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Asymmetric synthesis and structure elucidation of a glycerophospholipid from Mycobacterium tuberculosis.
Title | Asymmetric synthesis and structure elucidation of a glycerophospholipid from Mycobacterium tuberculosis. |
Publication Type | Journal Article |
Year of Publication | 2010 |
Authors | Horst, BTer, Seshadri, C, Sweet, L, Young, DC, Feringa, BL, D Moody, B, Minnaard, AJ |
Journal | J Lipid Res |
Volume | 51 |
Issue | 5 |
Pagination | 1017-22 |
Date Published | 2010 May |
ISSN | 0022-2275 |
Keywords | Biological Agents, Biological Markers, Glycerophospholipids, Mycobacterium tuberculosis, Stereoisomerism, Tandem Mass Spectrometry, Tuberculosis |
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. |
DOI | 10.1194/jlr.M001982 |
Alternate Journal | J. Lipid Res. |
PubMed ID | 19965610 |
PubMed Central ID | PMC2853428 |
Grant List | R01 049313 / / PHS HHS / United States T32 AI007061 / AI / NIAID NIH HHS / United States |