A matrix‐assisted laser desorption/ionization mass spectrometry approach to the lipid A from <i>Mesorhizobium loti</i>

Casabuono, Adriana C.; D'antuono, Alejandra Lorena; Sato, Yasuto; Nonami, Hiroshi; Ugalde, Rodolfo A.; Lepek, Viviana C.; Erra‐Balsells, Rosa; Couto, Alicia S.

doi:10.1002/rcm.2575

Cited by 11 publications

(8 citation statements)

References 38 publications

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“…nor ‐Harmane in the negative mode showed good results for detection of phosphorylated species. This matrix is useful for desorption and ionization of anionic substrates . Furthermore, the use of this MALDI matrix in the negative‐ion mode minimized the occurrence of prompt fragmentation giving good S/N ratio useful to perform MALDI‐TOF/TOF‐MS.…”

Section: Discussionmentioning

confidence: 99%

“…This matrix is useful for desorption and ionization of anionic substrates. [35] Furthermore, the use of this MALDI matrix in the negative-ion mode minimized the occurrence of prompt fragmentation giving good S/N ratio useful to perform MALDI-TOF/TOF-MS. During MS/MS measurements, preferential release of ester-bonded with respect to the amide-linked fatty acids occur, therefore determination of the acylation pattern was possible. This is very important since bacterial lipid A species are mixtures of similar molecules and the intensities of the spectra signals provide the relative proportions of the different species.…”

Section: Discussionmentioning

confidence: 99%

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Characterization of lipid A profiles from Shigella flexneri variant X lipopolysaccharide

Casabuono

Ploeg

Rogé

et al. 2012

Rapid Comm Mass Spectrometry

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RATIONALE In developing countries, Shigella flexneri (Sf) is the major causative agent of the endemic shigellosis (bacillary dysentery) responsible annually for one million fatalities mostly among infants. Lipopolysaccharides (LPSs) are characteristic components of the outer membrane of the overwhelming majority of Gram‐negative bacteria. Since lipid A is essential for the viability of the Gram‐negative bacteria, it is subject to extensive chemical studies with new analytical techniques. METHODS Lipid A was released by mild acid hydrolysis from the lipopolysaccharide which was obtained via the phenol/water extraction, purified and analyzed by matrix‐assisted laser desorption/ionization time‐of‐flight mass spectrometry (MALDI‐TOF‐MS) and matrix‐assisted laser desorption/ionization laser‐induced dissociation tandem mass spectrometry (MALDI‐LID‐MS/MS). RESULTS A detailed structural study of the whole lipid A obtained from S. flexneri variant X was carried out for the first time. Thus, we have shown that lipid A is a heterogeneous mixture having different numbers of acylated and phosphoethanolamine groups attached to the diglucosamine backbone. Furthermore, we found in the phenol phase an unusual hepta‐acylated lipid A species, although the abundance was very low. CONCLUSIONS MALDI‐TOF‐MS allowed us to unravel the lipid A heterogeneity, which was not previously reported in Sf LPS. It is well known that slight variations of the chemical structure of lipid A may change its biological activity. Thus, the knowledge of the detailed chemical structure represents an essential step for further development of new preventive or therapeutically active compounds. Copyright © 2012 John Wiley & Sons, Ltd.

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Section: Discussionmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

Characterization of lipid A profiles from Shigella flexneri variant X lipopolysaccharide

Casabuono

Ploeg

Rogé

et al. 2012

Rapid Comm Mass Spectrometry

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“…Therefore, an exquisitely sensitive analytical method is required to determine not only the major lipid A components, but also minor components directly from bacterial cells. Mass spectrometry has been widely used to gain knowledge about lipid A heterogeneity, i.e., the number of different species of the lipid A families and distribution of the fatty acids on each glucosamine group ( 11,(15)(16)(17)(18)(19). We have previously characterized lipid A species through analysis of the intact LPS ( 20 ).…”

Section: Lipid a Isolation From Cells Using Microwave-assisted Enzymamentioning

confidence: 99%

Microwave-assisted sample preparation for rapid and sensitive analysis of H. pylori lipid A applicable to a single colony

Zhou

Chandan

Liu

et al. 2009

Journal of Lipid Research

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This article is available online at http://www.jlr.org of H. pylori outer membrane. The H. pylori LPS consists of a lipid A region, a core region, and an O-chain polysaccharide (also known as the O-antigen) ( 3 ). Lipid A, the hydrophobic moiety of LPS and a glucosamine-based saccharolipid, is the principal structural component responsible for the range of biological activities of LPS ( 4, 5 ).Generally, lipid A is a glucosamine disaccharide that carries phosphates at positions 1 and 4 ′ and usually has four primary (glucosamine-linked) hydroxyacyl chains and one or more secondary acyl chains ( 3, 6, 7 ). However, H. pylori lipid A is different from that of other bacterial species, including both phosphorylation and acylation patterns ( 8 ). The lipid A of H. pylori contains a phosphoethanolamine ( P Etn) group directly linked to the 1-position of the disaccharide backbone. This is in contrast to the P Etn groups found in other pathogenic Gram-negative bacteria, which are attached to the lipid A phosphate group to form a pyrophosphate linkage ( 9, 10 ). In addition, the predominant absence of ester-bound 4'-phosphate and the presence of tetraacyl lipid A with fatty acids of 16 to 18 carbons in length differentiate H. pylori lipid A from that of other Gram-negative bacteria. H. pylori synthesizes two types of lipid A molecules: hexaacyl-and tetraacyl-lipid A. Hexaacyllipid A has two phosphates or phosphoethanolamines on the lipid A disaccharide backbone, whereas tetraacyllipid A contains only one phosphate ( 8 ). It has also been reported that H. pylori does not survive long before it is deacylated at the 3 ′ position from hexaacyl structure to form the tetraacyl major lipid A species ( 11 ). The toxicity of H. pylori tetraacyl-lipid A on human monocytes is ‫ف‬ 4-fold lower than that of the hexaacyl form ( 12 ). It has been suggested that the phosphorylation and acylation patterns in lipid A of H. pylori LPS are responsible for its low biological activity ( 13,14 ).

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“…It was applied to lipid A from Haemophilus influenzae and Bordetella holmesii. DHB, THAP, and ATT with ammonium citrate appear to be the preferred matrices for these compounds but Casabuono et al (2006) have obtained better spectra with nor-harmane as matrix than with DHB for studies of Lipid A from Mesorhizobium loti. Considerable heterogeneity was present in the spectra as the result of different chain lengths of the acyl groups c. Medical aspects.…”

Section: Lipopolysaccharides (Lps)mentioning

confidence: 99%

Analysis of carbohydrates and glycoconjugates by matrix‐assisted laser desorption/ionization mass spectrometry: An update for the period 2005–2006

Harvey

2010

Mass Spectrometry Reviews

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This review is the fourth update of the original review, published in 1999, on the application of MALDI mass spectrometry to the analysis of carbohydrates and glycoconjugates and brings coverage of the literature to the end of 2006. The review covers fundamental studies, fragmentation of carbohydrate ions, method developments, and applications of the technique to the analysis of different types of carbohydrate. Specific compound classes that are covered include carbohydrate polymers from plants, N- and O-linked glycans from glycoproteins, glycated proteins, glycolipids from bacteria, glycosides, and various other natural products. There is a short section on the use of MALDI-TOF mass spectrometry for the study of enzymes involved in glycan processing, a section on industrial processes, particularly the development of biopharmaceuticals and a section on the use of MALDI-MS to monitor products of chemical synthesis of carbohydrates. Large carbohydrate-protein complexes and glycodendrimers are highlighted in this final section.

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A matrix‐assisted laser desorption/ionization mass spectrometry approach to the lipid A from Mesorhizobium loti

Cited by 11 publications

References 38 publications

Characterization of lipid A profiles from Shigella flexneri variant X lipopolysaccharide

Characterization of lipid A profiles from Shigella flexneri variant X lipopolysaccharide

Microwave-assisted sample preparation for rapid and sensitive analysis of H. pylori lipid A applicable to a single colony

Analysis of carbohydrates and glycoconjugates by matrix‐assisted laser desorption/ionization mass spectrometry: An update for the period 2005–2006

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