1887

Chapter 20 : Lipids and Carbohydrates of

MyBook is a cheap paperback edition of the original book and will be sold at uniform, low price.

Ebook: Choose a downloadable PDF or ePub file. Chapter is a downloadable PDF file. File must be downloaded within 48 hours of purchase

Buy this Chapter
Digital (?) $15.00

Preview this chapter:
Zoom in
Zoomout

Lipids and Carbohydrates of , Page 1 of 2

| /docserver/preview/fulltext/10.1128/9781555818357/9781555819101_Chap20-1.gif /docserver/preview/fulltext/10.1128/9781555818357/9781555819101_Chap20-2.gif

Abstract:

This chapter presents a broad structural definition of complex mycobacterial lipids such as mycolyl-arabinogalactan-peptidoglycan complex (mAGP), lipoarabinomannan (LAM), lipomannan (LM), phosphatidyl-myo-inositol mannoside (PIM), sulfatide (SL), trehalose 6,6'-dimycolate (cord factor), other acylated trehaloses, phenolic glycolipid, lipooligosaccharides, and attenuation indicator lipid. It then discusses the possible roles of the lipids found within . A lipid apparently not present in other actinomycetes was isolated from by Noll and was degraded by lithium aluminum hydride to yield two products. The phospholipids found within mycobacterial species are almost invariably phosphodiacylglycerols based on phosphatide acid. Researchers observed that grows in the form of serpentine cords and also that avirulent and saprophytic species could be distinguished by an ability to absorb the cationic phenazine dye natural red. The development of thin-layer chromatographic systems has proved invaluable for the assignment of superficial mycolate patterns. Mycolates could be separated by their polar functions, giving rise to multispot thin-layer chromatograms. The most characteristic feature of the mycobacterial cell wall is the chemotype IV peptidoglycan, which is composed of substantial quantities of meso-diaminopimelic acid. A more comprehensive study of the L forms of mycobacteria may provide additional information concerning both the physical characterization and the biological functions of the complex carbohydrates and lipids of .

Citation: Besra G, Chatterjee D. 1994. Lipids and Carbohydrates of , p 285-306. In Bloom B (ed), Tuberculosis. ASM Press, Washington, DC. doi: 10.1128/9781555818357.ch20
Highlighted Text: Show | Hide
Loading full text...

Full text loading...

Figures

Image of Figure 1
Figure 1

Final stages of phthiocerol A biosynthesis, n = 20 or 22.

Citation: Besra G, Chatterjee D. 1994. Lipids and Carbohydrates of , p 285-306. In Bloom B (ed), Tuberculosis. ASM Press, Washington, DC. doi: 10.1128/9781555818357.ch20
Permissions and Reprints Request Permissions
Download as Powerpoint
Image of Figure 2
Figure 2

Phosphatidylinositol dimannoside.

Citation: Besra G, Chatterjee D. 1994. Lipids and Carbohydrates of , p 285-306. In Bloom B (ed), Tuberculosis. ASM Press, Washington, DC. doi: 10.1128/9781555818357.ch20
Permissions and Reprints Request Permissions
Download as Powerpoint
Image of Figure 3
Figure 3

Phosphatidyl--inositol hexamannoside. R, palmitic acid or tuberculostearic acid.

Citation: Besra G, Chatterjee D. 1994. Lipids and Carbohydrates of , p 285-306. In Bloom B (ed), Tuberculosis. ASM Press, Washington, DC. doi: 10.1128/9781555818357.ch20
Permissions and Reprints Request Permissions
Download as Powerpoint
Image of Figure 4
Figure 4

β--Arabinofuranosyl-l-phosphodecaprenol.

Citation: Besra G, Chatterjee D. 1994. Lipids and Carbohydrates of , p 285-306. In Bloom B (ed), Tuberculosis. ASM Press, Washington, DC. doi: 10.1128/9781555818357.ch20
Permissions and Reprints Request Permissions
Download as Powerpoint
Image of Figure 5
Figure 5

Trehalose 6,6′-dimycolate. RCO = mycolyl.

Citation: Besra G, Chatterjee D. 1994. Lipids and Carbohydrates of , p 285-306. In Bloom B (ed), Tuberculosis. ASM Press, Washington, DC. doi: 10.1128/9781555818357.ch20
Permissions and Reprints Request Permissions
Download as Powerpoint
Image of Figure 6
Figure 6

2,3,6,6′-Tetra--acyItrehalose 2′-sulfate.

Citation: Besra G, Chatterjee D. 1994. Lipids and Carbohydrates of , p 285-306. In Bloom B (ed), Tuberculosis. ASM Press, Washington, DC. doi: 10.1128/9781555818357.ch20
Permissions and Reprints Request Permissions
Download as Powerpoint
Image of Figure 7
Figure 7

Mycolipenic acids.

Citation: Besra G, Chatterjee D. 1994. Lipids and Carbohydrates of , p 285-306. In Bloom B (ed), Tuberculosis. ASM Press, Washington, DC. doi: 10.1128/9781555818357.ch20
Permissions and Reprints Request Permissions
Download as Powerpoint
Image of Figure 8
Figure 8

2,3-Di--acyltrehaloses.

Citation: Besra G, Chatterjee D. 1994. Lipids and Carbohydrates of , p 285-306. In Bloom B (ed), Tuberculosis. ASM Press, Washington, DC. doi: 10.1128/9781555818357.ch20
Permissions and Reprints Request Permissions
Download as Powerpoint
Image of Figure 9
Figure 9

Mycolipanolic acids.

Citation: Besra G, Chatterjee D. 1994. Lipids and Carbohydrates of , p 285-306. In Bloom B (ed), Tuberculosis. ASM Press, Washington, DC. doi: 10.1128/9781555818357.ch20
Permissions and Reprints Request Permissions
Download as Powerpoint
Image of Figure 10
Figure 10

Lipooligosaccharide (LOS-I) isolated from Canetti.

Citation: Besra G, Chatterjee D. 1994. Lipids and Carbohydrates of , p 285-306. In Bloom B (ed), Tuberculosis. ASM Press, Washington, DC. doi: 10.1128/9781555818357.ch20
Permissions and Reprints Request Permissions
Download as Powerpoint
Image of Figure 11
Figure 11

Phenolic glycolipid isolated from Canetti.

Citation: Besra G, Chatterjee D. 1994. Lipids and Carbohydrates of , p 285-306. In Bloom B (ed), Tuberculosis. ASM Press, Washington, DC. doi: 10.1128/9781555818357.ch20
Permissions and Reprints Request Permissions
Download as Powerpoint
Image of Figure 12
Figure 12

Reverse Claisen condensation reaction.

Citation: Besra G, Chatterjee D. 1994. Lipids and Carbohydrates of , p 285-306. In Bloom B (ed), Tuberculosis. ASM Press, Washington, DC. doi: 10.1128/9781555818357.ch20
Permissions and Reprints Request Permissions
Download as Powerpoint
Image of Figure 13
Figure 13

Biosynthesis of α-mycolic acids in H37Ra. А, Δ desaturase; В, tetracosanyl malonate CH(CH) CH(COOH).

Citation: Besra G, Chatterjee D. 1994. Lipids and Carbohydrates of , p 285-306. In Bloom B (ed), Tuberculosis. ASM Press, Washington, DC. doi: 10.1128/9781555818357.ch20
Permissions and Reprints Request Permissions
Download as Powerpoint
Image of Figure 14
Figure 14

Mycobactin T.

Citation: Besra G, Chatterjee D. 1994. Lipids and Carbohydrates of , p 285-306. In Bloom B (ed), Tuberculosis. ASM Press, Washington, DC. doi: 10.1128/9781555818357.ch20
Permissions and Reprints Request Permissions
Download as Powerpoint
Image of Figure 15
Figure 15

Schematic representation of the cell wall of M.

Citation: Besra G, Chatterjee D. 1994. Lipids and Carbohydrates of , p 285-306. In Bloom B (ed), Tuberculosis. ASM Press, Washington, DC. doi: 10.1128/9781555818357.ch20
Permissions and Reprints Request Permissions
Download as Powerpoint
Image of Figure 16
Figure 16

Mannose-capped LAM.

Citation: Besra G, Chatterjee D. 1994. Lipids and Carbohydrates of , p 285-306. In Bloom B (ed), Tuberculosis. ASM Press, Washington, DC. doi: 10.1128/9781555818357.ch20
Permissions and Reprints Request Permissions
Download as Powerpoint

References

/content/book/10.1128/9781555818357.chap20
1. Adam, A.,, M. Senn,, E. Vilkas,, and E. Lederer. 1967. Spectrometrie de masse de glycolipides. 2. Diesters de trehalose naturels et synthétiques. Eur. J. Biochem. 2:460468.
2. Alshamaony, L.,, M. Goodfellow,, and D. E. Minnikin. 1976a. Free mycolic acids as criteria in the classification of Nocardia and the "rhodochrous" complex. J. Gen. Microbiol. 92:188199.
3. Alshamaony, L.,, M. Goodfellow,, D. E. Minnikin,, and H. Mordarska. 1976b. Free mycolic acids as criteria in the classification of Gordona and the "rhodochrous" complex. J. Gen. Microbiol. 92:183187.
4. Anderson, L.,, and F. M. linger (ed.). 1983. Bacterial Lipopolysaccharides. ACS Symposium Series 231. American Chemical Society, Washington, D.C.
5. Anderson, R. J. 1939. The chemistry of the lipids of the tubercle bacillus and certain other microorganisms. Prog. Chem. Org. Nat. Prod. 3:145202.
6. Anderson, R. J. 1941. Structural peculiarities of acid-fast bacterial lipids. Chem. Rev. 29:225243.
7. Antoine, A. D.,, and B. S. Tepper. 1969. Environmental control of glycogen and lipid content of Mycobacterium phlei. J. Gen. Microbiol. 55:217226.
8. Asselineau, C.,, J. Asselineau,, R. Ryhage,, S. Stallberg-Stenhagen,, and E. Stenhagen. 1959. Synthesis of (-)-methyl 2D, 4D, 6D-trimethylnonacosanoate and identification of C32-mycocerosic acid as 2,4,6,8-tetramethyloctacosanoic acid. Acta Chem. Scand. 13:822824.
9. Asselineau, C.,, H. Montrozier,, and J. C. Prome. 1969. Structure des acides a-mycoliques isoles de la souche Canetti de Mycobacterium tuberculosis. Bull. Soc. Chim. Fr. 51:592596.
10. Azuma, I.,, H. Kimura,, T. Niinaka,, I. Aoki,, and Y. Yamamura. 1968. Chemical and immunological studies on mycobacterial polysaccharides. I. Purification and properties of polysaccharides from human tubercle bacilli. J. Bacteriol. 95:263271.
11. Ballou, C. E.,, E. Vilkas,, and E. Lederer. 1963. Structural studies on the myo-inositol phospholipids of Mycobacterium tuberculosis. J. Biol. Chem. 238: 6976.
12. Barksdale, L.,, and K.-S. Kim. 1977. Mycobacterium. Bacteriol. Rev. 41:217372.
13. Barnes, P. F.,, D. Chatterjee,, J. S. Abrams,, S. Lu,, E. Wang,, M. Yamamura,, P. J. Brennan,, and R. L. Modlin. 1992. Cytokine production induced by Mycobacterium tuberculosis lipoarabinomannan: relationship to chemical structure. J. Immunol. 149: 541547.
14. Besra, G. S.,, R. C. Bolton,, M. R. McNeil,, M. Ridell,, E. Simpson,, J. Glushka,, H. van Halbeek,, P. J. Brennan,, and D. E. Minnikin. 1992. Structural elucidation of a novel family of acyltrehaloses from Mycobacterium tuberculosis. Biochemistry 31: 98329837.
15. Bloch, H. 1950. Studies on the virulence of tubercle bacilli. Isolation and biological properties of a constituent of virulent organisms. J. Exp. Med. 91:197218.
16. Brennan, P. J., 1988. Mycobacterium and other actinomycetes, p. 203298. In C. Ratledge, and S. G. Wilkinson (ed.), Microbial Lipids, vol. I. Academic Press, London.
17. Brennan, P. J. 1989. Structures of mycobacteria: recent developments in denning cell wall carbohydrates and proteins. Rev. Infect. Dis. 11(Supp. 2):S420S430.
18. Brennan, P. J.,, and E. Ballou. 1968. Biosynthesis of mannophosphoinositides of Mycobacterium phlei. J. Biol. Chem. 243:29752984.
19. Brennan, P. J.,, D. P. Lehane,, and D. W. Thomas. 1970a. Acylglucoses of the corynebacteria and mycobacteria. Eur. J. Biochem. 13:117123.
20. Brennan, P. J.,, S. A. Rooney,, and F. G. Winder. 1970b. The lipids of Mycobacterium tuberculosis BCG: fractionation, composition, turnover, and the effects of isoniazid. Ir. J. Med. Sci. 3:371390.
21. Cason, J.,, G. L. Lange,, W. T. Miller,, and A. Weiss. 1964. The multibranched higher saturated acids from tubercle bacillus. Tetrahedron 20:91106.
22. Chan, J.,, X. Fan,, S. W. Hunter,, P. J. Brennan,, and B. R. Bloom. 1991. Lipoarabinomannan, a possible virulence factor involved in persistence of Mycobacterium tuberculosis within macrophages. Infect. Immun. 59:17551761.
23. Chargaff, E.,, and W. Schaefer. 1935. A specific polysaccharide from the bacillus Calmette Guerin. J. Biol. Chem. 112:393405.
24. Chatterjee, D.,, C. M. Bozic,, M. McNeil,, and P. J. Brennan. 1991. Structural features of the arabinan component of the lipoarabinomannan of Mycobacterium tuberculosis. J. Biol. Chem. 266:96529660.
25. Chatterjee, D.,, S. W. Hunter,, M. McNeil,, and P. J. Brennan. 1992a. Lipoarabinomannan: multiglycosylated form of the mycobacterial mannosylphosphati-dylinositols. J. Biol. Chem. 267:62286233.
26. Chatterjee, D.,, K. Lowell,, B. Rivoire,, M. R. McNeil,, and P. J. Brennan. 1992b. Lipoarabinomannan of Mycobacterium tuberculosis: capping with manno-syl residue in some strains. J. Biol. Chem. 267:62346239.
27. Chatterjee, D.,, A. D. Roberts,, K. Lowell,, P. J. Brennan,, and I. M. Orme. 1992c. Structural basis of capacity of lipoarabinomannan to induce secretion of tumor necrosis factor. Infect. Immun. 60:12491253.
28. Daffe, M.,, P. J. Brennan,, and M. McNeil. 1990. Predominant structural features of the cell wall arabinogalactan of Mycobacterium tuberculosis as revealed through characterization of oligoglycosyl alditol fragments by gas chromatography/mass spectrometry and by 1H and 13C-NMR analyses. J. Biol. Chem. 265:67346743.
29. Daffe, M.,, S.-N. Cho,, D. Chatterjee,, and P. J. Brennan. 1991a. Chemical synthesis and seroreactivity of a neoantigen containing the oligosaccharide hapten of the Mycobacterium tuberculosis-specific phenolic glycolipid. J. Infect. Dis. 163:161168.
30. Daffe, M.,, C. Lacave,, M. A. Laneelle,, M. Gillois,, and G. Laneelle. 1988. PolyphthienoyI trehalose, glycolipids specific for virulent strains of the tubercle bacillus. Eur. J. Biochem. 172:579584.
31. Daffe, M.,, C. Lacave,, M.-A. Laneelle,, and G. Laneelle. 1987. Structure of the major triglycosylphenol-phthiocerol of Mycobacterium tuberculosis strain Canetti. Eur. J. Biochem. 167:155160.
32. Daffe, M.,, M. R. McNeil,, and P. J. Brennan. 1991b. Novel type-specific lipooligosaccharides from Mycobacterium tuberculosis. Biochemistry 30:378388.
33. Dell, A., and E. Ballou. 1983. Fast-atom-bombardment, negative ion mass spectrometry of the mycobacterial O-methyl-deuterium glucose polysaccharides and lipopolysaccharides. Carbohydr. Res. 120: 95111.
34. Draper, P., 1982. The anatomy of mycobacteria, p. 952. In C. Ratledge, and J. Sanford (ed.), The Biology of Mycobacteria, vol. 1. Academic Press, London.
35. Etemadi, A.-H. 1967a. The use of pyrolysis gas chromatography and mass spectrometry in the study of the structure of mycolic acids. J. Gas Chromatogr. 5:447456.
36. Etemadi, A.-H. 1967b. Correlations structurales et biogenetiques des acides mycoliques en rapport avec la phylogenese de quelques genres d'actino-mycetales. Bull. Soc. Chim. Biol. 49:695706.
37. Etemadi, A.-H. 1967c. Les acides mycoliques structure, biogenese et interet phylogenetique. Expo. Annu. Biochim. Med. 28:77109.
38. Gastambide-Odier, M.,, J. M. Delaumeny,, and E. Le-derer. 1963. Biosynthesis of phthiocerol: incorporation of methionine and propionic acid. Chem. Ind. 1963:12851286.
39. Gastambide-Odier, M.,, and E. Lederer. 1960. Biosynthese de l'acide corynomycolique a partir de deux molecules d'acide palmitique. Biochem. Z. 333:285295.
40. Gastambide-Odier, M.,, and P. Sarda. 1970. Contribution a etude de la structure et de la biosynthese de glycolipides spécifiques isoles de mycobacterias: les mycosides A et B. Pneumologie 42:241255.
41. Ginger, L. G.,, and R. J. Anderson. 1945. The chemistry of the lipids of tubercle bacilli. LXXII. Fatty acids occurring in the wax prepared from tuberculin residues concerning mycocerosic acid. J. Biol. Chem. 157:203211.
42. Goodfellow, M.,, and T. Cross,. 1984. Classification, p. 7164. In M. Goodfellow,, M. Mordorski,, and S. T. Williams (ed.), The Biology of the Actinomycetes. Academic Press, London.
43. Goren, M. B. 1970a. Sulfolipid I of Mycobacterium tuberculosis strain H37Rv. I. Purification and properties. Biochim. Biophys. Acta 210:116126.
44. Goren, M. B. 1970b. Sulfolipid I of Mycobacterium tuberculosis strain H37Rv. II. Structural studies. Biochim. Biophys. Acta 210:127138.
45. Goren, M. B. 1972. Mycobacterial lipids: selected topics. Bacteriol. Rev. 36:3364.
46. Goren, M. B. 1977. Phagocyte lysosomes: interactions with infectious agents, phagosomes, and experimental perturbations in function. Annu. Rev. Microbiol. 31:507533.
47. Goren, M. B. 1982. Immunoreactive substances of mycobacteria. Am. Rev. Respir. Dis. 125(Part 2):5069.
48. Goren, M. B. 1987. Polyanionic agents do not inhibit phagosome-lysosome fusion in cultured macrophages. J. Leukocyte Biol. 41:122129.
49. Goren, M.,, and P. J. Brennan,. 1979. Mycobacterial lipids: chemistry and biologic activities, p. 69193. In G. P. Youmans (ed.), Tuberculosis. The W.B. Saunders Co., Philadelphia.
50. Goren, M., , O. Brokl,, P. Roller,, H. M. Fales,, and C. Das. 1976a. Sulfatides of Mycobacterium tuberculosis: the structure of the principle sulfatide (SL-I). Biochemistry 15:27282735.
51. Goren, M.,, O. Brokl,, and W. B. Schaefer. 1974. Lipids of putative relevance to virulence in Mycobacterium tuberculosis: correlation of virulence and elaboration of sulfatides and strongly acidic lipids. Infect. Immun. 9:150158.
52. Goren, M., , J. M. Grange,, V. R. Aber,, B. W. Allen,, and D. A. Mitchinson. 1982. Role of lipid content and hydrogen peroxide susceptibility in determining the guinea-pig virulence of Mycobacterium tuberculosis. Br. J. Exp. Pathol. 63:693700.
53. Goren, M., , P. D. Hart,, M. R. Young,, J. A. Armstrong. 1976b. Prevention of phagosome-lysosome fusion in cultured macrophages by sulfatides of Mycobacterium tuberculosis. Proc. Natl. Acad Sci. USA 73:25102514.
54. Hunter, S. W.,, and P. J. Brennan. 1990. Evidence for the presence of a phosphatidylinositol anchor on the lipoarabinomannan and lipomannan of Mycobacterium.tuberculosis. J. Biol. Chem. 265:92729279.
55. Hunter, S. W.,, H. Gaylord,, and P. J. Brennan. 1986. Structure and antigenicity of the phosphorylated lipopolysaccharide antigens from the leprosy and tubercle bacilli. J. Biol. Chem. 261:1234512351.
56. Imaeda, T.,, F. Kanetsuna,, and B. Galindo. 1968. Ultrastructure of cell walls of genus Mycobactc rium. J. Ultrastruct. Res. 25:4663.
57. Kaplan, G.,, R. R. Gandhi,, D. E. Weinstein,, W. R. Levis,, M. E. Patarroyo,, P. J. Brennan,, and Z. A. Cohn. 1987. Mycobacterium leprae antigen-induced suppression of T cell proliferation in vitro. J. Immunol. 138:30283034.
58. Kataoka, N.,, I. Toida,, I. Yano,, and A. Misaki. 1986. Isolation and characterization of new glycolipids from Mycobacterium tuberculosis H37Rv. Osaka City Med. J. 32:115.
59. Kato, M. 1973. Effect of anti-cord factor antibody on experimental tuberculosis in mice. Infect. Immun. 7:1421.
60. Kikuchi, S.,, D. L. Rainwater,, and P. E. Kolattukudy. 1992. Purification and characterization of an unusually large fatty acid synthase from Mycobacterium tuberculosis var. bovis BCG. Arch. Biochem. Biophys. 295:318326.
61. Koul, A. K.,, and M. Gastambide-Odier. 1977. Microanalyse rapide de dimycocerosate de phthiocerol de mycoside et de glycerides dans les extraits a l'ether de pétrole de Mycobacterium kansasii et du BCG, souchi Pasteur. Biochimie 59:535538.
62. Lacave, C.,, M. A. Laneelle,, M. Daffe,, H. Montrozier,, M. P. Rois,, and C. Asselineau. 1987. Etude structurale et métabolique des acides mycoliques de Mycobacterium fortuitum. Eur. J. Biochem. 163: 369378.
63. Lacave, C.,, M. A. Laneelle,, and G. Laneelle. 1990a. Mycolic acid synthesis by Mycobacterium aurum cell-free extracts. Biochim. Biophys. Acta 1042:315323.
64. Lacave, C., M. A. Laneelle,, H. Montrozier,, and G. Laneelle. 1989. Mycolic acid metabolic filiation and location in Mycobacterium aurum and Mycobacterium phlei. Eur. J. Biochem. 181:459466.
65. Lacave, C.,, A. Quemard,, and G. Laneelle. 1990b. Cell-free synthesis of mycolic acids in Mycobacterium aurum: radioactivity distribution in newly synthesized acids and presence of cell wall in the system. Biochim. Biophys. Acta 1045:5865.
66. Lechevalier, M. P. 1977. Lipids in bacterial taxonomy—a taxonomist's view. Crit. Rev. Microbiol. 1977:109210.
67. Lechevalier, M. P.,, and H. Lechevalier. 1970. Chemical composition as a criterion in the classification of aerobic actinomycetes. Int. J. Syst. Bacteriol. 20: 435444.
68. Lederer, E.,, A. Adam,, R. Ciorbaru,, J.-F. Petit,, and J. Wietzerbin. 1975. Cell walls of mycobacteria and related organisms; chemistry and immunostimulant properties. Mol. Cell. Biochem. 7:87104.
69. Lee, Y. C.,, and C. E. Ballou. 1964. Structural studies on the myo-inositol mannosides from the glycolipids of Mycobacterium tuberculosis and Mycobacterium phlei. J. Biol. Chem. 239:13161327.
70. Lee, Y. C.,, and C. E. Ballou. 1965. Complete structures of the glycophospholipids of mycobacteria. Biochemistry 4:13951404.
71. Lepoivre, M.,, J. P. Tenu,, G. Lemaire,, and J. F. Petit. 1982. Anti-tumor activity and hydrogen peroxide release by macrophages elicted by trehalose clusters. J. Immunol. 129:860866.
72. Manjula, M.,, and P. E. Kolattukudy. 1992. Molecular cloning and sequencing of the gene for mycocerosic acid synthase, a novel fatty acid elongating multifunctional enzyme from Mycobacterium tuberculosis var. bovis Bacillus Calmette-Guerin. J. Biol. Chem. 267:1938819395.
73. Marks, G. S.,, and N. Poigar. 1955. Mycoceranic acid. II. J. Chem. Soc. 1955(Part IV):38513857.
74. Matsunaga, I.,, S. Oka,, T. Inove,, and I. Yano. 1990. Mycolyl glycolipids stimulate macrophages to release chemotactic factors. FEMS Microbiol. Lett. 67:4954.
75. McNeil, M.,, and P. J. Brennan. 1991. Structure, function, and biogenesis of the cell envelope of mycobacteria in relation to bacterial physiology, pathogenesis, and drug resistance; some thoughts and possibilities arising from recent structural information. Res. Microbiol. 142:451463.
76. McNeil, M.,, M. Daffe,, and P. J. Brennan. 1990. Evidence for the nature of the link between the arabinogalactan and peptidoglycan components of mycobacterial cell walls. J. Biol. Chem. 265:1820018206.
77. McNeil, M.,, M. Daffe,, and P. J. Brennan. 1991. Location of the mycolyl ester substituent in the cell walls of mycobacteria. J. BioL Chem. 266:1321713223.
78. McNeil, M. R.,, K. G. Robuck,, M. Harter,, and P. J. Brennan. Enzymatic evidence for the presence of a critical terminal hexaarabinoside in the cell walls of Mycobacterium tuberculosis. Glycobiology, in press.
79. Menzel, A. E. O.,, and M. Heidelberger. 1939. Specific and nonspecific cell polysaccharides of bovine strain of tubercle bacillus. J. Biol. Chem. 127:221236.
80. Middlebrook, G.,, R. J. Dobos,, and C. Pierce. 1947. Virulence and morphological characteristics of mammalian tubercle bacilli. J. Exp. Med. 86:175184.
81. Minnikin, D. E., 1982. Lipids: complex lipids, their chemistry, biosynthesis and roles, p. 95184. In C. Ratledge, and J. L. Stanford (ed.), 7Vie Biology of the Mycobacteria, vol. 1. Academic Press, London.
82. Minnikin, D. E. 1991. Chemical principles in the organization of lipid components in the mycobacterial cell envelope. Res. Microbiol. 142:423427.
83. Minnikin, D. E.,, G. Dobson,, D. Sesardie,, and M. Ridel!. 1985. Mycolipenates and mycolipanolates of trehalose from Mycobacterium tuberculosis. J. Gen. Microbiol. 131:13691374.
84. Minnikin, D. E.,, and M. Goodfellow,. 1980. Lipid composition in the classification and identification of acid-fast bacteria, p. 189256. In M. Goodfellow, and R. G. Board (ed.), Microbiological Classification and Identification. Academic Press, London.
85. Minnikin, D. E.,, S. M. Minnikin,, I. G. Hutchinson,, M. Goodfellow,, and J. M. Grange. 1984a. Mycolic acid patterns of representative strains of Mycobacterium fortuitum, Mycobacterium peregrinum, and Mycobacterium smegmatis. J. Gen. Microbiol. 130:363367.
86. Minnikin, D. E.,, S. M. Minnikin,, J. H. Parlett,, M. Goodfellow,, and M. Magnusson. 1984b. Mycolic acid patterns of some species of Mycobacterium. Arch. Microbiol. 139:225231.
87. Minnikin, D. E.,, P. V. Patel,, and M. Goodfellow. 1974. Mycolic acids of representative strains of Nocardia and "rhodochrous" complex. FEBS Lett. 39:322324.
88. Minnikin, D. E.,, and N. Polgar. 1965. Phthiocerol B, a constituent of the lipids of the tubercle bacilli. Chem. Commun. 20:495.
89. Minnikin, D. E.,, and N. Polgar. 1966. Studies relating to phthiocerol. V. Phthiocerol A and B. J. Chem. Soc. (C) 1966:21072112.
90. Minnikin, D. E.,, and N. Polgar. 1967a. Studies relating to phthiocerol. VII. Phthiodiolone A. J. Chem. Soc. (C) 1967:803807.
91. Minnikin, D. E.,, and N. Polgar. 1967b. The mycolic acids from human and avian tubercle bacilli. Chem. Commun. 18:916918.
92. Minnikin, D. E.,, and N. Polgar. 1967c. The methoxymycolic and ketomycolic acids from human tubercle bacilli. Chem. Commun. 22:11721174.
93. Misaki, A.,, I. Azuma,, and Y. Yamamura. 1977. Structural and immunochemical studies on D-arabino-D-mannans and D-mannans of Mycobacterium tuberculosis and other Mycobacterium species. J. Biochem. 82:17591770.
94. Misaki, A.,, N. Ikawa,, T. Kato,, and S. Kotani. 1970. Cell wall arabinogalactan of Mycobacterium phlei. Biochim. Biophys. Acta 215:405408.
95. Misaki, A.,, N. Seto,, and I. Azuma. 1974. Structure and immunological properties of D-arabino-D-galactan isolated from cell walls of Mycobacterium species. J. Biochem. 76:1522.
96. Moreno, C.,, A. Mehlert,, and J. Lamb. 1988. The inhibitory effects of mycobacterial lipoarabinomannan and polysaccharides upon polyclonal human T-cell proliferation. Clin. Exp. Immunol. 74:206210.
97. Moreno, C.,, J. Taverne,, A. Mehlert,, C. A. W. Bate,, R. J. Brealey,, A. Meager,, G. A. W. Rook,, and J. H. L. Playfair. 1989. Lipoarabinomannan from Mycobacterium tuberculosis induces the production of tumor necrosis factor from human and murine macrophages. Clin. Exp. Immunol. 76:240245.
98. Nikaido, H.,, and V. Jarlier. 1991. Permeability of the mycobacterial cell wall. Res. Microbiol. 142:437443.
99. Noll, H. 1956. The chemistry of cord-factor, a toxic glycolipid of M. tuberculosis. Adv. Tuberc. Res. 7:149183.
100. Noll, H. 1957. The chemistry of some native constituents of the purified wax of Mycobacterium tuberculosis. J. Biol. Chem. 224:149164.
101. Ohashi, M. 1970. Studies on the chemical structure of serologically active arabinomannan from mycobacteria. Jpn. J. Exp. Med. 40:114.
102. Ohashi, M.,, and J. Tsumita. 1964. The fatty acid composition of the lipopolysaccharide of Mycobacterium tuberculosis, the hemagglutination antigen. Jpn. J. Exp. Med. 34:323328.
103. Orme, I. M.,, A. D. Roberts,, J. P. Griffin,, and J. S. Abrams. 1993. Cytokine secretion by CD4 T lymphocytes acquired in response to Mycobacterium tuberculosis infection. J. Immunol. 151:518525.
104. Pangborn, M. C.,, and J. A. McKinney. 1966. Purification of serologically active phosphoinositides of Mycobacterium tuberculosis. J. Lipid Res. 7:627637.
105. Polansky, J.,, E. Solar,, R. F. Toubiana,, K. Takayama,, M. S. Raju,, and E. Wankert. 1977. A carbon-13 nuclear magnetic resonance spectral analysis of cord-factors and related substances. Nouv. J. Chim. 2:317320.
106. Polgar, N.,, and W. Smith. 1963. Mycoceranic acid. III. J. Chem. Soc. (Part III) 1963:30813085.
107. Prome, J., , C. Lacave,, A. Ahibo-Coffy,, and A. Savagnac. 1976. Separation et etude structurale des especes moléculaires de monomycolates et de dimy-colates de ot-D-trehalose presents chez Mycobacterium phlei. Eur. J. Biochem. 63:543552.
108. Puzo, G.,, and J. C. Prome. 1978. Field desorption mass spectrometry of oligosaccharides and glycolip-ids in presence of metal salts. Adv. Mass Spectrom. 7:15961602.
109. Puzo, G.,, G. Tissie,, C. Lacave,, H. Aurelle,, and J. C. Prome. 1978. Structural determination of 'cord-factor' from a Cornybacterium diphtheriae strain by the use of combined ionization methods in mass spectrometry: field desorption cesium cationization and electron impact mass spectrometry. Biomed. Mass Spectrom. 5:699703.
110. Qureshi, N.,, N. Sathyamoorthy,, and K. Takayama. 1984. Biosynthesis of C30 to C56 fatty acids by an extract of Mycobacterium tuberculosis H37Ra. J. Bacteriol. 157:4652.
111. Rainwater, D. L.,, and P. E. Kolattukudy. 1983. Synthesis of mycocerosic acids from methylmalonyl coenzyme A by cell-free extracts of Mycobacterium tuberculosis var. bovis BCG. J. Biol. Chem. 258: 29792985.
112. Rainwater, D. L.,, and P. E. Kolattukudy. 1985. Fatty acid biosynthesis in Mycobacterium tuberculosis var. bovis Bacillus Calmette-Guerin. J. Biol. Chem. 260:616623.
113. Ratledge, C., 1987. Iron metabolism in mycobacteria, p. 207221. In G. Winkleman,, D. van der Jalm,, and J. Weilands (ed.), Iron Transport in Microbes, Plants, and Animals. VCH, Weinheim, Germany.
114. Roach, T. I., H. Barton,, D. Chatterjee,, and J. M. Blackwell. 1993. Macrophage activation: lipoarabinomannan from avirulent and virulent strains of Mycobacterium tuberculosis differentially induces the early genes c-fos, KC, JE, and tumor necrosis factor-a. J. Immunol. 150:18861896.
115. Seibert, F., , and D. W. Watson. 1941. Isolation of the polysaccharides and nucleic acid of tuberculin by electrophoresis. J. Biol. Chem. 140:5569.
116. Sibley, L. D.,, S. W. Hunter,, P. J. Brennan,, and J. L. Krahenbuhl. 1988. Mycobacterial lipoarabinomannan inhibits gamma interferon-mediated activation of macrophages. Infect. Immun. 56:12321236.
117. Spargo, B. J.,, L. M. Crowe,, T. Ioneda,, B. L. Beaman,, and J. H. Crowe. 1991. Cord-factor (a-a'-trehalose 6,6' dimycolate) inhibits fusion between phospholipid vesicles. Proc. Natl. Acad. Sci. USA 88:737740.
118. Steck, P. A.,, B. A. Schwartz,, M. S. Rosendahl,, and G. R. Gray. 1978. Mycolic acids: a reinvestigation. J. Biol. Chem. 253:56255709.
119. Stodola, F. H.,, A. Lesuk,, and R. J. Anderson. 1938. The chemistry of lipids of tubercle bacilli. LIV. The isolation and properties of mycolic acids. J. Biol. Chem. 126:505513.
120. Strain, S. M.,, R. Toubiana,, E. Ribi,, and R. Parker. 1977. Separation of the mixture of trehalose 6,6'-dimycolates comprising the mycobacterial glycolipid fraction. Biochem. Biophys. Res. Commun. 77:449456.
121. Takayama, K.,, and E. L. Armstrong. 1971. Mannolipid synthesis in a cell-free system of Mycobacterium smegmatis. FEBS Lett. 18:6769.
122. Takayama, K.,, and L. A. Davidson. 1979a. Antimyco-bacterial drugs that inhibit mycolic acid synthesis. Trends Biochem. Sci. 4:280282.
123. Takayama, K.,, and L. A. Davidson,. 1979b. isonicotinic acid hydrazide, p. 98119. In F. E. Hahn (ed.), Antibiotics VI, Mechanism of Action of Antibacterial Agents. Springer Verlag, Berlin.
124. Takayama, K.,, and D. S. Goldman. 1970. Enzymatic synthesis of mannosyl-l-phosphoryldecaprenol by a cell-free system of Mycobacterium tuberculosis. J. Biol. Chem. 245:62516257.
125. Takayama, K.,, H. K. Schnoes,, and E. J. Semmlier. 1973. Characterization of the alkali-stable mannophospholipids of Mycobacterium smegmatis. Biochim. Biophys. Acta 136:212221.
126. Thurman, P. F.,, W. Chai,, J. R. Rosankiewicz,, H. J. Rogers,, A. M. Lawson,, and P. Draper. 1993. Possible intermediates in the biosynthesis of mycoside B by Mycobacterium microti. Eur. J. Biochem. 212: 705711.
127. Tsumita, T.,, R. Matsumoto,, and D. Mizuno. 1959. The nature of the Middlebrook-Dubos haemagglutina-tion antigen of Mycobacterium tuberculosis. Jpn. J. Med. Sci. 12:167170.
128. Tsumita, T.,, R. Matsumoto,, and D. Mizuno. 1960. Chemical and biological properties of the- haemag-glutination antigen, a lipopolysaccharide of Mycobacterium tuberculosis. Jpn. J. Med. Sci. 13:131138.
129. Venisse, A.,, J.-H. Berjeaud,, P. Chaurand,, P. Gilleren,, and G. Puzo. 1993. Structural features of lipoarabinomannan from Mycobacterium bovis BCG. Determination of molecular mass by laser desorption mass spectrometry. J. Biol. Chem. 268:1240112411.
130. Vilkas, E.,, C. Amar,, J. Markovits,, J. G. F. Vliegenthart,, and J. P. Kamerling. 1973. Occurrence of a galactofuranose disaccharide in immunoadjuvant fractions of Mycobacterium tuberculosis (cell walls and wax D). Biochim. Biophys. Acta 297:423435.
131. Walker, R. W.,, H. Barakat,, and J. G. C. Hung. 1970. The positional distribution of fatty acids in the phospholipids and triglycerides of Mycobacterium smegmatis and M. bovis BCG. Lipids 5:684691.
132. Wallis, R. S.,, M. Amir-Tahmasseb,, and J. J. Ellner. 1990. Induction of interleukin 1 and tumor necrosis factor by mycobacterial proteins: the monocyte Western blot. Proc. Natl. Acad. Sci. USA 87:33483352.
133. Weber, P. L.,, and G. L. Gray. 1979. Structural and immunochemical characterization of the acidic arabinomannan of Mycobacterium smegmatis. Carbohydr. Res. 74:259278.
134. Weir, M. P.,, W. H. R. Langridge,, and R. H. Walker. 1972. Relationships between oleic acid uptake and lipid metabolism in Mycobacterium smegmatis. Am. Rev. Respir. Dis. 106:450457.
135. Wheeler, P. R.,, G. S. Besra,, D. E. Minnikin,, and C. Ratledge. 1993a. Stimulation of mycolic acid biosynthesis by incorporation of cis-tetracos-5-enoic acid in a cell wall preparation from Mycobacterium smegmatis. Biochim. Biophys. Acta 1167:182188.
136. Wheeler, P. R.,, G. S. Besra,, D. E. Minnikin,, and C. Ratledge. 1993b. Inhibition of mycolic acid biosynthesis in a cell wall preparation from Mycobacterium smegmatis by methyl 4-(2-octadecylcyclpro-pen-l-yl) butanoate, a structural analogue of a key precursor. Lett. Appl. Microbiol. 17:3336.
137. Winder, F. G., 1982. Mode of action of the antimyco-bacterial agents and associated aspects of the molecular biology of the mycobacterias, p. 354438. In C. Ratledge, and J. L. Stanford (ed.), The Biology of the Mycobacteria, vol. 1. Academic Press, London.
138. Wolucka, B. A.,, M. R. McNeil,, E. Hoffmann,, T. Chojnacki,, C. Cocito,, R. Comber,, and P. J. Brennan. Recognition of the likely carrier lipid for arab-inan biosynthesis and its relation to the mode of action of ethambutol in mycobacteria. Submitted for publication.
139. Wong, M. Y. H.,, and G. R. Gray. 1979. Structures of the homologous series of mono-alkene mycolic acids from Mycobacterium smegmatis. J. Biol. Chem. 254:57415744.
140. Yano, I.,, K. Kageyama,, Y. Ohno,, M. Masui,, E. Kusunose,, and M. Kusunose. 1978. Separation and analysis of molecular species of mycolic acids in Nocardia and related taxa by gas chromatography mass spectrometry. Biomed. Mass Spectrom. 5:1424.
141. Yokoyama, K., and E. Ballou. 1989. Synthesis of alpha 1—>6 mannooligosaccharides in Mycobacterium smegmatis. Function of beta-mannosylphos-phoryldecaprenol as the mannosyl donor. J. Biol. Chem. 264:2162121628.

Tables

Generic image for table
Table 1

Long-chain diols and fatty acids

Citation: Besra G, Chatterjee D. 1994. Lipids and Carbohydrates of , p 285-306. In Bloom B (ed), Tuberculosis. ASM Press, Washington, DC. doi: 10.1128/9781555818357.ch20
Generic image for table
Table 2

SLs of

Citation: Besra G, Chatterjee D. 1994. Lipids and Carbohydrates of , p 285-306. In Bloom B (ed), Tuberculosis. ASM Press, Washington, DC. doi: 10.1128/9781555818357.ch20
Generic image for table
Table 3

Structures of some mycobacterial mycolic acids

Citation: Besra G, Chatterjee D. 1994. Lipids and Carbohydrates of , p 285-306. In Bloom B (ed), Tuberculosis. ASM Press, Washington, DC. doi: 10.1128/9781555818357.ch20

This is a required field
Please enter a valid email address
Please check the format of the address you have entered.
Approval was a Success
Invalid data
An Error Occurred
Approval was partially successful, following selected items could not be processed due to error