Characterization of phthiocerol and phthiodiolone dimycocerosate esters of M. tuberculosis by multiple-stage linear ion-trap MS

Kelly N. Flentie, Christina L. Stallings, John Turk, Adriaan J. Minnaard, Fong Fu Hsu

Research output: Contribution to journalArticle

6 Scopus citations

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 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 MSn 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 biofi lm, differentiation of phthiocerol and phthiodiolone lipid families and complete structure identifi cation, including the phthiocerol and phthiodiolone backbones, and the mycocerosic acid substituents, including the locations of their multiple methyl side chains, can be achieved.

Original languageEnglish
Pages (from-to)142-155
Number of pages14
JournalJournal of lipid research
Volume57
Issue number1
DOIs
StatePublished - Jan 1 2016

Keywords

  • Biofilm
  • Electrospray ionization
  • Glycolipid
  • Higher collision energy dissociation
  • Lipidomics
  • Mass spectrometry
  • Microbial lipid
  • Mycobacterium tuberculosis

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