Abstract
Both phthiocerol/phthiodiolone dimycocerosate (PDIM) and phenolic glycolipids are abundant virulent lipids in the cell wall of various pathogenic mycobacteria, which can synthesize a wide range of complex high-molecular-mass lipids. In this article, we describe linear ion-trap MS(n) mass spectrometric approach for structural study of PDIMs, which were desorbed as the [M + Li](+) and [M + NH(4)](+) ions by ESI. We also applied charge-switch strategy to convert the mycocerosic acid substituents to their N-(4-aminomethylphenyl) pyridinium (AMPP) derivatives and analyzed them as M (+) ions, following alkaline hydrolysis of the PDIM to release mycocerosic acids. The structural information from MS(n) on the [M + Li](+) and [M + NH(4)](+) molecular species and on the M (+) ions of the mycocerosic acid-AMPP derivative affords realization of the complex structures of PDIMs in Mycobacterium tuberculosis biofilm, differentiation of phthiocerol and phthiodiolone lipid families and complete structure identification, including the phthiocerol and phthiodiolone backbones, and the mycocerosic acid substituents, including the locations of their multiple methyl side chains, can be achieved.
Highlights
E (PDIM) and phenolic glycolipids are abundant virulent lipids in the cell wall of various pathogenic mycobacteria, which can synthesize a wide range of complex high-molecular-mass lipids
They are among the most abundant lipids in the cell wall of various pathogenic mycobacteria, including M. tuberculosis, M. bovis, M. leprae, M. kansasii, M. microti, and M. marinum [7,8,9,10], which are known to synthesize a range of complex highmolecular-mass lipids [7]
The role of phthiodiolone dimycocerosate (PDIM) of M. tuberculosis was recognized by the studies that identified that mutants of M. tuberculosis were unable to either produce or properly localize PDIMs to the cell envelopeand that demonstrated that PDIM-deficient strains were attenuated in animal models of infection [8, 11, 13,14,15,16,17]
Summary
E (PDIM) and phenolic glycolipids are abundant virulent lipids in the cell wall of various pathogenic mycobacteria, which can synthesize a wide range of complex high-molecular-mass lipids. Both phthiocerol/phthiodiolone dimycocerosate (PDIM) esters and phenolic glycolipids (PGLs) are dimycocerosate esters (DIMs) produced by pathogenic mycobacteria. PDIMs were originally isolated from Mycobacterium tuberculosis [1,2,3,4] and are specific tuberculosis biomarkers [5, 6] They are among the most abundant lipids in the cell wall of various pathogenic mycobacteria, including M. tuberculosis, M. bovis, M. leprae, M. kansasii, M. microti, and M. marinum [7,8,9,10], which are known to synthesize a range of complex highmolecular-mass lipids [7]. The precise role of these molecules in the course of infection remains largely unknown, and their role in the multiplication of mycobacteria from the tuberculosis complex in organs other than the lungs is unclear
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