Asymmetric synthesis and structure elucidation of a glycerophospholipid from Mycobacterium tuberculosis

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.-ter Horst, B., C. Seshadri, L. Sweet, D. C. Young, B. L. Feringa, D. B. Moody, and A. J. Minnaard. Asymmetric synthesis and structure elucidation of a glycerophospholipid from Mycobacterium tuberculosis. J. Lipid Res. 2010. 51: 1017-1022.