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
Bjorn
B
Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747 AG, Groningen, The Netherlands. b.ter.horst@rug.nl
Seshadri
Chetan
C
Sweet
Lindsay
L
Young
David C
DC
Feringa
Ben L
BL
Moody
D Branch
DB
Minnaard
Adriaan J
AJ
D001688:Biological Products / Q000138:chemical synthesis / Q000737:chemistry / Q000302:isolation & purification; D015415:Biomarkers / Q000737:chemistry; D020404:Glycerophospholipids / Q000138:chemical synthesis* / Q000737:chemistry* / Q000302:isolation & purification; D009169:Mycobacterium tuberculosis / Q000737:chemistry*; D013237:Stereoisomerism; D053719:Tandem Mass Spectrometry; D014376:Tuberculosis
C550562:1-O-tuberculostearoyl-2-O-palmitoyl-sn-glycero-3-phosphoethanolamine; D001688:Biological Products; D015415:Biomarkers; D020404:Glycerophospholipids