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Chapter 20 : Lipids and Carbohydrates of Mycobacterium tuberculosis
Authors:
Gurdyal S. Besra1,
Delphi Chatterjee1
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Affiliations:
1: Department of Microbiology, Colorado State University, Fort Collins, Colorado 80523
Content Type: Monograph
Publication Year:
1994
Category: Fungi and Fungal Pathogenesis; Clinical Microbiology
Book DOI:
10.1128/9781555818357
Chapter DOI:
10.1128/9781555818357.ch20
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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 Mycobacterium tuberculosis. A lipid apparently not present in other actinomycetes was isolated from M. tuberculosis 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 M. tuberculosis 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 M. tuberculosis.
Citation:
Besra G, Chatterjee D.
1994.
Lipids and Carbohydrates of Mycobacterium tuberculosis,
p 285-306.
In
Bloom B (ed),
Tuberculosis.
ASM Press, Washington, DC.
doi: 10.1128/9781555818357.ch20
Figures
Lipids and Carbohydrates of Mycobacterium tuberculosis
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Citation:
Besra G, Chatterjee D.
1994.
Lipids and Carbohydrates of Mycobacterium tuberculosis,
p 285-306.
In
Bloom B (ed),
Tuberculosis.
ASM Press, Washington, DC.
doi: 10.1128/9781555818357.ch20
/content/10.1128/9781555818357.chap20.fig20-1
Figure 1
Final stages of phthiocerol A biosynthesis, n = 20 or 22.
10.1128/9781555818357/fig20-1_thmb.gif
10.1128/9781555818357/fig20-1.gif
Figure 1
Final stages of phthiocerol A biosynthesis, n = 20 or 22.
Citation:
Besra G, Chatterjee D.
1994.
Lipids and Carbohydrates of Mycobacterium tuberculosis,
p 285-306.
In
Bloom B (ed),
Tuberculosis.
ASM Press, Washington, DC.
doi: 10.1128/9781555818357.ch20
/content/10.1128/9781555818357.chap20.fig20-2
Figure 2
Phosphatidylinositol dimannoside.
10.1128/9781555818357/fig20-2_thmb.gif
10.1128/9781555818357/fig20-2.gif
Figure 2
Phosphatidylinositol dimannoside.
Citation:
Besra G, Chatterjee D.
1994.
Lipids and Carbohydrates of Mycobacterium tuberculosis,
p 285-306.
In
Bloom B (ed),
Tuberculosis.
ASM Press, Washington, DC.
doi: 10.1128/9781555818357.ch20
/content/10.1128/9781555818357.chap20.fig20-3
Figure 3
Phosphatidyl-myo-inositol hexamannoside. R, palmitic acid or tuberculostearic acid.
10.1128/9781555818357/fig20-3_thmb.gif
10.1128/9781555818357/fig20-3.gif
Figure 3
Phosphatidyl-myo-inositol hexamannoside. R, palmitic acid or tuberculostearic acid.
Citation:
Besra G, Chatterjee D.
1994.
Lipids and Carbohydrates of Mycobacterium tuberculosis,
p 285-306.
In
Bloom B (ed),
Tuberculosis.
ASM Press, Washington, DC.
doi: 10.1128/9781555818357.ch20
/content/10.1128/9781555818357.chap20.fig20-4
Figure 4
β-D-Arabinofuranosyl-l-phosphodecaprenol.
10.1128/9781555818357/fig20-4_thmb.gif
10.1128/9781555818357/fig20-4.gif
Figure 4
β-D-Arabinofuranosyl-l-phosphodecaprenol.
Citation:
Besra G, Chatterjee D.
1994.
Lipids and Carbohydrates of Mycobacterium tuberculosis,
p 285-306.
In
Bloom B (ed),
Tuberculosis.
ASM Press, Washington, DC.
doi: 10.1128/9781555818357.ch20
/content/10.1128/9781555818357.chap20.fig20-5
Figure 5
Trehalose 6,6′-dimycolate. RCO = mycolyl.
10.1128/9781555818357/fig20-5_thmb.gif
10.1128/9781555818357/fig20-5.gif
Figure 5
Trehalose 6,6′-dimycolate. RCO = mycolyl.
Citation:
Besra G, Chatterjee D.
1994.
Lipids and Carbohydrates of Mycobacterium tuberculosis,
p 285-306.
In
Bloom B (ed),
Tuberculosis.
ASM Press, Washington, DC.
doi: 10.1128/9781555818357.ch20
/content/10.1128/9781555818357.chap20.fig20-6
Figure 6
2,3,6,6′-Tetra-O-acyItrehalose 2′-sulfate.
10.1128/9781555818357/fig20-6_thmb.gif
10.1128/9781555818357/fig20-6.gif
Figure 6
2,3,6,6′-Tetra-O-acyItrehalose 2′-sulfate.
Citation:
Besra G, Chatterjee D.
1994.
Lipids and Carbohydrates of Mycobacterium tuberculosis,
p 285-306.
In
Bloom B (ed),
Tuberculosis.
ASM Press, Washington, DC.
doi: 10.1128/9781555818357.ch20
/content/10.1128/9781555818357.chap20.fig20-7
Figure 7
Mycolipenic acids.
10.1128/9781555818357/fig20-7_thmb.gif
10.1128/9781555818357/fig20-7.gif
Figure 7
Mycolipenic acids.
Citation:
Besra G, Chatterjee D.
1994.
Lipids and Carbohydrates of Mycobacterium tuberculosis,
p 285-306.
In
Bloom B (ed),
Tuberculosis.
ASM Press, Washington, DC.
doi: 10.1128/9781555818357.ch20
/content/10.1128/9781555818357.chap20.fig20-8
Figure 8
2,3-Di-O-acyltrehaloses.
10.1128/9781555818357/fig20-8_thmb.gif
10.1128/9781555818357/fig20-8.gif
Figure 8
2,3-Di-O-acyltrehaloses.
Citation:
Besra G, Chatterjee D.
1994.
Lipids and Carbohydrates of Mycobacterium tuberculosis,
p 285-306.
In
Bloom B (ed),
Tuberculosis.
ASM Press, Washington, DC.
doi: 10.1128/9781555818357.ch20
/content/10.1128/9781555818357.chap20.fig20-9
Figure 9
Mycolipanolic acids.
10.1128/9781555818357/fig20-9_thmb.gif
10.1128/9781555818357/fig20-9.gif
Figure 9
Mycolipanolic acids.
Citation:
Besra G, Chatterjee D.
1994.
Lipids and Carbohydrates of Mycobacterium tuberculosis,
p 285-306.
In
Bloom B (ed),
Tuberculosis.
ASM Press, Washington, DC.
doi: 10.1128/9781555818357.ch20
/content/10.1128/9781555818357.chap20.fig20-10
Figure 10
Lipooligosaccharide (LOS-I) isolated from M. tuberculosis Canetti.
10.1128/9781555818357/fig20-10_thmb.gif
10.1128/9781555818357/fig20-10.gif
Figure 10
Lipooligosaccharide (LOS-I) isolated from M. tuberculosis Canetti.
Citation:
Besra G, Chatterjee D.
1994.
Lipids and Carbohydrates of Mycobacterium tuberculosis,
p 285-306.
In
Bloom B (ed),
Tuberculosis.
ASM Press, Washington, DC.
doi: 10.1128/9781555818357.ch20
/content/10.1128/9781555818357.chap20.fig20-11
Figure 11
Phenolic glycolipid isolated from M. tuberculosis Canetti.
10.1128/9781555818357/fig20-11_thmb.gif
10.1128/9781555818357/fig20-11.gif
Figure 11
Phenolic glycolipid isolated from M. tuberculosis Canetti.
Citation:
Besra G, Chatterjee D.
1994.
Lipids and Carbohydrates of Mycobacterium tuberculosis,
p 285-306.
In
Bloom B (ed),
Tuberculosis.
ASM Press, Washington, DC.
doi: 10.1128/9781555818357.ch20
/content/10.1128/9781555818357.chap20.fig20-12
Figure 12
Reverse Claisen condensation reaction.
10.1128/9781555818357/fig20-12_thmb.gif
10.1128/9781555818357/fig20-12.gif
Figure 12
Reverse Claisen condensation reaction.
Citation:
Besra G, Chatterjee D.
1994.
Lipids and Carbohydrates of Mycobacterium tuberculosis,
p 285-306.
In
Bloom B (ed),
Tuberculosis.
ASM Press, Washington, DC.
doi: 10.1128/9781555818357.ch20
/content/10.1128/9781555818357.chap20.fig20-13
Figure 13
Biosynthesis of α-mycolic acids in M. tuberculosis H37Ra. А, Δ5 desaturase; В, tetracosanyl malonate CH3(CH2)23 CH(COOH)2.
10.1128/9781555818357/fig20-13_thmb.gif
10.1128/9781555818357/fig20-13.gif
Figure 13
Biosynthesis of α-mycolic acids in M. tuberculosis H37Ra. А, Δ5 desaturase; В, tetracosanyl malonate CH3(CH2)23 CH(COOH)2.
Citation:
Besra G, Chatterjee D.
1994.
Lipids and Carbohydrates of Mycobacterium tuberculosis,
p 285-306.
In
Bloom B (ed),
Tuberculosis.
ASM Press, Washington, DC.
doi: 10.1128/9781555818357.ch20
/content/10.1128/9781555818357.chap20.fig20-14
Figure 14
Mycobactin T.
10.1128/9781555818357/fig20-14_thmb.gif
10.1128/9781555818357/fig20-14.gif
Figure 14
Mycobactin T.
Citation:
Besra G, Chatterjee D.
1994.
Lipids and Carbohydrates of Mycobacterium tuberculosis,
p 285-306.
In
Bloom B (ed),
Tuberculosis.
ASM Press, Washington, DC.
doi: 10.1128/9781555818357.ch20
/content/10.1128/9781555818357.chap20.fig20-15
Figure 15
Schematic representation of the cell wall of M. tuberculosis.
10.1128/9781555818357/fig20-15_thmb.gif
10.1128/9781555818357/fig20-15.gif
Figure 15
Schematic representation of the cell wall of M. tuberculosis.
Citation:
Besra G, Chatterjee D.
1994.
Lipids and Carbohydrates of Mycobacterium tuberculosis,
p 285-306.
In
Bloom B (ed),
Tuberculosis.
ASM Press, Washington, DC.
doi: 10.1128/9781555818357.ch20
/content/10.1128/9781555818357.chap20.fig20-16
Figure 16
Mannose-capped LAM.
10.1128/9781555818357/fig20-16_thmb.gif
10.1128/9781555818357/fig20-16.gif
Figure 16
Mannose-capped LAM.
Citation:
Besra G, Chatterjee D.
1994.
Lipids and Carbohydrates of Mycobacterium tuberculosis,
p 285-306.
In
Bloom B (ed),
Tuberculosis.
ASM Press, Washington, DC.
doi: 10.1128/9781555818357.ch20
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Tables
Lipids and Carbohydrates of Mycobacterium tuberculosis
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Citation:
Besra G, Chatterjee D.
1994.
Lipids and Carbohydrates of Mycobacterium tuberculosis,
p 285-306.
In
Bloom B (ed),
Tuberculosis.
ASM Press, Washington, DC.
doi: 10.1128/9781555818357.ch20
/content/10.1128/9781555818357.chap20.tab20-1
Table 1
Long-chain diols and fatty acids
10.1128/9781555818357/tab20-1_thmb.gif
10.1128/9781555818357/tab20-1.gif
Table 1
Long-chain diols and fatty acids
Citation:
Besra G, Chatterjee D.
1994.
Lipids and Carbohydrates of Mycobacterium tuberculosis,
p 285-306.
In
Bloom B (ed),
Tuberculosis.
ASM Press, Washington, DC.
doi: 10.1128/9781555818357.ch20
/content/10.1128/9781555818357.chap20.tab20-2
Table 2
SLs of M. tuberculosis
10.1128/9781555818357/tab20-2_thmb.gif
10.1128/9781555818357/tab20-2.gif
Table 2
SLs of M. tuberculosis
Citation:
Besra G, Chatterjee D.
1994.
Lipids and Carbohydrates of Mycobacterium tuberculosis,
p 285-306.
In
Bloom B (ed),
Tuberculosis.
ASM Press, Washington, DC.
doi: 10.1128/9781555818357.ch20
/content/10.1128/9781555818357.chap20.tab20-3
Table 3
Structures of some mycobacterial mycolic acids
10.1128/9781555818357/tab20-3_thmb.gif
10.1128/9781555818357/tab20-3.gif
Table 3
Structures of some mycobacterial mycolic acids
Citation:
Besra G, Chatterjee D.
1994.
Lipids and Carbohydrates of Mycobacterium tuberculosis,
p 285-306.
In
Bloom B (ed),
Tuberculosis.
ASM Press, Washington, DC.
doi: 10.1128/9781555818357.ch20