ArticleJournal of the American Society for Mass Spectrometry2007
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.
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 23 papers.
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Who cites it
23 citing papers in PubMed.
- Multiple stage linear ion-trap mass spectrometry toward characterization of native bacterial lipids-a critical review.Biochimie · 2023Review
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- Complete Characterization of Polyacyltrehaloses fromBiochemistry · 2021Article
- Targeted Lipidomics of Mycobacterial Lipids and Glycolipids.Methods in molecular biology (Clifton, N.J.) · 2021Article
- Mass spectrometry-based shotgun lipidomics - a critical review from the technical point of view.Analytical and bioanalytical chemistry · 2018Review
- Structural determinants in a glucose-containing lipopolysaccharide fromThe Journal of biological chemistry · 2018Article
- Visualization of Mycobacterial Biomarkers and Tuberculosis Drugs in Infected Tissue by MALDI-MS Imaging.Analytical chemistry · 2018Article
- Purification and characterization of the acyltransferase involved in biosynthesis of the major mycobacterial cell envelope glycolipid--monoacylated phosphatidylinositol dimannoside.Protein expression and purification · 2014Article
- Structural studies on archaeal phytanyl-ether lipids isolated from membranes of extreme halophiles by linear ion-trap multiple-stage tandem mass spectrometry with electrospray ionization.Analytica chimica acta · 2013Article
- 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
- Article
- 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
- Regulation of antigen presentation by Mycobacterium tuberculosis: a role for Toll-like receptors.Nature reviews. Microbiology · 2010Review
- 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
- The glycerophosphoinositols: cellular metabolism and biological functions.Cellular and molecular life sciences : CMLS · 2009Review
- 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
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5 authors.
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Abstract
We described a multiple-stage ion-trap mass spectrometric approach to characterize the structures of phosphatidylinositol and phosphatidyl-myoinositol mannosides (PIMs) in a complex mixture isolated from Mycobacterium bovis Bacillus Calmette Guérin. The positions of the fatty acyl substituents of PIMs at the glycerol backbone can be easily assigned, based on the findings that the ions arising from losses of the fatty acid substituent at sn-2 as molecules of acid and of ketene, respectively (that is, the [M - H - R(2)CO(2)H](-) and [M - H - R(2)CHCO](-) ions), are respectively more abundant than the ions arising from the analogous losses at sn-1 (that is, the [M - H - R(1)CO(2)H](-) and [M - H - R(1)CHCO](-) ions) in the MS(2) product-ion spectra of the [M - H](-) ions desorbed by electrospray ionization (ESI). Further dissociation of the [M - H - R(2)CO(2)H](-) and [M - H - R(1)CO(2)H](-) ions gives rise to a pair of unique ions corresponding to losses of 74 and 56 Da (that is, [M - H - R(x)CO(2)H - 56](-) and [M - H - R(x)CO(2)H - 74](-) ions, x = 1, 2), respectively, probably arising from various losses of the glycerol. The profile of the ion-pair in the MS(3) spectrum of the [M - H - R(2)CO(2)H](-) ion is readily distinguishable from that in the MS(3) spectrum of the [M - H - R(1)CO(2)H](-) ion and thus the assignment of the fatty acid substituents at the glycerol backbone can be confirmed. The product-ion spectra of the [M - H](-) ions from 2-lyso-PIM and from 1-lyso-PIM are discernible and both spectra contain a unique ion that arises from primary loss of the fatty acid substituent at the glycerol backbone, followed by loss of a bicyclic glycerophosphate ester moiety of 136 Da. The combined structural information from the MS(2) and MS(3) product-ion spectra permit the complex structures of PIMs that consist of various isomers to be unveiled in detail.
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