ArticleJournal of the American Society for Mass Spectrometry2007
Structural characterization of phosphatidyl-myo-inositol mannosides from Mycobacterium bovis Bacillus Calmette Gúerin by multiple-stage quadrupole ion-trap mass spectrometry with electrospray ionization. II. Monoacyl- and diacyl-PIMs.
Article in Journal of the American Society for Mass Spectrometry, 2007. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 19 papers.
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19 citing papers in PubMed, 60 citations in OpenAlex.
- Multiple stage linear ion-trap mass spectrometry toward characterization of native bacterial lipids-a critical review.Biochimie · 2023Review
- Complete Characterization of Polyacyltrehaloses fromBiochemistry · 2021Article
- A concise review on lipidomics analysis in biological samples.ADMET & DMPK · 2021Review
- Targeted Lipidomics of Mycobacterial Lipids and Glycolipids.Methods in molecular biology (Clifton, N.J.) · 2021Article
- Lectins ofBeilstein journal of organic chemistry · 2019Review
- Novel long-chain diol phospholipids from some bacteria belonging to the class Thermomicrobia.Lipids · 2015Article
- Structural determination of glycopeptidolipids of Mycobacterium smegmatis by high-resolution multiple-stage linear ion-trap mass spectrometry with electrospray ionization.Journal of mass spectrometry : JMS · 2012Article
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- aprABC: a Mycobacterium tuberculosis complex-specific locus that modulates pH-driven adaptation to the macrophage phagosome.Molecular microbiology · 2011Article
- Lipidomic analyses of Mycobacterium tuberculosis based on accurate mass measurements and the novel "Mtb LipidDB".Journal of lipid research · 2011Article
- Characterization of mycolic acids from the pathogen Rhodococcus equi by tandem mass spectrometry with electrospray ionization.Analytical biochemistry · 2011Article
- Asymmetric synthesis and structure elucidation of a glycerophospholipid from Mycobacterium tuberculosis.Journal of lipid research · 2010Article
- Electrospray ionization multiple-stage linear ion-trap mass spectrometry for structural elucidation of triacylglycerols: assignment of fatty acyl groups on the glycerol backbone and location of double bonds.Journal of the American Society for Mass Spectrometry · 2010Article
- Electrospray ionization with low-energy collisionally activated dissociation tandem mass spectrometry of glycerophospholipids: mechanisms of fragmentation and structural characterization.Journal of chromatography. B, Analytical technologies in the biomedical and life sciences · 2009Review
- Mycobacterial phosphatidylinositol mannosides negatively regulate host Toll-like receptor 4, MyD88-dependent proinflammatory cytokines, and TRIF-dependent co-stimulatory molecule expression.The Journal of biological chemistry · 2009Article
- Electron transfer dissociation of doubly sodiated glycerophosphocholine lipids.Journal of the American Society for Mass Spectrometry · 2007Article
- Algorithm for processing raw mass spectrometric data to identify and quantitate complex lipid molecular species in mixtures by data-dependent scanning and fragment ion database searching.Journal of the American Society for Mass Spectrometry · 2007Article
- Structural characterization of phosphatidyl-myo-inositol mannosides from Mycobacterium bovis Bacillus Calmette Guérin by multiple-stage quadrupole ion-trap mass spectrometry with electrospray ionization. I. PIMs and lyso-PIMs.Journal of the American Society for Mass Spectrometry · 2007Article
- The cell envelope glycoconjugates of Mycobacterium tuberculosis.Critical reviews in biochemistry and molecular biologyReview
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Authors and funding
5 authors at 2 institutions in 1 country.
Funding
Abstract
The multiple-stage ion-trap mass spectrometric approaches towards to the structural characterization of the monoacyl-PIM (triacylated PIM) and the diacyl-PIM (tetracylated PIM), namely, the PIM (diacylated PIM) consisting of one or two additional fatty acid substituents attached to the glycoside, respectively, were described. While the assignment and confirmation of the fatty acid substituents on the glycerol backbone can be easily achieved by the methods described in the previous article, the identity of the glycoside moiety and its acylation state can be determined by the observation of a prominent acylglycoside ion arising from cleavage of the diacylglycerol moiety ([M - H - diacylglycerol](-)) in the MS(2)-spectra of monoacyl-PIM and diacyl-PIM. The distinction of the fatty acid substituents on the 2-O-mannoside (i.e., R(3)CO(2)H) from that on the inositol (i.e., R(4)CO(2)H) is based on the findings that the MS(3)-spectrum of [M - H - diacylglycerol](-) contains a prominent ion arising from further loss of the fatty acid at the 2-O-mannoside (i.e., the [M - H - diacylglycerol - R(3)CO(2)H](-) ion), while the ion arising from loss of the fatty acid substituent at the inositol (i.e., the [M - H - diacylglycerol - R(4)CO(2)H](-) ion) is of low abundance. The fatty acyl moiety on the inositol can also be identified by the product-ion spectrum from MS(4) of the [M - H - diacylglycerol - R(3)CO(2)H](-) ion, which gives rise to a prominent ion corresponding to loss of R(4)CO(2)H. An [M - H - acylmannose](-) ion was also observed in the MS(2)-spectra and, thus, the identity of the fatty acid substituent attached to 2-O-mannoside can be confirmed. The combined information obtained from the multiple-stage product-ion spectra from MS(2), MS(3), and MS(4) permit the assignment of the complex structures of monoacyl-PIMs and diacyl-PIMs in a mixture isolated from M. bovis Bacillus Calmette Guérin.
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