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Bioproducts pp 53-93 | Cite as

Extracellular microbial lipids as biosurfactants

  • Dieter Haferburg
  • Rolf Hommel
  • Reiner Claus
  • Hans-Peter Kleber
Conference paper
Part of the Advances in Biochemical Engineering/Biotechnology book series (ABE, volume 33)

Abstract

During the past 10 years there have been rapid developments in the detection and characterization of surface-active agents formed by bacteria, yeasts and fungi. The present paper reviews the available information on microbial processes which result in the formation of such compounds — biosurfactants —, i.e. appropriate conditions as well as the known chemical structures and physico-chemical properties of isolated biosurfactants. The physiological importance of extracellular surface-active compounds is discussed, particularly with respect to their possible role in the microbial degradation of water-insoluble carbon-sources and their possible biocidic effects. A survey on commercial applications is given and conclusions for further research work are presented.

Keywords

Biosurfactant Production Critical Micelle Concentration Mycolic Acid Extracellular Lipid Phase Inversion Temperature 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

Nomenclature and Definitions

AMP

adenosine-5′-monophosphate

CoA

coenzyme A

NAD+

nicotinamide adenine dinucleotide (oxidized)

TDP

thymidine-5′-diphosphate

UDP

uridine-5′-diphosphate

CMC

critical micelle concentration

C∶N

carbon-nitrogen ratio in growth medium

C∶P

carbon-phosphate ratio in growth medium

EOR

enhanced oil recovery

HLB

hydrophile-lipophile balance

PIT

phase inversion temperature

o/w

oil-in-water emulsion

w/o

water-in-oil emulsion

γi

interfacial tension

γs

surface tension

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References

  1. 1.
    Gerson, D. F., Zajic, J. E.: Process Biochem. 10, 20 (1979)Google Scholar
  2. 2.
    Layman, P. L.: Chem. Eng. News 60, 13 (1982)Google Scholar
  3. 3.
    Diekmann, H.: Nukleotid-Fermentationen mit Brevibacterium ammoniagenes, in: Fermentation (ed. Lafferty, R. M.) p. 121, Wien: Springer Verlag 1981Google Scholar
  4. 4.
    Bartha, R., Atlas, R. M.: Adv. Appl. Microbiol. 22, 225 (1977)PubMedGoogle Scholar
  5. 5.
    Cooney, J. J., Summers, R. J.: Hydrocarbon-using microorganisms in three freshwater ecosystems, in: Proc. of the IIIrd Intern. Biodegr. Symp. (eds. Sharpley, J. M., Kaplan, A. M.) p. 141, London: Applied Sciences Publishers 1976Google Scholar
  6. 6.
    Austin, B. et al.: Appl. Environ. Microbiol. 34, 60 (1977)PubMedGoogle Scholar
  7. 7.
    Polyakova, J. M.: Mikrobiologija 31, 1076 (1962)Google Scholar
  8. 8.
    Atlas, R. M. et al.: in: Proceedings of the Symp. on Assessment of the Environ. Impact of Accidental Oil Spills in the Oceans. Ann Arbor: Science Publ. 1980Google Scholar
  9. 9.
    Bhosle, N. B., Mavinkurve, S.: Marine Environ. Res. 4, 53 (1980)CrossRefGoogle Scholar
  10. 10.
    Platpira, W. P.: Latvijas PSR Zinatum Akademijas Vestis 3, 80 (1982)Google Scholar
  11. 11.
    Jarvis, F. G., Johnson, M. J.: J. Am. Chem. Soc. 71, 4124 (1949)CrossRefGoogle Scholar
  12. 12.
    Tulloch, A. P., Spencer, J. F. T.: Can. J. Chem. 42, 830 (1964)Google Scholar
  13. 13.
    Tulloch, A. P. et al.: ibid. 40, 1326 (1960)Google Scholar
  14. 14.
    Tulloch, A. P., Spencer, J. F. T.: ibid. 46, 1523 (1968)Google Scholar
  15. 15.
    Gorin, P. A. J., Spencer, J. F. T., Tulloch, A. P.: ibid. 39, 846 (1961)Google Scholar
  16. 16.
    Cooper, D. G., Zajic, J. E.: Adv. Appl. Microbiol. 26, 229 (1980)Google Scholar
  17. 17.
    Suzuki, T., Tanaka, H., Itoh, S.: Agric. Biol. Chem. 38, 557 (1974)Google Scholar
  18. 18.
    Itoh, S., Suzuki, T.: ibid. 38, 1443 (1974)Google Scholar
  19. 19.
    Gerson, D. F., Zajic, J. E.: Antonie van Leeuwenhoek 45, 81 (1979)CrossRefPubMedGoogle Scholar
  20. 20.
    Macdonald, C. R., Cooper, D. G., Zajic, J. E.: Appl. Environ. Microbiol. 41, 117 (1981)Google Scholar
  21. 21.
    Duvnjak, Z. et al.: Biotech. Bioeng. 24, 165 (1982)CrossRefGoogle Scholar
  22. 22.
    Margaritis, A., Zajic, J. E., Gerson, D. F.: ibid. 21, 1151 (1979)CrossRefGoogle Scholar
  23. 23.
    Akit, J. et al.: Current Microbiol. 6, 145 (1981)CrossRefGoogle Scholar
  24. 24.
    Cooper, D. G., Zajic, J. E., Gerson, D. F.: Appl. Environ. Microbiol. 37, 4 (1979)PubMedGoogle Scholar
  25. 25.
    Wagner, F., Bock, H., Kretschmer, A.: Gewinnung von Tensiden mit n-Alkan-oxidierenden Mikroorganismen, in: Fermentation (ed. Lafferty, R. M.) p. 181, Wien: Springer Verlag 1981Google Scholar
  26. 26.
    Lederer, E.: Angew. Chem. 72, 372 (1960)Google Scholar
  27. 27.
    Asselineau, J.: The Bacterial Lipids, San Francisco: Holden-Day 1966Google Scholar
  28. 28.
    Cundell, A. M.: Develop. Ind. Microbiol. 15, 250 (1974)Google Scholar
  29. 29.
    Mulkins-Philipps, G. J. et al.: Can. J. Microbiol. 20, 955 (1974)PubMedGoogle Scholar
  30. 30.
    Pareilleux, A.: Eur. J. Appl. Microbiol. Biotechnol. 8, 91 (1979)CrossRefGoogle Scholar
  31. 31.
    Illarionova, V. J. et al.: Mikrobiologija 53, 423 (1984)Google Scholar
  32. 32.
    Käppeli, O.: Ph. D. Thesis, Diss. No. 5661 E.T.H. Zürich (1976)Google Scholar
  33. 33.
    Reddy, P. G. et al.: Biotech. Bioeng. 25, 387 (1983)CrossRefGoogle Scholar
  34. 34.
    Itoh, S., Suzuki, T.: Agric. Biol. Chem. 36, 2233 (1972)Google Scholar
  35. 35.
    Hisatsuka, K. et al.: ibid. 35, 684 (1971)Google Scholar
  36. 36.
    Hisatsuka, K. et al.: ibid. 35, 686 (1971)Google Scholar
  37. 37.
    Hisatsuka, K. et al.: ibid. 36, 1361 (1972)Google Scholar
  38. 38.
    Hisatsuka, K. et al.: ibid. 41, 445 (1977)Google Scholar
  39. 39.
    Yamaguchi, M.: Chem. Ind. 17, 741 (1976)Google Scholar
  40. 40.
    Burger, M. M., Glaser, L., Burton, R. M.: J. Biol. Chem. 238, 2595 (1963)PubMedGoogle Scholar
  41. 41.
    Hauser, G. et al.: Fed. Proc. 12, 215 (1953)Google Scholar
  42. 42.
    Hauser, G. et al.: J. Bacteriol. 68, 645 (1954)CrossRefPubMedGoogle Scholar
  43. 43.
    Guerra-Santos, L., Käppeli, O., Fiechter, A.: Appl. Environ. Microbiol. 48, 301 (1984)PubMedGoogle Scholar
  44. 44.
    Haferburg, D. et al.: DD-WP 269 261 2, 08. 11. 1984Google Scholar
  45. 45.
    Syldatk, C. et al.: Z. Naturforsch. 40c, 61 (1985)Google Scholar
  46. 46.
    Li, Z. Y. et al.: Appl. Environ. Microbiol. 48, 610 (1984)Google Scholar
  47. 47.
    Zajic, J. E., Guignard, H., Gerson, D. F.: Biotech. Bioeng. 19, 1285 (1977)CrossRefGoogle Scholar
  48. 48.
    Zajic, J. E., Guignard, H., Gerson, D. F.: ibid. 19, 1303 (1977)CrossRefGoogle Scholar
  49. 49.
    Haurowitz, F.: Fed. Proc. 12, 215 (1953)Google Scholar
  50. 50.
    Tulloch, A. P. et al.: Can. J. Chem. 46, 3337 (1968)Google Scholar
  51. 51.
    Hommel, R. et al.: DD-WP 269 259 8, 08. 11. 1984Google Scholar
  52. 52.
    Botham, P. A., Ratledge, C.: J. Gen. Microbiol. 114, 361 (1979)PubMedGoogle Scholar
  53. 53.
    Tulloch, A. P., Spencer, J. F. T., Deinema, M. H.: Can. J. Chem. 46, 345 (1968)Google Scholar
  54. 54.
    Wickerham, L. J.: J. Bacteriol. 80, 484 (1960)PubMedGoogle Scholar
  55. 55.
    Stodola, F. H., Wickerham, L. J.: J. Biol. Chem. 235, 2584 (1960)Google Scholar
  56. 56.
    Takahara, Y. et al.: Agric. Biol. Chem. 40, 1901 (1976)Google Scholar
  57. 57.
    Cooper, D. G. et al.: Appl. Environ. Microbiol. 42, 408 (1981)Google Scholar
  58. 58.
    Arima, K., Kakinuma, A., Tamura, G.: Biochem. Biophys. Res. Commun. 31, 488 (1968)CrossRefPubMedGoogle Scholar
  59. 59.
    Kakinuma, A. et al.: Agric. Biol. Chem. 33, 971 (1969)Google Scholar
  60. 60.
    Kakinuma, A. et al.: ibid. 33, 973 (1969)Google Scholar
  61. 61.
    Weinberg, E. D.: Adv. Microbial Physiology 4, 1 (1970)Google Scholar
  62. 62.
    Kawashima, H. et al.: J. Ferment. Technol. 61, 143 (1983)Google Scholar
  63. 63.
    Deml, G. et al.: Phytochemistry 19, 83 (1980)CrossRefGoogle Scholar
  64. 64.
    Okazaki, H. et al.: Agric. Biol. Chem. 33, 764 (1969)Google Scholar
  65. 65.
    La Riviere, J. W. M.: Antonie van Leeuwenhoek 21, 1 (1955)PubMedGoogle Scholar
  66. 66.
    Knoche, H. W., Shiveley, J. M.: J. Biol. Chem. 247, 170 (1972)PubMedGoogle Scholar
  67. 67.
    Tahara, Y. et al.: Agric. Biol. Chem. 40, 243 (1976)Google Scholar
  68. 68.
    Kawanami, J. et al.: Chem. Phys. Lipids 7, 159 (1971)CrossRefPubMedGoogle Scholar
  69. 69.
    Käppeli, O., Finnerty, W. R.: J. Bacteriol. 140, 707 (1979)PubMedGoogle Scholar
  70. 70.
    Käppeli, O., Finnerty, W. R.: Biotech. Bioeng. 22, 495 (1980)CrossRefGoogle Scholar
  71. 71.
    Biotechnology A.G.: JP-P. 80, 112, 201; 29. 08. 1980Google Scholar
  72. 72.
    Zuckerberg, A. et al.: Appl. Environ. Microbiol. 37, 414 (1979)PubMedGoogle Scholar
  73. 73.
    Rosenberg, E. et al.: ibid. 37, 409 (1979)PubMedGoogle Scholar
  74. 74.
    Rosenberg, E. et al.: ibid. 37, 402 (1979)PubMedGoogle Scholar
  75. 75.
    Kessler, R. E.: J. Bacteriol. 137, 869 (1979)PubMedGoogle Scholar
  76. 76.
    Wicken, A. J., Knox, K. W.: Biochim. Biophys. Acta 604, 1 (1980)PubMedGoogle Scholar
  77. 77.
    Kosaric, N., Gray, N. C. C., Cairns, W. L.: Microbial emulsifiers and de-emulsifiers, in: Biotechnology Vol. 3, p. 575, Weinheim: Verlag Chemie 1983Google Scholar
  78. 78.
    Tanaka, A. et al.: J. Ferment. Technol. 46, 468 (1968)Google Scholar
  79. 79.
    Edwards, J. R., Hayashi, J. A.: Arch. Biochem. Biophys. 111, 415 (1965)CrossRefPubMedGoogle Scholar
  80. 80.
    Hirayama, T., Kato, J.: FEBS Lett. 139, 81 (1982)CrossRefGoogle Scholar
  81. 81.
    Jones, D. F.: J. Chem. Soc. (C) 479 (1967)Google Scholar
  82. 82.
    Jones, D. F., Howe, R.: ibid. 2801 (1968)Google Scholar
  83. 83.
    Jones, D. F.: J. Chem. Soc. 2809 (1968)Google Scholar
  84. 84.
    Jones, D. F., Howe, R.: ibid. 2816 (1968)Google Scholar
  85. 85.
    Jones, D. F., Howe, R.: ibid. 2827 (1968)Google Scholar
  86. 86.
    Tulloch, A. P., Spencer, J. F. T., Deinema, M. H.: Can. J. Chem. 46, 345 (1968)Google Scholar
  87. 87.
    Frautz, B., Lang, S., Wagner, F.: Eur. Cong. Biotech. 3rd, Abstracts I-79 (1984)Google Scholar
  88. 88.
    Anderson, R. J., Newman, M.: J. Biol. Chem. 101, 499 (1933)Google Scholar
  89. 89.
    Wilkinson, S. G.: Biochim. Biophys. Acta 270, 1 (1972)PubMedGoogle Scholar
  90. 90.
    Tahara, Y., Yamada, Y., Kondo, K.: Agric. Biol. Chem. 40, 1449 (1976)Google Scholar
  91. 91.
    Tahara, Y., Yamada, Y., Kondo, K.: ibid. 39, 2261 (1975)Google Scholar
  92. 92.
    Beebe, J. L., Umbreit, W.: J. Bacteriol. 108, 612 (1971)PubMedGoogle Scholar
  93. 93.
    Thiele, O. W., Oulevey, J., Hunneman, D. H.: Eur. J. Biochem. 139, 131 (1984)CrossRefPubMedGoogle Scholar
  94. 94.
    Bernheimer, A. W., Avigad, L.: J. Gen. Microbiol. 61, 361 (1970)PubMedGoogle Scholar
  95. 95.
    Tahara, J. et al.: Agric. Biol. Chem. 40, 243 (1976)Google Scholar
  96. 96.
    Godchaux, W., Leadbetter, E. R.: J. Biol. Chem. 259, 2983 (1984)Google Scholar
  97. 97.
    Pepoux, T., Michel, G., Decambe, L.: Eur. J. Biochem. 63, 391 (1976)CrossRefPubMedGoogle Scholar
  98. 98.
    Besson, F. et al.: ibid. 77, 61 (1977)CrossRefPubMedGoogle Scholar
  99. 99.
    Walton, R. B. et al.: J. Clin. Invest. 28, 924 (1949)Google Scholar
  100. 100.
    Heinemann, B. et al.: Antibiot. Chemother. 3, 1239 (1953)Google Scholar
  101. 101.
    Cooper, D. G.: J. Bacteriol. 137, 795 (1979)PubMedGoogle Scholar
  102. 102.
    Kretschmer, A., Wagner, F.: Biochim. Biophys. Acta 753, 306 (1983)Google Scholar
  103. 103.
    Lindam, E. et al.: J. Biochem. Microbiol. Technol. Eng. 3, 219 (1961)CrossRefGoogle Scholar
  104. 104.
    Odier, E.: Ann. Microbiol. 127b, 213 (1976)Google Scholar
  105. 105.
    Makula, R. A., Finnerty, W. R.: J. Bacteriol. 112, 398 (1972)PubMedGoogle Scholar
  106. 106.
    Shiio, J. et al.: Agric. Biol. Chem. 35, 2033 (1971)Google Scholar
  107. 107.
    Izuka, H. et al.: J. Gen. Appl. Microbiol. 12, 131 (1966)Google Scholar
  108. 108.
    Uchio, R. et al.: Agric. Biol. Chem. 36, 426 (1972)Google Scholar
  109. 109.
    Abbot, B. J. et al.: Adv. Appl. Microbiol. 14, 249 (1971)PubMedGoogle Scholar
  110. 110.
    Heringa, J. W. et al.: Antonie van Leeuwenhoek 27, 51 (1981)Google Scholar
  111. 111.
    Kester, A. S. et al.: J. Bacteriol. 85, 859 (1963)PubMedGoogle Scholar
  112. 112.
    Siporin, C., Cooney, J. J.: Appl. Microbiol. 29, 604 (1975)PubMedGoogle Scholar
  113. 113.
    Shively, J. M. et al.: J. Bacteriol. 94, 1679 (1967)PubMedGoogle Scholar
  114. 114.
    Nakao, Y. et al.: Agric. Biol. Chem. 37, 2399 (1973)Google Scholar
  115. 115.
    Kikuchi, M., Kanamura, T., Nakao, Y.: ibid. 37, 2405 (1973)Google Scholar
  116. 116.
    Cooper, D. G., Zajic, J. E., Denis, C.: J. Am. Oil Chem. Soc. 58, 77 (1981)Google Scholar
  117. 117.
    Ristau, E., Wagner, F.: Biotechnol. Lett. 5, 95 (1983)CrossRefGoogle Scholar
  118. 118.
    Gerson, D. F., Zajic, J. E.: Dev. Ind. Microbiol. 19, 577 (1978)Google Scholar
  119. 119.
    Zajic, J. E., Knetting, E.: US-P. 3,997,398; 14. 12. 1976Google Scholar
  120. 120.
    Tanaka, K., Suzuki, T.: US-P. 3,637,461; 25. 01. 1972Google Scholar
  121. 121.
    Wagner, F. et al.: US-P. 4,286,660; 01. 09. 1981Google Scholar
  122. 122.
    Zajic, J. E. et al.: US-P. 4,355,109; 19. 10. 1982Google Scholar
  123. 123.
    Spencer, J. F. T. et al.: US-P. 3,445,337; 20. 05. 1969Google Scholar
  124. 124.
    Spencer, J. F. T. et al.: US-P. 3,312,684; 04. 04. 1967Google Scholar
  125. 125.
    Tanaka, K., Suzuki, T.: DE-AS 1,965,975; 31. 01. 1969Google Scholar
  126. 126.
    Tanaka, K., Suzuki, T.: DE-AS 1,905,472; 31. 01. 1969Google Scholar
  127. 127.
    Ito, S. et al.: J. Antibiot. 24, 855 (1971)PubMedGoogle Scholar
  128. 128.
    Esders, T. W., Light, R. J.: J. Biol. Chem. 247, 7494 (1972)PubMedGoogle Scholar
  129. 129.
    Esders, T. W., Light, R. J.: ibid. 247, 1375 (1972)PubMedGoogle Scholar
  130. 130.
    Goldman, D. S., Lornitzo, F. A.: ibid. 237, 3332 (1962)PubMedGoogle Scholar
  131. 131.
    Elbein, A. D.: Adv. Carbohydr. Chem. Biochem. 30, 227 (1974)PubMedGoogle Scholar
  132. 132.
    Loomis, S. H., Madin, K. A. C., Crowe, J. H.: J. Exp. Zoology 211, 311 (1980)CrossRefGoogle Scholar
  133. 133.
    Walker, R. W., Prome, J. C., Lacave, C. S.: Biochim. Biophys. Acta 326, 52 (1973)PubMedGoogle Scholar
  134. 134.
    Kretschmer, A.: Ph.D. Thesis, Techn. Univ. Braunschweig (1981)Google Scholar
  135. 135.
    Ahibo-Coffy, A. et al.: Chem. Phys. Lipids 22, 185 (1978)CrossRefPubMedGoogle Scholar
  136. 136.
    Brennan, P. J., Lehane, D. P., Thomas, D. W.: Eur. J. Biochem. 13, 117 (1970)CrossRefPubMedGoogle Scholar
  137. 137.
    Nakahara, T., Kawashima, H., Tabuchi, T.: in: Advances in Biotechnology (eds. Moo-Young, M., Robinson, C. W., Vecina, C.) Vol. 1, pp. 149–153, Toronto: Pergamon Press 1981Google Scholar
  138. 138.
    Promè, J. C., Walker, R. W., Lacave, C.: Comptes Rendus Acad. Sci. Serie C t. 278, 1065 (1974)Google Scholar
  139. 139.
    Fulco, J. A.: Prog. Lipid Res. 22, 133 (1983)CrossRefPubMedGoogle Scholar
  140. 140.
    Dworkin, M., Keller, K. H., Weisberg, D.: J. Bacteriol. 155, 1367 (1983)PubMedGoogle Scholar
  141. 141.
    Rosenberg, M.: FEMS Microbiol. Lett. 22, 289 (1984)CrossRefGoogle Scholar
  142. 142.
    Egge, H.: in: Etherlipids: Biochemical and Biomedical Aspects, (eds. Mangold, H. K., Paltauf, F.) pp. 141–159, New York: Academic Press 1983Google Scholar
  143. 143.
    Cory, V. F. et al.: Biotech. Bioeng. 13, 825 (1971)CrossRefGoogle Scholar
  144. 144.
    Shennan, J. L., Levi, J. D.: Prog. Ind. Microbiol. 13, 1 (1974)PubMedGoogle Scholar
  145. 145.
    Watkinson, R. J.: in: Hydrocarbons in Biotechnology (eds. Harrison, D. E., Higgins, I. J., Watkinson, R. J.) pp. 11–24, London: Heyden and Son 1980Google Scholar
  146. 146.
    Ratledge, C.: in: Developments in Biodegradation of Hydrocarbons (ed. Watkinson, R. J.) pp. 1–46, London: Appl. Sci. Publ. 1978Google Scholar
  147. 147.
    Levi, J. D., Shennan, J. L., Ebbon, G. P.: Econ. Microbiol. 4, 361 (1979)Google Scholar
  148. 148.
    Miura, Y.: Adv. Biochem. Eng. 9, 31 (1978)Google Scholar
  149. 149.
    Goma, G., Pareilleux, A., Durand, G.: J. Ferment. Technol. 51, 616 (1976)Google Scholar
  150. 150.
    Roy, P. K. et al.: Biotech. Bioeng. 21, 955 (1979)CrossRefGoogle Scholar
  151. 151.
    Mallee, F. M. et al.: ibid. 19, 1793 (1977)CrossRefGoogle Scholar
  152. 152.
    Nakahara, T. et al.: ibid. 19, 9 (1977)CrossRefGoogle Scholar
  153. 153.
    Einsele, A. et al.: Adv. Biochem. Eng. 1, 169 (1971)Google Scholar
  154. 154.
    Kulkarni, K. et al.: Biotech. Bioeng. 21, 337 (1979)CrossRefGoogle Scholar
  155. 155.
    Einsele, A., Blanch, H. D., Fiechter, A.: ibid. Symp. 4, 455 (1973)Google Scholar
  156. 156.
    Milira, Y. et al.: ibid. 19, 701 (1977)CrossRefGoogle Scholar
  157. 157.
    McLee, A. G., Davies, S. L.: Can. J. Microbiol. 18, 315 (1972)PubMedGoogle Scholar
  158. 158.
    Käppeli, O., Fiechter, A.: Biotech. Bioeng. 18, 967 (1974)CrossRefGoogle Scholar
  159. 159.
    Kennedy, R. S. et al.: Arch. Microbiol. 102, 75 (1975)CrossRefPubMedGoogle Scholar
  160. 160.
    Rosenberg, M., Gutnick, D., Rosenberg, E.: FEMS Microbiol. Lett. 9, 29 (1980)CrossRefGoogle Scholar
  161. 161.
    Stuber, W.: Ph.D. Thesis, Karl-Marx-Universität Leipzig (1982)Google Scholar
  162. 162.
    Kefford, B., Kjelleberg, S., Marshall, K.: Arch. Microbiol. 133, 257 (1982)CrossRefGoogle Scholar
  163. 163.
    Miura, Y. et al.: Biotech. Bioeng. 19, 715 (1977)CrossRefGoogle Scholar
  164. 164.
    Mimura, A., Watanabe, S., Takeda, I.: J. Ferment. Technol. 49, 255 (1971)Google Scholar
  165. 165.
    Rosenberg, M., Rosenberg, E., Gutnick, D.: in: Microbial Adhesion to Surfaces (eds. Berkeley, R. C. W., Lynch, J. M., Helling, J., Rutter, P. R., Vincent, E.) Publ. for the Soc. of Chem. Ind. pp. 541–542, London 1980Google Scholar
  166. 166.
    Käppeli, O., Müller, M., Fiechter, A.: J. Bacteriol. 133, 952 (1978)PubMedGoogle Scholar
  167. 167.
    Käppeli, O., Fiechter, A.: ibid. 131, 917 (1977)PubMedGoogle Scholar
  168. 168.
    Rosenberg, M. et al.: Appl. Environ. Microbiol. 44, 929 (1982)Google Scholar
  169. 169.
    Scott, C. C. L., Finnerty, W. R.: J. Bacteriol. 127, 481 (1976)PubMedGoogle Scholar
  170. 170.
    Claus, R., Käppeli, O., Fiechter, A.: J. Gen. Microbiol. 130, 1035 (1984)Google Scholar
  171. 171.
    Tiurin, V. S., Ilchenko, A. P., Dimitriew, V. V.: Mikrobiologija 44, 481 (1975)Google Scholar
  172. 172.
    Petriuevic, S. B., Dovgum, L. I.: ibid. 49, 78 (1980)Google Scholar
  173. 173.
    Aiba, S. et al.: J. Ferment. Technol. 47, 211 (1969)Google Scholar
  174. 174.
    Müller, H. et al.: Z. Allg. Mikrobiol. 23, 645 (1983)Google Scholar
  175. 175.
    Moo-Young, M., Shimizu, T., Whitworth, D. A.: Biotech. Bioeng. 13, 841 (1971)Google Scholar
  176. 176.
    Erickson, L. E., Nakahara, T.: Proc. Biochem. 10, 9 (1975)Google Scholar
  177. 177.
    Gutnick, D. L., Rosenberg, E.: Annu. Rev. Microbiol. 31, 379 (1977)CrossRefPubMedGoogle Scholar
  178. 178.
    Koronelli, T. V.: Acta Biotechnol. 3, 309 (1983)CrossRefGoogle Scholar
  179. 179.
    Zajic, J. E., Panchal, C. J.: CRC Crit. Rev. Microbiol. 5, 39 (1976)PubMedGoogle Scholar
  180. 180.
    Tanaka, A., Fukui, S.: J. Ferment. Technol. 49, 809 (1971)Google Scholar
  181. 181.
    Wang, D. I. C., Ochoa, A.: Biotech. Bioeng. 14, 345 (1972)CrossRefGoogle Scholar
  182. 182.
    Whitworth, D. A., Moo-Young, M., Viswanatha, T.: ibid. 15, 649 (1973)CrossRefGoogle Scholar
  183. 183.
    Chakravarty, M. et al.: ibid. 17, 399 (1975)CrossRefGoogle Scholar
  184. 184.
    Whitworth, D. A.: Compt. Rend. Trav. Lab. Carlsberg 40, 33 (1974)Google Scholar
  185. 185.
    Nakahara, T., Hisatsuka, K., Minoda, V.: J. Ferment. Technol. 59, 415 (1981)Google Scholar
  186. 186.
    Nakahara, T. et al.: ibid. 61, 19 (1983)Google Scholar
  187. 187.
    Hisatsuka, K. et al.: ibid. 39, 999 (1975)Google Scholar
  188. 188.
    Koronelli, T. V., Koharova, T. I., Ignatshenko, A. V.: Mikrobiologija 52, 94 (1983)Google Scholar
  189. 189.
    Banerjee, S., Duttagupta, S., Chakrabarty, A. M.: Arch. Microbiol. 135, 110 (1983)CrossRefGoogle Scholar
  190. 190.
    Inoue, S., Ito, S.: Biotechnol. Lett. 4, 3 (1982)CrossRefGoogle Scholar
  191. 191.
    Ito, S., Inoue, S.: Appl. Environ. Microbiol. 43, 1278 (1982)PubMedGoogle Scholar
  192. 192.
    Ito, S., Kinta, M., Inoue, S.: Agric. Biol. Chem. 44, 2221 (1980)Google Scholar
  193. 193.
    Iguchi, T., Takeda, I., Ohsaiwa, H.: ibid. 33, 1657 (1969)Google Scholar
  194. 194.
    Bayer, E. A., Rosenberg, E., Gutnick, D. L.: J. Gen. Microbiol. 127, 295 (1981)PubMedGoogle Scholar
  195. 195.
    Reddy, P. G. et al.: Biotech. Bioeng. 25, 387 (1983)CrossRefGoogle Scholar
  196. 196.
    Neufeld, R. J., Zajic, J. E., Gerson, D. F.: Appl. Environ. Microbiol. 39, 511 (1980)Google Scholar
  197. 197.
    Rapp, P. et al.: J. Gen. Microbiol. 115, 491 (1979)Google Scholar
  198. 198.
    Kretschmer, A., Bock, H., Wagner, F.: Appl. Environ. Microbiol. 44, 864 (1982)Google Scholar
  199. 199.
    Cooper, D. G., Paddock, D. A.: ibid. 46, 1426 (1983)Google Scholar
  200. 200.
    Cooper, D. G., Paddock, D. A.: ibid. 47, 173 (1984)Google Scholar
  201. 201.
    Al-Dujaili, A. H.: J. Hygiene 77, 211 (1976)Google Scholar
  202. 202.
    Johnson, M. K., Allen, J. H.: Invest. Ophthalmal. Visual Sci. 17, 480 (1978)Google Scholar
  203. 203.
    Schachtele, C. F. et al.: Infect. Immun. 22, 714 (1978)PubMedGoogle Scholar
  204. 204.
    Romeo, D., Girard, A., Rothfield, L.: J. Mol. Biol. 53, 475 (1970)CrossRefPubMedGoogle Scholar
  205. 205.
    Lederer, E.: Chem. Phys. Lipids 1, 294 (1967)CrossRefGoogle Scholar
  206. 206.
    Bloch, H.: J. Exp. Med. 91, 197 (1950)CrossRefPubMedGoogle Scholar
  207. 207.
    Bloch, H.: ibid. 92, 507 (1950)CrossRefPubMedGoogle Scholar
  208. 208.
    Kato, M. et al.: Am. Rev. Respirat. Diseases 80, 240 (1955)Google Scholar
  209. 209.
    Kato, M.: Arch. Biochem. Biophys. 140, 379 (1970)CrossRefPubMedGoogle Scholar
  210. 210.
    Meyer, T. J. et al.: J. Natl. Cancer Inst. 52, 103 (1974)PubMedGoogle Scholar
  211. 211.
    Ribi, E. et al.: ibid. 55, 1253 (1975)PubMedGoogle Scholar
  212. 212.
    Jolles, P., Samouz, D., Lederer, E.: Arch. Biochem. Biophys. Suppl. 1, 283 (1962)Google Scholar
  213. 213.
    Diaz-Maurino, T., Perkins, H. R.: J. Gen. Microbiol. 80, 533 (1974)PubMedGoogle Scholar
  214. 214.
    Bateman, D. R., Basham, H. G.: in: Physiological Plant Pathology (ededs. Heitefuss, R., Williams, P. H.) pp. 316–355, New York: Springer Verlag 1976Google Scholar
  215. 215.
    Patil, S. S.: Ann. Rev. Phytopathol. 12, 259 (1974)CrossRefGoogle Scholar
  216. 216.
    Strobel, G. A.: Ann. Rev. Microbiol. 31, 205 (1977)CrossRefGoogle Scholar
  217. 217.
    Vidaver, A. K., Statt, M. P.: in: The Prokaryotes: A Handbook on Habitat, Isolation, and Identification of Bacteria (eds. Starr, M. P. et al.) Vol. 2, pp. 1878–1887, Berlin: Springer Verlag 1981Google Scholar
  218. 218.
    Vogel, P. et al.: Aust. J. Exp. Biol. Med. Sci. 59, 455 (1981)PubMedGoogle Scholar
  219. 219.
    Berry, P. H., Vogel, P.: ibid. 60, 129 (1982)PubMedGoogle Scholar
  220. 220.
    Vogel, P. et al.: Biochem. Biophys. Res. Commun. 105, 835 (1982)CrossRefPubMedGoogle Scholar
  221. 221.
    Stynes, B. A., Petterson, D. S.: Physiol. Plant. Path. 16, 163 (1980)Google Scholar
  222. 222.
    Kurioka, S., Liu, P. V.: J. Bacteriol. 93, 670 (1967)PubMedGoogle Scholar
  223. 223.
    O'Leary, W.: Bacteriol. Rev. 26, 421 (1962)Google Scholar
  224. 224.
    Kawashima, H. et al.: J. Ferment. Technol. 61, 143 (1983)Google Scholar
  225. 225.
    Haskins, R. H., Thorn, J. A., Boothroyd, D.: Can. J. Microbiol. 1, 749 (1955)PubMedGoogle Scholar
  226. 226.
    Bhattacharjee, S. S., Haskins, R. H., Gorin, P. A. J.: Carbohyd. Res. 13, 235 (1970)CrossRefGoogle Scholar
  227. 227.
    Bergström, S., Theorell, H., Davide, H.: Arch. Biochem. 10, 165 (1946)Google Scholar
  228. 228.
    Kosaric, N. et al.: J. Am. Oil Chem. Soc. 61, 1735 (1984)Google Scholar
  229. 229.
    McAuliffe, C.: Science 163, 478 (1969)Google Scholar
  230. 230.
    Franks, F.: Nature 210, 87 (1966)Google Scholar
  231. 231.
    Arima, K., Tamura, G., Kasinuma, A.: DE-OS 1803 987, 19. 10. 1968Google Scholar
  232. 232.
    Kimura, A., Otsuka, H.: Agric. Biol. Chem. 33, 1291 (1969)Google Scholar
  233. 233.
    Shryock, T. R. et al.: Current Microbiol. 10, 323 (1984)CrossRefGoogle Scholar
  234. 234.
    Bernheimer, A. W.: Science 159, 847 (1968)PubMedGoogle Scholar
  235. 235.
    Kakinuma, A., Arima, K.: Kagabu to Seibutu 6, 606 (1968)Google Scholar
  236. 236.
    Atlas, R. M., Bartha, R.: Antonie van Leeuwenhoek, J. Microbiol. Serol. 39, 257 (1973)Google Scholar
  237. 237.
    Galbraith, H. et al.: J. Appl. Bacteriol. 34, 803 (1971).PubMedGoogle Scholar
  238. 238.
    Nieman, C.: Bacteriol. Rev. 18, 147 (1954)PubMedGoogle Scholar
  239. 239.
    Niwano, M. et al.: Agric. Biol. Chem. 48, 1359 (1984)Google Scholar
  240. 240.
    Haska, G., Noren, B., Odham, G.: Physiol. Plant 27, 181 (1972)Google Scholar
  241. 241.
    Ved, H. S. et al.: J. Biol. Chem. 259, 8115 (1984)PubMedGoogle Scholar
  242. 242.
    Ved, H. S., Gustow, E., Pieringer, R. A.: ibid. 259, 8122 (1984)PubMedGoogle Scholar
  243. 243.
    Combes, C., Arnaudis, J.: Acta Tropica 39, 79 (1982)PubMedGoogle Scholar
  244. 244.
    Taber, J. J.: Pure Appl. Chem. 52, 1323 (1980)Google Scholar
  245. 245.
    Guerra-Santos, L., Käppeli, O., Fiechter, A.: Proceedings Intern. Conf. Microbial Enhancement Oil Recovery pp. 12–14, Afton 1982Google Scholar
  246. 246.
    Singer, M. E. et al.: Proceedings Intern. Conf. Microbial Enhancement Oil Recovery pp. 94–101, Afton 1982Google Scholar
  247. 247.
    Wagner, F. et al.: DE-PS 30 04 003; 4. 2. 1980Google Scholar
  248. 248.
    Zumbühl, O., Weder, H. G.: Biochem. Biophys. Res. Commun. 107, 869 (1982)CrossRefPubMedGoogle Scholar
  249. 249.
    Finnerty, W. R., Singer, M. E.: Biotechnol. 1, 47 (1983)CrossRefGoogle Scholar
  250. 250.
    Esuhi, K., Meguro, K., Honda, H.: Bull. Chem. Soc. Jpn. 6, 933 (1983)Google Scholar
  251. 251.
    Esuhi, K., Meguro, K., Honda, H.: ibid. 6, 3169 (1983)Google Scholar
  252. 252.
    Keese, C. R., Giaever, I.: Proc. Natl. Acad. Sci. 80, 5622 (1983)Google Scholar
  253. 253.
    Cirigliano, M. C., Carman, G. M.: Appl. Environm. Microbiol. 48, 747 (1984)Google Scholar
  254. 254.
    Boulton, C. A., Ratledge, C.: in: Topics in Enzyme and Fermentation Biotechnology (ed. Wiseman, A.) Vol. 9, pp. 11–77, New York, Chichester, Brisbane, Toronto: John Wiley & Sons 1984Google Scholar
  255. 255.
    Bühler, M., Schindler, J.: in: Biotechnology (eds. Rehm, H.-J., Reed, G.) Vol. 6a, pp. 329–385, Weinheim: Verlag Chemie 1984Google Scholar
  256. 256.
    Zajic, J. E., Seffens, W.: CRC Crit. Rev. Biotechnol. 1, 87 (1984)Google Scholar
  257. 257.
    Xiuyan, W. et al.: Acta Microbiologica Sinica 22, 269 (1982)Google Scholar

Copyright information

© Springer-Verlag 1986

Authors and Affiliations

  • Dieter Haferburg
    • 2
  • Rolf Hommel
    • 1
    • 2
  • Reiner Claus
    • 2
  • Hans-Peter Kleber
    • 2
  1. 1.Institut für Technische Mikrobiologie, Außenstelle LeipzigLeipzigGDR
  2. 2.Bereich Biochemie, Sektion BiowissenschaftenKarl-Marx-Universität LeipzigLeipzigGDR

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