Skip to main content
SpringerLink
Log in

Specific lipids of mycobacteria and related organisms

  • Published:
Chemistry of Natural Compounds Aims and scope

Abstract

Mycobacteria and related organisms contain specific lipids not found in other natural objects. The chemical structure, localization in the cell, physiological functions, and biological activities of four groups of such lipids are considered: fatty acid derivative of carbohydrates, mainly of α,α-D-trehalose; fatty acid amides of peptides; monoglycerides with mycolic acid residues; and mycosides C — specific glycopeptidolipids of nontubercular mycobacteria. Information is given on the biological activities of synthetic analogs of the bacterial glycolipids. A separate section is devoted to the structure and biosynthesis of the specific fatty acids forming components of the lipids discussed.

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

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

Literature cited

  1. T. V. Koronelli, Usp. Mikrobiol.,12, 164, (1977).

    Google Scholar 

  2. L. Barksdale and K.-S. Kim, Bacteriol. Rev.,41, 217 (1977).

    Google Scholar 

  3. M. B. Goren and P. Brennan, in: Tuberculosis, G. Youmans, ed., Saunders, Philadelphia (1979), p. 63.

    Google Scholar 

  4. E. Lederer, Chem. Phys. Lipids,16, 91 (1976).

    Google Scholar 

  5. C. Asselineau and J. Asselineau, Prog. Fats Other Lipids,16, 59 (1978).

    Google Scholar 

  6. C. Asselineau and J. Asselineau, Ann. Microbiol.,A129, 49 (1978).

    Google Scholar 

  7. E. Lederer, Springer Sem. Immunopathol.,2, 133 (1979).

    Google Scholar 

  8. T. Ioneda, C. L. Silva, and J.-L. Gesztesi, Z. Bakt. Mikrobiol. Hyg. 1 Abt., Suppl.11, 401 (1981).

    Google Scholar 

  9. J. Asselineau, Zentralkl. Bakteriol. Mikrobiol. Hyg. 1 Abt., Suppl.11, 391 (1981).

    Google Scholar 

  10. D. E. Minnikin, in: The Biology of the Mycobacteria, C. Ratledge and J. Stanford, eds., Academic Press, London, (1982), p. 95.

    Google Scholar 

  11. D. E. Minnikin and M. Goodfellow, Zentralkl. Bakteriol. Mikrobiol. Hyg., 1 Abt., Suppl.11, 99 (1981).

    Google Scholar 

  12. D. E. Minnikin and M. Goodfellow, in: Microbiological Classification and Identification, M. Goodfellow, and R. G. Board, eds., London (1980), p. 189.

  13. M. D. Collins, M. Goodfellow, and D. E. Minnikin, J. Gen. Microbiol.,128, 129 (1982).

    Google Scholar 

  14. S. Devi and D. E. S. Steward-Tull, Int. J. Leprosy,47, 484 (1979).

    Google Scholar 

  15. J. F. Tocanne and C. Asselineau, Bull. Soc. Chim. Fr., 4519 (1968).

  16. C. Asselineau, G. Tocanne, and J. F. Tocanne, Bull. Soc. Chim. Fr., 1455 (1970).

  17. I. Ioneda, M. Lenz, and J. Pudles, Biochem. Biophys. Res. Commun.,13, 110 (1963).

    Google Scholar 

  18. H. Wada, H. Okada, H. Suginaka, I. Tomiyasu, and I. Yano, FEMS. Microbiol. Lett.,11, 187 (1981).

    Google Scholar 

  19. H. Wada, and H. Kurihara, J. Osaka Univ. Dental Sch.,22, 115 (1982).

    Google Scholar 

  20. S. G. Batrakov, V. L. Sadovskaya, B. V. Rozynov, T. V. Koronelli and L. D. Bergel'son, Bioorg. Khim.,4, 667 (1978).

    Google Scholar 

  21. H. Okazaki, H. Sugino, T. Kanzaki, and H. Fukuda, Agr. Biol. Chem.,33, 764 (1969).

    Google Scholar 

  22. M. Welby-Gieusse, M.-A. Lanéelle, and J. Asselineau, Eur. J. Biochem.,13, 164 (1970).

    Google Scholar 

  23. G. Michel and C. Bordet, in: The Biology of the Nocardia, M. Goodfellow, G. H. Brownell, and J. A. Serrano, eds., Academic Press, London, (1976), p. 141.

    Google Scholar 

  24. D. E. Minnikin, and M. Goodfellow, in: The Biology of the Nocardia, M. Goodfellow, G. H. Brownell, and J. A. Serrano, eds., London (1976), p. 160.

  25. I. Tomiyasu, J. Bacteriol.,151, 828 (1982).

    Google Scholar 

  26. S. Toriyama, I. Yano, M. Masui, and M. Kusunose, FEBS Lett.,95, 111 (1978).

    Google Scholar 

  27. S. J. Danielson and G. R. Gray, J. Biol. Chem.,257, 12196 (1982).

    Google Scholar 

  28. G. R. Gray, M. Y. H. Wong, and S. J. Danielson, Prog. Lipid Res.,21, 91 (1982).

    Google Scholar 

  29. B. Mompon, C. Federici, R. Toubiana, and E. Lederer, Chem. Phys. Lipids,21, 97 (1978).

    Google Scholar 

  30. N. Qureshi, K. Takayama, H. C. Jordi, and H. K. Schnoes, J. Biol. Chem.,253, 5411 (1978).

    Google Scholar 

  31. M. Daffé, M. A., Lanéelle, D. Prome, and C. Asselineau, Ann. Microbiol.,B132, 3 (1981).

    Google Scholar 

  32. P. Draper, G. Dobson, D. E. Minnikin, and S. M. Minnikin, Ann. Microbiol.,B133, 39 (1982).

    Google Scholar 

  33. L. A. Davidson, P. Draper, and D. E. Minnikin, J. Gen. Microbiol.,128, 823 (1982).

    Google Scholar 

  34. D. E. Minnikin, S. M. Minnikin, and M. Goodfellow, Biochim. Biophys. Acta,712, 616 (1982).

    Google Scholar 

  35. M. Daffé, M.-A. Lanéelle, G. Puzo, and C. Asselineau, Tetrahedron Lett.,22, 4515 (1981).

    Google Scholar 

  36. M. A. Lanéelle and G. Lanéelle, Eur. Biochem.,12, 296 (1970).

    Google Scholar 

  37. J. C. Prome, C. Lacave, A. Ahibo-Coffy, and A. Savagnac, Eur. J. Biochem.,63, 543 (1976).

    Google Scholar 

  38. M. Gastambide-Odiea and E. Lederer, Biochem. Z.,333, 285 (1960).

    Google Scholar 

  39. S. Toriyama, S. Imaizumi, I. Tomiyasu, M. Masui, and I. Yano, Biochim. Biophys. Acta,712, 427 (1982).

    Google Scholar 

  40. N. Qureshi, Fed. Proc., Fed. Am. Soc. Exp. Biol.,37, 1707 (1978).

    Google Scholar 

  41. K. Takayama, M. Qureshi, and H. K. Schnoes, Lipids,13, 575 (1978).

    Google Scholar 

  42. K. Takayama, N. Qureshi, H. C. Jordi, and H. K. Schnoes, J. Liquid Chromatogr.,2, 861 (1979).

    Google Scholar 

  43. N. Qureshi, K. Takayama, and H. K. Schnoes, J. Biol. Chem.,255, 182 (1980).

    Google Scholar 

  44. K. Takayama and L. A. Davidson, Trends Biochem. Sci.,4, No. 12, 280 (1979).

    Google Scholar 

  45. K. Takayama and L. A. Davidson, in: Antibiotics, Vol. 1, Part 1, Mechanism of Action of Antibacterial Agents, F. E. Hahn, ed., Springer, Berlin (1979), p. 98.

    Google Scholar 

  46. N. Qureshi, K. Takayama, and H. K. Schnoes, J. Liquid Chromatogra.,4, 1207 (1981).

    Google Scholar 

  47. E. Lederer, A. Adam, R. Giorbaru, J.-F. Petit, and J. Wietzerbin, Molec. Cell. Biochem.,7, 87 (1975).

    Google Scholar 

  48. J.-F. Petit, Ann. Microbiol.,A129, 39 (1978).

    Google Scholar 

  49. H. A. Lechevalier, M. P. Lechevalier, and N. N. Gerber, Adv. Appl. Microbiol.,14, 47 (1971).

    Google Scholar 

  50. M. P. Lechevalier, H. Lechevalier, and A. C. Horan, Can. J. Microbiol.,19, 965 (1973).

    Google Scholar 

  51. G. O. Guerrant, M. A. Lambert, and W. C. Moss, J. Clin. Microbiol.,13, 899 (1981).

    Google Scholar 

  52. I. Yano, K. Kogeyama, Y. Ohno, M. Masui, E. Kusunose, M. Kusonose, and N. Akimori, Biomed. Mass Spectrom.,5, 14 (1978).

    Google Scholar 

  53. S. Toriyama, I. Yano, M. Masui, E. Kusunose, M. Kusunose, and N. Akimori, J. Biochem., (Tokyo),88, 211 (1980).

    Google Scholar 

  54. C. Gailly, P. Sandra, M. Verzele, and C. Cocito, Eur. J. Biochem.,125, 83 (1982).

    Google Scholar 

  55. M. Y. H. Wong and G. R. Gray, J. Biol. Chem.,254, 5741 (1979).

    Google Scholar 

  56. P. A. Steck, B. A. Schwartz, M. S. Rosendahl, and G. R. Gray, J. Biol. Chem.,253, 5625 (1978).

    Google Scholar 

  57. M. Y. H. Wong, P. A. Steck, and G. R. Gray, J. Biol. Chem.,254, 5734 (1979).

    Google Scholar 

  58. T. Kusaka, K. Kohsaka, Y. Fukuishi, and H. Akimori, Int. J. Leprosy,49, 406 (1981).

    Google Scholar 

  59. D. E. Minnikin, I. G. Hutchinson, A. B. Caldicott, and M. Goodfellow, J. Chromatogr.,188, 221 (1980).

    Google Scholar 

  60. M. Goodfellow and D. E. Minnikin, Tubercle,62, 285 (1981).

    Google Scholar 

  61. B. M. Ridell, M. Goodfellow, D. E. Minnikin, S. M. Minnikin, and I. G. Hutchinson, J. Gen. Microbiol.,128, 1299 (1982).

    Google Scholar 

  62. D. F. Gerson, D. G. Coper, B. Ramsay, and J. E. Zajic, Can. J. Microbiol.,26, 1498 (1980).

    Google Scholar 

  63. E. Rafidinarivo, A. Savagnac, C. Lacave, and J.-C. Promé, Biochim. Biophys. Acta,711, 266 (1982).

    Google Scholar 

  64. J. Julák, F. Turechec, and Z. Miková, J. Chromatogr.,190, 183 (1980).

    Google Scholar 

  65. A. Kretschmer, H. Bock, and F. Wagner, Appl. Enviorn. Microbiol.,44, 864 (1982).

    Google Scholar 

  66. H. Bloch, J. Exp. Med.,91, 197 (1950).

    Google Scholar 

  67. P. Rapp, H. Bock, V. Wray, and F. Wagner, J. Gen. Microbiol.,115, 491 (1979).

    Google Scholar 

  68. M. T. Pommier and G. Michel, Chem. Phys. Lipids,24, 149 (1979).

    Google Scholar 

  69. S. G. Batrakov, O. A. Mukhitdinova, T. V. Koronelli, and L. D. Bergel'son, Bioorg. Khim.,5, 83 (1979).

    Google Scholar 

  70. G. Puzo, G. Tissié, C. Lacave, H. Aurelle, and J.-C. Promé, Biomed. Mass Spectrom.,5, 699 (1978).

    Google Scholar 

  71. K. Takayama, and E. L. Armstrong, Biochemistry,15, 441 (1976).

    Google Scholar 

  72. S. G. Batrakov, O. A. Mukhitdinova, L. D. Bergel'son, and T. V. Koronelli, Bioorg. Khim.,5, 1495 (1979).

    Google Scholar 

  73. E. Vilkas and A. Rojas, Bull. Soc. Chim. Biol.,46, 689 (1964).

    Google Scholar 

  74. H. Tabaud, H. Tisnovska, and E. Volkas, Biochimie,53, 55 (1971).

    Google Scholar 

  75. S. G. Batrakov, B. V. Rozynov, T. V. Koronelli, and L. D. Bergelson, Chem. Phys. Lipids,29, 241 (1981).

    Google Scholar 

  76. G. Puzo, G. Tissié, H. Aurelle, C. Lacave, and J.-C. Promé, Eur. J. Biochem.,98, 99 (1979).

    Google Scholar 

  77. G. Puzo, H. Aurelle, C. Lacave, and J.-C. Promé, Adv. Mass Spectrom.,8B, 1283 (1980).

    Google Scholar 

  78. C. P. Asselineau, H. L. Montrozier, J.-C. Promé, A. M. Savagnac, and M. Welby, Eur. J. Biochem.,28, 102 (1972).

    Google Scholar 

  79. M. B. Goren, O. Brokl, B. C. Das, and E. Lederer, Biochemistry,10, 72 (1971).

    Google Scholar 

  80. M. B. Goren, O. Brokl, P. Roller, H. M. Fales, and B. C. Das, Biochemistry,15, 2728 (1976).

    Google Scholar 

  81. M. B. Goren, B. C. Das and O. Brokl, Nouv. J. Chim.,2, 379 (1978).

    Google Scholar 

  82. S. G. Batrakov, B. V. Rozynov, T. V. Koronelli, R. A. Kozhukhova, and L. D. Bergel'son, Bioorg. Khim.,3, 55 (1977).

    Google Scholar 

  83. N. Shaw and F. Dinglinger, Biochem. J.,109, 700 (1968).

    Google Scholar 

  84. N. Shaw and F. Dinglinger, Biochem. J.,112, 769 (1969).

    Google Scholar 

  85. A. E. Stepanov and V. I. Shvets, Usp. Biol. Khim.,20, 152 (1979).

    Google Scholar 

  86. M.-T. Pommier and G. Michel, Biochim. Biophys. Acta,441, 327 (1976).

    Google Scholar 

  87. M.-T. Pommier and G. Michel, Eur. J. Biochem.,118, 329 (1981).

    Google Scholar 

  88. P. J. Brennan, D. P. Lehane, and D. W. Thomas, Eur. J. Biochem.,13, 117 (1970).

    Google Scholar 

  89. S. Itoh, and T. Suzuki, Agr. Biol. Chem.,38, 1443 (1974).

    Google Scholar 

  90. T. Suzuki, H. Tanaka, and S. I. Itoh, Agr. Biol. Chem.,38, 557 (1974).

    Google Scholar 

  91. J. O. Kilburn, K. Takayama, and E. L. Armstrong, Biochem. Biophys. Res. Commun.,108, 132 (1982).

    Google Scholar 

  92. J. O. Kilburn and K. Takayama, Antimicrob. Agents Chemother.20, 401 (1981).

    Google Scholar 

  93. R. W. Walker, J.-C. Promé, and C. Lacave, Biochim. Biophys. Acta326, 52 (1973).

    Google Scholar 

  94. A. Ahibo-Coffy, H. Aurelle, C. Lacave, J.-C. Promé, G. Puzo, and A. Savagnac, Chem. Phys. Lipids,22, 185 (1978).

    Google Scholar 

  95. A. Ahibo-Coffy and J.-C. Promé, Tetrahedron Lett., 1503 (1976).

  96. H. Bloch and H. Noll, J. Exp. Med.,92, 1 (1953).

    Google Scholar 

  97. G. Middlebrook, C. Coleman and W. B. Schaefer, Proc. Natl. Acad. Sci., USA45, 1801 (1959).

    Google Scholar 

  98. F. C. Winder, J. Tighe, and P. J. Brennan, J. Gen. Microbiol.,73, 539 (1972).

    Google Scholar 

  99. M. Kato, Arch. Biochem. Biophys.,140, 379 (1970).

    Google Scholar 

  100. M. Kato, J. Bacteriol.,101, 709 (1970).

    Google Scholar 

  101. M. Kato and J. Maeda, Infect. Immun.,9, 8 (1974).

    Google Scholar 

  102. M. Kato and J. Asselineau, Eur. J. Biochem.,22, 364 (1971).

    Google Scholar 

  103. J. Asselineau and M. Kato, Biochemie,55, 559 (1973).

    Google Scholar 

  104. J. Asselineau and M. Kato, Japan J. Med. Sci. Biol.,28, 94 (1975).

    Google Scholar 

  105. R. Toubiana, B. C. Das, J. De Faye, B. Mompon, and M. J. Toubiana, Carbohydr. Res.,44, 308 (1975).

    Google Scholar 

  106. R. Toubiana, E. Ribi, C. McLaughlin, and S. M. Strain, Cancer Immunol. Immunother.,2, 189 (1977).

    Google Scholar 

  107. M. Kato, T. Tamura, G. Silve, and J. Asselineau, Eur. J. Biochem.,87, 497 (1978).

    Google Scholar 

  108. E. Durand, M. Gillois, J. F. Tocanne, and G. Lanéelle, Eur. J. Biochem.,94, 110 (1979).

    Google Scholar 

  109. J. Asselineau, E. Durand, G. Lanéelle, J.-M. Rouanet, and J.-F. Tocanne, Z. Bakt. Mikrobiol. Hyg. 1 Abt., Suppl. 11, 407 (1981).

    Google Scholar 

  110. J.-F. Tocanne and G. Lanéelle, Colloq. Natl. CNRS, No. 938, 111 (1979).

  111. M. B. Goren and K.-S. Jiang, Chem. Phys. Lipids,25, 209 (1979).

    Google Scholar 

  112. M. Kato, Am. Rev. Respirat. Diseases,100, 47 (1969).

    Google Scholar 

  113. G. Lanéellee and J.-F. Tocanne, Eur. J. Biochem.,109, 177 (1980).

    Google Scholar 

  114. R. Saito, A. Tanaka, K. Sugiyama, and M. Kato, Am. Rev. Respir. Dis.,112, 578 (1975).

    Google Scholar 

  115. A. Adam, R. Giorbaru, J.-F. Petit, and E. Lederer, Proc. Natl. Acad. Sci. USA,69, 851 (1972).

    Google Scholar 

  116. E. Durand, M. Welby, G. Lanéelle, and J.-F. Tocanne, Eur. J. Biochem.,93, 103 (1979).

    Google Scholar 

  117. E. Lederer, J. Med. Chem.,23, 103 (1980).

    Google Scholar 

  118. M. B. Goren, Am. Rev. Respir. Dis.,125, 50 (1982).

    Google Scholar 

  119. M. Kato, Infect. Immun.,5, 203 (1972).

    Google Scholar 

  120. M. Kato, Infect. Immun.,7, 9 (1973).

    Google Scholar 

  121. M. Kato, Infect. Immun.,7, 14 (1973).

    Google Scholar 

  122. Z. Reggiardo, E. Vazquez, and L. Schnaper, J. Immunol. Method.,34, 35 (1980).

    Google Scholar 

  123. A. Bekierkunst, E. Yarkoni, I. Flecher, S. Morecki, E. Vilkas, and E. Lederer, Infect. Immun.,4, 256 (1971).

    Google Scholar 

  124. R. Saito, S. Nagao, M. Takamoto, K. Sugiyama, and A. Tanaka, Infect. Immunol.,16, 725 (1977).

    Google Scholar 

  125. R. Saito, A. Tanaka, K. Sugiyama, I. Azuma, Y. Yamamura, M. Kato, and M. B. Goren, Infect. Immun.,13, 776 (1976).

    Google Scholar 

  126. M. Parant, F. Audibert, F. Parant, L. Chedid, E. Soler, J. Polonsky, and E. Lederer, Infect. Immunol.,20, 12 (1978).

    Google Scholar 

  127. L. F. Woodward, N. M. Toone, and C. A. McLaughlin, Infect. Immun.,30, 409 (1980).

    Google Scholar 

  128. D. L. Granger, K.-I. Yamamoto, and E. Ribi, J. Immunol.,116, 482 (1976).

    Google Scholar 

  129. T. J. Meyer, E. E. Ribi, and I. Azuma, Cell. Immunol.,16, 11 (1975).

    Google Scholar 

  130. Z. Reggiardo, and A. K. M. Shamsuddin, Infect. Immun.,14, 1369 (1976).

    Google Scholar 

  131. E. Yarkoni, L. Wang, and A. Bekierkunst, Infect. Immun.,16, 1 (1977).

    Google Scholar 

  132. V. D. Remanthan, J. Curtius, and J. L. Turk, Infect. Immun.,29, 30 (1980).

    Google Scholar 

  133. F. Kierszenbaum, and D. R. Walz, Infect. Immun.,33, 115 (1981).

    Google Scholar 

  134. E. Jarkoni and A. Bekierkunst, Infect. Immun.,14, 1125 (1976).

    Google Scholar 

  135. E. E. Ribi, K. C. Milner, D. L. Granger, M. T. Kelly, K. Yamamoto, W. Brehmer, R. Parker, R. E. Smith, and S. M. Strain, Ann. N. Y. Acad. Sci.,227, 228 (1976).

    Google Scholar 

  136. M. Parant, E. Parant, L. Chedid, J.-C. Drapier, J.-F. Petit, J. Wietzerbin, and E. Lederer, J. Infect. Dis.,135, 771 (1977).

    Google Scholar 

  137. E. Lederer, Biochem. Parasit. Proc. Satell. Conf. 13th. Meet. Fed. Eur. Biochem., Soc (FEBS), Jerusalem (1980), Oxford, (1981), p. 205.

  138. A. Bekierkunst, I. S. Levij, E. Yarkoni, E. Vilkas, and E. Lederer, Science,174, 1240 (1971).

    Google Scholar 

  139. A. Bekierkunst, L. Wang. R. Toubiana, and E. Lederer, Infect. Immun.,10, 1044 (1974).

    Google Scholar 

  140. I. Azuma, E. E. Ribi, T. J. Meyer, and B. Zbar, J. Natl. Cancer Inst.,52, 95 (1974).

    Google Scholar 

  141. T. J. Meyer, E. E. Ribi, I. Azuma, and B. Zbar, J. Natl. Cancer. Inst.,52, 103 (1974).

    Google Scholar 

  142. A. Bekierkunst, Int. J. Cancer,16, 442 (1975).

    Google Scholar 

  143. C. Leclerk, A. Lamensans, L. Chedid, J.-C. Drapier, J.-F. Petit, J. Wietzerbin, and E. Lederer, Cancer Immunol. Immunother.,1, 227 (1976).

    Google Scholar 

  144. E. Ribi, K. Takayama, K. Milner, G. R. Gray, M. B. Goren, R. Parker, C. McLaughlin, and M. Kelly, Cancer Immunol. Immunother.,1, 265 (1976).

    Google Scholar 

  145. E. Yarkoni, M. S. Meltzer, and H. J. Rapp, Int. J. Cancer,19, 818 (1977).

    Google Scholar 

  146. E. E. Ribi, D. L. Granger, K. C. Milner, and S. M. Strain, J. Natl. Cancer Inst.,55, 1253 (1975).

    Google Scholar 

  147. E. Yarkoni, and H. J. Rapp, Infect. Immun.,18, 552 (1977).

    Google Scholar 

  148. E. Yarkoni and H. J. Rapp, Infect. Immun.,20, 856 (1978).

    Google Scholar 

  149. G. Retzinger, S. Meredith, K. Takayama, T. Hunter, and F. Kézdy, J. Biol. Chem.,256, 8208 (1981).

    Google Scholar 

  150. G. S. Retzinger, S. C. Meredith, R. L. Hunter, K. Takayama, F. J. Kézdy, J. Immunol.,129, 735 (1982).

    Google Scholar 

  151. E. E. Ribi, T. Toubiana, S. M. Strain, K. C. Milner, C. McLaughlin, J. Cantrell, I. Azuma, B. C. Das, and R. Parker, Cancer Immunol. Immunother.,3, 171 (1978).

    Google Scholar 

  152. E. Yarkoni, H. J. Rapp, J. Polonsky, and E. Lederer, Int. J. Cancer,22, 564 (1978).

    Google Scholar 

  153. E. Yarkoni, H. J. Rapp, P. Polonsky, J. Varenne, and E. Lederer, Infect. Immun.,26, 462 (1979).

    Google Scholar 

  154. G. P. Youmans, in: Tuberculosis, G. P. Youmans, ed., Saunders, Philadelphia (1979), p. 46.

    Google Scholar 

  155. E. Yarkoni, M. B. Goren, and H. J. Rapp, Infect. Immun.,24, 586 (1979).

    Google Scholar 

  156. M. B. Goren and O. Brokl, Infect. Immun.,9, 142 (1974).

    Google Scholar 

  157. M. B. Goren, J. M. Grange, V. R. Aber, B. W. Allen, and D. A. Mitchison, Brit. J. Exp. Pathol.,63, 693 (1982).

    Google Scholar 

  158. M. Barber, P. Jolles, E. Vilkas, and E. Lederer, Biochem. Biophys. Res. Commu.,18, 469 (1965).

    Google Scholar 

  159. G. Lanéelle, J. Asselineau, W. A. Wolstenholme, and E. Lederer, Bull. Soc. Chim. Fr., 2133 (1965).

  160. M. Guinand and G. Michel, Biochim. Biophys. Acta,125, 75 (1966).

    Google Scholar 

  161. M. Ptak, A. Heitz, M. Guinand, and G. Michel, Biochem. Biophys. Res. Commun.,94, 1311 (1980).

    Google Scholar 

  162. M. Guinand, M. J. Vacheron, G. Michel, B. C. Das, E. Lederer, Tetrahedron, Suppl.,7, 271 (1966).

    Google Scholar 

  163. M. Guinand, G. Michel, B. C. Das, and E. Lederer, Vietnam. Chim. Acta,37, 1966.

  164. S. G. Batrakov, B. V. Muratov, L. D. Bergel'son, and T. V. Koronelli, Bioorg. Khim.,7, 1075 (1981).

    Google Scholar 

  165. S. G. Batrakov, V. B. Muratov, O. S. Reshetova, B. V. Rozynov, L. D. Bergel'son, and T. V. Koronelli, Bioorg. Khim.,7, 563 (1981).

    Google Scholar 

  166. S. G. Batrakov, V. B. Muratov, B. V. Rozynov, L. D. Bergel'son, and T. V. Koronelli, Bioorg. Khm.,7, 1087 (1981).

    Google Scholar 

  167. D. G. Cooper, J. E. Zajic, and D. F. Gerson, Appl. Environ. Microbiol.,37, 4 (1979).

    Google Scholar 

  168. M. Bodansky, G. P. Sigler, and A. Bodansky, J. Am. Chem. Soc.,95, 2352 (1973).

    Google Scholar 

  169. M. Nakajima, M. Inukai, T. Haneishi, A. Terahara, M. Arai, T. Kinoshita, and C. Tamura, J. Antibiot.,31, 426 (1978).

    Google Scholar 

  170. M. Nishii, T. Kihara, K. Isono, T. Higashijima, T. Miyazawa, S. K. Sethi, and J. A. McCloskey, Tetrahedron Lett.,21, 4627 (1980).

    Google Scholar 

  171. E. Vilkas, A. Rojas, and E. Lederer, C. R. Acad. Sci., Paris, Ser. C,261, 4258 (1965).

    Google Scholar 

  172. G. Lanéelle, and J. Asselineau, Eur. J. Biochem.,5, 487 (1968).

    Google Scholar 

  173. P. J. Brennan, M. Souhrada, B. Ullom, J. K. McClatchy, M. B. Goren, J. Clin. Microbiol.,8, 374 (1978).

    Google Scholar 

  174. P. J. Brennan and M. B. Goren, J. Biol. Chem.,254, 4205 (1979).

    Google Scholar 

  175. G. Lanéelle, J. Asselineau and G. Chamoiseau, FEBS Lett.,19, 109 (1971).

    Google Scholar 

  176. A. Voiland, M. Bruneteau, and G. Michel, Eur. J. Biochem.,21, 285 (1971).

    Google Scholar 

  177. E. Vilkas, C. R. Acad. Sci. Paris, Ser. C,262, 786 (1966).

    Google Scholar 

  178. E. Vilkas, A. Rojas, B. C. Das, W. A. Wolstenholm, and E. Lederer, Tetrahedron Lett.,22, 2809 (1966).

    Google Scholar 

  179. E. Vilkas, E. Lederer, and J. Massot, Tetrahedron Lett.,26, 3089 (1968).

    Google Scholar 

  180. E. Vilkas, C. Gros, and J. C. Massot, C. R. Acad. Sci., Paris, Ser. C,266, 837 (1968).

    Google Scholar 

  181. M. Chaput, G. Michel, and E. Lederer, Biochim. Biophys. Acta,63, 310 (1962).

    Google Scholar 

  182. K.-S. Kim, M. R. Salton, and L. Barksdale, J. Bacteriol.,125, 739 (1976).

    Google Scholar 

  183. W. B. Schaefer, Methods Microbiol.,13, 323 (1979).

    Google Scholar 

  184. E. Wolinsky and W. B. Schaefer, Int. J. Syst. Bacteriol.,23, 182 (1973).

    Google Scholar 

  185. M. Rennikey and D. J. Dowson, Appl. Microbiol.,26, 470 (1973).

    Google Scholar 

  186. W. W. Barrow, B. P. Ullom, and P. J. Brennan, J. Bacteriol.,144, 814 (1980).

    Google Scholar 

  187. P. J. Brennan, H. Mayer, G. O. Aspinall, and J. E. Nam Shin, Eur. J. Biochem.,115, 7 (1981).

    Google Scholar 

  188. P. J. Brennan, G. O. Aspinall, and J. E. Nam Shin, J. Biol. Chem.,256, 6817 (1981).

    Google Scholar 

  189. S.-I. Hakomori and A. Kobata, Antigens,2, 79 (1974).

    Google Scholar 

  190. P. J. Brennan, M. Heifets, and B. P. Ullom, J. Clin. Microbiol.,15, 447 (1982).

    Google Scholar 

  191. E. Wolinsky, Am. Rev. Respir. Dis.,119, 107 (1979).

    Google Scholar 

  192. P. Draper, J. Gen. Microbiol.,83, 431 (1974).

    Google Scholar 

  193. W. W. Barrow and P. J. Brennan, J. Bacteriol.,150, 381 (1982).

    Google Scholar 

  194. M. D. Yoshizumi, and A. K. Asbury, Acta Neuropathol.,24, 1 (1974).

    Google Scholar 

  195. P. Draper and R. J. W. Rees, Nature (London),228, 860 (1970).

    Google Scholar 

  196. P. Draper and R. J. W. Rees, J. Gen. Microbiol.,77, 79 (1974).

    Google Scholar 

  197. J. S. Stanford, J. Med. Microbiol.,6, 435 (1973).

    Google Scholar 

  198. P. J. Brennan and W. W. Barrow, Int. J. Leprosy,48, 382 (1980).

    Google Scholar 

  199. A. Furuchi and T. Tokunaga, J. Bacteriol.,111, 404 (1972).

    Google Scholar 

  200. M. B. Goren, J. K. McClatchy, B. Martens and O. Brokl. J. Virol.,9, 999 (1972).

    Google Scholar 

  201. T. Tokunaga, M. I. Sellers, and A. Furuchi, in: Host-Virus Relationships in Mycobacteria, Nocardia, and Actinomyces, S. E. Juhasz, and G. Plummer, eds., C. C. Thomas, Springfield (1970), p. 119.

    Google Scholar 

  202. H. Noll, J. Biol. Chem.,224, 149 (1957).

    Google Scholar 

  203. H. Bloch, I. Defaye, E. Lederer, and H. Noll, Biochim. Biophys. Acta23, 312 (1957).

    Google Scholar 

  204. C. L. Silva and T. Ioneda, Chem. Phys. Lipids,27, 43 (1980).

    Google Scholar 

  205. C. L. Silva and T. Ioneda, Rev. Microbiol., (S. Paulo),8, 39 (1977).

    Google Scholar 

  206. C. L. Silva, and T. Ioneda, Chem. Phys. Lipids,20, 217 (1977).

    Google Scholar 

  207. T. Ioneda and C. L. Silva, Chem. Phys. Lipids,25, 85 (1979).

    Google Scholar 

  208. C. L. Silva, J. L. Gesztesi, M. C. Zupo, M. Breda, and T. Ioneda, Chem. Phys Lipids,26, 197 (1980).

    Google Scholar 

Download references

Authors
  1. S. G. Batrakov
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

Institute of Immunology, Ministry of Public Health of the USSR, Moscow. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 147–172, March–April, 1985.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Batrakov, S.G. Specific lipids of mycobacteria and related organisms. Chem Nat Compd 21, 137–159 (1985). https://doi.org/10.1007/BF00714900

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00714900

Keywords

Search

Navigation