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结核分枝杆菌甘油磷脂的不对称合成与结构阐明。

Asymmetric synthesis and structure elucidation of a glycerophospholipid from Mycobacterium tuberculosis.

机构信息

Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747 AG, Groningen, The Netherlands.

出版信息

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

DOI:10.1194/jlr.M001982
PMID:19965610
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC2853428/
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.

摘要

从结核分枝杆菌参考株 H37Rv 中分离出一种甘油磷脂(1-O-结核硬脂酰-2-O-棕榈酰-sn-甘油-3-磷酸乙醇胺)。已经解析了这种结核硬脂酰 [(R)-10-甲基十八烷基] 和棕榈酰含有磷脂酰乙醇胺(PE)的分子结构。通过将该分离物与两种合成制备的立体异构体进行比较,可以确定甘油主链上的取代模式。通过 MS/MS 分析确定其分子结构。这种合成的分枝杆菌 PE 可以高产制备,具有立体化学正确和病原体特异性的脂肪酸酰基,可作为基于 LC-MS 的脂质组学分析中的标准品,用于检测人血液、痰或组织中痕量分枝杆菌 PE,作为分枝杆菌感染的标志物。

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本文引用的文献

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The synthesis of tuberculostearic acid.结核硬脂酸的合成
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