Chemistry of Natural Compounds

, Volume 20, Issue 4, pp 387–404 | Cite as

Gas-liquid chromatography of carbohydrates

  • E. V. Evtushenko
  • Yu. S. Ovodov
Article

Abstract

A review is given of materials on the use of the method of gas-liquid chromatography in carbohydrate chemistry.

Keywords

Xylose Monosaccharide Polyol Fucose Uronic Acid 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Literature cited

  1. 1.
    A. G. McInnes, D. H. Ball, F. R. Cooper, and T. Bishop, J. Chromatogr.,1, 556 (1958).Google Scholar
  2. 2.
    C. T. Bishop, Adv. Carbohydr. Chem.,19, 95 (1964); Yu. S. Ovolov, The Gas-Liquid Chromatography of the Carbohydrates [in Russian], Vladivostok (1970); G. G. S. Dutton, Adv. Carbohydr. Chem. Biochem.,28, 11 (1973); G. G. S. Dutton, Adv. Carbohyd. Chem. Biochem.,30, 9 (1974).PubMedGoogle Scholar
  3. 3.
    C. C. Sweeley, R. Bentley, M. Makita, and W. W. Wells, J. Am. Chem. Soc.,85, 2497 (1963).Google Scholar
  4. 4.
    W. E. Sable and G. W. Cathey, Agron. J.,62, 36 (1970).Google Scholar
  5. 5.
    C. Miyazaki, Kanzei, Chuo Bunsekishoho,15, 93 (1975); Chem. Abstr.,87, 290065 (1977).Google Scholar
  6. 6.
    A. E. Pierce, Silylation of Organic Compounds, Pierce Chemical Co. Rockford, Illinois (1968).Google Scholar
  7. 7.
    C. W. Ford, Anal. Biochem.,57, 413 (1974).PubMedGoogle Scholar
  8. 8.
    M. Martinez, D. Nurok, and A. Zlatkis, Anal. Biochem.,86, 552 (1978).Google Scholar
  9. 9.
    M. Donike, J. Chromatogr.,42, 103 (1969).Google Scholar
  10. 10.
    W. C. Ellis, J. Chromatogr.,41, 325 (1969).Google Scholar
  11. 11.
    A. Gindzienski and D. Kilczewska, Chem. Anal. (Warsaw),24, 167 (1979).Google Scholar
  12. 12.
    J. F. Kennedy, S. M. Robertson, and M. Stacey, Carbohydr. Res.,49, 243 (1976).PubMedGoogle Scholar
  13. 13.
    R. Malinen, E. Sjöström, Carbohydr. Res.,39, 335 (1975).Google Scholar
  14. 14.
    D. J. Leblanc and A. J. S. Ball, Anal. Biochem.,84, 574 (1978).PubMedGoogle Scholar
  15. 15.
    G. Petersson, Svensk. Papperstidn.,78, 27 (1975).Google Scholar
  16. 16.
    R. A. Laine and C. C. Sweeley, Carbohydr. Res.,27, 199 (1973).Google Scholar
  17. 17.
    S. Honda, K. Kakehi, and K. Okada, J. Chromatogr.,176, 367 (1979).PubMedGoogle Scholar
  18. 18.
    R. S. Selvendran, J. F. March, and S. Ring, Anal. Biochem.,96, 282 (1979).PubMedGoogle Scholar
  19. 19.
    R. Wachowaik, K. A. Connors, Anal. Chem.,51, 27 (1979).Google Scholar
  20. 20.
    G. D. McInnes, Carbohydr., Res.,108, 284 (1982).Google Scholar
  21. 21.
    Y. Arakawa, T. Imanari, and Z. Tamura, Chem. Pharm. Bull.,24, 2032 (1976).PubMedGoogle Scholar
  22. 22.
    M. M. Wrann and C. W. Todd, J. Chromatogr.,147, 309 (1978).Google Scholar
  23. 23.
    B. A. Rudenko, Capillary Chromatography [in Russian], Moscow (1978).Google Scholar
  24. 24.
    D. V. Phillips and A. E. Smith, Anal. Biochem.,54, 95 (1973).PubMedGoogle Scholar
  25. 25.
    V. L. Yarovenko, B. M. Nakhmanovich, D. M. Makeev, and E. M. Belov, Ferment. Spirt. Promst., 6 (1977).Google Scholar
  26. 26.
    B. Koop, J. Jurenitsch, and W. Kubelka, J. Chromatogr.,210, 291 (1981).Google Scholar
  27. 27.
    H. Jaddou and M. Al-Hakim, J. Agric. Food Chem.,28, 1208 (1980).PubMedGoogle Scholar
  28. 28.
    T. T. Gorovich and N. K. Abubakirov, Khim. Prir. Soedin., 241 (1975).Google Scholar
  29. 29.
    M. Yokota and T. Mori, Carbohydr. Res.,59, 289 (1977).PubMedGoogle Scholar
  30. 30.
    J. Mononen, Carbohydr. Res.,88, 39 (1981).Google Scholar
  31. 31.
    J. P. Kamerling, J. Gerwig, J. F. G. Vliegenthart, and J. R. Clamp, Biochem. J.,151, 491 (1975).PubMedPubMedCentralGoogle Scholar
  32. 32.
    A. A. Akhrem, G. V. Avvakumov, O. V. Sviridov, O. A. Strel'chonok, Vestsi Akad. Navuk BSSR, Ser. Khim. Navuk, No. 5, 95 (1978).Google Scholar
  33. 33.
    L. P. Stepovaya and Yu. I. Khol'kin, in: Chromatographic Analysis in Wood Chemistry [in Russian], Riga (1975), p. 18.Google Scholar
  34. 34.
    A. Ericsson, J. Hansen, and L. Dalgard, Anal. Biochem.,86, 552 (1978).PubMedGoogle Scholar
  35. 35.
    A. Patetta and A. Manino, Cron. Chim.,57, 9 (1978); Chem. Abstr.,91, 138942 (1979).Google Scholar
  36. 36.
    A. Doussin, S. Charonnat, and M. Guernet, Ann. Biol. Chem. (Paris),35, No. 1, 19 (1977); Chem. Abstr.,87, 64830 (1977).Google Scholar
  37. 37.
    J. Jurenitsch, B. Kopp, J. Gabber-Kolacsek, and W. Kubelka, J. Chromatogr.,210, 337 (1981).Google Scholar
  38. 38.
    T. Sakaki, S. Munakata, H. Sakuma, and S. Sugawara, Agric. Biol. Chem.,46, 827 (1982).Google Scholar
  39. 39.
    D. Anderle, J. Königstein, and V. Kováčik, Anal. Chem.,49, 137 (1977).Google Scholar
  40. 40.
    E. Jellum, P. Storseth, J. Alexander, P. Heiland, O. Stokke, and E. Teig, J. Chromatogr.,126, 487 (1976).PubMedGoogle Scholar
  41. 41.
    K. J. Schäffler, P. G. Morel du Boil, J. Chromatogr.,207, 251 (1981).Google Scholar
  42. 42.
    V. M. Svetlaeva, L. M. Kirshchenya, M. Ts. Yanotovskii, Khim.-Farm. Zh., 132 (1977).Google Scholar
  43. 43.
    D. Podhradsky, M. Podhradska, and J. Andrašina, Chem. Zvesti,31, 87 (1977).Google Scholar
  44. 44.
    Z. E. Bryantseva, V. R. Bretosh, and V. E. Moskaleva, in: Chromatographic Analysis in Wood Chemistry [in Russian], Riga (1975), p. 31.Google Scholar
  45. 45.
    R. A. Laine, W. J. Esselman, and C. C. Sweeley, Methods Enzymol.,28, 159 (1972); H. Sloneker, in: Methods in Carbohydrate Chemistry, Vol. VI, R. L. Whistler and J. N. BeMiller, eds., Academic Press, New York (1972), pp. 20–24.Google Scholar
  46. 46.
    A. Misaki, Y. Tsumuraya, M. Kakuta, H. Takemoto, and T. Igarashi, Carbohyd. Res.,75, C8 (1979).Google Scholar
  47. 47.
    N. E. Anderson and E. M. Clydesdale, J. Food, Sci.,45, No. 2, 336 (1980).Google Scholar
  48. 48.
    L. H. Krull and G. E. Inglett, J. Agric. Food Chem.,28, 917 (1980).PubMedGoogle Scholar
  49. 49.
    S. Hirase, K. Watanabe, and R. Takano, Agric. Biol. Chem.,42, 1065 (1978).Google Scholar
  50. 50.
    A. G. Darvill, D. P. Roberts, and M. A. Hall, J. Chromatogr.,115, 319 (1975).Google Scholar
  51. 51.
    J. Stadler, Anal. Biochem.,74, 62 (1976).PubMedGoogle Scholar
  52. 52.
    C. W. Gehrke, T. P. Waalkes, E. Borek, W. F. Swartz, T. F. Cole, K. C. Kuo, M. Aberloff, D. S. Ettinger, N. Rosenshen, and R. C. Yound, J. Chromatogr.162, 507 (1979).PubMedGoogle Scholar
  53. 53.
    R. Kanna, P. N. Seng, and H. Debuch, J. Chromatogr.,92, 95 (1974).Google Scholar
  54. 54.
    L. A. Torello, A. J. Yates, and D. K. Thomson, J. Chromatogr.,202, 195 (1980).PubMedGoogle Scholar
  55. 55.
    W. H. Porter, Anal. Biochem.,63, 27 (1975).PubMedGoogle Scholar
  56. 56.
    A. A. Akhrem, G. V. Avvakumov, O. V. Sviridov, and O. A. Strel'chonok, Vestsi Akad. Navuk BSSR, Ser. Khim. Navuk, No. 3, 98 (1978).Google Scholar
  57. 57.
    K. Schmid, and L.-C. H. Chen, Prep. Biochem.,6, 27 (1976).PubMedGoogle Scholar
  58. 58.
    W. Niedermeier and M. Tomana, Anal. Biochem.,57, 363 (1974).PubMedGoogle Scholar
  59. 59.
    P. Prehm and A. Scheid, J. Chromatogr.,166, 461 (1978).Google Scholar
  60. 60.
    R. Chaby and L. Szabo. Eur. J. Biochem.,70, 115 (1976).PubMedGoogle Scholar
  61. 61.
    G. Holzer, J. Oró, S. J. Smith, and V. M. Doctor, J. Chromatogr.,194, 410 (1980).Google Scholar
  62. 62.
    C. Green, V. M. Doctor, G. Holzer, and J. Oró, J. Chromatogr.,207, 268 (1981).Google Scholar
  63. 63.
    J. Klok, E. H. Niebérg-van Velzen, J. W. de Leeuw, and P. A. Schenck, J. Chromatogr.,207, 273 (1981).Google Scholar
  64. 64.
    R. Oshima, A. Yoshikawa, J. Kumanotani, J. Chromatogr.,213, 132 (1981).Google Scholar
  65. 65.
    B. A. Dmitriev, L. V. Backinowsky, O. S. Chizhov, B. M. Zolotarev, and N. K. Kochetkov, Carbohydr. Res.,19, 432 (1971).Google Scholar
  66. 66.
    J. K. Baird, M. J. Holroyde, and D. C. Ellwood, Carbohydr. Res.,27, 464 (1973).Google Scholar
  67. 67.
    R. Varma and R. S. Varma, J. Chromatogr.,128, 45 (1976).PubMedGoogle Scholar
  68. 68.
    R. Varma and R. S. Varma, J. Chromatogr.,139, 303 (1977).PubMedGoogle Scholar
  69. 69.
    F. R. Seymour, E. C. M. Chen, and S. H. Bishop, Carbohydr., Res.,73, 19 (1979).Google Scholar
  70. 70.
    R. Varma, R. S. Varma, and A. H. Wardi, J. Chromatogr.,77, 222 (1973).Google Scholar
  71. 71.
    R. Varma, R. S. Varma, W. S. Allen, and A. H. Wardi, J. Chromatogr.,86, 205 (1973).PubMedGoogle Scholar
  72. 72.
    T. T. Gorovich and N. K. Abubakirov, Khim. Prir. Soedin.,523, (1975).Google Scholar
  73. 73.
    C. D. Pfaffenberger, J. Szafrenek, M. G. Horning, and E. C. Horning, Anal. Biochem.,63, 501 (1975).PubMedGoogle Scholar
  74. 74.
    C. D. Pfaffenberger, J. Szafranek, and E. C. Horning, J. Chromatogr.,126, 535 (1976).PubMedGoogle Scholar
  75. 75.
    G. J. Mawnius, T. M. Li, and L.-F. L. Wen, Anal. Biochem.,99, 365 (1979).Google Scholar
  76. 76.
    T. P. Mawhinney, M. S. Feather, G. J. Barrero, and J. R. Martinez, Anal. Biochem.,101, 112 (1980).PubMedGoogle Scholar
  77. 77.
    S. H. Turner, and R. Cherniak, Carbohydr. Res.,95, 137 (1981).Google Scholar
  78. 78.
    J. Lehrfeld, Anal. Biochem.,115, 410 (1981).PubMedGoogle Scholar
  79. 79.
    M. Tomana, W. Niedermeier, and C. Spivey, Anal. Biochem.,89, 110 (1978).PubMedGoogle Scholar
  80. 80.
    T. Shinohara, J. Chromatogr.,207, 262 (1981).PubMedGoogle Scholar
  81. 81.
    S. Honda, N. Yamauchi, and K. Kakeni, J. Chromatogr.,169, 287 (1979).Google Scholar
  82. 82.
    S. Morgenlie, Carbohydr. Res.,41, 285 (1975).Google Scholar
  83. 83.
    S. Morgenlie, Carbohydr. Res.,80, 215 (1980).Google Scholar
  84. 84.
    P. J. Wood, J. R. Siddiqui, and J. Weisz, Carbohydr., Res.,42, 1 (1975).Google Scholar
  85. 85.
    R. J. Stroz, Carbohydr. Res.,72, 207 (1979).Google Scholar
  86. 86.
    H. Frank, H. J. C. Das Neves, and E. Bayer, J. Chromatogr.,207, 213 (1981).Google Scholar
  87. 87.
    P. Decker and H. Schweer, J. Chromatogr.,243, 372 (1982).Google Scholar
  88. 88.
    J. N. C. Whyte, J. Chromatogr.,87, 163 (1973).Google Scholar
  89. 89.
    J. R. Etchison and J. J. Holland, Anal. Biochem.,66, 87 (1975).PubMedGoogle Scholar
  90. 90.
    D. G. Pritchard and C. W. Todd, J. Chromatogr.,133, 133 (1977).PubMedGoogle Scholar
  91. 91.
    B. Kozulic, B. Ries, and P. Mildner, Anal. Biochem.,94, 36 (1979).PubMedGoogle Scholar
  92. 92.
    S. J. Rickart, C. C. Sweeley, J. Chromatogr.,147, 317 (1977).Google Scholar
  93. 93.
    A. A. Akhrem, G. V. A. Avvakumov, O. V. Sviridov, and O. A. Strel'chyonok, J. Chromatogr.,166, 123 (1978).Google Scholar
  94. 94.
    T. P. Mawhinney, M. S. Feather, J. R. Martinez, and G. J. Barbero, Carbohydr. Res.,75, C21 (1979).Google Scholar
  95. 95.
    J. Mononen and J. Karkkainen, FEBS Lett.,59, 190 (1975).PubMedGoogle Scholar
  96. 96.
    T. P. Mawhinney, M. A. Madson, R. H. Rice, M. S. Featherm and G. J. Barbero, Carbohydr. Res.,104, 169 (1982).Google Scholar
  97. 97.
    J. Szafranek, C. D. Pfaffenberger, and E. C. Horning, J. Chromatogr.,88, 149 (1974).Google Scholar
  98. 98.
    G. Petersson, J. Chromatogr. Sci.,15, 245 (1977).Google Scholar
  99. 99.
    M. Wurst, V. Vancura, and L. Kalachova, J. Chromatogr.,91, 469 (1974).PubMedGoogle Scholar
  100. 100.
    S. Inoue, M. Miyawaki, Anal. Biochem.,65, 164 (1975).PubMedGoogle Scholar
  101. 101.
    L. Vadas, H. S. Prihar, B. K. Pugasetti, and D. S. Feingold, Anal. Biochem.,114, 294 (1981).PubMedGoogle Scholar
  102. 102.
    R. M. Thompson and N. Gerber, J. Chromatogr.,124, 321 (1976).PubMedGoogle Scholar
  103. 103.
    H. Ehrsson, T. Walle, and S. Wikström, J. Chromatogr.,101, 206 (1974).PubMedGoogle Scholar
  104. 104.
    D. Nurok and T. J. Reardon, Carbohydr. Res.,56, 165 (1977).Google Scholar
  105. 105.
    G. A. Janauer, and P. Englmaier, J. Chromatogr.,153, 539 (1978).Google Scholar
  106. 106.
    K. A. Killick, Carbohydr. Res.,82, 1 (1980).Google Scholar
  107. 107.
    D. Nurok, J. Chromatogr. Sci.,14, 305 (1976).Google Scholar
  108. 108.
    P. L. Coduti and C. A. Buch, Anal. Biochem.,78, 21 (1977).PubMedGoogle Scholar
  109. 109.
    T. Pietrzykowski, H. Gruszecka, A. Borys, and S. Kubacki, Zes. Probl. Postepow Nauk Pol.,187, 145 (1977); Chem. Abstr.,87, 186359 (1977).Google Scholar
  110. 110.
    J. Copikova and F. Kvasnieka, Listy Cukrow,95, No. 4, 93 (1979).Google Scholar
  111. 111.
    A. Ostaniewicz, K. Wesolowska, S. Kubacki, and A. Borys, Gaz. Cukrow,85 (5), 110 (1977).Google Scholar
  112. 112.
    C. Womersley, Anal. Biochem.,112, 182 (1981).PubMedGoogle Scholar
  113. 113.
    M. Deki, and Y. Hakamada, Zanzei Chuo Bunsekishoho,15, 115 (1975); Chem. Abstr.,87, 95036 (1975).Google Scholar
  114. 114.
    H. Schwind, F. Scharbet, R. Schmidt, and R. Kattermann, J. Clin. Chem. Biochem.,16, 145 (1978).Google Scholar
  115. 115.
    M. J. Prager, M. A. Miskiewicz, J. Assoc. Off. Anal. Chem.,69, 262 (1979).Google Scholar
  116. 116.
    A. M. Jamiesson, J. Am. Soc. Brew. Chem.,34, 44 (1976); Chem. Abstr.,84, 178149 (1976).Google Scholar
  117. 117.
    K. Kuercher, H. Hadorn, C. Strack. Mitt. Geb. Lebensmittelunters. Hyg.66, 92 (1975); Chem. Abstr.,84, 313262 (1975).Google Scholar
  118. 118.
    S. Adam and W. G. Jennings, J. Chromatogr.,115, 218 (1975).Google Scholar
  119. 119.
    T. Toba and S. Adachi, J. Chromatogr.,135, 411 (1977).Google Scholar
  120. 120.
    S. E. Zurabyan, T. N. Mirzayanova, B. V. Rozynov, V. L. Sadovskaya, and A. Ya. Khorlin, Bioorg. Khim.,4, 1402 (1978).Google Scholar
  121. 121.
    J. Jones, in: Methods in Carbohydrate Chemistry, Academic Press, New York (1962ff) [Russian translation, Moscow (1975), p. 26].Google Scholar
  122. 122.
    B. Lindberg, Methods Enzymol.,28, 178 (1972).Google Scholar
  123. 123.
    K. Kato, K. Mutohi, T. Egashira, M. Kiura, and Y. Ueno, Agric. Biol. Chem.,42, 1073 (1978).Google Scholar
  124. 124.
    T. Mukumoto and H. Yamaguchi, Carbohydr. Res.,59, 614 (1977).Google Scholar
  125. 125.
    G. R. Woolard, E. B. Rathbone, and L. Novellie, Carbohydr. Res.,51, 239 (1976).Google Scholar
  126. 126.
    J.-P. Benedetto, M. Bruneteau, and G. Michel, Eur. J. Biochem.,63, 313 (1976).PubMedGoogle Scholar
  127. 127.
    A. K. Chakraborty, H. Friebolin, H. Niemann, and S. Stirm., Carbohydr. Res.,59, 525 (1977).Google Scholar
  128. 128.
    L. D. Kennedy and R. W. Bailey, Carbohydr. Res.,49, 451 (1976).PubMedGoogle Scholar
  129. 129.
    A. S. Rao and N. Roy, Carbohydr. Res.,74, 349 (1979).Google Scholar
  130. 130.
    J. F. Kennedy, J. S. Sandhy, and D. A. T. Southgate, Carbohydr. Res.,75, 265 (1979).Google Scholar
  131. 131.
    J. H. Pazur and L. S. Forsberg, Carbohydr. Res.,58, 222 (1977).PubMedGoogle Scholar
  132. 132.
    L. P. T. M. Zavenhuizen, Carbohydr. Res.,26, 409 (1973).Google Scholar
  133. 133.
    H. Rauvala, Carbohydr. Res.,26, 409 (1973).Google Scholar
  134. 134.
    A. A. Akhrem, G. V. Avvakumov, and O. A. Strelchonok, J. Chromotgr.,176, 207 (1979).Google Scholar
  135. 135.
    Y. M. Choy and G. G. S. Dutton, Can. J. Chem.,52, 684 (1974).Google Scholar
  136. 136.
    H. Parolis and D. McGarvie, Carbohydr. Res.,62, 363 (1978).Google Scholar
  137. 137.
    A. Amemura, M. Hisamatsum, S. K. Ghai, and T. Haraba, Carbohydr. Res.,91, 59 (1981).Google Scholar
  138. 138.
    P. N. Lipke, W. C. Raschke, and C. E. Ballou, Carbohydr. Res.,37, 23 (1974).PubMedGoogle Scholar
  139. 139.
    N. Shibuya, J. Chromatogr.,208, 96 (1981).Google Scholar
  140. 140.
    J. Radziejewska-Lebrecht, D. H. Shaw, D. Borowiak, I. Fromm, and H. Mayer, J. Chromatogr.,179, 113 (1979).Google Scholar
  141. 141.
    L.-E. Franzen and S. Svensson, Carbohydr. Res.,73, 309 (1979).Google Scholar
  142. 142.
    Y. V. Anjaneyalu and D. C. Gowda, Carbohydr. Res.,75, 251 (1979).Google Scholar
  143. 143.
    R. Geyer, H. Geyer, S. Kühnhardt, W. Mink, and S. Strim. Anal. Biochem.,121, 263 (1982).PubMedGoogle Scholar
  144. 144.
    D. P. Sweet, P. Albersheim, and R. H. Shapiro, Carbohydr. Res.,40, 199 (1975).Google Scholar
  145. 145.
    F. R. Seymour, R. D. Plattner, and M. E. Slodki, Carbohydr. Res.,44, 181 (1975).Google Scholar
  146. 146.
    F. R. Seymour, E. C. M. Chen, and S. H. Bishop, Carbohydr. Res.,68, 113 (1979).Google Scholar
  147. 147.
    F. R. Seymour, M. E. Slodki, R. D. Plattner, and A. Jeines, Carbohydr. Res.,53, 153 (1977).Google Scholar
  148. 148.
    D. Anderle and P. Kovac, Chem. Zvesti,30, 355 (1976).Google Scholar
  149. 149.
    B. W. Li, T. W. Cochran, and J. R. Vercellotti, Carbohydr. Res.,59, 567 (1977).Google Scholar
  150. 150.
    F. Janecek, R. Toman, S. Karácsonyi, and D. Anderle, J. Chromatogr.,173, 408 (1979).Google Scholar
  151. 151.
    B. Fournet, J.-M. Dhalluin, Y. Leroy, J. Montreuil, and H. Mayer, J. Chromatogr.,153, 91 (1978).Google Scholar
  152. 152.
    S. Ito and Y. Fujino, Agric. Biol. Chem.,44, 1181 (1980).Google Scholar
  153. 153.
    J. Jarý and M. Marek, Collect. Czech. Chem. Commun.,46, 2410 (1981).Google Scholar
  154. 154.
    S. Pekkala, B. Holmbom, and E. Avela, Kemia-kemi,1, 25 (1974).Google Scholar
  155. 155.
    T. Matsubura and A. Hayashi, Biomed. Mass Spectrom., 62 (1974).Google Scholar
  156. 156.
    Yu. N. El'kin, J. Chromatogr.,180, 163 (1979).Google Scholar
  157. 157.
    Yu. S. Ovodov and E. V. Evtushenko, Carbohydr. Res.,27, 169 (1973).Google Scholar
  158. 158.
    E. V. Evtushenko, and Yu. S. Ovodov, J. Chromatogr.,97, 99 (1974).Google Scholar
  159. 159.
    E. V. Evtushenko and Yu. S. Ovodov, Khim. Prir. Soedin., 677 (1975).Google Scholar
  160. 160.
    E. V. Evtushenko and Yu. S. Ovodov, Khim. Prir. Soedin., 753 (1977).Google Scholar
  161. 161.
    E. V. Evtushenko, N. M. Vakhrusheva, and Yu. S. Ovodov, Khim. Prir. Soedin., 142 (1979).Google Scholar
  162. 162.
    E. V. Evtushenko, N. M. Vakhrusheva, and Yu. S. Ovodov, J. Chromatogr.,196, 331 (1980).Google Scholar
  163. 163.
    B. Fournet, Y. Leroy, and J. Montreuil, J. Chromatogr.,92, 185 (1974).Google Scholar
  164. 164.
    E. V. Evtushenko and Yu. S. Ovodov, Khim. Prir. Soedin., 18 (1982); E. V. Evtushenko and Yu. S. Ovodov, Khim. Prir. Soedin., 21 (1982).Google Scholar
  165. 165.
    B. Fournet, G. Strecker, Y. Leroy, and J. Montreuil, Anal. Biochem.,116, 489 (1981).PubMedGoogle Scholar
  166. 166.
    S. K. Kundu, R. W. Ledeen, and P. A. J. Gorin, Carbohydr. Res.,39, 329 (1975).PubMedGoogle Scholar
  167. 167.
    S. K. Kundu, R. W. Ledeen, and P. A. J. Gorin, Carbohydr. Res.,39, 179 (1975).PubMedGoogle Scholar
  168. 168.
    T. Tai, K. Yamashita, and A. Kobata, J. Biochem. (Tokyo),78, 679 (1975).PubMedGoogle Scholar
  169. 169.
    J. Finne and H. Rauvala, Carbohydr. Res.,58, 57 (1977).PubMedGoogle Scholar
  170. 170.
    G. O. H. Schwarzmann and R. W. Jeanloz, Carbohydr. Res.,34, 161 (1974).Google Scholar
  171. 171.
    K. Stellner, H. Saito, and S.-I. Hakomori, Arch. Biochem. Biophys.,155, 464 (1973).PubMedGoogle Scholar
  172. 172.
    A. A. Akhrem, G. V. Avvakumov, I. V. Sidorova, and O. A. Strel'chonok, Vestsi Akad. Navuk BSSR. Ser. Khim. Navuk, No. 4, 111 (1979).Google Scholar
  173. 173.
    A. K. Bhattacharjee and H. J. Jennings, Carbohydr. Res.,51, 253 (1976).PubMedGoogle Scholar
  174. 174.
    S. Inoue and G. Matsumura, Carbohydr. Res.,74, 361 (1979).Google Scholar
  175. 175.
    I. Mononen, Carbohydr. Res.,104, 1 (1982).Google Scholar
  176. 176.
    H. Rauvala and J. Kärkkainen, Carbohydr. Res.,56, 1 (1977).PubMedGoogle Scholar
  177. 177.
    C. Bruvier, Y. Leroy, J. Montreuil, B. Fournet, and J. P. Kamerling, J. Chromatogr.,210, 487 (1981).Google Scholar
  178. 178.
    H. van Halbeek, J. Haverkamp, J. P. Kamerling, J. F. G. Vliegenthart, C. Verslius, and R. Schauer, Carbohydr. Res.,60, 51 (1978).Google Scholar
  179. 179.
    J. Haverkamp, J. P. Kamerling, J. F. G. Vliegenthart, and R. W. Ven, and R. Schauer, FEBS Lett.,73, 215 (1977).PubMedGoogle Scholar
  180. 180.
    D. Anderle and P. Cováč, J. Chromatogr.,91, 463 (1974).Google Scholar
  181. 181.
    S. Honda, K. Takeda and K. Kakehi, Carbohydr. Res.,73, 135 (1979).Google Scholar
  182. 182.
    S. Honda, N. Hamajima, and K. Kakehi, Carbohydr. Res.,68, 77 (1979).Google Scholar
  183. 183.
    S. Honda, S. Okuyama, Y. Kishi, S. Suzuki, and K. Kakehi, Carbohydr. Res.,164, 9 (1979).Google Scholar
  184. 184.
    O. Larm, E. Scholander, and O. Theander, Carbohydr. Res.,49, 69 (1976).PubMedGoogle Scholar
  185. 185.
    P. Decker and H. Schweer, Carbohydr. Res.,49, 201 (1976).Google Scholar
  186. 186.
    E. Wiren, L. Ahrgren, and N. de Belder, Carbohydr. Res.,49, 201 (1976).Google Scholar
  187. 187.
    P.-E. Jansson, L. Kenne, and S. Svensson, Acta Chem. Scand., B,30, 61 (1976).Google Scholar
  188. 188.
    S. Morgenlie, Carbohydr. Res.,73, 315 (1979).Google Scholar
  189. 189.
    G. J. Gerwig, J. R. Kamerling, and J. F. G. Vleigenthart, Carbohydr. Res.,62, 349 (1978).Google Scholar
  190. 190.
    G. J. Gerwig, J. P. Kamerling, and J. F. G. Vliegenthart, Carbohydr. Res.,77, 1 (1979).Google Scholar
  191. 191.
    K. Leontein, B. Lindberg, and J. Lönngren, Carbohydr. Res.,62, 359 (1978).Google Scholar
  192. 192.
    A. L. Leavitt, and W. R. Sherman, Carbohydr. Res.,103, 203 (1982).Google Scholar
  193. 193.
    W. Zablocki, E. J. Behrman, and G. A. Barber, J. Biochem. Biophys. Methods,1, 253 (1979).PubMedGoogle Scholar
  194. 194.
    M. R. Little, Carbohydr. Res.,105, 1 (1982).Google Scholar
  195. 195.
    L. B. Schroeder, K. M. Counts, and F. C. Haigh, Carbohydr. Res.,37, 368 (1974).Google Scholar
  196. 196.
    G. Wulff, U. Schroeder, and J. Wichelhaus, Carbohydr. Res.,72, 280 (1979).Google Scholar
  197. 197.
    E. V. Evtushenko and Yu. S. Ovodov, Khim. Prir. Soedin., 87 (1976).Google Scholar
  198. 198.
    J. Gelas and D. Horton, Carbohydr. Res.,45, 181 (1975).Google Scholar
  199. 199.
    J. Gelas and D. Horton, Carbohydr. Res.,67, 371 (1978).Google Scholar
  200. 200.
    J. Szafranek, A. Wisniewski, J. Gajdus, and J. Kusmiers, J. Chromatogr.,168, 445 (1979).Google Scholar
  201. 201.
    J. W. Mourits, H. G. Merkus, and L. de Gatan, Anal. Chem.,48, 1557 (1976).Google Scholar
  202. 202.
    A. Lipták, P. Fügedi, and P. Nánaśi, Carbohydr. Res.,65, 209 (1978).Google Scholar
  203. 203.
    J. M. Küster, H. Luftmann, and I. Dyong, Chem. Ber.,109, 2223 (1976).Google Scholar
  204. 204.
    J. Harangi and A. Liptak, J. Chromatogr.,147, 401 (1978).Google Scholar
  205. 205.
    K. Olsson, O. Theander, and P. Aman, Carbohydr. Res.,58, 1 (1977).PubMedGoogle Scholar
  206. 206.
    J. Eagles, G. R. Fenwick, and R. K. Heaney, Biomed. Mass Spectrom.,8, 278 (1981).Google Scholar
  207. 207.
    H. B. Boren, P. J. Garegg, L. Kenne, A. Pilotti, A. Svensson, and C.-G. Swahn, Acta Chem. Scand.,27, 3557 (1973).Google Scholar
  208. 208.
    K. Yoshimoto, K. Tahara, S. Suzuki, K. Sasaki, Y. Nishikawa, and Y. Tsuda, Chem. Pharm. Bull.,27, 2661 (1979).Google Scholar
  209. 209.
    J. P. Williams, G. R. Watson, M. Khan, S. Leung, A. Kuksas, O. Stachnyk, and J. J. Myher, Anal. Biochem.,66, 110 (1975).PubMedGoogle Scholar
  210. 210.
    H. Tokunaga, T. Kimura, and J. Kawamura, Yakugagku Zasshi,99, 800 (1979); Chem. Abstr.,91, 206577 (1979).Google Scholar
  211. 211.
    V. N. Reinhold, F. Wirtz-Peitz, and K. Biemann, Carbohydr. Res.,37, 203 (1974).Google Scholar
  212. 212.
    H. Tsuchida, K. Kitamura, H. Komoto, and N. Akimori, Carbohydr. Res.,67, 549 (1978).Google Scholar
  213. 213.
    A. Soler and R. P. A. Garcia, Ann. Univ. Murcia Cien.,32, 21 (1975) (Publ. 1978); Chem. Abstr.,90, 168843 (1979).Google Scholar
  214. 214.
    N. I. Kaletina, S. A. Pronkina, A. A. Bezzubov, and B. N. Stepanenko, Zh. Obshch. Khim.,50, 1195 (1980).Google Scholar
  215. 215.
    F. Shafizadeh, R. H. Furneaux, T. T. Stevenson, and T. G. Cochran, Carbohydr. Res.,67, 433 (1978).Google Scholar
  216. 216.
    C. von Sonntag and M. Dizdaroglu, Carbohydr. Res.,58, 21 (1977).Google Scholar
  217. 217.
    S. Kawakishi, Y. Kito, and M. Namiki, Carbohydr. Res.,39, 263 (1975).PubMedGoogle Scholar
  218. 218.
    J. M. Morrison, J. Chromatogr.,108, 361 (1975).PubMedGoogle Scholar
  219. 219.
    L. P. Kosheleva, G. Y. Il'chenko, and L. I. Glebko, Anal. Biochem.,73, 115 (1976).PubMedPubMedCentralGoogle Scholar
  220. 220.
    O. D. Livshits, M. I. Mazela, L. G. Sibiryakova, in: Chromatographic Analysis in Wood Chemistry [in Russian], Riga (1975), p. 39.Google Scholar
  221. 221.
    G. F. Aleksandrova and Yu. N. Khol'kin, in: All-Union Scientific Conference on the Chemistry and Technology of Furan Compounds. Abstracts of Lectures [in Russian], (Ya. P. Stradin', ed., Riga (1979), p. 75.Google Scholar
  222. 222.
    B. Fournet and J. Mountreuil, J. Chromatogr.,75, 29 (1973).Google Scholar

Copyright information

© Plenum Publishing Corporation 1985

Authors and Affiliations

  • E. V. Evtushenko
  • Yu. S. Ovodov

There are no affiliations available

Personalised recommendations