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. 2010 May;51(5):1017-22.
doi: 10.1194/jlr.M001982. Epub 2009 Nov 5.

Asymmetric synthesis and structure elucidation of a glycerophospholipid from Mycobacterium tuberculosis

Bjorn Ter Horst  1 , Chetan Seshadri, Lindsay Sweet, David C Young, Ben L Feringa, D Branch Moody, Adriaan J Minnaard
Affiliations

Asymmetric synthesis and structure elucidation of a glycerophospholipid from Mycobacterium tuberculosis

Bjorn Ter Horst et al. J Lipid Res. 2010 May.

Abstract

A glycerophospholipid (1-O-tuberculostearoyl-2-O-palmitoyl-sn-glycero-3-phosphoethanolamine) from Mycobacterium tuberculosis was isolated from the reference strain H37Rv. The molecular structure of this tuberculostearoyl [(R)-10-methyloctadecyl] and palmitoyl containing phosphatidylethanolamine (PE) has been resolved. The substitution pattern on the glycerol backbone could be determined by comparison of the isolate to the two synthetically prepared regioisomers. MS/MS analysis was used to determine its molecular structure. Production of this synthetic version of mycobacterial PE in high yield, with a stereochemically correct and pathogen-specific fatty acyl group, can be used as a standard in LC-MS based lipidomic analyses to detect trace amounts of mycobacterial PE in human blood, sputum, or tissues as a marker of infection by mycobacteria.

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Figures

Fig. 1.
Fig. 1.
Total synthesis of (R)-TBSA (3).
Fig. 2.
Fig. 2.
Synthesis of 1-O-TBSA-2-O-palmitoyl-sn-phos­pho­lipid (1).
Fig. 3.
Fig. 3.
The two possible structures of the natural phospholipid; 1-O-TBSA-2-O-palmitoyl-sn-phospholipid (1) and 1-O-palmitoyl-2-O-TBSA-sn-phospholipid (2).
Fig. 4.
Fig. 4.
A: Negative mode mass analysis of detected M. tuberculosis phosphatidylethanolamines (PE). B: Extracted ion chromatograms of PE's detected in M. tuberculosis compared to mammalian PE's from non-infected mouse lung homogenate, no ion at m/z 732.55 was detected in this region of the chromatogram for the mammalian PEs.
Fig. 5.
Fig. 5.
MS/MS (ESI) in negative mode.
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References

    1. Vance J. E. 2008. Phosphatidylserine and phosphatidylethanolamine in mammalian cells: two metabolically related aminophospholipids. J. Lipid Res. 49: 1377–1387. - PubMed
    1. Nicolaou K. C., Snyder S. A. 2005. Chasing molecules that were never there: misassigned natural products and the role of chemical synthesis in modern structure elucidation. Agnew. Chem. Int. Ed. 44: 1012–1044. - PubMed
    1. Smith P. B., Snyder A. P., Harden C. S. 1995. Characterization of bacterial phospholipids by electrospray ionization tandem mass spectrometry. Anal. Chem. 67: 1824–1830. - PubMed
    1. Cabrera G. M., Fernández Murga M. L., Font de Valdez G., Seldes A. M. 2000. Direct analysis by electrospray ionisation tandem mass spectrometry of mixtures of phosphatidyldiacylglycerols from Lactobacillus. J. Am. Soc. Mass Spectrom. 35: 1452–1459. - PubMed
    1. Jensen N. J., Tomer K. B., Gross M. L. 1987. FAB MS/MS for phosphatidylinostitol,-glycerol,-ethanolamine and other complex phospholipids. Lipids. 22: 480–489. - PubMed

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