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Category: Fungi and Fungal Pathogenesis; Clinical Microbiology
Lipids and Carbohydrates of Mycobacterium tuberculosis, Page 1 of 2
< Previous page | Next page > /docserver/preview/fulltext/10.1128/9781555818357/9781555819101_Chap20-1.gif /docserver/preview/fulltext/10.1128/9781555818357/9781555819101_Chap20-2.gifAbstract:
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.
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Final stages of phthiocerol A biosynthesis, n = 20 or 22.
Final stages of phthiocerol A biosynthesis, n = 20 or 22.
Phosphatidylinositol dimannoside.
Phosphatidylinositol dimannoside.
Phosphatidyl-myo-inositol hexamannoside. R, palmitic acid or tuberculostearic acid.
Phosphatidyl-myo-inositol hexamannoside. R, palmitic acid or tuberculostearic acid.
β-D-Arabinofuranosyl-l-phosphodecaprenol.
β-D-Arabinofuranosyl-l-phosphodecaprenol.
Trehalose 6,6′-dimycolate. RCO = mycolyl.
Trehalose 6,6′-dimycolate. RCO = mycolyl.
2,3,6,6′-Tetra-O-acyItrehalose 2′-sulfate.
2,3,6,6′-Tetra-O-acyItrehalose 2′-sulfate.
Mycolipenic acids.
Mycolipenic acids.
2,3-Di-O-acyltrehaloses.
2,3-Di-O-acyltrehaloses.
Mycolipanolic acids.
Mycolipanolic acids.
Lipooligosaccharide (LOS-I) isolated from M. tuberculosis Canetti.
Lipooligosaccharide (LOS-I) isolated from M. tuberculosis Canetti.
Phenolic glycolipid isolated from M. tuberculosis Canetti.
Phenolic glycolipid isolated from M. tuberculosis Canetti.
Reverse Claisen condensation reaction.
Reverse Claisen condensation reaction.
Biosynthesis of α-mycolic acids in M. tuberculosis H37Ra. А, Δ5 desaturase; В, tetracosanyl malonate CH3(CH2)23 CH(COOH)2.
Biosynthesis of α-mycolic acids in M. tuberculosis H37Ra. А, Δ5 desaturase; В, tetracosanyl malonate CH3(CH2)23 CH(COOH)2.
Mycobactin T.
Mycobactin T.
Schematic representation of the cell wall of M. tuberculosis.
Schematic representation of the cell wall of M. tuberculosis.
Mannose-capped LAM.
Mannose-capped LAM.
Long-chain diols and fatty acids
Long-chain diols and fatty acids
SLs of M. tuberculosis
SLs of M. tuberculosis
Structures of some mycobacterial mycolic acids
Structures of some mycobacterial mycolic acids