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1. Compound ID: 179
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R-3HOBut-(1-4)-+
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-3)-a-D-QuipNAc4N-(1-3)-a-L-Rhap-(1-2)-a-L-Rhap-(1-2)-S-2HOSuc-(4-2)-a-L-FucpN-(1- |
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Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide
Contained glycoepitopes: IEDB_133754,IEDB_136105,IEDB_142345,IEDB_225177,IEDB_885823
The structure is contained in the following publication(s):
- Article ID: 36
Caroff M, Karibian D "Structure of bacterial lipopolysaccharides" -
Carbohydrate Research 338(23) (2003) 2431-2447
Bacterial lipopolysaccharides are the major components of the outer surface of Gram-negative bacteria They are often of interest in medicine for their immunomodulatory properties. In small amounts they can be beneficial, but in larger amounts they may cause endotoxic shock. Although they share a common architecture, their structural details exert a strong influence on their activity. These molecules comprise: a lipid moiety, called lipid A, which is considered to be the endotoxic component, a glycosidic part consisting of a core of approximately 10 monosaccharides and, in 'smooth-type' lipopolysaccharides, a third region, named O-chain, consisting of repetitive subunits of one to eight monosaccharides responsible for much of the immunospecificity of the bacterial cell.
Lipopolysaccharide, structure, core, lipid A, endotoxin, O-chains
NCBI PubMed ID: 14670707Publication DOI: 10.1016/j.carres.2003.07.010Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: martine.carloff@bbmpc.u-psud.fr
Institutions: Equipe Endotoxines, UMR 8619 du Centre National de la Recherche Scientifique, IBBMC, Université de Paris-Sud, F-Orsay, France
- Article ID: 188
Vinogradov E, Korenevsky A, Beveridge TJ "The structure of the O-specific polysaccharide chain of the Shewanella algae BrY lipopolysaccharide" -
Carbohydrate Research 338(4) (2003) 385-388
An acidic O-specific polysaccharide was obtained by mild acid degradation of the Shewanella algae strain BrY lipopolysaccharide and was found to contain L-rhamnose, 2-acetamido-4-[D-3-hydroxybutyramido)]-2,4,6-trideoxy-D-glucose (D-BacNAc4NHbu), and 2-amino-2,6-dideoxy-L-galactose, N-acylated by the 4-carboxyl group of L-malic acid (L-malyl-(4→2)-α-L-FucN) in the ratio 2:1:1. 1H and 13C NMR spectroscopy was applied to the intact polysaccharide, and the following structure of the repeating unit was established:-3)-α-D-BacNAc4NHbu-(1→3)-α-L-Rha-(1→2)-α-L-Rha-(1→2)-L-malyl-(4→2)-α-L-FucN-(1- The repeating unit includes linkage via the residue of malic acid, reported here for the first time as a component of bacterial polysaccharides
Lipopolysaccharide, NMR, structure, Bacterial, strain, polysaccharide, repeating unit, polysaccharides, chain, group, Research, acidic, acid, NMR spectroscopy, O-specific, O-specific polysaccharide, biological, linkage, Bacterial polysaccharide, spectroscopy, degradation, 13C NMR, component, Shewanella, algae, bacterial polysaccharides, galactose, L-rhamnose, N-acylated, time
NCBI PubMed ID: 12559738Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: evguenii.vinogradov@nrc.ca
Institutions: Institute for Biological Sciences, National Research Council, 100 Sussex Dr., ON, K1A 0R6, Ottawa, Canada
Methods: NMR-2D, NMR, sugar analysis
- Article ID: 515
Vinogradov E, Korenevsky A, Beveridge TJ "The structure of the core region of the lipopolysaccharide from Shewanella algae BrY, containing 8-amino-3,8-dideoxy-D-manno-oct-2-ulosonic acid" -
Carbohydrate Research 339(3) (2004) 737-740
The structure of the carbohydrate backbone of the lipid A-core region of the LPS from Shewanella algae strain BrY was analysed. The LPS was N,O-deacylated to give three products, which were isolated and studied by chemical methods, NMR and mass spectrometry: where R=Ac or H [Formula: see text] All monosaccharides except l-rhamnose had the d-configuration. This LPS presents a second example (after S. oneidensis) of the structure with a novel linking unit between the core and lipid A moieties, 8-amino-3,8-dideoxy-d-manno-oct-2-ulosonic acid (8-amino-Kdo).
LPS, core, Kdo, Shewanella, 8-Amino-Kdo
NCBI PubMed ID: 15013415Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: evguenii.vinogradov@nrc-cnrc.gc.ca
Institutions: Institute for Biological Sciences, NRC, 100 Sussex Dr., Ottawa, ON, Canada K1A 0R6, Department of Microbiology, College of Biological Science, University of Guelph, Guelph, ON, Canada N1G 2W1
Methods: NMR-2D, methylation, NMR, de-O-acylation, MS, de-N-acylation
- Article ID: 1471
Korenevsky AA, Vinogradov E, Gorby Y, Beveridge TJ "Characterization of the lipopolysaccharides and capsules of Shewanella spp" -
Applied and Environmental Microbiology 68(9) (2002) 4653-4657
Electron microscopy, sodium dodecyl sulfate-polyacrylamide gel electrophoresis with silver staining and (1)H, (13)C, and (31)P-nuclear magnetic resonance (NMR) were used to detect and characterize the lipopolysaccharides (LPSs) of several Shewanella species. Many expressed only rough LPS; however, approximately one-half produced smooth LPS (and/or capsular polysaccharides). Some LPSs were affected by growth temperature with increased chain length observed below 25 degrees C. Maximum LPS heterogeneity was found at 15 to 20 degrees C. Thin sections of freeze-substituted cells revealed that Shewanella oneidensis, S. algae, S. frigidimarina, and Shewanella sp. strain MR-4 possessed either O-side chains or capsular fringes ranging from 20 to 130 nm in thickness depending on the species. NMR detected unusual sugars in S. putrefaciens CN32 and S. algae BrY(DL). It is possible that the ability of Shewanella to adhere to solid mineral phases (such as iron oxides) could be affected by the composition and length of surface polysaccharide polymers. These same polymers in S. algae may also contribute to this opportunistic pathogen's ability to promote infection
Lipopolysaccharide, capsular polysaccharide, Shewanella, surface polysaccharide, capsules, electron microscopy
NCBI PubMed ID: 12200327Journal NLM ID: 7605801Publisher: American Society for Microbiology
Correspondence: tjb@uoguelph.ca
Institutions: Department of Microbiology, College of Biological Science, University of Guelph, Guelph, Ontario, Canada, N1G 2W1, Institute for Biological Science, National Research Council of Canada, Ottawa, Ontario, Canada K1A 0R6, Pacific Northwest National Laboratory, Richland, Washington 99352
Methods: 13C NMR, 1H NMR, SDS-PAGE, 31P NMR, electron microscopy
- Article ID: 3820
Banoub JH, El Aneed A, Cohen AM, Joly N "Structural investigation of bacterial lipopolysaccharides by mass spectrometry and tandem mass spectrometry" -
Mass Spectrometry Reviews 29(4) (2010) 606-650
Mass spectrometric studies are now playing a leading role in the elucidation of lipopolysaccharide (LPS) structures through the characterization of antigenic polysaccharides, core oligosaccharides and lipid A components including LPS genetic modifications. The conventional MS and MS/MS analyses together with CID fragmentation provide additional structural information complementary to the previous analytical experiments, and thus contribute to an integrated strategy for the simultaneous characterization and correct sequencing of the carbohydrate moiety.
LPS, O-antigen, lipid A, core oligosaccharide, MS and MS/MS analyses
NCBI PubMed ID: 20589944Publication DOI: 10.1002/mas.20258Journal NLM ID: 8219702Publisher: Wiley
Correspondence: joe.banoub@dfo-mpo.gc.ca
Institutions: Fisheries and Oceans Canada, Science Branch, Special Projects, P.O. Box 5667, St. John's, Newfoundland, Canada A1C 5X1, Department of Chemistry, Memorial University of Newfoundland, St. John's, Newfoundland, Canada A1B 3V6, College of Pharmacy and Nutrition, University of Saskatchewan, Thorvaldson Building, 110 Science Place, Saskatoon, Saskatchewan, Canada S7N 5C9, Unité de Catalyse et de Chimie du Solide, Site de l'Artois—UMR CNRS 8181, I.U.T. de Béthune, Département Chimie, 1230 rue de l'Université, BP819, 62408 Béthune Cedex, France, Institute for Marine Biosciences Room 219A, (NRC-IMB), National Research Council of Canada, Government of Canada, 1411 Oxford Street, Halifax, NS, Canada B3H 3Z1
Methods: MS/MS, MS
- Article ID: 4328
Knirel YA "Structure of O-antigens" -
Book: Bacterial lipopolysaccharides: Structure, chemical synthesis, biogenesis and interaction with host cells (2011) Chapter 3, 41-115
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_3Publisher: Springer
Correspondence: knirel@ioc.ac.ru
Editors: Knirel YA, Valvano MA
Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
- Article ID: 4434
Nazarenko EL, Komandrova NA, Gorshkova RP, Tomshich SV, Zubkov VA, Kilcoyne M, Savage AV "Structures of polysaccharides and oligosaccharides of some Gram-negative marine Proteobacteria" -
Carbohydrate Research 338(23) (2003) 2449-2457
The chemical structures of polysaccharides and LPS core oligosaccharides, isolated from various Gram-negative marine bacteria from the genera Pseudoalteromonas and Shewanella belonging to the Alteromonadaceae family and gamma-subclass of Proteobacteria, are reviewed. The polysaccharides are distinguished by the acidic character (e.g., due to the presence of hexuronic and aldulosonic acids and their derivatives) and the occurrence of unusual sugars, including N-acyl derivatives of 6-deoxyamino sugars, such as N-acetyl-D-quinovosamine, N-acetyl-L-fucosamine and N-acetyl-6-deoxy-L-talosamine, and higher sugars like 2,6-dideoxy-2-acetamido-4-C-(3'-carboxamide-2',2'-dihydroxypropyl)-D-galac topyranose (shewanellose). Many constituent sugars have various uncommon non-sugar substituents, such as alanine, formic, lactic and hydroxybutyric acids, sulfate, phosphate, and 2-aminopropane-1,3-diol.
Lipopolysaccharide, oligosaccharide structure, O-antigen, polysaccharide structure, Shewanella, Pseudoalteromonas, Proteobacteria
NCBI PubMed ID: 14670708Publication DOI: 10.1016/j.carres.2003.06.004Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: A.V. Savage
Institutions: Department of Chemistry, National University of Ireland, Galway, Ireland, Pacific Institute of Bioorganic Chemistry, Far East Branch of the Russian Academy of Sciences, Vladivostok 690022, Russian Federation
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2. Compound ID: 432
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S-3HOBut-(1-4)-+ S-3HOBut-(1-3)-+
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-2)-a-L-Rhap-(1-4)-a-D-GalpNAcA-(1-3)-a-D-QuipNAc4N-(1-2)-b-D-Quip3N-(1- |
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Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_136105,IEDB_142345,IEDB_225177,IEDB_885823
The structure is contained in the following publication(s):
- Article ID: 159
Veremeychenko SN, Zdorovenko GM "Peculiarity of the structure of the lipopolysaccharide of Pseudomonas fluorescens IMV 247 (biovar II)" -
Mikrobiologiia = Microbiology [Russian] 69(3) (2000) 362-369
The results of the study of the Pseudomonas fluorescens IMV 247 (biovar II) lipopolysaccharide (LPS) isolated from the dry bacterial mass by Westphal's method and purified by repeated ultracentrifugation are presented. The macromolecular organization of the LPS is characterized by the presence of S and R forms of LPS molecules in a 1:1 ratio. The structural components of the LPS molecule → lipid A, the core oligosaccharide, and the O-specific polysaccharide -- were isolated and characterized. 3-Hydroxydecanoic, 2-hydroxydodecanoic, 3-hydroxydodecanoic, and dodecanoic acids proved to be the main lipid A fatty acids. Glucosamine, phosphoethanolamine, and phosphorus were identified as the components of the lipid A hydrophilic portion. Glucose, galactose, arabinose, rhamnose, glucosamine, alanine, phosphoethanolamine, phosphorus, and 2-keto-3-deoxyoctulonate (KDO) were revealed in the heterogeneous fraction of the core oligosaccharide. The O-specific polysaccharide chain was composed of repeating tetrasaccharide units consisting of L-rhamnose (L-Rha), 3,6-dideoxy-3-[(S)-3-hydroxybutyramido]-D-glucose (D-Qui3NHb), 2-acetamido-2,4,6-trideoxy-4[(S)-3-hydroxybutyramido-D-glucose (D-QuiNAc4NHb), and 2-acetamido-2-deoxy-D-galacturonic acid (D-GalNAcA) residues. A peculiarity of the O-specific polysaccharide was that it released, upon partial acid hydrolysis, the nonreducing disaccharide GalNAcA → QuiNAc4NHb with a 3-hydroxybutyryl group glycosylated intramolecularly with a QuiN4N residue. Double immunodiffusion in agar and lipopolysaccharide precipitation reactions revealed no serological interrelationship between the strain studied and the P. fluorescens strains studied earlier.
Lipopolysaccharide, LPS, structure, strain, characterization, Pseudomonas, fatty acid, O-chain, biovar, Pseudomonas fluorescens
NCBI PubMed ID: 10920806Journal NLM ID: 0376652Publisher: Moskva: Izdatelstvo Nauka
Institutions: Institute of Microbiology and Virology, National Academy of Sciences of Ukraine, Kiev, Ukraine.
Methods: NMR-2D, NMR
- Article ID: 4328
Knirel YA "Structure of O-antigens" -
Book: Bacterial lipopolysaccharides: Structure, chemical synthesis, biogenesis and interaction with host cells (2011) Chapter 3, 41-115
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_3Publisher: Springer
Correspondence: knirel@ioc.ac.ru
Editors: Knirel YA, Valvano MA
Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
- Article ID: 4334
Kondakova AN, Novototskaya-Vlasova KA, Shashkov AS, Drutskaya MS, Senchenkova SN, Shcherbakova VA, Gilichinsky DA, Nedospasov SA, Knirel YA "Structure of an acidic polysaccharide isolated from Psychrobacter maritimus 3pS containing a bacillosamine derivative" -
Carbohydrate Research 359 (2012) 7-10
An acidic polysaccharide was obtained from Psychrobacter maritimus 3pS isolated from a Siberian cryopeg sample (Kolyma lowland). The following structure of the tetrasaccharide repeating unit of the polysaccharide was established by sugar analysis along with (1)H and (13)C NMR spectroscopy: →2)-α-L-Rhap-(1→4)-α-D-GalpNAcA-(1→3)-α-D-QuipNAc4NHb-(1→3)-β-D-QuipNAc4NHb-(1→ where D-GalNAcA indicates 2-acetamido-2-deoxy-D-galacturonic acid and d-QuiNAc4NHb indicates 2-acetamido-2,4,6-trideoxy-4-[(S)-3-hydroxybutanoyl]amino-D-glucose.
acid, bacterial polysaccharide structure, 2, 4, 4-diamino-2, 2-acetamido-2-deoxy-D-galacturonic acid, Psychrobacter maritimus, 6-trideoxy-D-glucopyranose
NCBI PubMed ID: 22925757Publication DOI: 10.1016/j.carres.2012.07.007Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: annakond@gmail.com
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Institute for Physicochemical and Biological Problems in Soil Science, Russian Academy of Sciences, 142290 Pushchino, Russia, Engelhardt Institute of Molecular Biology, Russian Academy of Sciences, Moscow, Russia, Institute of Biochemistry and Physiology of Microorganisms, Russian Academy of Sciences,142290 Pushchino, Russia
Methods: 13C NMR, 1H NMR, NMR-2D, sugar analysis, ESI-MS, GLC, mild acid hydrolysis, DOC-PAGE, Smith degradation, GPC
- 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: 35750381Publication DOI: 10.1016/S1875-5364(22)60177-8Journal NLM ID: 101504416Publisher: 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
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3. Compound ID: 709
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S-3HOBut-(1-7)-+
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-4)-b-Sugp5Ac-(2-2)-S-2HOGlt-(5-4)-b-D-QuipNAc4N3Ac-(1-
Sug = 5,7,8-triamino-3,5,7,8,9-pentadeoxy-?-glycero-L-manno-non-2-ulosonic acid = SMILES CC({7}[C@@H]([C@@H]1O{2}[C@@](C(O)=O)(C{4}[C@@H]({5}[C@@H]1N)O)O)N)N |
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Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_142345
The structure is contained in the following publication(s):
- Article ID: 187
Vinogradov E, MacLean LL, Crump EM, Perry MB, Kay WW "Structure of the polysaccharide chain of the lipopolysaccharide from Flexibacter maritimus" -
European Journal of Biochemistry 270(8) (2003) 1810-1815
Flexibacter maritimus, a Gram-negative bacterium, is a fish pathogen responsible for disease in finfish species and a cause of cutaneous erosion disease in sea-caged salmonids. For the development of serology based diagnostics, protective vaccines, and a study of pathogenesis, the structural analysis of the lipopolysaccharide (LPS) produced by the bacterium has been undertaken. We now report that an acidic O-specific polysaccharide, obtained by mild acid degradation of the F. maritimus LPS was found to be composed of a disaccharide repeating unit built of 2-acetamido-3-O-acetyl-4-[(S)-2-hydroxyglutar-5-ylamido]-2,4,6-trideoxy-β-glucose and 5-acetamido-7-[(S)-3-hydroxybutyramido]-8-amino-3,5,7,8,9-pentadeoxynonulopyranosonic acid (Sug) having the structure: The configuration of the C-2-C-7 fragment of the latter monosaccharide (B) was assigned β-manno; however, the configuration at C-8 could not be established. NMR data indicate that the two monosaccharides have opposite absolute configurations. The repeating unit includes a linkage via a (S)-2-hydroxyglutaric acid residue, reported here for the first time as a component of a bacterial polysaccharide. The LPS was also found to contain a minor amount of a disaccharide β-Sug-(2-3)-l-Rha, isolated from the products of the acidic methanolysis of the LPS
Lipopolysaccharide, NMR, polysaccharide, Flexibacter maritimus
NCBI PubMed ID: 12694194Publication DOI: 10.1046/j.1432-1033.2003.03543.xJournal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Correspondence: Malcolm.Perry@nrc.ca
Institutions: Institute for Biological Sciences, National Research Council, Ottawa, Ontario, Canada
Methods: NMR-2D, NMR, chemical analysis
- Article ID: 4049
Knirel YA, Shevelev SD, Perepelov AV "Higher aldulosonic acids: components of bacterial glycans" -
Mendeleev Communications 21(4) (2011) 173-182
Recent data on the natural occurrence, chemistry, and biochemistry of C8 and C9 aldulosonic acids (3-deoxy-d-manno-oct-2-ulosonic acid, sialic acids, N-acyl derivatives of 5,7-diamino-3,5,7,9-tetradeoxynon-2-ulosonic acids, and some others) as well as on the structures and biological significance of bacterial glycans containing these higher acidic monosaccharides are summarized.
structure, Bacterial, glycan, aldulosonic acid, higher acidic monosaccharides, sialic acids
Publication DOI: 10.1016/j.mencom.2011.07.001Journal NLM ID: 9425965Publisher: Moscow: Academy of Sciences of the USSR; Cambridge,UK : Royal Society of Chemistry
Correspondence: knirel@ioc.ac.ru
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
- Article ID: 6049
Di Lorenzo F, Duda KA, Lanzetta R, Silipo A, De Castro C, Molinaro A "A Journey from Structure to Function of Bacterial Lipopolysaccharides" -
Chemical Reviews (2021)
Lipopolysaccharide (LPS) is a crucial constituent of the outer membrane of most Gram-negative bacteria, playing a fundamental role in the protection of bacteria from environmental stress factors, in drug resistance, in pathogenesis, and in symbiosis. During the last decades, LPS has been thoroughly dissected, and massive information on this fascinating biomolecule is now available. In this Review, we will give the reader a third millennium update of the current knowledge of LPS with key information on the inherent peculiar carbohydrate chemistry due to often puzzling sugar residues that are uniquely found on it. Then, we will drive the reader through the complex and multifarious immunological outcomes that any given LPS can raise, which is strictly dependent on its chemical structure. Further, we will argue about issues that still remain unresolved and that would represent the immediate future of LPS research. It is critical to address these points to complete our notions on LPS chemistry, functions, and roles, in turn leading to innovative ways to manipulate the processes involving such a still controversial and intriguing biomolecule.
Lipopolysaccharide, LPS, structure, Pathogenesis, carbohydrate, function, gram negative bacteria
NCBI PubMed ID: 34286971Publication DOI: 10.1021/acs.chemrev.0c01321Journal NLM ID: 2985134RPublisher: Chem Rev
Correspondence: Antonio Molinaro
Institutions: Department of Chemical Sciences, University of Naples Federico II, via Cinthia 4, 80126 Naples, Italy, Task Force on Microbiome Studies, University of Naples Federico II, Via Cinthia 4, 80126 Naples, Italy, Research Center Borstel Leibniz Lung Center, Parkallee 4a, 23845 Borstel, Germany, Department of Agricultural Sciences, University of Naples Federico II, Via Universita 96, 80055 Portici, Naples, Italy, Department of Chemistry, School of Science, Osaka University, 1-1 Osaka University Machikaneyama, Toyonaka, Osaka 560-0043, Japan
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4. Compound ID: 786
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S-3HOBut-(1-4)-+
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-4)-a-D-GlcpNAc6(50%)Ac-(1-4)-a-D-GalpNAcA-(1-3)-b-D-QuipNAc4N-(1- |
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Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_141807,IEDB_142345,IEDB_151531
The structure is contained in the following publication(s):
- Article ID: 203
Vinogradov EV, Brade L, Brade H, Holst O "Structural and serological characterisation of the O-antigenic polysaccharide of the lipopolysaccharide from Acinetobacter baumannii strain 24" -
Carbohydrate Research 338(23) (2003) 2751-2756
Extraction of dry bacteria of Acinetobacter baumannii strain 24 by phenol-water yielded a lipopolysaccharide (LPS) that was studied by serological methods and fatty acid analysis. After immunisation of BALB/c mice with this strain, monoclonal antibody S48-3-13 (IgG(3) isotype) was obtained, which reacted with the LPS in western blot and characterized it as S-form LPS. Degradation of the LPS in aqueous 1% acetic acid followed by GPC gave the O-antigenic polysaccharide, whose structure was determined by compositional analyses and NMR spectroscopy of the polysaccharide and O-deacylated polysaccharide as [carbohydrate structure: see text] where QuiN4N is 2,4-diamino-2,4,6-trideoxyglucose and GalNAcA 2-acetamido-2-deoxygalacturonic acid. The amino group at C-4 of the QuipN4N residues is acetylated in about 2/3 of LPS molecules and (S)-3-hydroxybutyrylated in the rest
Lipopolysaccharide, NMR, LPS, structure, strain, structural, polysaccharide, analysis, group, molecule, O-antigenic, O-antigenic polysaccharide, acid, Acinetobacter, Acinetobacter baumannii, antibodies, antibody, monoclonal, monoclonal antibodies, monoclonal antibody, mice, NMR spectroscopy, bacteria, serological, spectroscopy, fatty acid, method, degradation, methods, acetylated, amino, amino group, aqueous, extraction, O-deacylated, phenol-water, S-form
NCBI PubMed ID: 14670733Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: oholst@fz-borstel.de
Institutions: Division of Medical and Biochemical Microbiology, Research Center Borstel, D-23845 Borstel, Germany, Division of Structural Biochemistry, Research Center Borstel, D-23845 Borstel, Germany
Methods: NMR-2D, NMR, chemical methods
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5. Compound ID: 1654
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-4)-a-D-GalpNAcA6NH2-(1-4)-a-D-GalpNAcA6NH2-(1-4)-a-D-GalpNAcA6NH2-(1-3)-a-D-QuiNAc4NAc-(1- |
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Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_142345
The structure is contained in the following publication(s):
- Article ID: 514
Vinogradov E, Conlan WJ, Gunn JS, Perry MB "Characterization of the lipopolysaccharide O-antigen of Francisella novicida (U112)" -
Carbohydrate Research 339(3) (2004) 649-654
Francisella novicida (U112), a close relative of the highly virulent bacterium F. tularensis, was shown to produce a lipopolysaccharide in which the antigenic O-polysaccharide component was found by chemical, (1)H and (13)C NMR and MS analyses to be an unbranched neutral linear polymer of a repeating tetrasaccharide unit composed of 2-acetamido-2-deoxy-d-galacturonamide (d-GalNAcAN) and 2,4-diacetamido-2,4,6-trideoxy-d-glucose (d-Qui2NAc4NAc, di-N-acetylbacillosamine) residues (3:1) and had the structure: [Formula: see text] With polyclonal murine antibody, the F. novicida O-antigen did not show serological cross-reactivity with the O-antigen of F. tularensis despite the occurrence of a common →4)-d-GalpNAcAN-(1→4)-α-D-GalpNAcAN-(1→ disaccharide unit in their respective O-antigens. Thus, O-PS serology offers a practical way to distinguish between the two Francisella species.
Lipopolysaccharide, NMR, structure, common, tetrasaccharide, characterization, O-antigen, antigenic, O antigen, polymer, Research, antibodies, antibody, O-polysaccharide, O antigens, O polysaccharide, O-antigens, bacteria, neutral, serological, serology, biological, chemical, component, MS, disaccharide, linear, occurrence, lipopolysaccharide O-antigen, species, cross-reactivity, crossreactivity, virulent, PDF, murine
NCBI PubMed ID: 15013402Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: malcolm.perry@nrc-cnrc.gc.ca
Institutions: Institute for Biological Sciences, National Research Council, Ottawa, Ontario, Canada K1A OR6, Department of Virology, Immunology and Medical Genetics, Department of Medicine, Division of Infectious Diseases, The Center for Microbial Interface Biology, The Ohio State University, Columbus, OH, USA
Methods: NMR-2D, methylation, NMR, sugar analysis, MS
- Article ID: 4328
Knirel YA "Structure of O-antigens" -
Book: Bacterial lipopolysaccharides: Structure, chemical synthesis, biogenesis and interaction with host cells (2011) Chapter 3, 41-115
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_3Publisher: Springer
Correspondence: knirel@ioc.ac.ru
Editors: Knirel YA, Valvano MA
Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
- 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: 35750381Publication DOI: 10.1016/S1875-5364(22)60177-8Journal NLM ID: 101504416Publisher: 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
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6. Compound ID: 1662
|
a-D-Glcp-(1-2)-b-D-Glcp-(1-2)-+
|
a-D-GalpNAc-(1-2)-+ |
| |
a-D-GalpNAcA6NH2-(1-4)-a-D-GalpNAcA6NH2-(1-4)-a-D-GalpNAcA6NH2-(1-3)-b-D-QuipNAc4NAc-(1-4)-b-D-Manp-(1-4)-a-D-Manp-(1-5)-Kdo
|
a-D-Glcp-(1-3)-+ |
Show graphically |
Structure type: oligomer
Compound class: core oligosaccharide with O-unit
Contained glycoepitopes: IEDB_130648,IEDB_130650,IEDB_130701,IEDB_137473,IEDB_137485,IEDB_1391961,IEDB_141584,IEDB_142345,IEDB_142488,IEDB_144983,IEDB_144998,IEDB_146664,IEDB_152206,IEDB_153219,IEDB_244149,IEDB_885822,IEDB_983930,IEDB_983931,SB_192,SB_44,SB_67,SB_72
The structure is contained in the following publication(s):
- Article ID: 516
Vinogradov E, Perry MB "Characterisation of the core part of the lipopolysaccharide O-antigen of Francisella novicida (U112)" -
Carbohydrate Research 339(9) (2004) 1643-1648
Francisella novicida (U112), a close relative of the highly virulent bacterium F. tularensis, is known to produce a lipopolysaccharide that is significantly different in biological properties from the LPS of F. tularensis. Here we present the results of the structural analysis of the F. novicida LPS core part, which is found to be similar to that of F. tularensis, differing only by one additional α-Glc residue:where R is an O-chain, linked via a β-bacillosamine (2,4-diamino-2,4,6-trideoxyglucose) residue. The lipid part of F. novicida LPS contains no phosphate substituent and apparently has a free reducing end, a feature also noted in F. tularensis LPS.
LPS, core structure, Francisella, Francisella novicida
NCBI PubMed ID: 15183739Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: evguenii.vinogradov@nrc-cnrc.gc.ca
Institutions: Institute for Biological Sciences, National Research Council, Ottawa, Ontario, Canada K1A 0R6
Methods: NMR-2D, methylation, NMR, MS
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7. Compound ID: 1663
|
a-D-Glcp-(1-2)-b-D-Glcp-(1-2)-+
|
a-D-GalpNAc-(1-2)-+ |
| |
a-D-GalpNAcA6NH2-(1-4)-a-D-GalpNAcA6NH2-(1-4)-a-D-GalpNAcA6NH2-(1-3)-a-D-QuipNAc4NAc-(1-4)-a-D-GalpNAcA6NH2-(1-4)-a-D-GalpNAcA6NH2-(1-4)-a-D-GalpNAcA6NH2-(1-3)-b-D-QuipNAc4NAc-(1-4)-b-D-Manp-(1-4)-a-D-Manp-(1-5)-Kdo
|
a-D-Glcp-(1-3)-+ |
Show graphically |
Structure type: oligomer
Compound class: core oligosaccharide with two O-units
Contained glycoepitopes: IEDB_130648,IEDB_130650,IEDB_130701,IEDB_137473,IEDB_137485,IEDB_1391961,IEDB_141584,IEDB_142345,IEDB_142488,IEDB_144983,IEDB_144998,IEDB_146664,IEDB_152206,IEDB_153219,IEDB_244149,IEDB_885822,IEDB_983930,IEDB_983931,SB_192,SB_44,SB_67,SB_72
The structure is contained in the following publication(s):
- Article ID: 516
Vinogradov E, Perry MB "Characterisation of the core part of the lipopolysaccharide O-antigen of Francisella novicida (U112)" -
Carbohydrate Research 339(9) (2004) 1643-1648
Francisella novicida (U112), a close relative of the highly virulent bacterium F. tularensis, is known to produce a lipopolysaccharide that is significantly different in biological properties from the LPS of F. tularensis. Here we present the results of the structural analysis of the F. novicida LPS core part, which is found to be similar to that of F. tularensis, differing only by one additional α-Glc residue:where R is an O-chain, linked via a β-bacillosamine (2,4-diamino-2,4,6-trideoxyglucose) residue. The lipid part of F. novicida LPS contains no phosphate substituent and apparently has a free reducing end, a feature also noted in F. tularensis LPS.
LPS, core structure, Francisella, Francisella novicida
NCBI PubMed ID: 15183739Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: evguenii.vinogradov@nrc-cnrc.gc.ca
Institutions: Institute for Biological Sciences, National Research Council, Ottawa, Ontario, Canada K1A 0R6
Methods: NMR-2D, methylation, NMR, MS
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8. Compound ID: 1666
|
a-D-Glcp-(1-2)-b-D-Glcp-(1-2)-+
|
a-D-GalpN-(1-2)-+ |
| |
b-L-4dthrHexp4enNA-(1-3)-b-D-QuipNAc4NAc-(1-4)-b-D-Manp-(1-4)-a-D-Manp-(1-5)-a-Kdo-(2-6)-b-D-GlcpN-(1-6)-D-GlcN-ol
|
a-D-Glcp-(1-3)-+ |
Show graphically |
Structure type: oligomer
Compound class: LPS
Contained glycoepitopes: IEDB_130650,IEDB_130701,IEDB_137340,IEDB_137473,IEDB_137485,IEDB_141807,IEDB_142345,IEDB_142488,IEDB_144983,IEDB_144998,IEDB_146664,IEDB_151531,IEDB_152206,IEDB_153219,IEDB_983930,IEDB_983931,SB_192,SB_44,SB_67,SB_72
The structure is contained in the following publication(s):
- Article ID: 516
Vinogradov E, Perry MB "Characterisation of the core part of the lipopolysaccharide O-antigen of Francisella novicida (U112)" -
Carbohydrate Research 339(9) (2004) 1643-1648
Francisella novicida (U112), a close relative of the highly virulent bacterium F. tularensis, is known to produce a lipopolysaccharide that is significantly different in biological properties from the LPS of F. tularensis. Here we present the results of the structural analysis of the F. novicida LPS core part, which is found to be similar to that of F. tularensis, differing only by one additional α-Glc residue:where R is an O-chain, linked via a β-bacillosamine (2,4-diamino-2,4,6-trideoxyglucose) residue. The lipid part of F. novicida LPS contains no phosphate substituent and apparently has a free reducing end, a feature also noted in F. tularensis LPS.
LPS, core structure, Francisella, Francisella novicida
NCBI PubMed ID: 15183739Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: evguenii.vinogradov@nrc-cnrc.gc.ca
Institutions: Institute for Biological Sciences, National Research Council, Ottawa, Ontario, Canada K1A 0R6
Methods: NMR-2D, methylation, NMR, MS
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9. Compound ID: 1667
|
a-D-Glcp-(1-2)-b-D-Glcp-(1-2)-+
|
a-D-GalpNAc-(1-2)-+ |
| |
b-L-4dthrHexp4enNA-(1-3)-b-D-QuipNAc4NAc-(1-4)-b-D-Manp-(1-4)-a-D-Manp-(1-5)-a-Kdo-(2-6)-b-D-GlcpNAc-(1-6)-D-GlcNAc-ol
|
a-D-Glcp-(1-3)-+ |
Show graphically |
Structure type: oligomer
Compound class: LPS
Contained glycoepitopes: IEDB_130648,IEDB_130650,IEDB_130701,IEDB_135813,IEDB_137340,IEDB_137473,IEDB_137485,IEDB_1391961,IEDB_141584,IEDB_141807,IEDB_142345,IEDB_142488,IEDB_144983,IEDB_144998,IEDB_146664,IEDB_151531,IEDB_152206,IEDB_153219,IEDB_244149,IEDB_885822,IEDB_983930,IEDB_983931,SB_192,SB_44,SB_67,SB_72
The structure is contained in the following publication(s):
- Article ID: 516
Vinogradov E, Perry MB "Characterisation of the core part of the lipopolysaccharide O-antigen of Francisella novicida (U112)" -
Carbohydrate Research 339(9) (2004) 1643-1648
Francisella novicida (U112), a close relative of the highly virulent bacterium F. tularensis, is known to produce a lipopolysaccharide that is significantly different in biological properties from the LPS of F. tularensis. Here we present the results of the structural analysis of the F. novicida LPS core part, which is found to be similar to that of F. tularensis, differing only by one additional α-Glc residue:where R is an O-chain, linked via a β-bacillosamine (2,4-diamino-2,4,6-trideoxyglucose) residue. The lipid part of F. novicida LPS contains no phosphate substituent and apparently has a free reducing end, a feature also noted in F. tularensis LPS.
LPS, core structure, Francisella, Francisella novicida
NCBI PubMed ID: 15183739Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: evguenii.vinogradov@nrc-cnrc.gc.ca
Institutions: Institute for Biological Sciences, National Research Council, Ottawa, Ontario, Canada K1A 0R6
Methods: NMR-2D, methylation, NMR, MS
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10. Compound ID: 1682
Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide
Contained glycoepitopes: IEDB_1394181,IEDB_142345
The structure is contained in the following publication(s):
- Article ID: 519
Vinogradov E, Nossova L, Swierzko A, Cedzynski M "The structure of the O-specific polysaccharide from Ralstonia pickettii" -
Carbohydrate Research 339(11) (2004) 2045-2047
The following structure of the Ralstonia pickettii have been determined using NMR and chemical methods: [Formula: see text]
LPS, structure, O-chain, Ralstonia, Ralstonia pickettii
NCBI PubMed ID: 15261599Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: evguenii.vinogradov@nrc-cnrc.gc.ca
Institutions: Institute for Biological Sciences, National Research Council, 100 Sussex Dr., Ottawa, ON, Canada K1A 0R6, The Laboratory of Immunobiology of Infections, Centre for Medical Biology, Polish Academy of Sciences, Lodowa 106,93-232 Lodz, Poland
Methods: NMR-2D, methylation, NMR, sugar analysis, methanolysis
- Article ID: 4328
Knirel YA "Structure of O-antigens" -
Book: Bacterial lipopolysaccharides: Structure, chemical synthesis, biogenesis and interaction with host cells (2011) Chapter 3, 41-115
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_3Publisher: Springer
Correspondence: knirel@ioc.ac.ru
Editors: Knirel YA, Valvano MA
Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
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11. Compound ID: 1683
Structure type: oligomer
Contained glycoepitopes: IEDB_142345
The structure is contained in the following publication(s):
- Article ID: 519
Vinogradov E, Nossova L, Swierzko A, Cedzynski M "The structure of the O-specific polysaccharide from Ralstonia pickettii" -
Carbohydrate Research 339(11) (2004) 2045-2047
The following structure of the Ralstonia pickettii have been determined using NMR and chemical methods: [Formula: see text]
LPS, structure, O-chain, Ralstonia, Ralstonia pickettii
NCBI PubMed ID: 15261599Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: evguenii.vinogradov@nrc-cnrc.gc.ca
Institutions: Institute for Biological Sciences, National Research Council, 100 Sussex Dr., Ottawa, ON, Canada K1A 0R6, The Laboratory of Immunobiology of Infections, Centre for Medical Biology, Polish Academy of Sciences, Lodowa 106,93-232 Lodz, Poland
Methods: NMR-2D, methylation, NMR, sugar analysis, methanolysis
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12. Compound ID: 2068
|
a-D-QuipNAc4NAc-(1-4)-+
|
S-3HOBut-(1-2)-+ |
| |
-4)-b-D-GlcpA-(1-4)-b-D-GlcpA-(1-3)-b-D-QuipN4N-(1-2)-a-L-IdopA-(1-
|
S-3HOBut-(1-4)-+ |
Show graphically |
Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_115136,IEDB_140630,IEDB_142345,IEDB_423153
The structure is contained in the following publication(s):
- Article ID: 674
Hanniffy O, Shashkov AS, Senchenkova SN, Tomshich SV, Komandrova NA, Romanenko LA, Knirel YA, Savage AV "Structure of a highly acidic O-specific polysaccharide from Pseudoalteromonas haloplanktis KMM 223 (44-1) containing L-iduronic acid and D-QuiNHb4NHb" -
Carbohydrate Research 307 (1998) 291-298
An acidic O-specifc polysaccharide was obtained by mild acid degradation of the lipopolysaccharide isolated by phenol±water extraction of Pseudoalteromonas haloplanktis strain KMM 223 (44-1). l-Iduronic acid (IdoA) was found to be a component of the polysaccharide and identifed by NMR spectroscopy and after carboxyl-reduction followed by acid hydrolysis and acetylation, by GLC-MS as 2,3,4-tri-O-acetyl-1,6-anhydroidose. On the basis of 1H and 13C NMR spectroscopic studies, including 1D NOE, 2D NOESY, HSQC and HMBC experiments, the following structure of the branched pentasaccharide repeating unit of the polysaccharide was established:
structure, strain, polysaccharide, capsular polysaccharide, acidic, acid, NMR spectroscopy, O-specific, O-specific polysaccharide, 2, 4, Pseudoalteromonas haloplanktis, Pseudoalteromonas, iduronic acid, L-iduronic acid, 4-diamino-2, 6-trideoxy-D-glucose, (S)-3-hydroxybutyric acid
NCBI PubMed ID: 9675369Journal NLM ID: 0043535Publisher: Elsevier
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Department of Chemistry, University College, Galway, Ireland, Pacifc Institute of Bioorganic Chemistry, Far East Branch of the Russian Academy of Sciences, Vladivostok 690022, Russian Federation
Methods: NMR-2D, NMR
- Article ID: 4099
Raedts J, Kengen SW, van der OJ "Occurrence of L-iduronic acid and putative D-glucuronyl C5-epimerases in prokaryotes" -
Glycoconjugate Journal 28(2) (2011) 57-66
Glycosaminoglycans (GAGs) are polysaccharides that are typically present in a wide diversity of animal tissue. Most common GAGs are well-characterized and pharmaceutical applications exist for many of these compounds, e.g. heparin and hyaluronan. In addition, also bacterial glycosaminoglycan-like structures exist. Some of these bacterial GAGs have been characterized, but until now no bacterial GAG has been found that possesses the modifications that are characteristic for many of the animal GAGs such as sulfation and C5-epimerization. Nevertheless, the latter conversion may also occur in bacterial and archaeal GAGs, as some prokaryotic polysaccharides have been demonstrated to contain L-iduronic acid. However, experimental evidence for the enzymatic synthesis of L-iduronic acid in prokaryotes is as yet lacking. We therefore performed an in silico screen for D-glucuronyl C5-epimerases in prokaryotes. Multiple candidate C5-epimerases were found, suggesting that many more microorganisms are likely to exist possessing an L-iduronic acid residue as constituent of their cell wall polysaccharides.
Lipopolysaccharide, glycosaminoglycans, capsule polysaccharide, L-iduronic acid, D-glucuronyl C5-epimerase
NCBI PubMed ID: 21347714Journal NLM ID: 8603310Publisher: Kluwer Academic Publishers
Correspondence: John.Raedts@wur.nl
Institutions: Laboratory of Microbiology, Wageningen University, Dreijenplein 10, 6703 HB Wageningen, The Netherlands
- Article ID: 5157
Goyette-Desjardins G, Vinogradov E, Okura M, Takamatsu D, Gottschalk M, Segura M "Streptococcus suis serotype 3 and serotype 18 capsular polysaccharides contain di-N-acetyl-bacillosamine" -
Carbohydrate Research 466 (2018) 18-29
Streptococcus suis serotype 3 is counted among the S. suis serotypes causing clinical disease in pigs. Yet, limited information is available on this serotype. Here we determined for the first time the chemical composition and structure of serotype 3 capsular polysaccharide (CPS), a major bacterial virulence factor and the antigen at the origin of S. suis classification into serotypes. Chemical and spectroscopic data gave the repeating unit sequence for serotype 3: [4)D-GlcA (β1-3)d-QuiNAc4NAc(β1-]n. To the best of our knowledge, this is the first report of di-N-acetyl-d-bacillosamine (QuiNAc4NAc) containing polysaccharides in Streptococci and the second time this rare diamino sugar has been observed in a Gram-positive bacterial species since its initial report. This led to the identification of homologues of UDP-QuiNAc4NAc synthesis genes in S. suis serotype 18. Thus, the repeating unit sequence for serotype 18 is: [3)d-GalNAc(α1-3)[d-Glc (β1-2)]d-GalA4OAc(β1-3)d-GalNAc(α1-3)d-QuiNAc4NAc(α1-]n. A correlation between S. suis serotypes 3 and 18 CPS sequences and genes of these serotypes' cps loci encoding putative glycosyltransferases and polymerase responsible for the biosynthesis of the repeating unit was tentatively established. Knowledge of CPS structure and composition will contribute to better dissect the role of this bacterial component in the pathogenesis of S. suis serotypes 3 and 18.
polysaccharide, capsular polysaccharide, polysaccharides, carbohydrate structure, Streptococcus suis, Di-N-Acetyl-bacillosamine, Serotype 18, Serotype 3
NCBI PubMed ID: 30014879Publication DOI: 10.1016/j.carres.2018.07.003Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: mariela.segura@umontreal.ca
Institutions: Swine and Poultry Infectious Diseases Research Center, Faculty of Veterinary Medicine, University of Montreal, 3200 Sicotte St., St-Hyacinthe, Quebec, J2S 2M2, Canada, Canadian Glycomics Network (GlycoNet), University of Alberta, 11227 Saskatchewan Dr., Edmonton, Alberta, T6G 2G2, Canada, National Research Council, 100 Sussex Dr., Ottawa, Ontario, K1A 0R6, Canada, Division of Bacterial and Parasitic Disease, National Institute of Animal Health, National Agriculture and Food Research Organization, 3-1-5 Kannondai, Tsukuba, Ibaraki, 305-0856, Japan, The United Graduate School of Veterinary Sciences, Gifu University, 1-1 Yanagido, Gifu, Gifu, 501-1193, Japan
Methods: gel filtration, 13C NMR, 1H NMR, NMR-2D, GC-MS, de-O-acylation, sugar analysis, methanolysis, SEC-MALS, periodate oxidation, bioinformatic analysis
- 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: 35750381Publication DOI: 10.1016/S1875-5364(22)60177-8Journal NLM ID: 101504416Publisher: 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
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13. Compound ID: 2069
|
D-Ala2Ac-(1-3)-+
|
-4)-a-L-GalpNAcA-(1-3)-b-D-QuipNAc4NAc-(1-2)-b-D-Quip3N-(1-4)-a-D-GalpNAcA-(1-4)-a-D-Galp2(60%)Ac6(60%)Ac-(1- |
Show graphically |
Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_136906,IEDB_137472,IEDB_141794,IEDB_142345,IEDB_151528,IEDB_190606,SB_36,SB_7
The structure is contained in the following publication(s):
- Article ID: 675
Hanniffy O, Shashkov AS, Senchenkova SN, Tomshich SV, Komandrova NA, Romanenko LA, Knirel YA, Savage AV "Structure of an acidic O-specific polysaccharide of Pseudoalteromonas haloplanktis type strain ATCC14393 containing 2-acetamido-2-deoxy-D- and -L-galacturonic acids and 3-(N-acetyl-D-alanyl)amino-3,6-dideoxy-D-glucose" -
Carbohydrate Research 321(1-2) (1999) 132-138
An acidic O-specific polysaccharide was obtained from the lipopolysaccharide of Pseudoalteromonas haloplanktis ATCC14393 and found to contain D-galactose, 3-(N-acetyl-D-alanyl)amino-3,6-dideoxy-D-glucose (DQui3NxDAlaAc), 2,4-diacetamido-2,4,6-trideoxy-D-glucose (D-QuiNAc4NAc), 2-acetamido-2-deoxy-D- and -L-galacturonic acids (D- and L-GalNAcA), and O-acetyl groups. On the basis of Smith degradation and 1H and 13C NMR spectroscopic studies, including 2D COSY, TOCSY, NOESY, 1H, 13C HMQC, and HMBC experiments, the following structure of the pentasaccharide repeating unit of the polysaccharide was established: -4)-a-L-GalpNAcA-(1-3)-b-D-QuipNAc4NAc-(1-2)-b-D-Quip3NxDAlaAc-(1-4)-a-D-GalpNAcA-(1-4)-a-D-Galp2,6Ac2-(1- where O-acetylation of the galactose residue at each position is partial (50-70%).
NMR spectroscopy, O-Specific polysaccharide structure, 2, 4, Pseudoalteromonas haloplanktis, L-iduronic acid, 4-diamino-2, 6-trideoxy-D-glucose, (S)-3-hydroxybutyric acid
Publication DOI: 10.1016/S0008-6215(97)10108-2Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: angela.savage@nuigalway.ie
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Department of Chemistry, National University of Ireland, Galway, Ireland, Pacific Institute of Bioorganic Chemistry, Far East Branch of the Russian Academy of Sciences, Vladivostok 690022, Russian Federation
Methods: NMR-2D, NMR, Smith degradation
- Article ID: 4434
Nazarenko EL, Komandrova NA, Gorshkova RP, Tomshich SV, Zubkov VA, Kilcoyne M, Savage AV "Structures of polysaccharides and oligosaccharides of some Gram-negative marine Proteobacteria" -
Carbohydrate Research 338(23) (2003) 2449-2457
The chemical structures of polysaccharides and LPS core oligosaccharides, isolated from various Gram-negative marine bacteria from the genera Pseudoalteromonas and Shewanella belonging to the Alteromonadaceae family and gamma-subclass of Proteobacteria, are reviewed. The polysaccharides are distinguished by the acidic character (e.g., due to the presence of hexuronic and aldulosonic acids and their derivatives) and the occurrence of unusual sugars, including N-acyl derivatives of 6-deoxyamino sugars, such as N-acetyl-D-quinovosamine, N-acetyl-L-fucosamine and N-acetyl-6-deoxy-L-talosamine, and higher sugars like 2,6-dideoxy-2-acetamido-4-C-(3'-carboxamide-2',2'-dihydroxypropyl)-D-galac topyranose (shewanellose). Many constituent sugars have various uncommon non-sugar substituents, such as alanine, formic, lactic and hydroxybutyric acids, sulfate, phosphate, and 2-aminopropane-1,3-diol.
Lipopolysaccharide, oligosaccharide structure, O-antigen, polysaccharide structure, Shewanella, Pseudoalteromonas, Proteobacteria
NCBI PubMed ID: 14670708Publication DOI: 10.1016/j.carres.2003.06.004Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: A.V. Savage
Institutions: Department of Chemistry, National University of Ireland, Galway, Ireland, Pacific Institute of Bioorganic Chemistry, Far East Branch of the Russian Academy of Sciences, Vladivostok 690022, Russian Federation
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14. Compound ID: 2077
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D-Ala-(2-6)-+
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-4)-a-D-GalpNAcA-(1-4)-a-D-GalpNAcA-(1-3)-b-D-QuipNAc4NAc-(1- |
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Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen, CPS
Contained glycoepitopes: IEDB_142345
The structure is contained in the following publication(s):
- Article ID: 684
Haseley SR, Holst O, Brade H "Structural and serological characterisation of the O-antigenic polysaccharide of the lipopolysaccharide from Acinetobacter haemolyticus strain ATCC17906" -
European Journal of Biochemistry 244 (1997) 761-766
A polysaccharide containing 2-acetamido-2-deoxy-D-galacturonic acid (GalNAcA), 2.4-diacetamido-2,4,6-trideoxy-D-glucose (QuiNAc4NAc), and D-alanine (Ala) was isolated from the water-soluble lipopolysaccharide (LPS) originating from the reference strain for Acinetobacter haemolyticus (DNA group 4) strain ATCC17906. The polysaccharide, characterised by means of monosaccharide analyses and NMR studies, was shown to be based on a linear trisaccharide repeating unit, as shown below, with the alanine group amide-bound to position 6 of one GalNAcA residue. It was specifically recognised in western blots by polyclonal rabbit antisera. [structure: see text]
Lipopolysaccharide, LPS, strain, polysaccharide, O-antigenic, O-antigenic polysaccharide, Acinetobacter, Acinetobacter haemolyticus, Alanine, structura
NCBI PubMed ID: 9108245Journal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Institutions: Division of Biochemical Microbiology, Research Centre Borstel, Germany.
Methods: NMR-2D, NMR, Western blotting, methanolysis
- Article ID: 4328
Knirel YA "Structure of O-antigens" -
Book: Bacterial lipopolysaccharides: Structure, chemical synthesis, biogenesis and interaction with host cells (2011) Chapter 3, 41-115
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_3Publisher: Springer
Correspondence: knirel@ioc.ac.ru
Editors: Knirel YA, Valvano MA
Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
- Article ID: 5157
Goyette-Desjardins G, Vinogradov E, Okura M, Takamatsu D, Gottschalk M, Segura M "Streptococcus suis serotype 3 and serotype 18 capsular polysaccharides contain di-N-acetyl-bacillosamine" -
Carbohydrate Research 466 (2018) 18-29
Streptococcus suis serotype 3 is counted among the S. suis serotypes causing clinical disease in pigs. Yet, limited information is available on this serotype. Here we determined for the first time the chemical composition and structure of serotype 3 capsular polysaccharide (CPS), a major bacterial virulence factor and the antigen at the origin of S. suis classification into serotypes. Chemical and spectroscopic data gave the repeating unit sequence for serotype 3: [4)D-GlcA (β1-3)d-QuiNAc4NAc(β1-]n. To the best of our knowledge, this is the first report of di-N-acetyl-d-bacillosamine (QuiNAc4NAc) containing polysaccharides in Streptococci and the second time this rare diamino sugar has been observed in a Gram-positive bacterial species since its initial report. This led to the identification of homologues of UDP-QuiNAc4NAc synthesis genes in S. suis serotype 18. Thus, the repeating unit sequence for serotype 18 is: [3)d-GalNAc(α1-3)[d-Glc (β1-2)]d-GalA4OAc(β1-3)d-GalNAc(α1-3)d-QuiNAc4NAc(α1-]n. A correlation between S. suis serotypes 3 and 18 CPS sequences and genes of these serotypes' cps loci encoding putative glycosyltransferases and polymerase responsible for the biosynthesis of the repeating unit was tentatively established. Knowledge of CPS structure and composition will contribute to better dissect the role of this bacterial component in the pathogenesis of S. suis serotypes 3 and 18.
polysaccharide, capsular polysaccharide, polysaccharides, carbohydrate structure, Streptococcus suis, Di-N-Acetyl-bacillosamine, Serotype 18, Serotype 3
NCBI PubMed ID: 30014879Publication DOI: 10.1016/j.carres.2018.07.003Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: mariela.segura@umontreal.ca
Institutions: Swine and Poultry Infectious Diseases Research Center, Faculty of Veterinary Medicine, University of Montreal, 3200 Sicotte St., St-Hyacinthe, Quebec, J2S 2M2, Canada, Canadian Glycomics Network (GlycoNet), University of Alberta, 11227 Saskatchewan Dr., Edmonton, Alberta, T6G 2G2, Canada, National Research Council, 100 Sussex Dr., Ottawa, Ontario, K1A 0R6, Canada, Division of Bacterial and Parasitic Disease, National Institute of Animal Health, National Agriculture and Food Research Organization, 3-1-5 Kannondai, Tsukuba, Ibaraki, 305-0856, Japan, The United Graduate School of Veterinary Sciences, Gifu University, 1-1 Yanagido, Gifu, Gifu, 501-1193, Japan
Methods: gel filtration, 13C NMR, 1H NMR, NMR-2D, GC-MS, de-O-acylation, sugar analysis, methanolysis, SEC-MALS, periodate oxidation, bioinformatic analysis
- Article ID: 5789
Kenyon JJ, Senchenkova SN, Shashkov AS, Shneider MM, Popova AV, Knirel YA, Hall RM "K17 capsular polysaccharide produced by Acinetobacter baumannii isolate G7 contains an amide of 2-acetamido-2-deoxy-D-galacturonic acid with D-alanine" -
International Journal of Biological Macromolecules 144 (2020) 857-862
The K17 capsular polysaccharide (CPS) produced by Acinetobacter baumannii G7, which carries the KL17 configuration at the capsule biosynthesis locus, was isolated and studied by chemical methods along with one- and two-dimensional 1H and 13C NMR spectroscopy. Selective cleavage of the glycosidic linkage of a 2,4-diacetamido-2,4,6-trideoxy-D-glucose (D-QuiNAc4NAc) residue by (i) trifluoroacetic acid solvolysis or (ii) alkaline β-elimination (NaOH-NaBH4) of the 4-linked D-alanine amide of a 2-acetamido-2-deoxy-D-galacturonic acid residue (d-GalNAcA6DAla) yielded trisaccharides that were isolated by Fractogel TSK HW-40 gel-permeation chromatography and identified by using NMR spectroscopy and high-resolution electrospray ionization mass spectrometry. The following structure was established for the trisaccharide repeat (K unit) of the CPS: →4)-α-D-GalpNAcA6DAla-(1→4)-α-D-GalpNAcA-(1→3)-β-D-QuipNAc4NAc-(1→. The presence of the itrA1 gene coding for the initial glycosylphosphotransferase in the KL17 gene cluster established the first sugar of the K unit as D-QuipNAc4NAc. KL17 includes genes for three transferases that had been annotated previously as glycosyltransferases (Gtrs). As only two Gtrs are required for the K17 structure and one D-GalpNAcA residue is modified by a D-alanine amide, these assignments were re-assessed. One transferase was found to belong to the ATPgrasp_TupA protein family that includes D-alanine-D-alanine ligases, and thus was renamed Alt1 (alanine transferase). Alt1 represents a novel family that amidate the carboxyl group of D-GalpNAcA or D-GalpA.
capsular polysaccharide, Acinetobacter baumannii, D-alanine, K locus, KL17
NCBI PubMed ID: 31715229Publication DOI: 10.1016/j.ijbiomac.2019.09.163Journal NLM ID: 7909578Publisher: Butterworth-Heinemann
Correspondence: johanna.kenyon@qut.edu.au
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, M. M. Shemyakin & Y. A. Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, Moscow, Russia, State Research Center for Applied Microbiology and Biotechnology, Obolensk, Moscow Region, Russia, Moscow Institute of Physics and Technology, Dolgoprudny, Moscow Region, Russia, Institute of Health and Biomedical Innovation, School of Biomedical Sciences, Faculty of Health, Queensland University of Technology, Brisbane, Australia, School of Life and Environmental Sciences, The University of Sydney, Sydney, Australia, Institute of Antimicrobial Chemotherapy, Smolensk State Medical University, Smolensk, Russia
Methods: 13C NMR, NMR-2D, GLC, chemical methods, NMR-1D, GPC, bioinformatic analysis, solvolysis with anhydrous CF3CO2H, HR-ESI-MS1H NMR
- Article ID: 5791
Knirel YA, Van Calsteren M "Bacterial exopolysaccharides" -
Book: Comprehensive Glycoscience: From Chemistry to Systems Biology. Reference Module in Chemistry, Molecular Sciences and Chemical Engineering (2021) 1-75
Bacterial extracellular polysaccharides are known as a cell-bound capsule, a sheath, or a slime, which is excreted into the environment. They play an important role in virulence of medical bacteria and plant-to-symbiont interaction and are used for serotyping of bacteria and production of vaccines. Some exopolysaccharides have commercial applications in industry, and claims of health benefits have been documented for an increasing number of them. Exopolysaccharides have diverse composition and structure, and some contain sugar and non-sugar components that are found in bacterial carbohydrates only. The present article provides an updated collection of the data on exopolysaccharides of various classes of gram-negative and gram-positive bacteria reported until the end of 2019. When known, biosynthesis pathways of exopolysaccharides are treated in a summary manner. References are made to structure and biosynthesis relatedness between exopolysaccharides of different bacterial taxa as well as between bacterial polysaccharides and mammalian glycosaminoglycans.
polysaccharide structure, Gram-negative bacteria, capsule, Biofilm, polysaccharide biosynthesis, gram-positive bacteria, Monosaccharide composition, Bacterial exopolysaccharide, non-sugar component
Publication DOI: 10.1016/B978-0-12-819475-1.00005-5Publisher: Elsevier
Correspondence: marie-rose.vancalsteren@canada.ca; yknirel@gmail.com
Editors: Barchi J, Kamerling H
Institutions: N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Saint-Hyacinthe Research and Development Centre, Agriculture and Agri-Food Canada, Saint-Hyacinthe, QC, Canada
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15. Compound ID: 2149
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D-Ala2Ac-(1-3)-+
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a-L-GalpNAcA-(1-3)-b-D-QuipNAc4NAc-(1-2)-b-D-Quip3N-(1-4)-a-D-GalpNAcA-(1-2)-D-Thre-ol |
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Structure type: oligomer
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_114709,IEDB_142345
The structure is contained in the following publication(s):
- Article ID: 675
Hanniffy O, Shashkov AS, Senchenkova SN, Tomshich SV, Komandrova NA, Romanenko LA, Knirel YA, Savage AV "Structure of an acidic O-specific polysaccharide of Pseudoalteromonas haloplanktis type strain ATCC14393 containing 2-acetamido-2-deoxy-D- and -L-galacturonic acids and 3-(N-acetyl-D-alanyl)amino-3,6-dideoxy-D-glucose" -
Carbohydrate Research 321(1-2) (1999) 132-138
An acidic O-specific polysaccharide was obtained from the lipopolysaccharide of Pseudoalteromonas haloplanktis ATCC14393 and found to contain D-galactose, 3-(N-acetyl-D-alanyl)amino-3,6-dideoxy-D-glucose (DQui3NxDAlaAc), 2,4-diacetamido-2,4,6-trideoxy-D-glucose (D-QuiNAc4NAc), 2-acetamido-2-deoxy-D- and -L-galacturonic acids (D- and L-GalNAcA), and O-acetyl groups. On the basis of Smith degradation and 1H and 13C NMR spectroscopic studies, including 2D COSY, TOCSY, NOESY, 1H, 13C HMQC, and HMBC experiments, the following structure of the pentasaccharide repeating unit of the polysaccharide was established: -4)-a-L-GalpNAcA-(1-3)-b-D-QuipNAc4NAc-(1-2)-b-D-Quip3NxDAlaAc-(1-4)-a-D-GalpNAcA-(1-4)-a-D-Galp2,6Ac2-(1- where O-acetylation of the galactose residue at each position is partial (50-70%).
NMR spectroscopy, O-Specific polysaccharide structure, 2, 4, Pseudoalteromonas haloplanktis, L-iduronic acid, 4-diamino-2, 6-trideoxy-D-glucose, (S)-3-hydroxybutyric acid
Publication DOI: 10.1016/S0008-6215(97)10108-2Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: angela.savage@nuigalway.ie
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Department of Chemistry, National University of Ireland, Galway, Ireland, Pacific Institute of Bioorganic Chemistry, Far East Branch of the Russian Academy of Sciences, Vladivostok 690022, Russian Federation
Methods: NMR-2D, NMR, Smith degradation
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