 75–84.

    PubMed  CAS  Article  Google Scholar 

  48. Howarth, O., Jones, A.S., Walker, R.T., and Wyatt, P.G.,J. Chem. Soc., Perkin Trans. 2, 1984, no. 3, pp. 261–265.

  49. Borchardt, R.T., Wu, Y.S., and Wu, B.S.,Biochemistry, 1978, vol. 20, pp. 4145–4153.

    Article  Google Scholar 

  50. Lowe, P.N. and Beechey, R.B.,Bioorg. Chem., 1982, vol. 11, pp. 55–71.

    CAS  Article  Google Scholar 

  51. Jones, A.S., Markham, A.F., and Walker, R.T.,J. Chem. Soc., Perkin Trans. 1, 1976, no. 14, pp. 1567–1570.

  52. Mikhailov, S.N. and Yakovlev, G.I.,Khimiya Prirod. Soedin., 1987, no. 1, pp. 40–43.

  53. Ermolinsky, B.S., Modified Oligonucleotides Containing Hexapyranosylnucleosides and Disaccharide Nucleosides. Synthesis and Properties,Cand Sc. (Chem.) Dissertation, Moscow: Engelhardt Institute of Molecular Biology, 2000.

    Google Scholar 

  54. Meyerhof, O. and Lohman, K.,Biochem. Z., 1934, vol. 271, pp. 89–110.

    CAS  Google Scholar 

  55. Schwartz, D.E. and Gilham, P.T.,J. Am. Chem. Soc., 1972, vol. 94, pp. 8921–8922.

    PubMed  CAS  Article  Google Scholar 

  56. Grant, A.J. and Lerner, L.M.,J. Med. Chem., 1980, vol. 23, pp. 795–798.

    PubMed  CAS  Article  Google Scholar 

  57. Brown, D.M., Fried, M., and Todd, A.R.,Chem. Ind., 1953, no. 4, pp. 352–353.

  58. Brown, D.M., Fried, M., and Todd, A.R.,J. Chem. Soc., 1955, no. 7, pp. 2206–2213.

  59. Whitfeld, P.R. and Markham, R.,Nature, 1953, vol. 171, pp. 1151–1152.

    PubMed  CAS  Article  Google Scholar 

  60. Whitfeld, P.R.,Biochem. J., 1954, vol. 58, pp. 390–396.

    PubMed  CAS  Google Scholar 

  61. Steinschneider, A.,Biochemistry, 1971, vol. 10, pp. 173–178.

    PubMed  CAS  Article  Google Scholar 

  62. Hansske, F. and Cramer, F.,Meth. Enzymol., 1979, vol. 59, pp. 172–181.

    PubMed  CAS  Google Scholar 

  63. Khym, J.X.,Biochemistry, 1963, vol. 2, pp. 344–350.

    PubMed  CAS  Article  Google Scholar 

  64. Neu, H.C. and Heppel, L.A.,J. Biol. Chem., 1964, vol. 239, pp. 2927–2933.

    PubMed  CAS  Google Scholar 

  65. Rammler, D.H.,Biochemistry, 1971, vol. 10, pp. 4699–4705.

    PubMed  CAS  Article  Google Scholar 

  66. Uziel, M.,Biochemistry, 1973, vol. 12, pp. 938–942.

    PubMed  CAS  Article  Google Scholar 

  67. Yu, C.-T. and Zamecnic, P.C.,Biochim. Biophys. Acta, 1960, vol. 45, pp. 148–154.

    PubMed  CAS  Article  Google Scholar 

  68. Whitfeld, P.R.,Biochim. Biophys. Acta, 1965, vol. 108, pp. 202–210.

    PubMed  CAS  Google Scholar 

  69. Schmidt, G.,Meth. Enzymol., 1968, vol. 12, pp. 230–235.

    CAS  Google Scholar 

  70. Fraenkel-Conrat, H. and Steinschneider, A.,Meth. Enzymol., 1968, vol. 12, pp. 243–246.

    CAS  Google Scholar 

  71. Uziel, M. and Khym, J.X.,Biochemistry, 1969, vol. 8, pp. 3254–3260.

    PubMed  CAS  Article  Google Scholar 

  72. Hunt, J.A.,Biochem. J., 1970, vol. 120, pp. 353–363.

    PubMed  CAS  Google Scholar 

  73. Trim, A.R. and Parker, J.E.,Anal. Biochem., 1972, vol. 46, pp. 482–488.

    PubMed  CAS  Article  Google Scholar 

  74. Keith, G. and Gilham, P.T.,Biochemistry, 1974, vol. 13, pp. 3601–3606.

    PubMed  CAS  Article  Google Scholar 

  75. Randerath, K., Randerath, E., Gupta, R.C., and Chia, L.S.Y.,FEBS Lett., 1974, vol. 40, pp. 187–191.

    PubMed  CAS  Article  Google Scholar 

  76. Randerath, K., Chia, L.S.Y., Randerath, E., and Gupta, R.C.,FEBS Lett., 1974, vol. 40, pp. 183–186.

    PubMed  CAS  Article  Google Scholar 

  77. Shine, J. and Dalgarno, L.,Biochem. J., 1974, vol. 141, pp. 605–609.

    Google Scholar 

  78. Shine, J. and Dalgarno, L.,Proc. Natl. Acad. Sci. USA, 1974, vol. 71, pp. 1342–1346.

    PubMed  CAS  Article  Google Scholar 

  79. Dubin, D.T. and Shine, J.,Nucleic Acids Res., 1976, vol. 3, pp. 102–111.

    Google Scholar 

  80. Randerath, K., Randerath, E., Gupta, R.C., Chia, L.S.Y., and Sivarajan, M.,Nucleic Acids Res., 1974, vol. 1, pp. 1121–1142.

    PubMed  CAS  Article  Google Scholar 

  81. Limbach, P.A., Crain, P.F., and McCloskey, J.A.,Nucleic Acids Res., 1994, vol. 22, pp. 2183–2196.

    PubMed  CAS  Article  Google Scholar 

  82. Desgres, J., Keith, G., Kuo, K.C., and Gehrke, C.W.,Nucleic Acids Res., 1989, vol. 17, pp. 865–882.

    PubMed  CAS  Article  Google Scholar 

  83. Keith, G., Glasser, A.-L., Desgres, J., Kuo, K.C., and Gehrke, C.W.,Nucleic Acids Res., 1990, vol. 18, pp. 5989–5993.

    PubMed  CAS  Article  Google Scholar 

  84. Glasser, A.-L., Desgres, J., Heitzler, J., Gehrke, C.W., and Keith, G.,Nucleic Acids Res., 1991, vol. 19, pp. 5199–5203.

    PubMed  CAS  Article  Google Scholar 

  85. Kiesewetter, S., Ott, G., and Sprinzl, M.,Nucleic Acids Res., 1990, vol. 18, pp. 4677–4682.

    PubMed  CAS  Article  Google Scholar 

  86. Khym, J.X. and Cohn, W.E.,J. Am. Chem. Soc., 1960, vol. 82, pp. 6380–6386.

    CAS  Article  Google Scholar 

  87. Lerner, L.M.,Carbohydr. Res., 1970, vol. 13, pp. 465–469.

    CAS  Article  Google Scholar 

  88. Lerner, L.M. and Rossi, R.R.,J. Med. Chem., 1973, vol. 16, pp. 457–459.

    PubMed  Article  Google Scholar 

  89. Smrt, J., Mikhailov, S.N., Hynie, S., and Florentiev, V.L.,Collect. Czech. Chem. Commun., 1975, vol. 40, pp. 3399–3403.

    CAS  Google Scholar 

  90. Kritsyn, A.M., Mikhailov, S.N., Misharin, A.Yu., Padyukova, N.Sh., and Florentiev, V.L.,Bioorg. Khim., 1976, vol. 2, pp. 1338–1350.

    CAS  Google Scholar 

  91. Lerner, L.M.,Carbohydr. Res., 1984, vol. 127, pp. 141–145.

    PubMed  CAS  Article  Google Scholar 

  92. Mikhailov, S.N., Florentiev, V.L., and Pfleiderer, W.,Synthesis, 1985, vol. 41, pp. 399–400.

    Article  Google Scholar 

  93. Jones, A.S., Walker, R.T., Wyatt, P.G., Balzarini, J., and De Clecrq, E.,J. Chem. Res., 1985, vol. 15, pp. 336–337.

    Google Scholar 

  94. Jones, A.S., McClean, M.J., Tanaka, H., Walker, R.T., Balzarini, J., and De Clecrq, E.,Tetrahedron, 1985, vol. 41, pp. 5965–5972.

    CAS  Article  Google Scholar 

  95. Jones, A.S., Niwas, S., Tanaka, H., and Walker, R.T.,Nucleic Acids Res., 1986, vol. 14, pp. 5409–5416.

    PubMed  CAS  Article  Google Scholar 

  96. McGee, D.P.C. and Martin, J.C.,Can. J. Chem, 1986, vol. 64, pp. 1885–1889.

    CAS  Article  Google Scholar 

  97. Prisbe, E.J.,J. Med. Chem., 1986, vol. 29, pp. 2445–2450.

    PubMed  CAS  Article  Google Scholar 

  98. Kumar, A. and Walker, R.T.,Tetrahedron, 1990, vol. 46, pp. 3101–3110.

    CAS  Article  Google Scholar 

  99. Van Aerschot, A., Janssen, G., and Herdewijn, P.,Bull. Soc. Chim. Belg., 1990, vol. 99, pp. 769–777.

    Article  Google Scholar 

  100. Maggio, A.-F., Boyer, V., Aubertin, A.M., Obert, G., Kirn, A., and Imbach, J.-L.,Nucleosides Nucleotides, 1991, vol. 10, pp. 1431–1449.

    CAS  Article  Google Scholar 

  101. Neenan, J.P., Opitz, S.M., Cooke, C.L., Ussery, M.A., Morril, T.C., and Eckel, L.M.,Bioorg. Med. Chem. Lett., 1996, vol. 6, pp. 1381–1386.

    CAS  Article  Google Scholar 

  102. Rosenthal, L.P., Hogenkamp, H.P.C., and Bodley, J.W.,Carbohydr. Res., 1982, vol. 111, pp. 85–91.

    CAS  Article  Google Scholar 

  103. Stolarski, R., Kaziemierczuk, Z., Lassota, P., and Shugar, D.,Z. Naturforsch., 1986, vol. 41, pp. 758–770.

    CAS  Google Scholar 

  104. Oivanen, M., Lonnberg, H., Kaziemierczuk, Z., and Shugar, D.,Nucleosides Nucleotides, 1989, vol. 8, pp. 133–144.

    CAS  Article  Google Scholar 

  105. Oivanen, M., Rajamaki, M., Varila, J., Hovinen, J., Mikhailov, S.N., and Lonnberg, H.,J. Chem. Soc., Perkin Trans. 2, 1994, no. 3, pp. 309–314.

  106. Lerner, L.M. and Rossi, R.R.,Biochemistry, 1972, vol. 11, pp. 2772–2777.

    PubMed  CAS  Article  Google Scholar 

  107. Zavgorodnii, S.G., Efimtseva, E.V., Mikhailov, S.N., Tsilevich, T.L., Yavorskii, A.E., and Florentiev, V.L.,Khim. Geterotsikl. Soed., 1988, no. 2, pp. 223–228.

  108. Mikhailov, S.N. and Efimtseva, E.V.,Khim. Geterotsikl. Soed., 1988, no. 5, pp. 947–951.

  109. Herdewijn, P., van Aerschot, A., Russon, R., Claes, P., and De Clerq, E.,Nucleosides Nucleotides, 1991, vol. 10, pp. 1525–1549.

    CAS  Article  Google Scholar 

  110. Mikhailov, S.N.,Bioorg. Khim., 1978, vol. 4, pp. 639–644.

    CAS  Google Scholar 

  111. Mikhailov, S.N. and Grishko, N.B.,Khim. Geterotsikl. Soed., 1988, no. 4, pp. 91–94.

  112. McGree, D.P.C. and Martin, J.C.,Can. J. Chem., 1986, vol. 64, pp. 1885–1889.

    Article  Google Scholar 

  113. Baud, M.-V., Chavis, C., Lucas, M., and Imbach, J.-L.,Tetrahedron, 1991, vol. 47, pp. 9993–10002.

    CAS  Article  Google Scholar 

  114. RajBhandary, U.L.,J. Biol. Chem., 1968, vol. 243, pp. 556–564.

    PubMed  CAS  Google Scholar 

  115. Karpeisky, M. Ya., Mamaeva, O.K., Mikhailov, S.N., Padyukova, N.Sh., Yakovlev, G.I., and Smrt, I.,Bioorg. Khim., 1983, vol. 9, pp. 496–504.

    Google Scholar 

  116. Leppla, S.H., Bjoraker, B., and Bock, R.M.,Meth. Enzymol., 1968, vol. 112, pp. 237–240.

    Google Scholar 

  117. Von der Haar, F., Schlimme, E., Gomez-Guillen, M., and Cramer, F.,Eur. J. Biochem., 1971, vol. 24, pp. 296–302.

    PubMed  Article  Google Scholar 

  118. Von der Haar, F., Schlimme, E., and Gauss, D.H., inProcedures in Nucleic Acids Research, New York: Happer and Row, 1971, vol. 2, pp. 643–664.

    Google Scholar 

  119. Randerath, E., Yu, C.-T., and Randerath, K.,Anal. Biochem., 1972, vol. 48, pp. 172–198.

    PubMed  CAS  Article  Google Scholar 

  120. Itkes, A.V., Karpeisky, M. Ya., Kartasheva, O.N., Mikhailov, S.N., Moiseyev, G.P., Pfleiderer, W., Charubala, R., and Yakovlev, G.I.,FEBS Lett., 1988, vol. 236, pp. 325–328.

    PubMed  CAS  Article  Google Scholar 

  121. Itkes, A.V., Karpeisky, M.Ya., Kartasheva, O.N., Mikhailov, S.N., Moiseev, G.P., Pfleiderer, W., Charubala, R., and Yakovlev, G.I.,Mol. Biol., 1988, vol. 22, pp. 1393–1398.

    CAS  Google Scholar 

  122. Mikhailov, S.N. and Pfleiderer, W.,Tetrahedron Lett., 1985, vol. 26, pp. 2059–2062.

    CAS  Article  Google Scholar 

  123. Brown, D.M. and Read, A.P.,J. Chem. Soc., 1965, no. 11, pp. 5072–5074.

  124. Van Aerschot, A., Janssen, G., and Herdewijn, P.,Bull. Soc. Chim. Belg., 1990, vol. 99, pp. 769–777.

    Article  Google Scholar 

  125. Imai, J., Johnston, M.J., and Torrence, P.F.,J. Biol. Chem., 1982, vol. 257, pp. 12739–12745.

    PubMed  CAS  Google Scholar 

  126. Rayford, R., Anthony, D.D., O’Neil, R.E., and Merrick, W.C.,J. Biol. Chem., 1985, vol. 260, pp. 15 708–15 713.

    CAS  Google Scholar 

  127. Lemaitre, M., Bayard, B., and Lebleu, B.,Proc. Natl. Acad. Sci. USA, 1987, vol. 84, pp. 648–652.

    PubMed  CAS  Article  Google Scholar 

  128. Bayard, B., Bisbal, C., and Lebleu, B.,Biochemistry, 1986, vol. 25, pp. 3730–3736.

    PubMed  CAS  Article  Google Scholar 

  129. Stirchak, E.P., Summerton, J.E., and Weller, D.D.,Nucleic Acids Res., 1989, vol. 17, pp. 6129–6141.

    PubMed  CAS  Article  Google Scholar 

  130. Wang, H. and Weller, D.D.,Tetrahedron Lett., 1991, vol. 32, pp. 7385–7388.

    CAS  Article  Google Scholar 

  131. Antivirals Technical Report No. 3. Morpholino-Type NEU-GENES™: The Next Generation of Antisense.,Antisense. Res. Develop., 1993, vol. 3, pp. 1–12.

  132. Sakatsume, O., Tanaka, H., and Takaku, H.,Chem. Lett., 1993, no. 2, pp. 201–204.

  133. Lesiak, K. and Torrence, P.F.,Bioconjugate Chem., 1997, vol. 8, pp. 199–293.

    CAS  Article  Google Scholar 

  134. Bellon, L., Workman, C., Scherrer, J., Usman, N., and Wincott, F.,J. Amer. Chem. Soc., 1996, vol. 118, pp. 3771–3772.

    CAS  Article  Google Scholar 

  135. Hunt, J.A.,Biochem. J., 1965, vol. 95, pp. 541–545.

    PubMed  CAS  Google Scholar 

  136. Hunt, J.A.,Meth. Enzymol., 1968, vol. 112, pp. 240–243.

    Google Scholar 

  137. Midgley, J.E.M.,Biochim. Biophys. Acta, 1965, vol. 108, pp. 340–347.

    PubMed  CAS  Google Scholar 

  138. Jones, A.S. and Walker, R.T.,Carbohydr. Res., 1973, vol. 26, pp. 255–257.

    PubMed  CAS  Article  Google Scholar 

  139. Hansske, F. and Cramer, F.,Meth. Enzymol., 1979, vol. 59, pp. 172–181.

    PubMed  CAS  Article  Google Scholar 

  140. Randerath, K.,Anal. Biochem., 1981, vol. 115, pp. 391–397.

    PubMed  CAS  Article  Google Scholar 

  141. Agrawal, S., Christodopulou, C., and Gait, M.J.,Nucleic Acids Res., 1986, vol. 14, pp. 6227–6245.

    PubMed  CAS  Article  Google Scholar 

  142. Wilchek, M. and Miron, T.,Meth. Enzymol., 1974, vol. 34, pp. 72–76.

    PubMed  CAS  Google Scholar 

  143. Wilchek, M. and Lamed, R.,Meth. Enzymol., 1974, vol. 34, pp. 475–479.

    PubMed  CAS  Google Scholar 

  144. Barker, R., Trayer, I.P., and Hill, R.L.,Meth. Enzymol., 1974, vol. 34, pp. 479–491.

    PubMed  CAS  Google Scholar 

  145. Gribnau, T.C.J.,Affinity Cromatography, Dean, P.D.G., Johnson, W.S., and Middle, F.A., Eds., Oxford: IRL, 1985. Translated under the titleAffinnaya khromatografiya. Metody, Moscow: Mir, 1988, pp. 66–71.

    Google Scholar 

  146. Knorre, D.G., Myzina, S.D., and Sandakhchiev, L.S.,Izv. SO AN SSSR, Ser. Khim., 1964, no. 5, pp. 135–142.

  147. Robberson, D.L. and Davidson, D.,Biochemistry, 1972, vol. 11, pp. 533–537.

    PubMed  CAS  Article  Google Scholar 

  148. Grosjean, H., Takada, C., and Petre, J.,Biochem. Biophys. Res. Commun., 1973, vol. 53, pp. 882–893.

    PubMed  CAS  Article  Google Scholar 

  149. Khrapko, K.R., Lysov, Yu.P., Khorlin, A.A., Ivanov, I.B., Yershov, G.M., Vasilenko, S.K., Florentiev, V.L., and Mirzabekov, A.D.,DNA Sequence, 1991, vol. 1, pp. 375–388.

    PubMed  CAS  Article  Google Scholar 

  150. Timofeev, E.N., Kochetkova, S.V., Mirzabekov, A.D., and Florentiev, V.L.,Nucleic Acids Res., 1996, vol. 24, pp. 3142–3148.

    PubMed  CAS  Article  Google Scholar 

  151. Steinschneider, A. and Frankel-Conrat, H.,Biochemistry, 1966, vol. 5, pp. 2729–2734.

    PubMed  CAS  Article  Google Scholar 

  152. Dulbecco, R. and Smith, J.D.,Biochim. Biophys. Acta, 1960, vol. 39, pp. 358–361.

    PubMed  CAS  Article  Google Scholar 

  153. Nedospasov, A.A. and Khomutov, R.M.,Bioorg. Khim., 1978, vol. 4, pp. 645–653.

    CAS  Google Scholar 

  154. Hansske, F. and Cramer, F.,Carbohydr. Res., 1975, vol. 41, pp. 366–369.

    PubMed  CAS  Article  Google Scholar 

  155. Szarek, W.E., Pinto, B.M., and Iwakawa, M.,Can. J. Chem., 1985, vol. 63, pp. 2149–2161.

    CAS  Article  Google Scholar 

  156. Baer, H.H.,Adv. Carbohydr. Chem. Biochem., 1969, vol. 24, pp. 67–138.

    PubMed  CAS  Article  Google Scholar 

  157. Watanabe, K.A., Beranek, J., Friedman, H.A., and Fox, J.J.,J. Org. Chem., 1965, vol. 30, pp. 2735–2747.

    PubMed  CAS  Article  Google Scholar 

  158. Lichtenthaler, F.W. and Albrecht, H.P.,Chem. Ber., 1966, vol. 99, pp. 575–585.

    PubMed  CAS  Article  Google Scholar 

  159. Ohta, N., Minamoto, K., Yamamoto, T., Koide, N., and Sakoda, R.,Nucleosides Nucleotides, 1996, vol. 15, pp. 833–855.

    CAS  Article  Google Scholar 

  160. Tsuboike, K., Minamoto, K., Mizuno, G., and Yanagihara, K.,Nucleosides Nucleotides, 1998, vol. 17, pp. 745–758.

    CAS  Article  Google Scholar 

  161. Chiara, J.L., Cabri, W., and Hanessian, S.,Tetrahedron Lett., 1991, vol. 32, pp. 1125–1128.

    CAS  Article  Google Scholar 

  162. Hays, D.S. and Fu, G.C.,J. Am. Chem. Soc., 1995, vol. 117, pp. 7283–7284.

    CAS  Article  Google Scholar 

  163. Hays, D.S. and Fu, G.C.,J. Org. Chem. Soc., 1998, vol. 63, pp. 6375–6381.

    CAS  Article  Google Scholar 

  164. Kaufman, J. and Mittelman, A.,Cancer Chemother. Rep., 1975, vol. 59, pp. 1007–1014.

    PubMed  CAS  Google Scholar 

  165. Plagemann, P.G., Graff, J.C., and Behrens, M.,Cancer Res., 1977, vol. 37, pp. 2188–2195.

    PubMed  CAS  Google Scholar 

  166. Bell, J.P., Faures, M.L., LePage, G.A., and Kimball, A.P.,Cancer Res., 1968, vol. 28, pp. 782–787.

    PubMed  CAS  Google Scholar 

  167. Cory, J.G. and Parker, S.H.,Biochem. Pharmacol., 1979, vol. 28, pp. 867–871.

    PubMed  CAS  Article  Google Scholar 

  168. Mirkin, B.L., O’Dea, R.F., and Hogenkamp, H.P.,Cancer Res., 1987, vol. 47, pp. 3650–3655.

    PubMed  CAS  Google Scholar 

  169. Sheid, B., Saggar, M., Gaetjens, E., and Lerner, L.M.,Cancer Chemother. Pharmacol., 1991, vol. 28, pp. 339–343.

    PubMed  CAS  Article  Google Scholar 

  170. Keller, B.T. and Borchardt, R.T.,Mol. Pharmacol., 1987, vol. 31, pp. 485–492.

    PubMed  CAS  Google Scholar 

  171. Cools, M. and De Clercq, E.,Biochem. Pharmacol., 1990, vol. 40, pp. 2259–2264.

    PubMed  CAS  Article  Google Scholar 

  172. Cools, M. and De Clercq, E.,Biochem. Pharmacol., 1989, vol. 38, pp. 1061–1067.

    PubMed  CAS  Article  Google Scholar 

  173. Andrei, G. and De Clercq, E.,Antiviral Res., 1990, vol. 14, pp. 287–299.

    PubMed  CAS  Article  Google Scholar 

  174. Pizarro, J.M., Pizarro, J.L., Fernandez, J., Sandino, A.M., and Spencer, E.,Virology, 1991, vol. 184, pp. 768–772.

    PubMed  CAS  Article  Google Scholar 

  175. Kinnamon, K.E., Steck, E.A., and Rane, D.S.,Antimicrob. Agents Chemother., 1979, vol. 15, pp. 157–160.

    PubMed  CAS  Google Scholar 

  176. Spoor, T.C., Evans, J.E., and Kimball, A.P.,Proc. Soc. Exp. Biol. Med., 1971, vol. 136, pp. 605–607.

    PubMed  CAS  Google Scholar 

  177. Ohmstede, C.A. and Cory, J.G.,Biochem. Pharmacol., 1985, vol. 34, pp. 1717–1724.

    PubMed  CAS  Article  Google Scholar 

  178. Kimball, A.P., Wilson, M.J., Bell, J.P., and LePage, G.A.,Cancer Res., 1968, vol. 28, pp. 661–665.

    PubMed  CAS  Google Scholar 

  179. Grant, A.J. and Lerner, L.M.,Biochemistry, 1979, vol. 18, pp. 2838–2842.

    PubMed  CAS  Article  Google Scholar 

  180. Grant, A.J. and Lerner, L.M.,J. Med. Chem., 1980, vol. 23, pp. 39–42.

    PubMed  CAS  Article  Google Scholar 

  181. Cory, J.G. and Mansell, M.M.,Cancer Res., 1975, vol. 35, pp. 390–396.

    PubMed  CAS  Google Scholar 

  182. Cory, J.G., Mansell, M.M., and Whitford, T.W.,Cancer Res., 1976, vol. 36, pp. 3166–3170.

    PubMed  CAS  Google Scholar 

  183. Houston, D.M., Dolence, E.K., Keller, B.T., Patel-Thombre, U., and Borchardt, R.T.,J. Med. Chem., 1985, vol. 28, pp. 471–477.

    PubMed  CAS  Article  Google Scholar 

  184. Cysyk, R.L. and Adamson, R.H.,Cancer Treat. Rep., 1976, vol. 60, pp. 563–570.

    PubMed  CAS  Google Scholar 

  185. Senapathy, P., Ali, M.A., and Jacob, M.T.,FEBS Lett., 1985, vol. 190, pp. 337–341.

    PubMed  CAS  Article  Google Scholar 

  186. Nuhn, E., Schiling, E., Wagner, G., Hemmerling, J., Malberg, K., Schlimke, R., Stulpner, H., and Amrosius, H.,Pharmazie, 1977, vol. 32, pp. 558–561.

    PubMed  CAS  Google Scholar 

  187. Brusentsov, N.A., Bukhman, V.M., Belitskii, G.A., Slavina, E.G., Leipunskaya, I.L., Kikot’, B.S., and Preobrazhenskaya, M.N.,Khim.-Farm. Zh., 1980, no. 5, pp. 5–13.

  188. Gritsenko, O.M. and Gromova, E.S.,Uspekhi Khim., 1999, vol. 68, pp. 267–278.

    Google Scholar 

  189. Afinnaya modifikatsiya polimerov (Affinity Modification of Polymers), Knorre, D.G., Ed., Novosibirsk: Nauka, 1983.

    Google Scholar 

  190. Spoor, T.C., Hodnett, J.L., and Kimball, A.P.,Cancer Res., 1973, vol. 33, pp. 856–858.

    PubMed  CAS  Google Scholar 

  191. Wu, F.Y.-H. and Wu, C.-W.,Biochemistry, 1974, vol. 13, pp. 2562–2566.

    PubMed  CAS  Article  Google Scholar 

  192. Easterbook-Smith, S.B., Wallage, J.C., and Keech, D.B.,Eur. J. Biochem., 1976, vol. 62, pp. 125–130.

    Article  Google Scholar 

  193. Kochetkov, S.N., Bulgarina, T.V., Sashenko, L.P., and Severin, E.S.,Eur. J. Biochem., 1977, vol. 81, pp. 111–118.

    PubMed  CAS  Article  Google Scholar 

  194. Westcott, K.R., Olwin, B.B., and Storm, D.R.,J. Biol. Chem., 1980, vol. 255, pp. 8767–8771.

    PubMed  CAS  Google Scholar 

  195. Borchardt, R.T., Schasteen, C.S., and Wu, S.E.,Biochim. Biophys. Acta, 1982, vol. 708, pp. 280–293.

    PubMed  CAS  Google Scholar 

  196. Kozlov, I.A. and Milgrom, Y.M.,Eur. J. Biochem., 1980, vol. 106, pp. 457–462.

    PubMed  CAS  Article  Google Scholar 

  197. Favilla, R. and Bayley, P.M.,Eur. J. Biochem., 1982, vol. 125, pp. 209–214.

    PubMed  CAS  Article  Google Scholar 

  198. Chang, G.G., Shiao, M.S., Lee, K.R., and Wu, J.J.,Biochem. J., 1990, vol. 272, pp. 683–690.

    PubMed  CAS  Google Scholar 

  199. Hohenegger, M. and Makinose, M.,Eur. J. Biochem., 1992, vol. 205, pp. 173–179.

    PubMed  CAS  Article  Google Scholar 

  200. Peter, M.E., Wittmann-Liebold, B., and Sprinzl, M.,Biochemistry, 1988, vol. 27, pp. 9132–9139.

    PubMed  CAS  Article  Google Scholar 

  201. Low, A., Sprinzl, M., and Faulhammer, H.G.,Eur. J. Biochem., 1993, vol. 215, pp. 473–479.

    PubMed  CAS  Article  Google Scholar 

  202. Patel-Thombre, U. and Borchardt, R.T.,Biochemistry, 1985, vol. 24, pp. 1130–1136.

    PubMed  CAS  Article  Google Scholar 

  203. Wakagi, T. and Ohta, T.,J. Biochem. (Tokyo), 1982, vol. 92, pp. 1403–1412.

    CAS  Google Scholar 

  204. Hinrichs, M.V.,Biochim. Biophys. Acta, 1982, vol. 704, pp. 177–185.

    PubMed  CAS  Google Scholar 

  205. Mignaco, J., Scofano, H.M., and Barrabin, H.,Biochim. Biophys. Acta, 1990, vol. 1039, pp. 305–312.

    PubMed  CAS  Google Scholar 

  206. Lowe, P.L. and Beechey, R.B.,Biochemistry, 1982, vol. 21, pp. 4073–4082.

    PubMed  CAS  Article  Google Scholar 

  207. King, M.M. and Colman, R.F.,Biochemistry, 1983, vol. 22, pp. 1656–1665.

    PubMed  CAS  Article  Google Scholar 

  208. Colman, R.F.,Annu. Rev. Biochem., 1983, vol. 52, pp. 67–91.

    PubMed  CAS  Article  Google Scholar 

  209. Tsai, P.K. and Hogenkamp, H.P.,Arch. Biochem. Biophys., 1983, vol. 226, pp. 276–284.

    PubMed  CAS  Article  Google Scholar 

  210. Rabinkov, A.G. and Amontov, S.V.,Biochim. Biophys. Acta, 1990, vol. 1037, pp. 216–220.

    PubMed  CAS  Google Scholar 

  211. Baltzinger, M., Fasiolo, F., and Remy, P.,Eur. J. Biochem., 1979, vol. 97, pp. 481–494.

    PubMed  CAS  Article  Google Scholar 

  212. Fayat, G., Hountondji, C., and Blanquet, S.,Eur. J. Biochem., 1979, vol. 96, pp. 87–92.

    PubMed  CAS  Article  Google Scholar 

  213. Gerlo, E. and Charlier, J.,FEBS Lett., 1979, vol. 99, pp. 25–28.

    PubMed  CAS  Article  Google Scholar 

  214. Efimtseva, E.V., Ermolinsky, B.S., Fomitcheva, M.V., Meshkov, S.V., Padyukova, N.Sh., Mikhailov, S.N., van Aerschot, A., Rozenski, J., and Herdewijn, P.,Collection. Special Issue, 1996, vol. 61, pp. 206–209.

    Google Scholar 

  215. Mikhailov, S.N., Efimtseva, E.V., Ermolinsky, B.S., Fomitcheva, M.V., Gritsenko, O.M., Brevnov, M.G., Gromova, E.S., Schepers, G., van Aerschot, A., and Herdewijn, P.,Collection. Special Issue, 1996, vol. 61, pp. 210–212.

    Google Scholar 

  216. Efimtseva, E.V., Victorova, L.S., Rodionov, A.A., Ermolinsky, B.S., Fomitcheva, M.V., Mikhailov, S.N., Oivanen, M., van Aerschot, A., and Herdewijn, P.,Nucleosides Nucleotides, 1998, vol. 17, pp. 1681–1684.

    CAS  Article  Google Scholar 

  217. Mikhailov, S.N., Ermolinsky, B.S., Efimtseva, E.V., Brevnov, M.G., Gritsenko, O.M., Gromova, E.S., van Aerschot, A., and Herdewijn, P.,Nucleosides Nucleotides, 1999, vol. 18, pp. 1469–1470.

    CAS  Article  Google Scholar 

  218. Ermolinsky, B.S., Fomitcheva, M.V., Efimtseva, E.V., Meshkov, S.V., Mikhailov, S.N., Esipov, D.S., Boldyreva, E.F., and Korobko, V.G.,Nucleosides Nucleotides, 1996, vol. 15, pp. 1619–1634.

    CAS  Article  Google Scholar 

  219. Mikhailov, S.N., Efimtseva, E.V., Gurskaya, G.V., Zavodnik, V.E., De Bruyn, A., Rozenski, J., and Herdewijn, P.,J. Carbohydr. Chem., 1997, vol. 16, pp. 75–92.

    CAS  Article  Google Scholar 

  220. Brevnov, M.G., Gritsenko, O.M., Mikhailov, S.N., Efimtseva, E.V., Ermolinsky, B.S., van Aerschot, A., Herdewijn, P., Repyk, A.V., and Gromova, E.S.,Nucleic Acids Res., 1997, vol. 25, pp. 3302–3309.

    PubMed  CAS  Article  Google Scholar 

  221. Tunitskaya, V.L., Rusakova, E.E., Memelova, L.V., Kochetkov, S.N., van Aerschot, A., Herdewijn, P., Efimtseva, E.V., Ermolinsky, B.S., and Mikhailov, S.N.,FEBS Lett., 1999, vol. 442, pp. 20–24.

    PubMed  CAS  Article  Google Scholar 

  222. Mikhailov, S.N., Ermolinsky, B.S., Efimtseva, E.V., Moiseyev, G.P., Tunitskaya, V.L., Rusakova, E.E., Kochetkov, S.N., Gritsenko, O.M., Gromova, E.S., van Aerschot, A., and Herdewijn, P.,Collection. Special Issue, 1999, vol. 2, pp. 141–144.

    CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to S. N. Mikhailov.

Rights and permissions

Reprints and Permissions

About this article

Cite this article

Ermolinsky, B.S., Mikhailov, S.N. Periodate oxidation in chemistry of nucleic acids: Dialdehyde derivatives of nucleosides, nucleotides, and oligonucleotides (Review). Russ J Bioorg Chem 26, 429–449 (2000). https://doi.org/10.1007/BF02758613

Download citation

  • Received:

  • Revised:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF02758613

Key words

  • dialdehyde derivatives of nucleosides
  • nucleotides
  • and oligonucleotides
  • periodate oxidation