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Lipopolysaccharide (LPS) was isolated from Yersinia enterocolitica serovar O:10 and O:10 KL, and the structural pattern of O-specific sugar chain elucidated. The rhamnan and L-xylulose (L-threo-pent-2-ulose) as constituents of the O-specific polysaccharide were obtained by autohydrolysis of the LPS. The rhamnan was shown to be a linear, a-(1-3)-linked polysaccharide in the D configuration. L-Xylulose was purified using paper chromatography on a preparative scale and its structre was confirmed by 13C NMR spectroscopy. Using sugar and methylation analysis and 13C NMR spectroscopy of the LPS and the rhamnan, the structural features of the disaccharide repeating unit of from Y. enterocolitica serovar O:10 O-specific polysaccharide were elucidated as: [-3)[bLXulf(2-2)]aDRhap(1-]

Lipopolysaccharide, O-specific polysaccharide, d-Rhamnan, Yersinia enterocolitica, L-xylulose (L-threo-pent-2-ulose)

NCBI PubMed ID: 7537629
Publication DOI: 10.1016/0008-6215(94)00339-H
Journal NLM ID: 0043535
Publisher: Elsevier
Institutions: Pacific Institute of Bioorganic Chemistry, Far East Branch of the Russian Academy of Sciences, Vladivostok 690022, Russia
Methods: 13C NMR, methylation, sugar analysis, paper chromatography, autohydrolysis

The lipopolysaccharide (LPS) is the major constituent of the outer leaflet of the outer membrane of Gram-negative bacteria. Its lipid A moiety is embedded in the membrane and serves as an anchor for the rest of the LPS molecule. The outermost repetitive glycan region of the LPS is linked to the lipid A through a core oligosaccharide (OS), and is designated as the O-specific polysaccharide (O-polysaccharide, OPS) or O-antigen. The O-antigen is the most variable portion of the LPS and provides serological specificity, which is used for bacterial serotyping. The OPS also provides protection to the microorganisms from host defenses such as complement mediated killing and phagocytosis, and is involved in interactions of bacteria with plants and bacteriophages. Studies of the OPSs ranging from the elucidation of their chemical structures and conformations to their biological and physico-chemical properties help improving classification schemes of Gram-negative bacteria. Furthermore, these studies contributed to a better understanding of the mechanisms of pathogenesis of infectious diseases, as well as provided information to develop novel vaccines and diagnostic reagents.

Lipopolysaccharide, synthesis, lipopolysaccharides, structure, Bacterial, host, O-antigen, O antigen, cell, O antigens, O-antigens, chemical, interaction, cells, PDF, chemical synthesis, biogenesis

Publication DOI: 10.1007/978-3-7091-0733-1_3
Publisher: Springer
Correspondence: knirel@ioc.ac.ru
Editors: Knirel YA, Valvano MA
Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia

The antigenic polysaccharide was obtained from the cell wall of Eubacterium saburreum strain T15 by trypsin digestion followed by gel permeation and ion-exchange chromatography. Its structure was determined using acid hydrolysis, methylation analysis, and 1D and 2D NMR spectroscopy. It contained L-threo-pent-2-ulose (Xul), D-fucose (Fuc), and D-glycero-D-galacto-heptose (Hep) in 2:3:3 ratio. Methylation analysis indicated an octasaccharide repeating-unit containing five branches. The 1H and 13C signals in NMR spectra of the sugar residues were assigned by COSY, HOHAHA, and HMQC 2D experiments, and the sequence of sugar residues in the repeating unit was determined by NOESY and HMBC experiments. The polysaccharide also contains two O- acetyl groups in the repeating unit, located on the Hep residue. The repeating structure can be written as:This is a novel structure in bacterial cell-wall polysaccharides from Gram-positive bacteria

NMR, structure, Bacterial, strain, polysaccharide, methylation analysis, repeating unit, analysis, cell, group, acid, infection, signal, NMR spectroscopy, bacteria, hydrolysis, cell wall, sugar, polysaccharides, methylation, spectroscopy, sequence, antigenic, chromatography, Japan, 2D NMR spectroscopy, antigenic polysaccharide, acetyl, 2D NMR, cell wall polysaccharides, HMQC, cell wall polysaccharide, Gram-positive, HMBC, D-fucose, NOESY, medical, gel, acetyl group, COSY, D-glycero-D-galacto-heptose, ecology, Eubacterium, Eubacterium saburreum, HOHAHA, ion-exchange, ion-exchange chromatography, oral, Trypsin

NCBI PubMed ID: 12681915
Journal NLM ID: 0043535
Publisher: Elsevier
Correspondence: sa-naomi@dent.niigata-u.ac.jp
Institutions: Department of Oral Health Science, Division of Oral Ecology in Health and Infection, Course for Oral Life Science, Niigata University Graduate School of Medical and Dental Sciences Gakkocho-dori 2, 951- 8514, Niigata, Japan
Methods: NMR