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Structure type: monomer

• Article ID: 124
  Tsvetkov YE, Shashkov AS, Knirel YA, Backinowsky LV, Zähringer U "Synthesis of 5,7-diacetamido-3,5,7,9-tetradeoxy-L-glycero-D-galacto- and -L-glycero-D-talo-nonulosonic acids, putative components of bacterial lipopolysaccharide" - Mendeleev Communications 10(3) (2000) 90-91
  

  The title acids were synthesised by condensation of 2,4-diacetamido-2,4,6-trideoxy-L-guIose with oxalacetic acid and characterised by 1H and I3C NMR spectroscopy.

  Lipopolysaccharide, synthesis, LPS, 5, 7-diamino-3, 7, 9-teradeoxy-L-glycero-D-galacto-nonulosonic acid, 9-teradeoxy-L-glycero-D-talo-nonulosonic acid, Legionella pneumophila

  Publication DOI: 10.1070/MC2000v010n03ABEH001287
  Journal NLM ID: 9425965
  Publisher: Moscow: Academy of Sciences of the USSR; Cambridge,UK : Royal Society of Chemistry
  Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Forschungszentrum Borstel, Zentrum fiir Medizin und Biowissenschaften, 23845 Borstel, Germany
  Methods: 13C NMR, 1H NMR
  
   
  
  Legionella pneumophila
  CSDB ID 5237 (all data & tools)
• Article ID: 126
  Tsvetkov YE, Shashkov AS, Knirel YA, Zähringer U "Synthesis and NMR spectroscopy of nine stereoisomeric 5,7-diacetamido-3,5,7,9-tetradeoxynon-2-ulosonic acids" - Carbohydrate Research 335(4) (2001) 221-243
  

  Derivatives of 5,7-diamino-3,5,7,9-tetradeoxynon-2-ulosonic acids are essential constituents of some bacterial polysaccharides and glycoproteins. In order to establish reliably the configuration of the natural sugars, nine stereoisomeric 5,7-diacetamido-3,5,7,9-tetradeoxynon-2-ulosonic acids were synthesized, including di-N-acetyl-legionaminic and -pseudaminic acids (the D-glycero-D-galacto and L-glycero-L-manno isomers, respectively) and their isomers at C-4, C-5, C-7, and C-8 having the L-glycero-D-galacto, D-glycero-D-talo, L-glycero-D-talo, D-glycero-L-altro, L-glycero-L-altro, D-glycero-L-manno, and L-glycero-L-gluco configurations. Synthesis was performed by condensation of 2,4-diacetamido-2,4,6-trideoxy-L-gulose, -D-mannose, -D-talose, and -L-allose with oxalacetic acid under basic conditions, the reaction of the last two precursors being accompanied by epimerisation at C-2. The 1H and 13C NMR data of the synthetic compounds are discussed. Acetylated methyl esters of the C-7 and C-8 isomeric nonulosonic acids were prepared and used for analysis of the side-chain conformation by NMR spectroscopy.

  NMR, synthesis, LPS, Bacterial, acid, NMR spectroscopy, pseudaminic acid, putative, identification, spectroscopy, 5, 7-diamino-3, 7, 9-tetradeoxynon-2-ulosonic acid, lipopolysaccharide components, 7-diacetamido-3, 9-tetradeoxynon-2-ulosonic acids, 2, 4-diacetamido-2, 4, 6-trideoxyhexoses, legionaminic acid, 9-teradeoxynonulosonic acid, component, isomer

  NCBI PubMed ID: 11595217
  Publication DOI: 10.1016/S0008-6215(01)00235-X
  Journal NLM ID: 0043535
  Publisher: Elsevier
  Correspondence: tsvetkov@ioc.ac.ru
  Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospeckt 47, Moscow, Russian Federation, Forschungszentrum Borstel, Zentrum fur Medizin und Biowissenschaften, Borstel, Germany.
  Methods: 13C NMR, 1H NMR
  
   
  
  (bacteria)
  CSDB ID 5350 (all data & tools)
• Article ID: 1231
  Shashkov AS, Torgov VI, Nazarenko EL, Zubkov VA, Gorshkova NM, Gorshkova RP, Widmalm G "Structure of the phenol-soluble polysaccharide from Shewanella putrefaciens strain A6" - Carbohydrate Research 337(12) (2002) 1119-1127
  

  The structure of the phenol-soluble polysaccharide from Shewanella putrefaciens strain A6 has been elucidated. Chemical modifications of the polymer in conjunction with 1H and 13C NMR spectroscopy, including 2D techniques, were employed in the analysis. It is concluded that the repeating unit is composed of two nine-carbon sugars as follows: →4)-α-NonpA-(2→3)-β-Sugp-(1→ where α-NonpA is 5-acetamido-7-acetamidino-8-O-acetyl-3,5,7,9-tetradeoxy-L-glycero-α-D-galacto-non-2-ulosonic acid (8eLeg) and β-Sugp is 2-acetamido-2,6-dideoxy-4-C-(3'-carboxamide-2',2'-dihydroxypropyl)-β-D-galactopyranose, with the proposed name Shewanellose (She).

  biosynthesis, polysaccharide, NMR spectroscopy, nonulosonic acid, shewanellose, Shewanella putrefaciens

  NCBI PubMed ID: 12062527
  Publication DOI: 10.1016/S0008-6215(02)00101-5
  Journal NLM ID: 0043535
  Publisher: Elsevier
  Correspondence: G. Widmalm
  Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Pacific Institute of Bioorganic Chemistry, Far East Branch of the Russian Academy of Sciences, Vladivostok 690022, Russian Federation, Arrhenius Laboratory, Department of Organic Chemistry, Stockholm University, Stockholm, Sweden
  Methods: NMR
  
   
  
  Shewanella putrefaciens A6
  CSDB ID 4785 (all data & tools)

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Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_135813,IEDB_137340,IEDB_141807,IEDB_151531,SB_74,SB_85

• Article ID: 381
  Skurnik M, Zhang L "Molecular genetics and biochemistry of Yersinia lipopolysaccharide" - APMIS: Acta Pathologica, Microbiologica, et Immunologica Scandinavica 104(12) (1996) 849-872
  

  Studies on the molecular genetics of bacterial LPS serve at least two main purposes: (i) to help develop an understanding of the biology, biochemistry and genetics of this bacterial surface macromolecule, and (ii) to provide a basis for both vaccine development and virulence experiments. Both of these goals have been the driving force in studies of Yersinia LPS carried out during the last decade. Here we will review the progress made in the molecular genetics and biochemistry of Yersinia LPS. A deep understanding has been achieved with respect to Y. enterocolitica serotype O:3, reaching as far as a detailed analysis of the gene clusters directing the biosynthesis of the outer core oligosaccharide and of the O-ag. The O-ag gene clusters of Y. enterocolitica serotype O:8 and Y. pseudotuberculosis serotypes O:2a and O:5a have also been cloned and partially characterized LPS biosynthesis of these Yersinia species includes examples of the two major variations recognized in the biosynthesis of this macromolecule: (i) homopolymeric or O-antigen polymerase-independent biosynthesis, and (ii) heteropolymeric or O-antigen polymerase-dependent biosynthesis.

  Lipopolysaccharide, genetic, gene, genetics, O-antigen, biochemistry, Yersinia, molecular genetics

  NCBI PubMed ID: 9048864
  Publication DOI: 10.1111/j.1699-0463.1996.tb04951.x
  Journal NLM ID: 8803400
  Publisher: Copenhagen: Munksgaard
  Institutions: Turku Centre for Biotechnology, University of Turku, Finland, department of Medical Microbiology, University of Turku, Turku, Finland
  
   
  
  Yersinia ruckeri O1
  CSDB ID 31547 (all data & tools)
• Article ID: 2299
  Beynon LM, Richards JC, Perry MB "The structure of the lipopolysaccharide O antigen from Yersinia ruckeri serotype O1" - Carbohydrate Research 256 (1994) 303-317
  

  The O antigen obtained from the lipopolysaccharide of Yersinia ruckeri serotype 01, by mild acid hydrolysis, is composed of a branched tetrasaccharide repeating unit containing 2-acetamidino-2,6-dideoxy-l-galactose (l-FucAm), 2-acetamido-2-deoxy-d-glucose (D-GlcNac), and 7-acetamido-3,5,7,9-tetradeoxy-5-(4-hydroxybutyramido)-d-glycero-l-galacto-nonulosonic acid (l-Sug). Partial hydrolysis of the O antigen with 0.1 M HClafforded a trisaccharide and a tetrasaccharide having nonulosonic acid at their reducing ends. Cleavage of the O antigen with anhydrous methanolic hydrogen fluoride afforded the methyl glycoside derivatives of a trisaccharide and a tetrasaccharide. 1H and 13C NMR analysis, including 1H-13C heteronuclear multiple bond correlation spectroscopy to locate the N-acyl substituents, together with mass spectrometric analysis of the above oligosaccharides, allowed the structure of the O-specific polysaccharide to be assigned as: [formula: see text].

  NCBI PubMed ID: 7514497
  Publication DOI: 10.1016/0008-6215(94)84215-9
  Journal NLM ID: 0043535
  Publisher: Elsevier
  Institutions: Institute for Biological Sciences, National Research Council of Canada, Ottawa, Ontario
  
   
  
  Yersinia ruckeri O1
  CSDB ID 117883 (all data & tools)
• Article ID: 6301
  Qin CJ, Ding MR, Tian GZ, Zou XP, Fu JJ, Hu J, Yin J "Chemical approaches towards installation of rare functional groups in bacterial surface glycans" - Chinese Journal of Natural Medicines = Zhongguo Tianran Yaowu 20(6) (2022) 401-420
  

  Bacterial surface glycans perform a diverse and important set of biological roles, and have been widely used in the treatment of bacterial infectious diseases. The majority of bacterial surface glycans are decorated with diverse rare functional groups, including amido, acetamidino, carboxamido and pyruvate groups. These functional groups are thought to be important constituents for the biological activities of glycans. Chemical synthesis of glycans bearing these functional groups or their variants is essential for the investigation of structure-activity relationships by a medicinal chemistry approach. To date, a broad choice of synthetic methods is available for targeting the different rare functional groups in bacterial surface glycans. This article reviews the structures of naturally occurring rare functional groups in bacterial surface glycans, and the chemical methods used for installation of these groups.

  chemical synthesis, acetamidino group, amido group, bacterial surface glycan, carboxamido group, pyruvyl ketal

  NCBI PubMed ID: 35750381
  Publication DOI: 10.1016/S1875-5364(22)60177-8
  Journal NLM ID: 101504416
  Publisher: Beijing: Science Press; Elsevier
  Correspondence: J. Yin
  Institutions: Key Laboratory of Carbohydrate Chemistry and Biotechnology, Ministry of Education, School of Biotechnology, Jiangnan University, Wuxi, China, Wuxi School of Medicine, Jiangnan University, Wuxi, China
  
   
  
  Yersinia ruckeri O1
  CSDB ID 9100 (all data & tools)

Show legend Show as text

Structure type: polymer chemical repeating unit
Contained glycoepitopes: IEDB_137340,IEDB_141807,IEDB_151531

• Article ID: 688
  Haseley SR, Wilkinson SG "Structural studies of the putative O-specific polysaccharide of Acinetobacter baumannii O24 containing 5,7-diamino-3,5,7,9-tetradeoxy-L-glycero-D-galacto-nonulosonic acid" - European Journal of Biochemistry 250 (1997) 617-623
  

  A polysaccharide containing D-GlcN, 2-amino-2,6-dideoxy-L-galactose (L-FucN), and 7-acetamido-5-acylamino-3,5,7,9-tetradeoxy-L-glycero-D-galacto-nonulo sonic acid (LegAX), in which the acyl group (X) is either S-3-hydroxybutyryl (50%) or acetyl (50%), was isolated by mild acid hydrolysis treatment, followed by gel-permeation chromatography, of the water-soluble lipopolysaccharide from Acinetobacter baumannii serogroup O24. The polysaccharide, characterised by means of monosaccharide analyses, partial acid hydrolysis, methylation analysis and NMR studies, was shown to have a linear tetrasaccharide repeating unit, as depicted below. Serological tests indicated that the polymer corresponded to the O24 antigen. [→6)-α-D-GlcpNAc-(1→3)-α-L-FucpNAc-(1→3)-α-D-Glcp NAc-(1→4)-β-LegpAX-(1→].

  Lipopolysaccharide, O antigen, Acinetobacter baumannii, structural studies

  NCBI PubMed ID: 9428717
  Publication DOI: 10.1111/j.1432-1033.1997.0617a.x
  Journal NLM ID: 0107600
  Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
  Correspondence: S.G.Wilkinson@chem.hull.ac.uk
  Institutions: School of Chemistry, University of Hull, England., School of Chemistry, University of Hull, England
  Methods: methylation, partial acid hydrolysis, NMR
  
   
  
  Acinetobacter baumannii O24
  CSDB ID 491 (all data & tools)

Show legend Show as text

Structure type: polymer chemical repeating unit
Contained glycoepitopes: IEDB_137340,IEDB_141807,IEDB_151531

• Article ID: 688
  Haseley SR, Wilkinson SG "Structural studies of the putative O-specific polysaccharide of Acinetobacter baumannii O24 containing 5,7-diamino-3,5,7,9-tetradeoxy-L-glycero-D-galacto-nonulosonic acid" - European Journal of Biochemistry 250 (1997) 617-623
  

  A polysaccharide containing D-GlcN, 2-amino-2,6-dideoxy-L-galactose (L-FucN), and 7-acetamido-5-acylamino-3,5,7,9-tetradeoxy-L-glycero-D-galacto-nonulo sonic acid (LegAX), in which the acyl group (X) is either S-3-hydroxybutyryl (50%) or acetyl (50%), was isolated by mild acid hydrolysis treatment, followed by gel-permeation chromatography, of the water-soluble lipopolysaccharide from Acinetobacter baumannii serogroup O24. The polysaccharide, characterised by means of monosaccharide analyses, partial acid hydrolysis, methylation analysis and NMR studies, was shown to have a linear tetrasaccharide repeating unit, as depicted below. Serological tests indicated that the polymer corresponded to the O24 antigen. [→6)-α-D-GlcpNAc-(1→3)-α-L-FucpNAc-(1→3)-α-D-Glcp NAc-(1→4)-β-LegpAX-(1→].

  Lipopolysaccharide, O antigen, Acinetobacter baumannii, structural studies

  NCBI PubMed ID: 9428717
  Publication DOI: 10.1111/j.1432-1033.1997.0617a.x
  Journal NLM ID: 0107600
  Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
  Correspondence: S.G.Wilkinson@chem.hull.ac.uk
  Institutions: School of Chemistry, University of Hull, England., School of Chemistry, University of Hull, England
  Methods: methylation, partial acid hydrolysis, NMR
  
   
  
  Acinetobacter baumannii O24
  CSDB ID 600 (all data & tools)

Show legend Show as text

Structure type: oligomer
Contained glycoepitopes: IEDB_137340,IEDB_141807,IEDB_151531

• Article ID: 688
  Haseley SR, Wilkinson SG "Structural studies of the putative O-specific polysaccharide of Acinetobacter baumannii O24 containing 5,7-diamino-3,5,7,9-tetradeoxy-L-glycero-D-galacto-nonulosonic acid" - European Journal of Biochemistry 250 (1997) 617-623
  

  A polysaccharide containing D-GlcN, 2-amino-2,6-dideoxy-L-galactose (L-FucN), and 7-acetamido-5-acylamino-3,5,7,9-tetradeoxy-L-glycero-D-galacto-nonulo sonic acid (LegAX), in which the acyl group (X) is either S-3-hydroxybutyryl (50%) or acetyl (50%), was isolated by mild acid hydrolysis treatment, followed by gel-permeation chromatography, of the water-soluble lipopolysaccharide from Acinetobacter baumannii serogroup O24. The polysaccharide, characterised by means of monosaccharide analyses, partial acid hydrolysis, methylation analysis and NMR studies, was shown to have a linear tetrasaccharide repeating unit, as depicted below. Serological tests indicated that the polymer corresponded to the O24 antigen. [→6)-α-D-GlcpNAc-(1→3)-α-L-FucpNAc-(1→3)-α-D-Glcp NAc-(1→4)-β-LegpAX-(1→].

  Lipopolysaccharide, O antigen, Acinetobacter baumannii, structural studies

  NCBI PubMed ID: 9428717
  Publication DOI: 10.1111/j.1432-1033.1997.0617a.x
  Journal NLM ID: 0107600
  Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
  Correspondence: S.G.Wilkinson@chem.hull.ac.uk
  Institutions: School of Chemistry, University of Hull, England., School of Chemistry, University of Hull, England
  Methods: methylation, partial acid hydrolysis, NMR
  
   
  
  Acinetobacter baumannii O24
  CSDB ID 560 (all data & tools)

Show legend Show as text

Structure type: monomer

• Article ID: 1231
  Shashkov AS, Torgov VI, Nazarenko EL, Zubkov VA, Gorshkova NM, Gorshkova RP, Widmalm G "Structure of the phenol-soluble polysaccharide from Shewanella putrefaciens strain A6" - Carbohydrate Research 337(12) (2002) 1119-1127
  

  The structure of the phenol-soluble polysaccharide from Shewanella putrefaciens strain A6 has been elucidated. Chemical modifications of the polymer in conjunction with 1H and 13C NMR spectroscopy, including 2D techniques, were employed in the analysis. It is concluded that the repeating unit is composed of two nine-carbon sugars as follows: →4)-α-NonpA-(2→3)-β-Sugp-(1→ where α-NonpA is 5-acetamido-7-acetamidino-8-O-acetyl-3,5,7,9-tetradeoxy-L-glycero-α-D-galacto-non-2-ulosonic acid (8eLeg) and β-Sugp is 2-acetamido-2,6-dideoxy-4-C-(3'-carboxamide-2',2'-dihydroxypropyl)-β-D-galactopyranose, with the proposed name Shewanellose (She).

  biosynthesis, polysaccharide, NMR spectroscopy, nonulosonic acid, shewanellose, Shewanella putrefaciens

  NCBI PubMed ID: 12062527
  Publication DOI: 10.1016/S0008-6215(02)00101-5
  Journal NLM ID: 0043535
  Publisher: Elsevier
  Correspondence: G. Widmalm
  Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Pacific Institute of Bioorganic Chemistry, Far East Branch of the Russian Academy of Sciences, Vladivostok 690022, Russian Federation, Arrhenius Laboratory, Department of Organic Chemistry, Stockholm University, Stockholm, Sweden
  Methods: NMR
  
   
  
  Shewanella putrefaciens A6
  CSDB ID 4786 (all data & tools)

Show legend Show as text

Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_137340,IEDB_141807,IEDB_151531

• Article ID: 1470
  Knirel YA, Shashkov AS, Tsvetkov YE, Jansson P, Zähringer U "5,7-Diamino-3,5,7,9-tetradeoxynon-2-ulosonic acids in bacterial glycopolymers: chemistry and biochemistry" - Book: Advances in Carbohydrate Chemistry and Biochemistry (2003) Vol. 58, 371-417
  

  This chapter provides an overview of the chemistry of 5,7-diamino-3,5,7,9-tetradeoxynon-2-ulosonic acids in bacterial glycopolymers. Ald-2-ulosonic acids are the important components of natural glycoconjugates. Sialic acids—namely, N- and O-acyl derivatives of 5-amino-3,5-dideoxy-D-glycero-D-galacto-non-2-ulosonic acid (neuraminic acid, Neu), generally occur in glycoconjugates of vertebrates and play a significant role in their recognition, regulation, and protection. A deamino analogue of neuraminic acid—3-deoxy-D-glycero-D-galacto-non-2-ulosonic acid (Kdn)—has also been found in a variety of animal tissues. 3-Deoxy-D-manno-oct-2-ulosonic acid (Kdo) is an essential component of lipopolysaccharides (LPSs) of Gram-negative bacteria that functions to link the carbohydrate portion to the lipid moiety. In rare cases, Kdo in LPS is replaced with a 3-hydroxylated analogue—D-glycero-D-talo-oct-2-ulosonic acid. The chapter focuses on the occurrence and characterization of derivatives of 5,7-diamino-3,5,7,9-tetradeoxynon-2-ulosonic acids and presents experimental approaches that are used to identify them and to elucidate the structures of the bacterial polysaccharides that contain the nonulosonic acids. It also presents the recent data on the biosynthesis of these sugars and discusses their role in immune recognition.

  Lipopolysaccharide, LPS, structure, polysaccharide, Bacterial polysaccharide, 5, 7-diamino-3, 7, higher sugar, 9-tetradeoxynonulosonic acid

  NCBI PubMed ID: 14719362
  Publication DOI: 10.1016/S0065-2318(03)58007-6
  Publisher: Elsevier Inc.
  Correspondence: knirel@ioc.ac.ru
  Editors: Horton D
  Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Research Center Borstel, Center for Medicine and Biosciences, Borstel, Germany, Karolinska Institute, Clinical Research Center, Huddinge University Hospital, Huddinge, Sweden
  
   
  
  Salmonella arizonae O61
  CSDB ID 31936 (all data & tools)
• Article ID: 3847
  Gajdus J, Glosnicka R, Szafranek J "Primary structure of Salmonella spp. O-antigens" - Wiadomosci Chemiczne [Polish] 60(9-10) (2006) 621-653
  

  Salmonella spp. are pathogenic Gram-negative bacteria that belong to Enterobacteriaceae family with lipopolysaccharide (LPS) as a constituent of cell wall. This is an integral component of the outer membrane of the wall. Salmonella smooth (S) forms produce LPS, which is composed of three parts, chemically bonded together viz. polysaccharide O-antigen, oligosaccharide core region and lipid A. Antigens O (O-PS) together with H flagella antigens are the foundation of serological classification of these bacteria. O-chain, which is built with up to 50 oligosaccharide repeating units, is one of the products of mild acidic hydrolysis of LPS. Due to the fact that polysaccharide antigens are the sites of specific antibody complexing, any difference in primary and secondary structures of O-antigens reflect serological specificity of bacteria. Taking this fact into consideration, we can distinguish about 2541 Salmonella serotypes with O and H antigenic formulas defined [4]. In this review we present 55 chemical structures of O-antigenic repeating units of Salmonella strains including their heterogeneity structures. The structures can have 22 different monosaccharide residues usually in 3 to 6 sugar repeating units. We describe here selected chemical and spectroscopic (MS, NMR) methods for primary structure examination of these bacterial O-PS. Enzymatic and immunochemical methods are also described. Cross-reactions of Salmonella spp. with any other bacteria or blood group A, B, 0 antigens are explained on the molecular level. Thus, structural assignments of somatic antigens of Salmonella spp. allow us to understand the molecular level of the classification system of these bacteria.

  NMR spectroscopy, O-antigens, Salmonella, MS, primary structure

  WWW link: http://baztech.icm.edu.pl/baztech/cgi-bin/btgetdoc.cgi?BUS2-0016-0014
  Publisher: Polish Chemical Society
  Correspondence: jerzyg@chemik.chem.univ.gda.pl
  Institutions: Wydzial Chemii, Uniwersytet Gdanski, ul. Sobieskiego 18, 80-952 Gdansk
  
   
  
  Salmonella arizonae O61
  CSDB ID 25646 (all data & tools)

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Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen

• Article ID: 1778
  Knirel YA, Kochetkov NK "The structure of lipopolysaccharides of gram-negative bacteria. III. The structure of O-antigens: A review" - Biochemistry (Moscow) 59(12) (1994) 1325-1383
  

  This review summarizes data on the composition and structure of the O-antigens, the polysaccharide chains of the outer-membrane lipopolysaccharides (LPS) of Gram-negative bacteria defining the immunospecificity of these microbial cells. Special reference is given to some structural features of the O-antigens, such as the presence of unique monosaccharides and noncarbohydrate components, masked regularity, and the occurrence in one microorganism of LPS with structurally different polysaccharide chains. Antigenic relationships between microorganisms belonging to different taxonomic groups are discussed.

  structure, O-antigen, chemical composition, bacterial lipopolysaccharides, Salmonella livingstone C1

  NCBI PubMed ID: 7533007
  Journal NLM ID: 0376536
  Publisher: Nauka/Interperiodica
  Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
  
   
  
  Pseudomonas aeruginosa O12
  CSDB ID 108470 (all data & tools)
• Article ID: 2402
  Knirel YA, Vinogradov EV, Shashkov AS, Dmitriev BA, Kochetkov NK, Stanislavsky ES, Mashilova GM "Somatic antigens of Pseudomonas aeruginosa. The structure of the O-specific polysaccharide chain of the lipopolysaccharide from P. aeruginosa O13 (Lányi)" - European Journal of Biochemistry 163 (1987) 627-637
  

  The O-specific polysaccharide, obtained on mild acid degradation of lipopolysaccharide of Pseudomonas aeruginosa O13 (Lányi classification), is built up of trisaccharide repeating units involving 2-acetamidino-2,6-dideoxy-D-glucose (N-acetyl-D-quinovosamine, D-QuiNAc), 2-acetamidino-2,6-dideoxy-L-galactose (L-fucosacetamidine, L-FucAm), and a new sialic-acid-like sugar, 5,7-diacetamido-3,5,7,9-tetradeoxy-D-glycero-L-galacto-nonulosonic acid (Sug), and thus contains simultaneously both acidic and basic functions. Cleavage of the polysaccharide with hydrogen fluoride in methanol revealed the high stability of the glycosidic linkage of the ulosonic acid and afforded methyl glycosides of a disaccharide and a trisaccharide. The structures of the new ulosonic acid and acetamidino group were established by analysing the oligosaccharide fragments by 1H, 13C nuclear magnetic resonance spectrometry, as well as on the basis of their chemical conversions: alkaline hydrolysis of the acetamidino group into acetamido group, reductive deamination with lithium borohydride into the ethylamino group and acetylation with acetic anhydride in pyridine accompanied by intramolecular acylation of the acetamidino function by the ulosonic acid to form a six-membered lactam ring. Identification of the oligosaccharide fragments and comparative analysis of the 13C nuclear magnetic resonance spectra of the oligosaccharides and polysaccharide revealed the following structure of the repeating unit: →3)D-QuiNAcp(α1→3)Sugp(α2→3)L-FucAmp(α1→.

  NCBI PubMed ID: 3104040
  Publication DOI: 10.1111/j.1432-1033.1987.tb10912.x
  Journal NLM ID: 0107600
  Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
  Methods: 13C NMR
  
   
  
  Pseudomonas aeruginosa O13, Pseudomonas aeruginosa Lányi
  CSDB ID 123023 (all data & tools)
• Article ID: 5748
  Chidwick HS, Fascione MA "Mechanistic and structural studies into the biosynthesis of the bacterial sugar pseudaminic acid (Pse5Ac7Ac)" - Organic and Biomolecular Chemistry 18(5) (2020) 799-809
  

  The non-mammalian nonulosonic acid sugar pseudaminic acid (Pse) is present on the surface of a number of human pathogens including Campylobacter jejuni and Helicobacter pylori and other bacteria such as multidrug resistant Acinetobacter baumannii. It is likely important for evasion of the host immune sysyem, and also plays a role in bacterial motility through flagellin glycosylation. Herein we review the mechanistic and structural characterisation of the enzymes responsible for the biosynthesis of the Pse parent structure, Pse5Ac7Ac in bacteria.

  biosynthesis, structure, Acinetobacter baumannii, Campylobacter jejuni, pseudaminic acid, nonulosonic acid, Helicobacter pylori, structural studies, Enzymes, glycosylation, immune, Flagellin

  NCBI PubMed ID: 31913385
  Publication DOI: 10.1039/c9ob02433f
  Journal NLM ID: 101154995
  Publisher: The Royal Society of Chemistry
  Correspondence: martin.fascione@york.ac.uk
  Institutions: Department of Chemistry, University of York, York, YO10 5DD, UK
  
   
  
  Pseudomonas aeruginosa O13
  CSDB ID 5157 (all data & tools)
• Article ID: 6301
  Qin CJ, Ding MR, Tian GZ, Zou XP, Fu JJ, Hu J, Yin J "Chemical approaches towards installation of rare functional groups in bacterial surface glycans" - Chinese Journal of Natural Medicines = Zhongguo Tianran Yaowu 20(6) (2022) 401-420
  

  Bacterial surface glycans perform a diverse and important set of biological roles, and have been widely used in the treatment of bacterial infectious diseases. The majority of bacterial surface glycans are decorated with diverse rare functional groups, including amido, acetamidino, carboxamido and pyruvate groups. These functional groups are thought to be important constituents for the biological activities of glycans. Chemical synthesis of glycans bearing these functional groups or their variants is essential for the investigation of structure-activity relationships by a medicinal chemistry approach. To date, a broad choice of synthetic methods is available for targeting the different rare functional groups in bacterial surface glycans. This article reviews the structures of naturally occurring rare functional groups in bacterial surface glycans, and the chemical methods used for installation of these groups.

  chemical synthesis, acetamidino group, amido group, bacterial surface glycan, carboxamido group, pyruvyl ketal

  NCBI PubMed ID: 35750381
  Publication DOI: 10.1016/S1875-5364(22)60177-8
  Journal NLM ID: 101504416
  Publisher: Beijing: Science Press; Elsevier
  Correspondence: J. Yin
  Institutions: Key Laboratory of Carbohydrate Chemistry and Biotechnology, Ministry of Education, School of Biotechnology, Jiangnan University, Wuxi, China, Wuxi School of Medicine, Jiangnan University, Wuxi, China
  
   
  
  Pseudomonas aeruginosa O13
  CSDB ID 9105 (all data & tools)

Show legend Show as text

Structure type: oligomer
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_135813,IEDB_137340,IEDB_141807,IEDB_151531,SB_74,SB_85

• Article ID: 2299
  Beynon LM, Richards JC, Perry MB "The structure of the lipopolysaccharide O antigen from Yersinia ruckeri serotype O1" - Carbohydrate Research 256 (1994) 303-317
  

  The O antigen obtained from the lipopolysaccharide of Yersinia ruckeri serotype 01, by mild acid hydrolysis, is composed of a branched tetrasaccharide repeating unit containing 2-acetamidino-2,6-dideoxy-l-galactose (l-FucAm), 2-acetamido-2-deoxy-d-glucose (D-GlcNac), and 7-acetamido-3,5,7,9-tetradeoxy-5-(4-hydroxybutyramido)-d-glycero-l-galacto-nonulosonic acid (l-Sug). Partial hydrolysis of the O antigen with 0.1 M HClafforded a trisaccharide and a tetrasaccharide having nonulosonic acid at their reducing ends. Cleavage of the O antigen with anhydrous methanolic hydrogen fluoride afforded the methyl glycoside derivatives of a trisaccharide and a tetrasaccharide. 1H and 13C NMR analysis, including 1H-13C heteronuclear multiple bond correlation spectroscopy to locate the N-acyl substituents, together with mass spectrometric analysis of the above oligosaccharides, allowed the structure of the O-specific polysaccharide to be assigned as: [formula: see text].

  NCBI PubMed ID: 7514497
  Publication DOI: 10.1016/0008-6215(94)84215-9
  Journal NLM ID: 0043535
  Publisher: Elsevier
  Institutions: Institute for Biological Sciences, National Research Council of Canada, Ottawa, Ontario
  
   
  
  Yersinia ruckeri O1
  CSDB ID 117881 (all data & tools)

Show legend Show as text

Structure type: oligomer
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_137340,IEDB_141807,IEDB_151531

• Article ID: 2299
  Beynon LM, Richards JC, Perry MB "The structure of the lipopolysaccharide O antigen from Yersinia ruckeri serotype O1" - Carbohydrate Research 256 (1994) 303-317
  

  The O antigen obtained from the lipopolysaccharide of Yersinia ruckeri serotype 01, by mild acid hydrolysis, is composed of a branched tetrasaccharide repeating unit containing 2-acetamidino-2,6-dideoxy-l-galactose (l-FucAm), 2-acetamido-2-deoxy-d-glucose (D-GlcNac), and 7-acetamido-3,5,7,9-tetradeoxy-5-(4-hydroxybutyramido)-d-glycero-l-galacto-nonulosonic acid (l-Sug). Partial hydrolysis of the O antigen with 0.1 M HClafforded a trisaccharide and a tetrasaccharide having nonulosonic acid at their reducing ends. Cleavage of the O antigen with anhydrous methanolic hydrogen fluoride afforded the methyl glycoside derivatives of a trisaccharide and a tetrasaccharide. 1H and 13C NMR analysis, including 1H-13C heteronuclear multiple bond correlation spectroscopy to locate the N-acyl substituents, together with mass spectrometric analysis of the above oligosaccharides, allowed the structure of the O-specific polysaccharide to be assigned as: [formula: see text].

  NCBI PubMed ID: 7514497
  Publication DOI: 10.1016/0008-6215(94)84215-9
  Journal NLM ID: 0043535
  Publisher: Elsevier
  Institutions: Institute for Biological Sciences, National Research Council of Canada, Ottawa, Ontario
  
   
  
  Yersinia ruckeri O1
  CSDB ID 117882 (all data & tools)

Show legend Show as text

Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen

• Article ID: 2812
  Knirel YA "New sialic acid-like sugars: components of bacterial lipopolysaccharides" - Proceedings of Sialic acids 1998: Japanese-German Symposium on Sialic Acids (1st : 1988 : Berlin) (1988) 160-161
  
  Book NLM ID: 9012728
  Publisher: Kiel: Kieler Verlag Wissenschaft + Bildung
  Editors: Schauer R, Yamakawa T
  
   
  
  Pseudomonas aeruginosa 10
  CSDB ID 148513 (all data & tools)

Show legend Show as text

Structure type: oligomer
Trivial name: repeating unit
Contained glycoepitopes: IEDB_115136,IEDB_137340,IEDB_140630,IEDB_141807,IEDB_151531,IEDB_423153

• Article ID: 3344
  Shashkov AS, Kocharova NA, Zatonsky GV, Blaszczyk A, Knirel YA, Rozalski A "Structure of the O-antigen of Providencia stuartii O20, a new polysaccharide containing 5,7-diacetamido-3,5,7,9-tetradeoxy-L-glycero-D-galacto-non-2-ulosonic acid" - Carbohydrate Research 342(3-4) (2007) 653-658
  

  The O-polysaccharide chain of the lipopolysaccharide (LPS) of Providencia stuartii O20 was found to contain d-glucuronic acid, N-acetyl-d-glucosamine, and a rarely occurring higher sugar 5,7-diacetamido-3,5,7,9-tetradeoxy-l-glycero-d-galacto-non-2-ulosonic acid (di-N-acetyl-8-epilegionaminic acid, 8eLeg5Ac7Ac). Degradation of the LPS with dilute acetic acid caused depolymerization of the polysaccharide chain by the ketosidic linkage to give a tetrasaccharide corresponding to the repeating unit of the polysaccharide. Based on sugar and methylation analyses of the tetrasaccharide and O-deacylated LPS as well as ESIMS, (1)H and (13)C NMR spectroscopy data, the structure of the O-polysaccharide of P. stuartii O20 was established.

  Lipopolysaccharide, polysaccharide structure, 5, 7, 9-tetradeoxynon-2-ulosonic acid, 7-diacetamido-3, Providencia stuartii, 8-epilegionaminic acid

  NCBI PubMed ID: 16949059
  Journal NLM ID: 0043535
  Publisher: Elsevier
  Correspondence: koch@ioc.ac.ru
  Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
  Methods: 13C NMR, 1H NMR, methylation, GLC-MS, NMR-2D, sugar analysis, ESI-MS, GLC, mild acid hydrolysis, NMR-1D, alkaline hydrolysis
  
   
  
  Providencia stuartii O20
  CSDB ID 22035 (all data & tools)

Show legend Show as text

Structure type: oligomer

• Article ID: 3490
  King JD, Mulrooney EF, Vinogradov E, Kneidinger B, Mead K, Lam JS "lfnA from Pseudomonas aeruginosa O12 and wbuX from Escherichia coli O145 encode membrane-associated proteins and are required for expression of 2,6-dideoxy-2-acetamidino-L-galactose in lipopolysaccharide O antigen" - Journal of Bacteriology 190(5) (2008) 1671-1679
  

  The rare sugar 2,6-dideoxy-2-acetamidino-L-galactose (L-FucNAm) is found only in bacteria and is a component of cell surface glycans in a number of pathogenic species, including the O antigens of Pseudomonas aeruginosa serotype O12 and Escherichia coli O145. P. aeruginosa is an important opportunistic pathogen, and the O12 serotype is associated with multidrug-resistant epidemic outbreaks. O145 is one of the classic non-O157 serotypes associated with Shiga toxin-producing, enterohemorrhagic E. coli. The acetamidino (NAm) moiety of L-FucNAm is of interest, because at neutral pH it contributes a positive charge to the cell surface, and we aimed to characterize the biosynthesis of this functional group. The pathway is not known, but expression of NAm-modified sugars coincides with the presence of a pseA homologue in the relevant biosynthetic locus. PseA is a putative amidotransferase required for synthesis of a NAm-modified sugar in Campylobacter jejuni. In P. aeruginosa O12 and E. coli O145, the pseA homologues are lfnA and wbuX, respectively, and we hypothesized that these genes function in L-FucNAm biosynthesis. Sodium dodecyl sulfate-polyacrylamide gel electrophoresis, Western blotting, and nuclear magnetic resonance analysis of the lfnA mutant O-antigen structure indicated that the mutant expresses 2,6-dideoxy-2-acetamido-L-galactose (L-FucNAc) in place of L-FucNAm. The mutation could be complemented by expression of either His(6)-tagged lfnA or wbuX in trans, confirming that these genes are functional homologues and that they are required for NAm moiety synthesis. Both proteins retained their activity when fused to a His(6) tag and localized to the membrane fraction. These data will assist future biochemical investigation of this pathway.

  biosynthesis, O-antigen, Pseudomonas aeruginosa, Membrane Proteins, lfnA, wbuX

  NCBI PubMed ID: 18156256
  Journal NLM ID: 2985120R
  Publisher: American Society for Microbiology
  Correspondence: jlam@uoguelph.ca
  Institutions: Department of Molecular and Cellular Biology, University of Guelph, Guelph, Ontario N1G 2W1, Canada
  Methods: 13C NMR, 1H NMR, GLC-MS, NMR-2D, SDS-PAGE, sugar analysis, mild acid hydrolysis, Western blotting, genetic methods
  
   
  
  Pseudomonas aeruginosa O12 lfnA
  CSDB ID 23006 (all data & tools)

Show legend Show as text

Structure type: oligomer
Trivial name: repeating unit
Compound class: cell wall polysaccharide
Contained glycoepitopes: IEDB_137340,IEDB_141807,IEDB_151531

• Article ID: 4735
  Vinogradov E, MacLean L, Xu HH, Chen W "The structure of the polysaccharide isolated from Acinetobacter baumannii strain LAC-4" - Carbohydrate Research 390 (2014) 42-45
  

  The structure of the surface polysaccharide from a hypervirulent for mice Acinetobacter baumannii strain LAC-4 was studied. The polysaccharide was built of trisaccharide repeating units containing α-l-fucosamine, α-d-glucosamine, and α-8-epi-legionaminic acid. The structure interpretation was based mostly on NMR data. Polysaccharide was obtained using a procedure of LPS O-chain preparation, although whether it is an LPS O-chain or capsular polysaccharide remained unclear.

  NMR, LPS, structure, strain, polysaccharide, Acinetobacter, Acinetobacter baumannii, O-polysaccharide, PDF

  NCBI PubMed ID: 24690675
  Publication DOI: 10.1016/j.carres.2014.03.001
  Journal NLM ID: 0043535
  Publisher: Elsevier
  Correspondence: E. Vinogradov ; L. MacLean ; H.H. Xu ; W. Chen
  Institutions: Human Health Therapeutics Portfolio, National Research Council Canada, 100 Sussex Drive, Ottawa, Ontario K1A 0R6, Canada, Department of Biological Sciences, California State University, 5151 State University Dr., Los Angeles, CA 90032-8201, USA
  Methods: 13C NMR, 1H NMR, NMR-2D, GC-MS, sugar analysis, mild acid hydrolysis, de-O-acylation with hydrazine, NMR-1D
  
   
  
  Acinetobacter baumannii LAC-4
  CSDB ID 30523 (all data & tools)

Show legend Show as text

Structure type: oligomer
Trivial name: di-repeating unit
Compound class: cell wall polysaccharide
Contained glycoepitopes: IEDB_137340,IEDB_141807,IEDB_151531

• Article ID: 4735
  Vinogradov E, MacLean L, Xu HH, Chen W "The structure of the polysaccharide isolated from Acinetobacter baumannii strain LAC-4" - Carbohydrate Research 390 (2014) 42-45
  

  The structure of the surface polysaccharide from a hypervirulent for mice Acinetobacter baumannii strain LAC-4 was studied. The polysaccharide was built of trisaccharide repeating units containing α-l-fucosamine, α-d-glucosamine, and α-8-epi-legionaminic acid. The structure interpretation was based mostly on NMR data. Polysaccharide was obtained using a procedure of LPS O-chain preparation, although whether it is an LPS O-chain or capsular polysaccharide remained unclear.

  NMR, LPS, structure, strain, polysaccharide, Acinetobacter, Acinetobacter baumannii, O-polysaccharide, PDF

  NCBI PubMed ID: 24690675
  Publication DOI: 10.1016/j.carres.2014.03.001
  Journal NLM ID: 0043535
  Publisher: Elsevier
  Correspondence: E. Vinogradov ; L. MacLean ; H.H. Xu ; W. Chen
  Institutions: Human Health Therapeutics Portfolio, National Research Council Canada, 100 Sussex Drive, Ottawa, Ontario K1A 0R6, Canada, Department of Biological Sciences, California State University, 5151 State University Dr., Los Angeles, CA 90032-8201, USA
  Methods: 13C NMR, 1H NMR, NMR-2D, GC-MS, sugar analysis, mild acid hydrolysis, de-O-acylation with hydrazine, NMR-1D
  
   
  
  Acinetobacter baumannii LAC-4
  CSDB ID 30524 (all data & tools)