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[Identification of 3-acetamidino-2-acetamido-2,3-dideoxy-L-guluronic acid in lipopolysaccharide from Pseudomonas aeruginosa immunotype 7]. 1986

Iu A Knirel', and N A Paramonov, and E V Vinogradov, and A S Shashkov, and N K Kochetkov

O-Specific polysaccharide chain of Pseudomonas aeruginosa immunotype 7 lipopolysaccharide is composed of 3-acetamidino-2-acetamido-2,3-dideoxy-L-guluronic acid (GulNAcAmA), 2,3-diacetamido-2,3-dideoxy-D-mannuronic acid (ManN2Ac2A), and N-acetyl-D-fucosamine (FucNAc). On solvolysis with anhydrous hydrogen fluoride, the polysaccharide afforded a trisaccharide containing all its components. Borohydride reduction of the trisaccharide in boric acid solution resulted in conversion of reducing fucosamine into fucosaminitol, whereas in water the reduction was accompanied by reductive deamination of acetamidino function into ethylamino group. On hydrolysis with aqueous triethylamine, acetamidino group gave acetamido group. Analysis of the trisaccharides thus obtained by 1H NMR spectroscopy (including nuclear Overhauser effect), 13C NMR spectroscopy, and fast-atom bombardment mass spectrometry allowed the determination of the structure of the unusual uronic acid derivative and the following structure of the polysaccharide repeating unit: -4)-alpha-L-GulNAcAmA-(1-4)-beta-D-ManN2Ac2A-(1-3)-alpha-D-+ ++FucNAc-(1-.

UI MeSH Term Description Entries
D008070 Lipopolysaccharides Lipid-containing polysaccharides which are endotoxins and important group-specific antigens. They are often derived from the cell wall of gram-negative bacteria and induce immunoglobulin secretion. The lipopolysaccharide molecule consists of three parts: LIPID A, core polysaccharide, and O-specific chains (O ANTIGENS). When derived from Escherichia coli, lipopolysaccharides serve as polyclonal B-cell mitogens commonly used in laboratory immunology. (From Dorland, 28th ed) Lipopolysaccharide,Lipoglycans
D009682 Magnetic Resonance Spectroscopy Spectroscopic method of measuring the magnetic moment of elementary particles such as atomic nuclei, protons or electrons. It is employed in clinical applications such as NMR Tomography (MAGNETIC RESONANCE IMAGING). In Vivo NMR Spectroscopy,MR Spectroscopy,Magnetic Resonance,NMR Spectroscopy,NMR Spectroscopy, In Vivo,Nuclear Magnetic Resonance,Spectroscopy, Magnetic Resonance,Spectroscopy, NMR,Spectroscopy, Nuclear Magnetic Resonance,Magnetic Resonance Spectroscopies,Magnetic Resonance, Nuclear,NMR Spectroscopies,Resonance Spectroscopy, Magnetic,Resonance, Magnetic,Resonance, Nuclear Magnetic,Spectroscopies, NMR,Spectroscopy, MR
D011550 Pseudomonas aeruginosa A species of gram-negative, aerobic, rod-shaped bacteria commonly isolated from clinical specimens (wound, burn, and urinary tract infections). It is also found widely distributed in soil and water. P. aeruginosa is a major agent of nosocomial infection. Bacillus aeruginosus,Bacillus pyocyaneus,Bacterium aeruginosum,Bacterium pyocyaneum,Micrococcus pyocyaneus,Pseudomonas polycolor,Pseudomonas pyocyanea
D002621 Chemistry A basic science concerned with the composition, structure, and properties of matter; and the reactions that occur between substances and the associated energy exchange.
D006603 Hexuronic Acids Term used to designate tetrahydroxy aldehydic acids obtained by oxidation of hexose sugars, i.e. glucuronic acid, galacturonic acid, etc. Historically, the name hexuronic acid was originally given to ascorbic acid. Hexouronic Acids,Acids, Hexouronic,Acids, Hexuronic
D000942 Antigens, Bacterial Substances elaborated by bacteria that have antigenic activity. Bacterial Antigen,Bacterial Antigens,Antigen, Bacterial
D012703 Serotyping Process of determining and distinguishing species of bacteria or viruses based on antigens they share. Serotypings
D014574 Uronic Acids Acids derived from monosaccharides by the oxidation of the terminal (-CH2OH) group farthest removed from the carbonyl group to a (-COOH) group. (From Stedmans, 26th ed) Uronic Acid,Acid, Uronic,Acids, Uronic
D055598 Chemical Phenomena The composition, structure, conformation, and properties of atoms and molecules, and their reaction and interaction processes. Chemical Concepts,Chemical Processes,Physical Chemistry Concepts,Physical Chemistry Processes,Physicochemical Concepts,Physicochemical Phenomena,Physicochemical Processes,Chemical Phenomenon,Chemical Process,Physical Chemistry Phenomena,Physical Chemistry Process,Physicochemical Phenomenon,Physicochemical Process,Chemical Concept,Chemistry Process, Physical,Chemistry Processes, Physical,Concept, Chemical,Concept, Physical Chemistry,Concept, Physicochemical,Concepts, Chemical,Concepts, Physical Chemistry,Concepts, Physicochemical,Phenomena, Chemical,Phenomena, Physical Chemistry,Phenomena, Physicochemical,Phenomenon, Chemical,Phenomenon, Physicochemical,Physical Chemistry Concept,Physicochemical Concept,Process, Chemical,Process, Physical Chemistry,Process, Physicochemical,Processes, Chemical,Processes, Physical Chemistry,Processes, Physicochemical
D019081 O Antigens The lipopolysaccharide-protein somatic antigens, usually from gram-negative bacteria, important in the serological classification of enteric bacilli. The O-specific chains determine the specificity of the O antigens of a given serotype. O antigens are the immunodominant part of the lipopolysaccharide molecule in the intact bacterial cell. (From Singleton & Sainsbury, Dictionary of Microbiology and Molecular Biology, 2d ed) O-Antigen,O-Specific Polysaccharides,O Antigen,O Antigen, Bacterial,O-Antigens,O-Specific Polysaccharide,Antigen, Bacterial O,Antigen, O,Antigens, O,Bacterial O Antigen,O Specific Polysaccharide,O Specific Polysaccharides,Polysaccharide, O-Specific,Polysaccharides, O-Specific

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