Journal
JOURNAL OF LIPID RESEARCH
Volume 57, Issue 1, Pages 142-155Publisher
ELSEVIER
DOI: 10.1194/jlr.D063735
Keywords
glycolipid; microbial lipid; lipidomics; biofilm; mass spectrometry; electrospray ionization; higher collision energy dissociation; Mycobacterium tuberculosis
Categories
Funding
- U.S. Public Health Service [P41-GM103422, P60-DK-20579, P30-DK56341, 1R21HL120760-01]
- Arnold and Mabel Beckman Foundation
- Children's Discovery Institute of Washington University
- St. Louis Children's Hospital
- Center for Women's Infectious Disease Research at Washington University School of Medicine
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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 MSn mass spectrometric approach for structural study of PDIMs, which were desorbed as the [M + Li](+) and [M + NH4](+) 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 on the [M + Li](+) and [M + NH4](+) molecular species and on the M ions of the mycocerosic acid-AMPP derivative affords realization of the complex structures of PDIMs in Mycobacterium tuberculosis biofilin, 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.
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