Structure of an acidic O-specific polysaccharide of Pseudoalteromonashaloplanktis type strain ATCC 14393 containing 2-acetamido-2-deoxy-d- and -l-galacturonic acids and 3-(N-acetyl-d-alanyl)amino-3,6-dideoxy-d-glucose

Hanniffy, Orla M.; Shashkov, Alexander S.; Senchenkova, Sof’ya N.; Tomshich, Svetlana V.; Komandrova, Nadezhda A.; Romanenko, Lyudmila A.; Knirel, Yuriy A.; Savage, Angela V.

doi:10.1016/s0008-6215(99)00182-2

Cited by 55 publications

(15 citation statements)

References 17 publications

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“…O Deacetylated polysaccharide 2 was studied by two dimensional NMR spectroscopy, including 1 H, 1 H homo nuclear COSY, TOCSY, and ROESY correlation experi ments and 1 H, 13 C heteronuclear HSQC and HMBC ex periments. As a result, we made the assignment of the signals for the protons of spin systems of two α galacto pyranose residues (A and B), an α mannopyranose resi due (C), and an α rhamnopyranose residue (D) and three spin systems (H(1)-H(3), H(5)-H (8), and H(1´)-H(2´)) of erwiniose (Table 2).…”

Section: Resultsmentioning

confidence: 99%

Structure of the O-polysaccharide of Erwinia carotovora ssp. atroseptica GSPB 9205 containing a new higher branched monosaccharide

et al. 2005

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An O polysaccharide was prepared by mild acid hydrolysis of a lipopolysaccharide of Erwinia carotovora ssp. atroseptica GSPB 9205 and was found to contain a new higher branched monosaccharide, viz., 3,6,8 trideoxy 4 C (R 1 hydroxyethyl) D gulo octose, which we called erwiniose. The structure of the pentasaccharide repeating unit of the O polysaccharide was established by monosaccharide analysis, including the determination of absolute configura tions, methylation analysis, O deacetylation, Smith degradation, and one and two dimen sional NMR spectroscopy. The configuration of erwiniose was determined based on the cou pling constants of vicinal protons combined with the nuclear Overhauser effect data and the results of periodate oxidation of the polysaccharide followed by reduction of the resultant 4 keto sugar (the C(1)-C(4)-C(1´)-C(2´) fragment) to give 3,6 dideoxy D ribo hexose (paratose) and oxidation of 3 hydroxybutyraldehyde (the C(5)-C(8) fragment) to give R 3 hydroxybutyric acid.Lipopolysaccharide (LPS) forms the outer layer of the outer membrane of the Gram negative bacteria cell walls. The fine structure of the O polysaccharide chain of the LPS is responsible for intraspecies diversity of strains and specificity of interactions of bacterial cells with other bio logical systems. Classification schemes of many Gram negative bacteria necessary for epidemiologic monitoring are based on O polysaccharide structures.Lipopolysaccharides of phytopathogenic bacteria are involved in plant pathogenesis, for example, in soft rot caused by Erwinia carotovora strains. The structure of LPS of bacteria belonging to the Erwinia genus was poorly studied. 1-5 The structures of O polysaccharides were es tablished only for two strains, viz., E. carotovora ssp. atroseptica GSPB 436 1 and Erwinia amylovara T. 4 The classification scheme of bacteria Erwinia is lacking. With the aim of classifying strains of phytopathogenic bacteria, we perform a series of structural studies of their O poly saccharides. In the present study, we established the structure of the O polysaccharide of E. carotovora ssp. atroseptica GSPB 9205. We found and identified a new higher branched monosaccharide in this O polysaccharide and called it erwiniose. Results and DiscussionMild acid degradation of LPS, which was isolated from E. carotovora ssp. atroseptica GSPB 9205 cells by aque ous phenol extraction, afforded an O polysaccharide (1). Monosaccharide analysis by GLC of alditol acetates ob tained upon total acid hydrolysis of polysaccharide 1 re vealed the presence of galactose, mannose, and rhamnose in a ratio of 2 : 1 : 1. The GLC analysis of acetylated glycosides with an optically active alcohol, viz., S octan 2 ol, revealed D configuration for galactose and mannose and L configuration for rhamnose. Methylation analysis of the polysaccharide revealed 3 substituted galactose resi dues, a 4 substituted rhamnose residue, and a 2,3 disub stituted mannose residue. The presence of the latter monosaccharide is indicative of a branched structure of the polys...

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Section: Resultsmentioning

confidence: 99%

Structure of the O-polysaccharide of Erwinia carotovora ssp. atroseptica GSPB 9205 containing a new higher branched monosaccharide

et al. 2005

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“…A mixing time of 60 ms and a spin‐lock time of 200 ms were used in TOCSY and ROESY experiments, respectively. Other NMR experimental parameters were set essentially as described (Hanniffy et al ., ).…”

Section: Methodsmentioning

confidence: 97%

Structure and genetics of the O-antigen ofCronobacter turicensisG3882 from a new serotype,C. turicensisO2, and identification of a serotype-specific gene

Sun

Arbatsky

Wang

et al. 2012

FEMS Immunol Med Microbiol

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Lipopolysaccharides on the cell surface of Gram‐negative bacteria are an important factor in pathogenicity, and the O‐specific polysaccharide chain (O‐polysaccharide, O‐antigen) defines the immunospecificity of different bacterial strains. Cronobacter turicensis is an emerging foodborne pathogen which causes severe invasive infections in neonates. In this study, a new O serotype, C. turicensis O2, was established, the structure and genetics of the O‐antigen were investigated, and a serotype‐specific gene was identified. Sugar and methylation analyses, and nuclear magnetic resonance spectroscopy indicated that the O‐polysaccharide contains d‐galactose (d‐Gal), N‐acetyl‐d‐glucosamine (d‐GlcNAc), l‐rhamnose (l‐Rha) and 5,7‐diacetamido‐3,5,7,9‐tetradeoxy‐d‐glycero‐d‐galacto‐non‐2‐ulosonic acid (di‐N‐acetyllegionaminic acid, Leg5Ac7Ac). The structure of the tetrasaccharide repeat of the O‐polysaccharide was established as: .5mm→4)‐α‐Legp5Ac7Ac‐(2→3)‐α‐d‐Galp‐(1→3)‐β‐l‐Rhap‐(1→4)‐β‐d‐GlcpNAc‐(1→ The O‐antigen gene cluster of C. turicensis O2 was sequenced and compared with related gene clusters from available databases. Putative genes for the synthesis of l‐Rha and Leg5Ac7Ac, and genes encoding sugar transferases and O‐antigen processing genes (wzx and wzy) were found. The tentatively assigned functions of the O‐antigen genes were in agreement with the structure of the O‐polysaccharide. In addition, primers based on the wzy gene were shown to be specific for C. turicensis O2 in a screen against 145 strains.

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“…Other NMR spectroscopic experimental parameters were essentially as described previously. [26] NMR spectra of the fraction-A oligosaccharides were measured at 25 8C on a Varian UNITY/Inova 500 spectrometer (USA). Mixing times of 120, 300, and 80 ms were used in TOCSY, NOESY, and HSQC-TOCSY/HMQC-TOCSY experiments, respectively.…”

Section: Methodsmentioning

confidence: 99%

Full Structure of the Carbohydrate Chain of the Lipopolysaccharide of Providencia rustigianii O34

Kocharova

Kondakova

Vinogradov

et al. 2008

Chemistry A European J

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A lipopolysaccharide isolated from an opportunistic pathogen of the Enterobacteriaceae family Providencia rustigianii O34 was found to be a mixture of R-, SR-, and S-forms consisting of a lipid moiety (lipid A) that bears a core oligosaccharide, a core with one O-polysaccharide repeating unit attached, and a long-chain O-polysaccharide, respectively. The corresponding carbohydrate moieties were released from the lipopolysaccharide by mild acid hydrolysis and studied by sugar and methylation analyses along with one- and two-dimensional NMR spectroscopy and high-resolution electrospray ionization mass spectrometry. As a result, the structures of the core and the O-polysaccharide were established, including the structure of the biological repeating unit (an oligosaccharide that is preassembled and polymerized in biosynthesis of the O-polysaccharide), as well as the mode of the linkage between the O-polysaccharide and the core. Combining the structure of the carbohydrate moiety thus determined and the known structure of lipid A enabled determination of the full lipopolysaccharide structure of P. rustigianii O34.

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Structure of an acidic O-specific polysaccharide of Pseudoalteromonashaloplanktis type strain ATCC 14393 containing 2-acetamido-2-deoxy-d- and -l-galacturonic acids and 3-(N-acetyl-d-alanyl)amino-3,6-dideoxy-d-glucose

Cited by 55 publications

References 17 publications

Structure of the O-polysaccharide of Erwinia carotovora ssp. atroseptica GSPB 9205 containing a new higher branched monosaccharide

Structure of the O-polysaccharide of Erwinia carotovora ssp. atroseptica GSPB 9205 containing a new higher branched monosaccharide

Structure and genetics of the O-antigen ofCronobacter turicensisG3882 from a new serotype,C. turicensisO2, and identification of a serotype-specific gene

Full Structure of the Carbohydrate Chain of the Lipopolysaccharide of Providencia rustigianii O34

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