Asymmetric synthesis and structure elucidation of a glycerophospholipid from Mycobacterium 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.

journal_name

J Lipid Res

authors

Ter Horst B,Seshadri C,Sweet L,Young DC,Feringa BL,Moody DB,Minnaard AJ

doi

10.1194/jlr.M001982

subject

Has Abstract

pub_date

2010-05-01 00:00:00

pages

1017-22

issue

5

eissn

0022-2275

issn

1539-7262

pii

jlr.M001982

journal_volume

51

pub_type

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