Mycolic acids: Structure, biosynthesis and physiological functions

Progress in Lipid Research

Volumn 37, Issue 2-3, 1998, Pages 143-179

  Barry III, Clifton E ^a,b   Lee, Richard E ^a   Mdluli, Khisimusi ^a   Sampson, Andrea E ^a   Schroeder, Benjamin G ^a   Slayden, Richard A ^a   Yuan, Ying ^a  

^a NATIONAL INSTITUTE OF ALLERGY AND INFECTIOUS DISEASES   (United States)

^b NONE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; MEMBRANE LIPID; MYCOLIC ACID;

ARTICLE; BACTERIAL CELL WALL; CHEMICAL STRUCTURE; FATTY ACID DESATURATION; FATTY ACID SYNTHESIS; IMMUNE RESPONSE; IMMUNOGENICITY; LIPID ANALYSIS; LIPID OXIDATION; MYCOBACTERIOSIS; MYCOBACTERIUM; NONHUMAN; POLYMERIZATION; PRIORITY JOURNAL; SPECIES DIFFERENCE; TAXONOMY;

BACTERIA (MICROORGANISMS); MYCOBACTERIUM;

EID: 0032126742     PISSN: 01637827     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0163-7827(98)00008-3     Document Type: Review

References (288)

1. 1. Stodola, F. H., Lesuk, A. and Anderson, R. J., J. Biol. Chem., 1938, 126, 505-513.
2. 2. Anderson, R. J., Chem. Rev., 1941, 29, 225-243.
3. 3. Anderson, R. J., Fortschritte. Chem. Org. Naturst., 1939, 3, 145-202.
4. 4. Minnikin, D. E., in The Biology of the Mycobacteria, Vol. 1, eds C. Ratledge and J. Standford. Academic Press, London, 1982, pp. 95-184.
5. 5. Asselineau, J., Compte Rendu Acad. Sci., 1950, 230, 1620-1622.
6. 6. Asselineau, J. and Lederer, E., Nature, 1950, 166, 782-783.
7. 7. Luquin, M., Ausina, V., Calahorra, F. L., Belda, F., Barcelo, M. G., Celma, C. and Prats, G., J. Clin. Microbiol., 1991, 29, 120-130.
8. 8. Larsson, L., Jiménez, J., Valero-Guillén, P., Martín-Luengo, F. and Kubín, M., J. Clin. Microbiol., 1989, 27, 2388-2390.
9. 9. Minnikin, D. E. and Polgar, N., Chem. Comm., 1966, 648-649..
10. 10. Etemadi, A. H., Expos. Annu. Biochim. Med., 1967, 28, 77-109.
11. 11. Asselineau, J., Tocanne, G. and Tocanne, J. F., Bull. Chim. Soc. Fr., 1970, 1455-1459..
12. 12. Daffé, M., Lanéelle, M. A. and Valero-Guillen, P. L., Eur. J. Biochem., 1988, 177, 339-344.
13. 13. Lacave, C., Lanéelle, M. A., Daffé, M., Montrozier, H., Rols, M. P. and Asselineau, C., Europ. J. Biochem., 1987, 163, 369-378.
14. 14. Rafidinarivo, E., Prome, J. C. and Levy-Frebault, V., Chem. Phys. Lipids, 1985, 36, 215-228.
15. 15. Daffé, M., Lanéelle, M. A. and Lacave, C., Res. Microbiol., 1991, 142, 397-403.
16. 16. Ioneda, T. and Ishige, M., Chem. Phys. Lipids, 1996, 83, 93-109.
17. 17. Minnikin, D. E., in Bacterial Cell Surface Techniques, eds I. Hancock and I. Poxton. John Wiley and Sons, Chichester, 1988, pp. 125-135.
18. 18. Minnikin, D. E., Hutchinson, I. G., Caldicott, A. B. and Goodfellow, M., J. Chromatog., 1980, 188, 221-233.
19. 19. Valero-Guillén, P. L., Pacheco, F. and Martin-Luengo, F., J. Appl. Bacteriol., 1985, 59, 113-126.
20. 20. George, K. M., Yuan, Y., Sherman, D. R. and Barry, C. E., III., J. Biol. Chem., 1995, 270, 27292-27298.
21. 21. Guerrant, G. O., Lambert, M. A. and Moss, C. W., J. Clin. Microbiol., 1981, 13, 899-907.
22. 22. Kusaka, T. and Mori, T., J. Gen. Microbiol., 1986, 132, 3403-3406.
23. 23. Chun, J., Kang, S. O., Hah, Y. C. and Goodfellow, M., J. Ind. Microbiol., 1996, 17, 205-213.
24. 24. Collins, M. D., Goodfellow, M. and Minnikin, D. E., J. Gen. Microbiol., 1982, 128, 129-149.
25. 25. Goodfellow, M., Weaver, C. R. and Minnikin, D. E., J. Gen. Microbiol., 1982, 128, 731-745.
26. 26. Butler, W. R., Ahearn, D. G. and Kilburn, J. O., J. Clin. Microbiol., 1986, 23, 182-185.
27. 27. Glickman, S. E., Kilburn, J. O., Butler, W. R. and Ramos, L. S., J. Clin. Microbiol., 1994, 32, 740-745.
28. 28. Hamid, M. E., Minnikin, D. E. and Goodfellow, M., J. Gen. Microbiol., 1993, 139, 2203-2213.
29. 29. De Briel, D., Couderc, F., Riegel, P., Jehl, F. and Minck, R., J. Clin. Microbiol., 1992, 30, 1407-1417.
30. 30. Lee, R. E., Armour, J. W., Takayama, K., Brennan, P. J. and Besra, G. S., Biochim. Biophys. Acta, 1997, 1346, 275-284.
31. 31. Rainey, F. A., Klatte, S., Kroppenstedt, R. M. and Stackebrandt, E., Int. J. Syst. Bacteriol., 1995, 45, 32-36.
32. 32. Koronelli, T. V., Rozynov, B. V., Kvasnikov, E. I., Nogina, T. M. and Nesterenko, O. A., Mikrobiologiia, 1984, 53, 371-373.
33. 33. Baba, T., Nishiuchi, Y. and Yano, I., Int. J. Syst. Bacteriol., 1997, 47, 795-801.
34. 34. Wallace, R. J., Jr., Brown, B. A., Blacklock, Z., Ulrich, R., Jost, K., Brown, J. M., McNeil, M. M., Onyi, G., Steingrube, V. A. and Gibson, J., J. Clin. Microbiol., 1995, 33, 1528-1533.
35. 35. Tomiyasu, I., J. Bacteriol., 1982, 151, 828-837.
36. 36. Beaman, B. L. and Moring, S. E., Infect. Immun., 1988, 56, 557-563.
37. 37. Beaman, B. L., Moring, S. E. and Ioneda, T., J. Bacteriol., 1988, 170, 1137-1142.
38. 38. Koda, S., Fujioka, M. and Shigi, M. et al., J. Gen. Microbiol., 1986, 132, 1547-1551.
39. 39. Ioneda, T. and de Almeida, E. T., Chem. Phys. Lipids, 1991, 59, 225-231.
40. 40. Alshamaony, L., Goodfellow, M., Minnikin, D. E. and Mordarska, H., J. Gen. Microbiol., 1976, 92, 183-187.
41. 41. Bendinger, B., Rainey, F. A., Kroppenstedt, R. M., Moormann, M. and Klatte, S., Int. J. Syst. Bacteriol., 1995, 45, 544-548.
42. 42. Collins, M. D., Simda, J., Dorsch, M. and Stackenbrandt, E., Int. J. Sys. Bacteriol., 1988, 38, 385-391.
43. 43. Tomiyasu, I. and Yano, I., Eur. J. Biochem., 1984, 139, 173-180.
44. 44. Savagnac, A., Aurelle, H., Casas, C., Couderc, F., Gavard, P., Prome, D. and Prome, J. C., Chem. Phys. Lipids, 1989, 51, 31-38.
45. 45. Valero-Guillén, P., Martin-Luengo, F., Jimenez, J. and Larsson, L., Acta Pathol. Microbiol. Immunol. Scand. [B], 1986, 94, 373-376.
46. 46. Minnikin, D. E. and Goodfellow, M., in Microbiological Classification and Identification, eds M. Goodfellow and R. G. Board. Academic Press, London, 1980, pp. 189-256.
47. 47. Minnikin, D. E., Minnikin, S. M., Parlett, J. H., Goodfellow, M. and Magnusson, M., Arch. Microbiol., 1984, 139, 225-231.
48. 48. Minnikin, D. E., Minnikin, S. M., Parlett, J. H. and Goodfellow, M., Zbl. Bakt. Hyg. [A], 1985, 259, 446-460.
49. 49. Minnikin, D. E. and Goodfellow, M., in Twenty-Five Years of Mycobacterial Taxonomy, eds G. P. Kubica, L. G. Wayne and L. S. Good. CDC, US Dept. Health and Human Services, Atlanta, 1980, pp. 159-179.
50. 50. Butler, W. R. and Kilburn, J. O., J. Clin. Microbiol., 1988, 26, 50-53.
51. 51. Butler, W. R. and Kilburn, J. O., J. Clin. Microbiol., 1990, 28, 2094-2098.
52. 52. Butler, W. R., Jost, K. C., Jr and Kilburn., J. O., J. Clin. Microbiol., 1991, 29, 2468-2472.
53. 53. Floyd, M. M., Silcox, V. A., Jones, W. D., Jr., Butler, W. R. and Kilburn, J. O., J. Clin. Microbiol., 1992, 30, 1327-1330.
54. 54. Duffey, P. S. and Guthertz, L. S., FEMS Microbiol. Lett., 1992, 74, 27-36.
55. 55. Cage, G. D., J. Clin. Microbiol., 1992, 30, 2402-2407.
56. 56. Butler, W. R., Thibert, L. and Kilburn, J. O., J. Clin. Microbiol., 1992, 30, 2698-2704.
57. 57. Thibert, L. and Lapierre, S., J. Clin. Microbiol., 1993, 31, 1759-1763.
58. 58. Guthertz, L. S., Lim, S. D., Jang, Y. and Duffey, P. S., J. Clin. Microbiol., 1993, 31, 1876-1881.
59. 59. Hagen, S. R. and Thompson, J. D., J. Chromatogr. A, 1995, 692, 167-172.
60. 60. Tortoli, E., Bartoloni, A., Burrini, C., Mantella, A. and Simonetti, M. T., Eur. J. Clin. Microbiol. Infect. Dis., 1995, 14, 240-243.
61. 61. Duffey, P. S., Guthertz, L. S. and Evans, G. C., J. Clin. Microbiol., 1996, 34, 1939-1943.
62. 62. Ritter, D., Carlson, L. D. C., Logan, B. K., Ramos, L. S., Kilburn, J. O. and Coyle, M. B., J. Clin. Microbiol., 1996, 34, 2004-2006.
63. 63. Tortoli, E., Bartoloni, A., Bozzetta, E., Burrini, C., Lacchini, C., Mantella, A., Penati, V., Tullia Simonetti, M. and Ghittino, C., Comp. Immunol. Microbiol. Infect. Dis., 1996, 19, 25-29.
64. 64. Lumb, R., Goodwin, A., Ratcliff, R., Stapledon, R., Holland, A. and Bastian, I., J. Clin. Microbiol., 1997, 35, 2782-2785.
65. 65. Lambert, M. A., Moss, C. W., Silcox, V. A. and Good, R. C., J. Clin. Microbiol., 1986, 23, 731-736.
66. 66. Larsson, L., Jantzen, E. and Johnsson, J., Eur. J. Clin. Microbiol., 1985, 4, 483-487.
67. 67. Kaneda, K., Naito, S., Imaizumi, S., Yano, I., Mizuno, S., Tomiyasu, I., Baba, T., Kusunose, E. and Kusunose, M., J. Clin. Microbiol., 1986, 24, 1060-1070.
68. 68. Kaneda, K., Imaizumi, S. and Yano, I., Microbiol. Immunol., 1995, 39, 563-570.
69. 69. Kaneda, K., Imaizumi, S., Mizuno, S., Baba, T., Tskamura, M. and Yano, I., J. Gen. Microbiol., 1988, 134, 2213-2229.
70. 70. Daffé, M., Lanéelle, M. A., Asselineau, C., Lévy-Frébault, V. and David, H., Ann. Microbiol. (Inst. Pasteur), 1983, 134(B), 241-256.r,
71. 71 Levy-Frebault, V., Goh, K. S. and David, H. L., J.Clin. Microbiol., 1986, 24, 835-839.
72. 72. Dobson, G., Minnikin, D. E., Minnikin, S. M., Parle≪, J. H., Goodfellow, M., Ridell, M. and Magnusson, M., in Chemical Methods in Bacterial Systematics. (Academic Press, Inc., London, 1985.
73. 73. Minnikin, D. E., Parle≪, J. H., Magnusson, M., Ridell, M. and Lind, A., J. Gen. Microbio., 1984, 130, 2733-2736.
74. 74. Minnikin, D. E., Minnikin, S. M., Dobson, G., Goodfellow, M., Portaels, F., Breen, L. V. D. and Sesardic, D., Journal of General Microbiology, 1983, 129, 889-891.
75. 75. Koukila-Kähkölä, P., Springer, Böttger, E. C., Paulin, L., Jantzen, E. and Katila, M. L., Int. J. Syst. Bacterial, 1995, 45, 549-553.
76. 76. Brander, E., Jantzen, E., Huttunen,R., Julkunen, A. and Katila, M. L., J. Cun. Microbiol., 1992, 30, 1972-1975.
77. 77. Butler, W.R., O'Connor, S.P., Yakrus, M.A., Smithwick, R.W., Plikaytis, B.B., Moss, C.W., Floyd, M.M., Woodley, C.L., Kilburn, J.O., Vadney, F.S., Gross, W.M., Int. J. Syst. Bacteriol., 1993, 43, 539-548.
78. 78. Springer, B., Tortoli, E., Richter, I., Grünewald, R., Rüsch-Gerdes, S., Uschmann, K., Suter, F., Collins, M. D., Kroppenstedt, R. M. and Bottger, E. C., J. Clin. Microbiol., 1995, 33, 2805-2811.
79. 79. Minnikin, D. E., Minnikin, S. M. and Goodfellow, M., Biochim. Biophys. Acta, 1982, 712, 616-620.
80. 80. Ridell, M., Goodfellow, M., Minnikin, D. E., Minnikin, S. M. and Hutchinson, I. G., J. Gen. Microbiol., 1982, 128, 1299-1307.
81. 81. Böttger, E. C., Hirschel, B. and Coyle, M. B., Int. J. Syst. Bacteriol., 1993, 43, 841-843.
82. 82. Coyle, M. B., Carlson, L. C., Wallis, C. K., Leonard, R. B., Raisys, V. A., Kilburn, J. O., Samadpour, M. and Böttger, E. C., J. Clin. Microbiol., 1992, 30, 3206-3212.
83. 83. Portaels, F., Dawson, D. J., Larsson, L. and Rigouts, L., J. Clin. Microbiol., 1993, 31, 26-30.
84. 84. Haas, W. H., Butler, W. R., Kirschner, P., Plikaytis, B. B., Coyle, M. B., Amthor, B., Steigerwalt, A. G., Brenner, D. J., Salfinger, M., Crawford, J. T., Böttger, E. C. and Bremer, H. J., J. Clin. Microbiol., 1997, 35, 3203-3209.
85. 85. Springer, B., Kirschner, P., Rost-Meyer, G., Schroder, K. H., Kroppenstedt, R. M. and Böttger, E. C., J. Clin. Microbiol., 1993, 31, 3083-3089.
86. 86. Meier, A., Kirschner, P., Schröder, K. H., Wolters, J., Kroppenstedt, R. M. and Böttger, E. C., Int. J. Syst. Bacteriol., 1993, 43, 204-209.
87. 87. Springer, B., Wu, W. K., Bodmer, T., Haase, G., Pfyffer, G. E., Kroppenstedt, R. M., Schröder, K. H., Emler, S., Kilburn, J. O., Kirschner, P., Telenti, A., Coyle, M. B. and Bottger, E. C., J. Clin. Microbiol., 1996, 34, 1100-1107.
88. 88. Datta, A. K., Katoch, V. M., Katoch, K., Sharma, V. D. and Shivannavar, C. T., Int. J. Lepr., 1987, 55, 680-684.
89. 89. Minnikin, D. E., Dobson, G., Goodfellow, M., Draper, P. and Magnusson, M., J. Gen. Microbiol., 1985, 131, 2013-2021.
90. 90. Datta, A. K., Katoch, V. M., Sharma, V. D. and Katoch, K., Int. J. Leprosy, 1985, 53, 45-51.
91. 91. Davidson, L. A., Draper, P. and Minnikin, D. E., J. Gen. Microbiol., 1982, 128, 823-828.
92. 92. Floyd, M. M., Guthertz, L. S., Silcox, V. A., Duffey, P. S., Jang, Y., Desmond, E. P., Crawford, J. T. and Butler, W. R., J. Clin. Microbiol., 1996, 34, 2963-2967.
93. 93. Hinrikson, H. P. and Pfyffer, G. E., Med. Microbiol. Lett., 1994, 3, 49-57.
94. 94. Luquin, M., Lopez, F. and Ausina, V., J. Clin. Microbiol., 1989, 27, 1403-1406.
95. 95. Kazda, J., Stackebrandt, E., Smida, J., Minnikin, D. E., Daffé, M., Parlett, J. H. and Pitulle, C., Int. J. Syst. Bacteriol., 1990, 40, 217-223.
96. 96. Kazda, J., Cooney, R., Monaghan, M., Quinn, P. J., Stackebrandt, E., Dorsch, M., Daffé, M., Müller, K., Cook, B. R. and Tarnok, Z. S., Int. J. Syst. Bacteriol., 1993, 43, 352-357.
97. 97. Lévy-Frébault, V., Rafidinarivo, E. and Prome, J. C. et al., Int. J. Syst. Bacteriol., 1983, 33, 336-343.
98. 98. Levy-Frebault, V., Daffé, M., Goh, K. S., Lanéelle, M. A., Asselineau, C. and David, H. L., J. Clin. Microbiol., 1983, 17, 744-752.
99. 99. Minnikin, D. E., Minnikin, S. M., Goodfellow, M. and Stanford, J. L., J. Gen. Microbiol., 1982, 128, 817-822.
100. 100. Luquin, M., Lanéelle, M. A., Ausina, V., Garcia Barcelo, M., Belda, F., Alonso, C. and Prats, G., Int. J. Syst. Bacteriol., 1991, 41, 390-394.
101. 101. Lacave, C., Lanéelle, M. A., Daffé, M., Montrozier, H., Rols, M. P. and Asselineau, C., Eur. J. Biochem., 1987, 163, 369-378.
102. 102. Minnikin, D. E., Minnikin, S. M., Hutchinson, I. G., Goodfellow, M. and Grange, J. M., J. Gen. Microbiol., 1984, 130, 363-367.
103. 103. Domenech, P., Jimenez, M. S., Menendez, M. C., Bull, T. J., Samper, S., Manrique, A. and Garcia, M. J., Int. J. Syst. Bacteriol., 1997, 47, 535-540.
104. 104. Munoz, M., Julian, E., Garcia-Barcelo, M., Ausina, V. and Luquin, M., J. Chromatogr. B Biomed. Sci. Appl., 1997, 689, 341-347.
105. 105. Wallace, R. J., Jr., Silcox, V. A., Tsukamura, M., Brown, B. A., Kilburn, J. O., Butler, W. R. and Onyi, G., J. Clin. Microbiol., 1993, 31, 3231-3239.
106. 106. Shojaei, H., Goodfellow, M., Magee, J. G., Freeman, R., Gould, F. K. and Brignall, C. G., Int. J. Syst. Bacteriol., 1997, 47, 1205-1207.
107. 107. Luquin, M., Margarit, L., Condom, M. J. and Ausina, V., Int. J. Syst. Bacteriol., 1987, 37, 75-77.
108. 108. Ausina, V., Luquin, M., Margarit, L. and Prats, G., in Mycobacteria of Clinical Interest, ed. M. Casal. Elsevier Science Publishers B.V., London, 1986, pp. 70-74.
109. 109. Ausina, V., Luquin, M., Garcia Barcelo, M., Lanéelle, M. A., Levy-Frebault, V., Belda, F. and Prats, G., Int. J. Syst. Bacteriol., 1992, 42, 529-535.
110. 110. Luquin, M., Roussel, J., Lopez-Calahorra, F., Lanéelle, G., Ausina, V. and Lanéelle, M. A., Eur. J. Biochem., 1990, 192, 753-759.
111. 111. Luquin, M., Ausina, V., Levy-Frebault, V., Lanéelle, M. A., Belda, F., Barcelo, M. G., Prats, G. and Daffé, M., Int. J. Syst. Bacteriol., 1993, 43, 405-413.
112. 112. Ausina, V., Luquin, M. and Margarit, L., J. Gen. Microbiol., 1985, 131, 2237-2239.
113. 113. Haggblom, M. M., Nohynek, L. J., Palleroni, N. J., Kronqvist, K., Nurmiaho-Lassila, E. L., Salkinoja-Salonen, M. S., Klatte, S. and Kroppenstedt, R. M., Int. J. Syst. Bacteriol., 1994, 44, 485-493.
114. 114. Kirschner, P., Teske, A., Schroder, K. H., Kroppenstedt, R. M., Wolters, J. and Bottger, E. C., Int. J. Syst. Bacteriol., 1992, 42, 257-262.
115. 115. Kleespies, M., Kroppenstedt, R. M., Rainey, F. A., Webb, L. E. and Stackebrandt, E., Int. J. Syst. Bacteriol., 1996, 46, 683-687.
116. 116. Kazda, J., Muller, H. J., Stackebrandt, E., Daffé, M., Muller, K. and Pitulle, C., Int. J. Syst. Bacteriol., 1992, 42, 524-528.
117. 117. Valero-Guillen, P. L. and Martin-Luengo, F., FEMS Microbiol Lett, 1986, 35, 59-63.
118. 118. Levy-Frebault, V., Daffé, M., Restrepo, E., Grimont, F., Grimont, P. A. D. and David, H. L., Ann. Inst. Pasteur/Microbiol., 1986, 2, 143-151.
119. 119. Padgitt, P. J. and Moshier, S. E., Int. J. Syst. Bacteriol., 1987, 37, 186-191.
120. 120. Baba, T., Kaneda, K., Kusunose, E., Kusunose, M. and Yano, I., Lipids, 1988, 23, 1132-1138.
121. 121. Yuan, Y., Crane, D. C., Musser, J. M., Sreevatsan, S. and Barry, C. E., III., J. Biol. Chem., 1997, 272, 10041-10049.
122. 122. Wong, M. Y. H. and Gray, G. R., J. Biol. Chem., 1979, 254, 5741-5744.
123. 123. Danielson, S. J. and Gray, G. R., J. Biol. Chem., 1982, 257, 12196-12203.
124. 124. Magnuson, K., Jackowski, S., Rock, C. O. and Cronan, J. E., Jr., Microbiol. Rev., 1993, 57, 522-542.
125. 125. Wakil, S. J., Stoops, J. K. and Joshi, V. C., Ann. Rev. Biochem., 1983, 52, 537-579.
126. 126. Stoops, J. K., Arslanian, M. J., Oh, Y. H., Aune, K. C., Vanaman, T. C. and Wakil, S. J., Proc. Natl. Acad. Sci. USA, 1975, 72, 1940-1944.
127. 127. Mattick, J. S., Tsukamoto, Y., Nickless, J. and Wakil, S. J., J. Biol.Chem., 1983, 258, 15291-15299.
128. 128. Wong, H., Mattick, J. S. and Wakil, S. J., J. Biol. Chem., 1983, 258, 15305-15311.
129. 129. Jackowski, S., Cronan, J. E., Jr and Rock, C. O., in Biochemistry of Lipids, Lipoproteins and Membranes, eds D. E. Vance and J. Vance. Elsevier Science, 1991, pp. 43-85.
130. 130. Cronan, J. E., Jr and Rock, C. O., in Escherichia coli and Salmonella Cellular and Molecular Biology, ed. Neidhardt. ASM, Washington DC, 1987, pp. 474-497.
131. 131. Cronan, J. E., Jr and Rock, C. O., in Escherichia coli and Salmonella Cellular and Molecular Biology, ed. Neidhardt. ASM Press, Washington DC, 1996, pp. 612-636.
132. 132. Kass, L. R., Brock, D. J. H. and Bloch, K., J. Biol. Chem., 1967, 242, 4418-4431.
133. 133. Bergler, H., Wallner, P., Ebeling, A., Leitinger, B., Fuchsbichler, S., Aschauer, H., Kollenz, G., Hogenauer, G. and Turnowsky, F., J. Biol. Chem., 1994, 269, 5493-5496.
134. 134. Bloch, K., Meth. Enzymol., 1975, 35, 84-90.
135. 135. Brindley, D., Matsumura, S. and Bloch, K., Nature, 1969, 224, 666-669.
136. 136. Bloch, K., Adv. Enzymol. Relat. Areas Mol. Biol., 1977, 45, 1-84.
137. 137. Kikuchi, S., Rainwater, D. L. and Kolattukudy, P. E., Arch. Biochem. Biophys., 1992, 295, 318-326.
138. 138. Fernandes, N. D. and Kolattukudy, P. E., Gene, 1996, 170, 95-99.
139. 139. Kiho, T. and Ballou, C. E., Biochemistry, 1988, 27, 5824-5828.
140. 140. Maggio, J. E., Proc. Natl. Acad. Sci. USA, 1980, 77, 2582-2586.
141. 141. Qureshi, N., Sathyamoorthy, N. and Takayama, K., J. Bacteriol., 1984, 157, 46-52.
142. 142. Takayama, K., Wang, L. and David, H. L., Antimicrob. Agents Chemother., 1972, 2, 29-35.
143. 143. Takayama, K., Schnoes, H. K., Armstrong, E. L. and Boyle, R. W., J. Lipid Res., 1975, 16, 308-317.
144. 144. Mdluli, K., Slayden, R. A., Zhu, Y., Ramaswamy, S., Pan, X., Mead, D., Crane, D. D., Musser, J. M. and Barry, C. E. III (1998) Science 1988, 280, 1607-1610.
145. 145. Hopwood, D. A., Chem. Rev., 1997, 97, 2465-2497.
146. 146. Banerjee, A., Dubnau, E., Quemard, A., Balasubramanian, V., Um, K.S., Wilson, T., Collins, D., Lisle, G.d. and Jacobs, W.R., Jr, Science, 1994, 263, 227-230.
147. 147. Dessen, A., Quenmard, A., Blanchard, J. S., Jacobs, W. R., Jr and Sacchettini., J. C., Science, 1995, 267, 1638-1641.
148. 148. Quemard, A., Sacchettini, J. C., Dessen, A., Vilcheze, C., Bittman, R., Jacobs, W. R., Jr and Blanchard., J. S., Biochemistry, 1995, 34, 8235-8241.
149. 149. Sacchettini, J. C. and Blanchard, J. S., Res. Microbiol., 1996, 147, 36-43.
150. 150. Mdluli, K., Sherman, D. R., Hickey, M. J., Kreiswirth, B. N., Morris, S., Stover, C.K. and Barry, C. E., III., J. Inf. Dis., 1996, 174, 1085-1090.
151. 151. Qureshi, N., Takayama, K. and Schnoes, H. K., J. Biol. Chem., 1980, 255, 182-189.
152. 152. Takayama, K., Qureshi, N. and Schnoes, H. K., Lipids, 1978, 13, 575-579.
153. 153. Sathyamoorthy, N., Qureshi, N. and Takayama, K., Can. J. Microbiol., 1985, 31, 214-219.
154. 154. Couderc, F., Lipids, 1995, 30, 691-699.
155. 155. Jackson, M., Portnoi, D., Catheline, D., Dumail, L., Rauzier, J., Legrand, P. and Gicquel, B., Infect Immun., 1997, 65, 2883-2889.
156. 156. Gastambide-Odier, M., Delaumeny, J. M. and Lederer, E., Compte rendu Hebd. Acad. Sci., 1964, 259, 3404-3407.
157. 157. Etemadi, A. H. and Lederer, E., Biochim. Biophys. Acta, 1965, 98, 160-167.
158. 158. Wong, M. Y. H., Steck, P. A. and Gray, G. R., J. Biol. Chem., 1979, 254, 5734-5740.
159. 159. Lederer, E., Q. Rev. Chem. Soc., 1969, 23, 453-481.
160. 160. Grogan, D. W. and Cronan, J. E., Jr., Microbiol. Mol. Biol. Rev., 1997, 61, 429-441.
161. 161. Yuan, Y., Lee, R. E., Besra, G. S., Belisle, J. T. and Barry, C. E., III., Proc. Natl. Acad. Sci. USA, 1995, 92, 6630-6634.
162. 162. Wang, A.-Y., Grogan, D. W. and Cronan, J. E., Jr., Biochemistry, 1992, 31, 11020-11028.
163. 163. Minnikin, D. E. and Polgar, N., Chem. Comm., 1967, 1064, 1172-1174.
164. 164. Yuan, Y. and Barry, C. E., III., Proc. Natl. Acad. Sci. USA, 1996, 93, 12828-12833.
165. 165. Quemard, A., Lanéelle, M. A., Marrakchi, H., Prome, D., Dubnau, E. and Daffé, M., Eur. J. Biochem., 1997, 250, 758-763.
166. 166. Minnikin, D. E. and Polgar, N., Chem. Comm., 1967, 785, 916-918.
167. 167. Dubnau, E., Lanéelle, M. A., Soares, S., Benichou, A., Vaz, T., Prome, D., Prome, J. C., Daffé, M. and Quemard, A., Mol. Microbiol., 1997, 23, 313-322.
168. 168. Dougherty, D. A., Science, 1996, 271, 163-168.
169. 169. Etemadi, A. H. and Gasche, J., Bull. Soc. Chim. Biol. (Paris), 1965, 47, 2095-2104.
170. 170. Toriyama, S., Imaizumi, S., Tomiyasu, I., Masui, M. and Yano, I., Biochim. Biophys. Acta, 1982, 712, 427-429.
171. 171. Reiser, S. and Somerville, C., J. Bacteriol., 1997, 179, 2969-2975.
172. 172. Wang, L., Takayama, K., Goldman, D. S. and Schnoes, H. K., Biochim. Biophys. Acta, 1972, 260, 41-48.
173. 173. Takayama, K. and Davidson, L. A., Trends Biochem. Sci., 1979, 14, 280-282.
174. 174. Takayama, K. and Qureshi, N., in The Mycobacteria: A Sourcebook, Part A, Vol. 15, eds G. P. Kubica and L. G. Wayne. Marcel Dekker, New York, 1984, pp. 315-344..
175. 175. Gastambide-Odier, M. and Lederer, E., Nature, 1959, 184, 1563-1564.
176. 176. Gastambide-Odier, M. and Lederer, E., Biochem. Z., 1960, 333, 285-295.
177. 177. Chevalier, J., Pommier, M. T., Cremieux, A. and Michel, G., J. Gen. Microbiol., 1988, 134, 2457-2461.
178. 178. Couderc, F., De Briel, D., Demont, N., Guard, V. and Prome, J. C., J. Gen. Microbiol., 1991, 137, 1903-1909.
179. 179. Etemadi, A. H., Bull. Soc. Chim. Biol., 1967, 49, 695-706.
180. 180. Walker, R. W., Prome, J. and Lacave, C. S., Biochim. Biophys. Acta, 1973, 326, 52-62.
181. 181. Prome, J. C., Walker, R. W. and Lacave, C., C.R. Acad. Sci. Paris, Ser. G., 1974, 278, 1065-1068.
182. 182. Ahibo-Coffy, A., Aurelle, H. and Lacave, C., Chem. Phys. Lipids, 1978, 22, 185-195.
183. 183. Shimakata, T., Iwaki, M. and Kusaka, T., Arch. Biochem. Biophys., 1984, 229, 329-339.
184. 184. Shimakata, T., Iwaki, M. and Kusaka, T., Arch. Biochem. Biophys., 1985, 238, 497-508.
185. 185. Puzo, G., Tissie, G., Aurelle, H., Lacave, C. and Prome, J. C., Eur. J. Biochem., 1979, 98, 99-105.
186. 186. Datta, A. K. and Takayama, K., Biochim. Biophys. Acta, 1993, 1169, 135-145.
187. 187. Besra, G. S., Sievert, T., Lee, R. E., Slayden, R. A., Brennan, P. J. and Takayama, K., Proc. Natl. Acad. Sci. USA, 1994, 91, 12735-12739.
188. 188. Belisle, J. T., Vissa, V. D., Sievert, T., Takayama, K., Brennan, P. J. and Besra, G. S., Science, 1997, 276, 1420-1422.
189. 189. Walsh, C., Enzymatic Reaction Mechanisms. W. H. Freeman and Company, New York, 1979..
190. 190. Lacave, C., Quemard, A. and Lanéelle, G., Biochim. Biophys. Acta, 1990, 1045, 58-68.
191. 191. Lacave, C., Lanéelle, M. A. and Lanéelle, G., Biochim. Biophys. Acta, 1990, 1042, 315-323.
192. 192. Lopez-Marin, L. M., Quemard, A., Lanéelle, G. and Lacave, C., Biochim. Biophys. Acta, 1991, 1086, 22-28.
193. 193. Wheeler, P. R., Besra, G. S., Minnikin, D. E. and Ratledge, C., Biochim. Biophys. Acta, 1993, 1167, 182-188.
194. 194. Besra, G. S., Minnikin, D. E., Wheeler, P. R. and Ratledge, C., Chem. Phys. Lipids, 1993, 66, 23-34.
195. 195. Rastogi, N., Res. Microbiol., 1991, 142, 464-476.
196. 196. Nikaido, H., Science, 1994, 264, 382-388.
197. 197. Barry, C. E., III and Mdluli., K., Trends Microbiol., 1996, 4, 275-281.
198. 198. Clemens, D. L., Trends Microbiol., 1997, 5, 383-385.
199. 199. Armstrong, J. A. and D'Arcy Hart, P., J. Exp. Med., 1971, 134, 713-740.
200. 200. Jarlier, V. and Nikaido, H., J. Bacteriol., 1990, 172, 1418-1423.
201. 201. Trias, J. and Benz, E., Mol. Microbiol., 1994, 14, 283-290.
202. 202. Chambers, H. F., Moreau, D., Yajko, D., Miick, C., Wagner, C., Hackbarth, C., Kocagoz, S., Rosenberg, E., Hadley, W. K. and Nikaido, H., Antimicrob. Agents Chemother., 1995, 39, 2620-2624.
203. 203. Liu, J., Barry, C. E. III and Nikaido, H., in Mycobacteria: Molecular Biology and Virulence, eds C. Ratledge and J. W. Dale. Chapman and Hall, 1998, pp. 1-44.
204. 204. Jarlier, V. and Nikaido, H., FEMS Microbiol. Lett., 1994, 123, 11-18.
205. 205. Bendinger, B., Rijnaarts, H. H. M., Altendorf, K. and Zehnder, A. J. B., Appl. Environ. Microbiol., 1993, 59, 3973-3977.
206. 206. Barksdale, L. and Kim, K.-S., Bacteriol. Rev., 1977, 41, 217-372.
207. 207. Goren, M. B., Cernich, M. and Brokl, O., Am. Rev. Respir. Dis., 1978, 118, 151-154.
208. 208. Trias, J., Jarlier, V. and Benz, R., Science, 1992, 258, 1479-1481.
209. 209. Trias, J. and Benz, R., J. Biol. Chem., 1993, 268, 6234-6240.
210. 210. Duchene, M., Schweizer, A., Lottspeich, F., Krauss, G., Marget, M., Vogel, K., von Sprecht, B. U. and Domdey, H., J. Bacteriol., 1988, 170, 155-162.
211. 211. Daffé, M. and Draper, P., Adv. Microb. Physiol., 1998, 39, 131-203.
212. 212. Brennan, P. J. and Nikaido, H., Annu. Rev. Biochem., 1995, 64, 29-63.
213. 213. Imaeda, T., Kanetsuna, F. and Galindo, B., J. Ultrastructural Res., 1968, 25, 46-63.
214. 214. Mdluli, K., Swanson, J., Fischer, E., Lee, R. E. and Barry, C. E. III. Mol. Microbiol. 1998, 27, 1223-1233.
215. 215. Paul, T. R. and Beveridge, T. J., J. Bacteriol., 1992, 174, 6508-6517.
216. 216. Paul, T. R. and Beveridge, T. J., Zbl. Bakt., 1993, 279, 450-457.
217. 217. Paul, T. R. and Beveridge, T. J., Infect. Immun., 1994, 62, 1542-1550.
218. 218. Lee, R. E., Brennan, P. J. and Besra, G. S., Curr. Top. Microbiol. Immunol., 1996, 215, 1-27.
219. 219. Goren, M. B., in The Mycobacteria: A Sourcebook, Part A., eds G. P. Kubica and L. G. Wayne. Marcell Dekker, Inc., New York and Basel, 1984, pp. 379-415..
220. 220. Nikaido, H., Kim, S.-H. and Rosenberg, E. Y., Mol. Microbiol., 1993, 8, 1025-1030.
221. 221. Liu, J., Rosenberg, E. Y. and Nikaido, H., Proc. Natl. Acad. Sci. USA, 1995, 92, 11254-11258.
222. 222. Liu, J., Barry, C. E., III., Besra, G. S. and Nikaido, H., J. Biol. Chem., 1996, 271, 29545-29551.
223. 223. Singer, S. J. and Nicolson, G. L., Science, 1972, 175, 720-731.
224. 224. Wilson, M. A. and Pohorille, A., J. Am. Chem. Soc., 1996, 118, 6580-6587.
225. 225. Durand, E., Welby, M., Laneele, G. and Tocanne, J.-F., Eur. J. Biochem., 1979, 93, 103-112.
226. 226. Durand, E., Gillois, M., Tocanni, J.-F. and Laneele, G., Eur. J. Biochem., 1979, 94, 109-118.
227. 227. Sinensky, M., Proc. Nat. Acad. Sci. USA, 1974, 71, 522-525.
228. 228. Toriyama, S., Yano, I., Masui, M., Kusunose, M. and Kusunose, E., FEBS Lett., 1978, 95, 111-115.
229. 229. Toriyama, S., Yano, I., Masui, M., Kusunose, E., Kusunose, M. and Akimori, N., J. Biochem., 1980, 88, 211-221.
230. 230. Tomiyasu, I., Toriyama, S., Yano, I. and Masui, M., Chem. Phys. Lipids, 1981, 28, 41-54.
231. 231. Baba, T., Kaneda, K., Jusunose, E., Kusunose, M. and Yano, I., J. Biochem., 1989, 106, 81-86.
232. 232. Macdonald, P. M., Sykes, B. D. and McElhaney, R. N., Biochemistry, 1985, 24, 4651-4659.
233. 233. Silvius, J. R. and McElhaney, R. N., Chem. Phys. Lipids, 1979, 25, 125-134.
234. 234. McGarrity, J. T. and Armstrong, J. B., Biochim. Biophys. Acta, 1981, 640, 544-548.
235. 235. Perly, B., Smith, I. C. P. and Jarrell, H. C., Biochemistry, 1985, 24, 1055-1063.
236. 236. Dufourc, E. J., Smith, I. C. P. and Jarrell, H. C., Chem. Phys. Lipids, 1983, 33, 153-177.
237. 237. Dufourc, E. J., Smith, I. C. P. and Jarrell, H. C., Biochemistry, 1984, 23, 2300-2309.
238. 238. Jarrell, H. C., Tulloch, A. and Smith, I. C. P., Biochemistry, 1983, 22, 5611-5619.
239. 239. Wang, A.-Y. and Cronan, J. E., Jr., Mol. Microbiol., 1994, 11, 1009-1017.
240. 240. Guckert, J. B., Hood, M. A. and White, D. C., Appl. Environ. Microbiol., 1986, 52, 794-801.
241. 241. Grogan, D. W. and Cronan, J. E., Jr., J. Bacteriol., 1984, 158, 286-295.
242. 242. Grogan, D. W. and Cronan, J. E., Jr., J. Bacteriol., 1986, 166, 872-877.
243. 243. Harley, J. B., Santangelo, G. M., Rasmussen, H. and Goldfine, H., J. Bacteriol., 1978, 134, 808-820.
244. 244. Sherman, D. R., Sabo, P. J., Hickey, M. J., Arain, T. M., Mahairas, G. G., Yuan, Y., Barry, C. E., III and Stover., C. K., Proc. Natl. Acad. Sci. USA, 1995, 92, 6625-6629.
245. 245. Calabi, F. and Milstein, C., Nature, 1986, 323, 540-543.
246. 246. Terhorst, C., Agthoven, K. L., Snow, P., Reinherz, E. and Schlossman, S., Cell, 1981, 23, 771-780.
247. 247. Calabi, F., Jarvis, J. M., Martin, L. and Milstein, C., Eur. J. Immun., 1989, 19, 285-292.
248. 248. Balk, S. P., Bleicher, P. A. and Terhorst, C., Proc. Natl. Acad. Sci. USA, 1989, 86, 252-256.
249. 249. Porcelli, S., Brenner, M. B. and Band, H., Immun. Rev., 1991, 120, 137-183.
250. 250. Porcelli, S., Morita, C. T. and Brenner, M. B., Nature, 1992, 360, 593-597.
251. 251. Porcelli, S., Brenner, M. B., Greenstein, J. L., Balk, S. P., Terhorst, C. and Bleicher, P. A., Nature, 1989, 341, 447-450.
252. 252. Faure, F., Jitsukawa, S., Miossec, C. and Hercend, T., Eur. J. Immun., 1990, 20, 703-706.
253. 253. Balk, S. P., Ebert, E. C., Blumenthal, R. L., McDermott, F. V., Wucherpfennig, K. W., Landau, S. B. and Blumberg, R. S., Science, 1991, 253, 1411-1415.
254. 254. Beckman, E. M., Porcelli, S. A., Morita, C. T., Behar, S. M., Furlong, S. T. and Brenner, M. B., Nature, 1994, 372, 691-694.
255. 255. Zeng, Z. H., Castano, A. R., Segelke, B. W., Stura, P. A., Peterson, E. A. and Wilson, I. A., Science, 1997, 277, 339-345.
256. 256. Lalonde, J. M., Levenson, M. A., Roe, J. J., Bernlohr, D. A. and Banaszak, L. J., J. Biol. Chem., 1994, 269, 25339-25347.
257. 257. Shin, D. H., Lee, J. Y., Hwang, K. Y., Kim, K. K. and Suh, S. W., Structure, 1995, 3, 189-199.
258. 258. Bloch, H., J. Exp. Med., 1950, 91, 197-217.
259. 259. Artman, M., Bekierkunst, A. and Goldberg, I., Arch. Biochem. Biophys., 1964, 105, 80-85.
260. 260. Kato, M., Arch. Biochem. Biophys., 1970, 140, 379-390.
261. 261. Yarkoni, E. and Rapp, H. J., Infect. Immun., 1977, 18, 552-554.
262. 262. Saito, R., Tanaka, A., Sugiyama, K. and Kato, M., Am. Rev. Resp. Dis., 1975, 112, 578-580.
263. 263. Adam, A., Ciorbaru, R., Petit, J. F. and Lederer, E., Proc. Natl. Acad. Sci. USA, 1972, 69, 851-854.
264. 264. Bekierkunst, A., Int. J. Cancer, 1975, 16, 442-447.
265. 265. McLaughlin, C. A., Parker, R., Hadlow, W. J., Toubiana, R. and Ribi, E. E., Cell. Immunol., 1978, 38, 14-24.
266. 266. Meyer, J. T., Ribi, E. E. and Azuma, I., Cell. Immunol., 1975, 16, 11-24.
267. 267. Rastogi, N. and David, H. L., Biochimie, 1988, 70, 1101-1120.
268. 268. Han, Y., He, H., Oka, S. and Yano, I., Acta Lepr., 1989, 7, 130-132.
269. 269. Kaneda, K., Sumi, Y., Kurano, F., Kato, Y. and Yano, I., Infect. Immun., 1986, 54, 869-875.
270. 270. Matsunaga, I., Oka, S., Fujiwara, N. and Yano, I., J. Biochem., 1996, 120, 663-670.
271. 271. Gotoh, K., Mitsuyama, M., Imaizumi, S., Kawamura, I. and Yano, I., Microbiol. Immunol., 1991, 35, 175-185.
272. 272. Bekierkunst, A., Levij, I. S., Yarkoni, E., Vilkas, E. and Lederer, E., Science, 1971, 174, 1240-1242.
273. 273. Numata, F., Ishida, H., Nishimura, K., Sekikawa, I. and Azuma, I., J. Carb. Chem., 1986, 5, 127-138.
274. 274. Bekierkunst, A., J. Bacteriol., 1968, 96, 958-961.
275. 275. Ribi, E. E., Milner, K. C., Granger, D. L., Kelly, M. T., Yamamoto, K., Brehmer, W., Parker, R., Smith, R. F. and Strain, S. M., Ann. NY Acad. Sci., 1976, 277, 228-235.
276. 276. Yarkoni, E. and Bekierkunst, A., Infect. Immun., 1976, 14, 1125-1129.
277. 277. Parant, M., Prant, F., Chedid, L., Draier, J. C., Petit, J. F., Wietzerbin, J. and Lederer, E., J. Infect. Dis., 1977, 135, 771-777.
278. 278. Parant, M., Audibert, F., Parant, F., Chedid, L., Soler, E., Polonsky, J. and Lederer, E., Infect. Immun., 1978, 20, 12-19.
279. 279. Mahmoud, A. A. F., Civil, R. H. D., Lederer, E. and Chedid, L., Clin. Res., 1977, 25, 380A-385A.
280. 280. Olds, G. R., Chedid, L., Lederer, E. and Mahmoud, A. F., J. Inf. Dis., 1980, 141, 473-478.
281. 281. Bekierkunst, A., Wang, L., Toubiana, R. and Lederer, E., Infect. Immun., 1974, 10, 1044-1050.
282. 282. Leclerc, C., Lamensans, A., Chedid, L., Drapier, J. C., Petit, J. F., Wietzerbin, J. and Lederer, E., Cancer Immunol. Immunother., 1976, 1, 227-232.
283. 283. Furukawa, M., Ohtsubo, Y., Sugimoto, N., Katoh, Y. and Dohi, Y., FEMS Microbiol. Immunol., 1990, 64, 83-88.
284. 284. Kato, M., Am. Rev. Respir. Dis., 1969, 100, 47-53.
285. 285. Ofek, I. and Bekierkunst, A., J. Natl. Cancer Inst., 1976, 57, 1379-1381.
286. 286. Yarkoni, E., Wang, L. and Bekierkunst, A., Infect. Immun., 1977, 16, 1-8.
287. 287. Matsunaga, I., Oka, S., Inoue, T. and Yano, I., FEMS Microbiol. Lett., 1990, 67, 49-54.
288. 288. Goren, M. B. and Brennan, P. J., in Tuberculosis, ed. G. P. Youmans. W.B. Saunders Co., Philadelphia, 1979, pp. 63-193.