Structural analysis of the carbohydrate backbone of Vibrioparahaemolyticus O2 lipopolysaccharides

Hashii, Noritaka; Isshiki, Yasunori; Iguchi, Takehiro; Kondo, Seiichi

doi:10.1016/s0008-6215(03)00078-8

Cited by 27 publications

(28 citation statements)

References 18 publications

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“…The structural variation thus, resides mainly in the oligosaccharide portion of the LOSs. Similar types of LOSs are also found in some parahaemolyticus O2 has been reported to contain 5,7-diacetamido-3,5,7,9-tetradeoxy-D-glycero-D-galacto-non-2-ulosonic acid [7], where as, a O-untypable strain KX-V212 contains 5-acetamido-7-(N-acetyl-D-alanyl)amido-3,5,7,9-tetradeoxy-D-glycero-D-galacto-non-2-ulosonic acid [8]. The chemical structure of the lipooligosaccharide of V. parahaemolyticus O2 [7] and V. parahaemolyticus Ountypable strain KX-V212 [9] have been established, recently.…”

Section: Introductionsupporting

confidence: 69%

“…The NonlA is in the α-anomeric form as is evident from the chemical shift of H-3 (equatorial, δ H 2.98), which is shifted, downfield by 0.67 ppm compared to the β-anomer [7,16]. The NOESY spectrum of the OS (DMSO-d 6 ) showed strong correlation of C-5 amide proton (δ H 7.52) with the methyl protons of 5-N-acetyl group.…”

Section: Isolation Of the Lipooligosaccharide And Oligosaccharidementioning

confidence: 91%

“…

A novel sugar,5,5,7,8,, has been identified as a component of the oligosaccharide (OS) isolated from the lipooligosaccharide (LOS) of the emerging strain of Vibrio parahaemolyticus O3:K6 associated with a global pandemic. In the present study we report the identification and characterization of this novel sugar present in the OS of V. parahaemolyticus O3:K6, using chemical analysis, NMR spectroscopy and mass spectrometry.

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confidence: 99%

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Identification of a novel sugar 5,7-diacetamido-8-amino-3,5,7,8,9-pentadeoxy-d-glycero-d-galacto-non-2-ulosonic acid present in the lipooligosaccharide of Vibrio parahaemolyticus O3:K6

Mazumder

Choudhury²,

Nair

et al. 2007

Glycoconj J

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A novel sugar, 5,7-diacetamido-8-amino-3,5,7,8,9-pentadeoxy-D-glycero-D-galacto-non-2-ulosonic acid (NonlA), has been identified as a component of the oligosaccharide (OS) isolated from the lipooligosaccharide (LOS) of the emerging strain of Vibrio parahaemolyticus O3:K6 associated with a global pandemic. In the present study we report the identification and characterization of this novel sugar present in the OS of V. parahaemolyticus O3:K6, using chemical analysis, NMR spectroscopy and mass spectrometry.

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Section: Introductionsupporting

confidence: 69%

Section: Isolation Of the Lipooligosaccharide And Oligosaccharidementioning

confidence: 91%

“…

…”

mentioning

confidence: 99%

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Identification of a novel sugar 5,7-diacetamido-8-amino-3,5,7,8,9-pentadeoxy-d-glycero-d-galacto-non-2-ulosonic acid present in the lipooligosaccharide of Vibrio parahaemolyticus O3:K6

Mazumder

Choudhury²,

Nair

et al. 2007

Glycoconj J

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“…Most of the components (Hep, Glc, Kdo, GalNAc, PEA, and phosphate) seen in the core are prototypical constituents of core components found in numerous Gram-negative bacteria, including other Vibrio spp. (24,(42)(43)(44)(45)(46)(47)(48). In addition to these typical components, the V. fischeri core also contains the unusual sugar 8-epi-legionaminic acid.…”

Section: Discussionmentioning

confidence: 99%

O-antigen and Core Carbohydrate of Vibrio fischeri Lipopolysaccharide

Post

Krasity

et al. 2012

Journal of Biological Chemistry

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Background:The structure and function of the Vibrio fischeri O-antigen were unknown. Results: The O-antigen structure was determined using an O-antigen ligase mutant. Conclusion: This mutant had a motility defect, and comparison of its LPS with wild-type LPS showed that the O-antigen contains some unusual sugars. Significance: The O-antigen mutation results in a significantly slower rate of bacterial colonization of the squid light organ.

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“…Traditionally, to obtain the level of structural detail required for LOS structure/activity studies, the two domains of the molecule were analyzed separately following selective cleavage of the labile ketosidic linkage between the lipid A and the oligosaccharide moieties by mild acid hydrolysis [4,24]. Alternatively, LOS can be O-deacylated to remove O-linked fatty acids from the lipid A, or fully O-and N-deacylated to generate Bbackbone^LOS [25,26]. However, other acid-labile moieties, such as phosphate groups and Neu5Ac, can also be removed [10] and the release of biologically interesting O-linked moieties, such as acetate and glycine, occurs as an unwanted consequence of O-deacylation [27].…”

mentioning

confidence: 99%

Analysis of Bacterial Lipooligosaccharides by MALDI-TOF MS with Traveling Wave Ion Mobility

Phillips

John

Jarvis

2016

J. Am. Soc. Mass Spectrom.

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LOS MALDI IMS-MSAbstract. Lipooligosaccharides (LOS) are major microbial virulence factors displayed on the outer membrane of rough-type Gram-negative bacteria. These amphipathic glycolipids are comprised of two domains, a core oligosaccharide linked to a lipid A moiety. Isolated LOS samples are generally heterogeneous mixtures of glycoforms, with structural variability in both domains. Traditionally, the oligosaccharide and lipid A components of LOS have been analyzed separately following mild acid hydrolysis, although important acid-labile moieties can be cleaved. Recently, an improved method was introduced for analysis of intact LOS by MALDI-TOF MS using a thin layer matrix composed of 2,4,6-trihydroxyacetophenone (THAP) and nitrocellulose. In addition to molecular ions, the spectra show in-source Bprompt^fragments arising from regiospecific cleavage between the lipid A and oligosaccharide domains. Here, we demonstrate the use of traveling wave ion mobility spectrometry (TWIMS) for IMS-MS and IMS-MS/MS analyses of intact LOS from Neisseria spp. ionized by MALDI. Using IMS, the singly charged prompt fragments for the oligosaccharide and lipid A domains of LOS were readily separated into resolved ion plumes, permitting the extraction of specific subspectra, which led to increased confidence in assigning compositions and improved detection of less abundant ions. Moreover, IMS separation of precursor ions prior to collision-induced dissociation (CID) generated time-aligned, clean MS/MS spectra devoid of fragments from interfering species. Incorporating IMS into the profiling of intact LOS by MALDI-TOF MS exploits the unique domain structure of the molecule and offers a new means of extracting more detailed information from the analysis.

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Structural analysis of the carbohydrate backbone of Vibrioparahaemolyticus O2 lipopolysaccharides

Cited by 27 publications

References 18 publications

Identification of a novel sugar 5,7-diacetamido-8-amino-3,5,7,8,9-pentadeoxy-d-glycero-d-galacto-non-2-ulosonic acid present in the lipooligosaccharide of Vibrio parahaemolyticus O3:K6

Identification of a novel sugar 5,7-diacetamido-8-amino-3,5,7,8,9-pentadeoxy-d-glycero-d-galacto-non-2-ulosonic acid present in the lipooligosaccharide of Vibrio parahaemolyticus O3:K6

O-antigen and Core Carbohydrate of Vibrio fischeri Lipopolysaccharide

Analysis of Bacterial Lipooligosaccharides by MALDI-TOF MS with Traveling Wave Ion Mobility

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