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Chapter 20 : Lipids and Carbohydrates of

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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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

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