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1. Compound ID: 264
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a-D-GlcpNAc-(1-2)-+ a-D-Galp-(1-6)-+
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a-L-Rhap-(1-3)-a-L-Rhap-(1-2)-a-D-Galp-(1-3)-a-D-GlcpNAc-(1-4)-a-D-Glcp-(1-2)-a-D-Galp-(1-3)-D-Glc |
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Structure type: oligomer
Contained glycoepitopes: IEDB_125611,IEDB_130669,IEDB_130693,IEDB_136105,IEDB_136906,IEDB_137340,IEDB_137472,IEDB_140529,IEDB_141794,IEDB_141807,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_151528,IEDB_151531,IEDB_167069,IEDB_190606,IEDB_225177,IEDB_885823,IEDB_983931,SB_192,SB_7
The structure is contained in the following publication(s):
- Article ID: 69
Falt IC, Mills D, Schweda EKH, Timmis KN, Lindberg AA "Construction of recombinant aroA salmonellae stably producing the Shigella dysenteriae serotype 1 O-antigen and structural characterization of the Salmonella/Shigella hybrid LPS" -
Microbial Pathogenesis 20(1) (1996) 11-30
The TN501 mercury resistant transposon containing the rfp and rfb loci encoding biosynthesis of the O-antigen of Shigella dysenteriae serotype 1 lipopolysaccharide (LPS) was constructed and introduced into aroA mutants of Salmonella typhimurium and Salmonella dublin. In five recombinant strains, both homologous LPS and hybrid LPS, consisting of Salmonella lipid A-core and Shigella O-antigen, were produced. All derivatives but one (SL3235) stably inherited the new trait. Immunofluorescence microscopy, using mixtures of differentially-labelled antibodies specific for either the Salmonella or the Shigella O-antigen, demonstrated that individual bacteria produced both types of LPS. Qualitative and quantitative analysis of polysaccharides obtained by mild hydrolysis of purified LPS was carried out by methylation analysis and NMR spectroscopy, and revealed that the ratio of Salmonella to Shigella O-antigen repeating units in the high molecular weight fraction of isolated polysaccharides varied from 1.3: 1 to 8.4:1 as based on the relative proportions of 1,4,5-tri-O-acetyl-2,3-di-O-methyl-L-rhamnitol (Salmonella repeating unit) and 1,3,5-tri-O-acetyl-2,4-di-O-methyl-L-rhamnitol (Shigella repeating unit). The attachment site of the Shigella O-antigen to the Salmonella core was investigated by construction of a mutant rfp-rfb gene cluster encoding the synthesis of only one repeat unit of the Shigella dysenteriae type 1 O-antigen, and its introduction into a rough Salmonella strain. This hybrid organism produced a polysaccharide with the following structure, [formula: see text] demonstrating that the Shigella dysenteriae type 1 O-antigen is linked at position O-4 of the subterminal D-glucose unit in the Salmonella core
LPS, Salmonella, Shigella dysenteriae type 1, hybrids, vaccine.
NCBI PubMed ID: 8692007Journal NLM ID: 8606191Publisher: Academic Press
Institutions: Department of Immunology, Microbiology, Pathology and Infectious Diseases, Karolinska Institute, Huddinge Hospital, Sweden, Department of Medical Biochemistry, University of Geneva, Switzerland, Division of Microbiology, National Research Centre for Biotechnology, Braunschweig, Germany, Clinical Research Centre, Karolinska Institute, Novum, Huddinge Hospital, Sweden
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2. Compound ID: 328
Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen, LPS, cell wall polysaccharide
Contained glycoepitopes: IEDB_130648,IEDB_136906,IEDB_137472,IEDB_137473,IEDB_140529,IEDB_141794,IEDB_142488,IEDB_146664,IEDB_151528,IEDB_167069,IEDB_190606,IEDB_983931,SB_192,SB_7
The structure is contained in the following publication(s):
- Article ID: 91
Galbraith L, Sharples JL, Wilkinson SG "Structure of the O-specific polysaccharide for Acinetobacter baumannii serogroup O1" -
Carbohydrate Research 319(1-4) (1999) 204-208
A polymeric fraction containing D-galactose, N-acetyl-D-galactosamine, and N-acetyl-D-glucosamine was isolated from the lipopolysaccharide produced by the reference strain for Acinetobacter baumannii serogroup O1. By means of NMR spectroscopy, methylation analysis, and chemical degradation, the repeating unit of the polymer was identified as a branched trisaccharide of the following structure. [formula: see text]
structure, polysaccharide, Acinetobacter, Acinetobacter baumannii, O-specific, O-specific polysaccharide, serogroup
NCBI PubMed ID: 10520267Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: S.G.Wilkison@chem.hull.ac.uk
Institutions: Department of Chemistry, University of Hull, UK
Methods: methylation, NMR-2D, NMR, sugar analysis
- Article ID: 2303
Haseley SR, Galbraith L, Wilkinson SG "Structure of a surface polysaccharide from Acinetobacter baumannii strain 214" -
Carbohydrate Research 258 (1994) 199-206
Journal NLM ID: 0043535Publisher: Elsevier
- Article ID: 4329
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: 4534
Hu D, Liu B, Dijkshoorn L, Wang L, Reeves PR "Diversity in the major polysaccharide antigen of Acinetobacter baumannii assessed by DNA sequencing, and development of a molecular serotyping scheme" -
PLoS One 8(7) (2013) e70329
We have sequenced the gene clusters for type strains of the Acinetobacter baumannii serotyping scheme developed in the 1990s, and used the sequences to better understand diversity in surface polysaccharides of the genus. We obtained genome sequences for 27 available serovar type strains, and identified 25 polysaccharide gene cluster sequences. There are structures for 12 of these polysaccharides, and in general the genes present are appropriate to the structure where known. This greatly facilitates interpretation. We also find 53 different glycosyltransferase genes, and for 7 strains can provisionally allocate specific genes to all linkages. We identified primers that will distinguish the 25 sequence forms by PCR or microarray, or alternatively the genes can be used to determine serotype by 'molecular serology'. We applied the latter to 190 Acinetobacter genome-derived gene-clusters, and found 76 that have one of the 25 gene-cluster forms. We also found novel gene clusters and added 52 new gene-cluster sequence forms with different wzy genes and different gene contents. Altogether, the strains that have one of the original 25 sequence forms include 98 A. baumannii (24 from our strains) and 5 A. nosocomialis (3 from our strains), whereas 32 genomes from 12 species other than A. baumannii or A. nosocomialis, all have new sequence forms. One of the 25 serovar type sequences is found to be in European clone I (EC I), 2 are in EC II but none in EC III. The public genome strains add an additional 52 new sequence forms, and also bring the number found in EC I to 5, in EC II to 9 and in EC III to 2.
antigen, structure, Acinetobacter baumannii, gene cluster, glycosyltransferase, serotyping, genome, surface polysaccharide, polysaccharide antigen
NCBI PubMed ID: 23922982Publication DOI: 10.1371/journal.pone.0070329Journal NLM ID: 101285081Publisher: San Francisco, CA: Public Library of Science
Correspondence: Peter R. Reeves
Institutions: TEDA School of Biological Sciences and Biotechnology, Nankai University, Tianjin, China, Department of Infectious Diseases, Leiden University Medical Center, Leiden, The Netherlands, School of Molecular Bioscience, University of Sydney, Sydney, Australia
Methods: PCR, DNA sequencing, DNA techniques, genetic methods
- Article ID: 4819
Giguere D "Surface polysaccharides from Acinetobacter baumannii: Structures and syntheses" -
Carbohydrate Research 418 (2015) 29-43
The emergence of multidrug-resistance Acinetobacter baumannii requires novel approaches for prevention, treatment and diagnosis. The structures of surface polysaccharides from A. baumannii are valuable tools to understand pathogenesis, virulence and immunogenicity. The synthesis of bacterial mono- or polysaccharides may result in novel probes to become important therapeutic options in the fight against A. baumannii. This report exemplifies the relevance of glycochemistry for the development of new antibiotics.
lipopolysaccharides, capsular polysaccharides, Acinetobacter, Acinetobacter baumannii, polysaccharide synthesis, surface polysaccharides
NCBI PubMed ID: 26531136Publication DOI: 10.1016/j.carres.2015.10.001Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: denis.giguere@chm.ulaval.ca
Institutions: Département de Chimie, Université Laval, Québec City, Québec, Canada G1V 0A6
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3. Compound ID: 550
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R-CetEtN-(1--P--6)--+
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-3)-a-D-Galp-(1-6)-b-D-Glcp-(1-3)-b-D-Galp-(1-3)-b-D-GlcpNAc-(1- |
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Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_135813,IEDB_136044,IEDB_136906,IEDB_137340,IEDB_137472,IEDB_1391962,IEDB_140529,IEDB_141794,IEDB_141807,IEDB_142078,IEDB_142488,IEDB_143794,IEDB_146664,IEDB_150899,IEDB_151528,IEDB_151531,IEDB_167069,IEDB_190606,IEDB_983931,SB_137,SB_156,SB_165,SB_166,SB_173,SB_187,SB_192,SB_195,SB_29,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 114
Toukach FV, Shashkov AS "Computer-assisted structural analysis of regular glycopolymers on the basis of 13C NMR data" -
Carbohydrate Research 335(2) (2001) 101-104
A computer-assisted approach to the prediction of the primary structures of regular glycopolymers is described. The analysis is based on comparing the calculated 13C NMR spectra of all the possible structures of the repeating unit (for the given monomeric composition) to an experimental 13C NMR spectrum. The spectra generation is based on the spectral database containing information on the 13C chemical shifts of monomers, di- and trimeric fragments. If the required data are missing from this database, the special database for average glycosylation effects is used. The analysis reveals those structures with the calculated 13C NMR spectrum most close to observed. The structures of repeating units of any topology containing up to six residues linked by glycosidic, amidic or phospho-diester bridges can be predicted. Unambiguous selection of the proper structure from the output list of possible structures may require additional experimental data. Testing the created program and databases on bacterial polysaccharides and their derivatives containing up to three non-sugar residues (alditols, amino acids, phosphate groups etc.) per repeating unit revealed the good convergence of prediction with independently obtained structural data.
NMR, structural, analysis, structural analysis, 13C NMR, calculation, computer, glycopolymer, regular
NCBI PubMed ID: 11567641Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: tou@cacr.ioc.ac.ru
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospect 47, 117913 Moscow, Russian Federation.
Methods: NMR simulation
- Article ID: 494
Torzewska A, Kocharova NA, Maszewska A, Knirel YA, Rozalski A "Serological characterization of the O-specific polysaccharide of Providencia alcalifaciens O23" -
Archivum Immunologiae et Therapiae Experimentalis 52(1) (2004) 43-49
INTRODUCTION: The genus Providencia belongs to the Enterobacteriaceae family and currently consists of five species: P. alcalifaciens, P. heimbachae, P. rettgerii, P. rustigianii and P. stuartii. The serological classification scheme of P. alcalifaciens, P. rustigianii and P. stuartii includes 63 O-serogroups and 30 H-serogroups. The O-antigenic specificity is defined by the structure of the O-antigen (O-specific polysaccharide--OPS), a part of the lipopolysaccharide (LPS, endotoxin), one of the major components of the outer membrane of gram-negative bacteria and an important virulence factor of these bacteria. Among the bacteria of the Enterobacteriaceae family, the genus Providencia is one of the least studied in respect to its LPS structure and antigenic specificity. Studies of the chemical structures and the serological specificity of the O-antigens aim at the elucidation of the molecular basis of the serological classification of Providencia sp. MATERIALS AND METHODS: LPS and alkali-treated LPS of P. alcalifaciens O23 and serologically related P. rustigianii O14, P. mirabilis O13 and P. myxofaciens as well as O-antiserum against P. alcalifaciens O23 were used. Serological characterization of P. alcalifaciens O23 O-specific polysaccharide was done by use enzyme immunosorbent assay (EIA), passive hemolysis test (PHT) as well as by inhibition and sodium deoxycholate polyacrylamide gel electrophoresis (DOC-PAGE) of LPS and Western blot. RESULTS AND CONCLUSIONS: The OPS of P. alcalifaciens, O23, contains an N-(D-glucuronoyl)-N-[(R)-1-carboxyethyl]-L-lysine residue (GlcAAlaLys). The LPS of P. alcalifaciens, O23, and other LPSs containing AlaLys from Providencia and Proteus strains were tested with rabbit anti-P. alcalifiaciens O23 serum. The serological data showed that a GlcAAlaLys-associated epitope plays a role as an antigenic determinant in the P. alcalifaciens O23 OPS and revealed the particular importance of glucuronic acid and the carboxyethyl group for the binding of O23-specific antibodies.
Lipopolysaccharide, structure, characterization, polysaccharide, O-antigen, O-specific, O-specific polysaccharide, Providencia, Providencia alcalifaciens, serological, O-serogroups, Ne-[(R)-1-carboxyethyl]-L-lysine
NCBI PubMed ID: 15053232Journal NLM ID: 0114365Publisher: Basel, Boston: Birkhaüser
Correspondence: rozala@biol.uni.lodz.pl
Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Institute of Microbiology and Immunology, University of Lodz, Lodz, Poland
- Article ID: 1467
Knirel YA, Kaca W, Rozalski A, Sidorczyk Z "Structure of the O-antigenic polysaccharides of Proteus bacteria" -
Polish Journal of Chemistry 73 (1999) 895-907
Data on the composition and structure of the O-specific polysaccharides (O-antigens) of the lipopolysaccharides of the genus Proteus are summarized and discussed as the molecular basis for serotyping of these medically important bacteria.
structure, O-antigen, Proteus, Bacterial polysaccharide, epitope specificity
Journal NLM ID: 7901356WWW link: http://www.ichf.edu.pl/pjch/pj-1999/pj0699.htm#0895Publisher: Państwowe Wydawnictwo Naukowe
Correspondence: knirel@ioc.ac.ru
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences,Leninsky Prospekt 47, Moscow, Russia, Institute of Microbiology and Immunology, University of Łódź, Banacha 12/16, 90-237 Łódź, Poland, Center of Microbiology and Virology, Polish Academy of Sciences, Lodowa 106, 93-232 Łódź, Poland
- Article ID: 1873
Vinogradov EV, Kaca W, Shashkov AS, Pietrasik D, Rozalski A, Knirel YA, Kochetkov NK "Structure of Proteus mirabilis O3 O-specific polysaccharide containing N-(2-hydroxyethyl)-D-alanine" -
Bioorganicheskaya Khimia = Bioorganic Chemistry [Russian] 15 (1989) 1431-1434
O-Specific polysaccharide, obtained by mild acid degradation of the Proteus mirabilis 03 lipopolysaccharide, was dephosphorylated with 48% HF to give a linear polysaccharide and an amino acid, N-(2-hydroxyethyl)-D-alanine. The structure of the polysaccharide was determined by methylation, the Smith degradation and computer-assisted analysis of the 13C NMR spectra of original and dephosphorylated polymers and oligomers. The structure of the amino acid was elucidated by using 1H and 13C NMR spectroscopy and mass spectrometry (applied to the acetylated methyl ester derivative), optical rotation and CD spectrum data and comparison with the synthetic sample. The repeating unit of P. mirabilis 03 O-specific polysaccharide is shown to have the following structure: (formula: see text)
NCBI PubMed ID: 2483615Journal NLM ID: 7804941Publisher: Moskva: Nauka
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Academy of Sciences of the USSR, Moscow, Russia
Methods: 13C NMR, 1H NMR, methylation, Smith degradation, HF treatment
- Article ID: 2423
Vinogradov EV, Kaca W, Shashkov AS, Krajewska-Pietrasik D, Rozalski A, Knirel YA, Kochetkov NK "The structure of Proteus mirabilis O3 O-specific polysaccharide containing N-(2-hydroxyethyl)-D-alanine" -
European Journal of Biochemistry 188 (1990) 645-651
O-Specific polysaccharide was obtained by mild acid degradation of Proteus mirabilis O3 lipopolysaccharide. The polysaccharide was dephosphorylated with 48% HF to give a linear polysaccharide and an amino acid, N-(2-hydroxyethyl)-D-alanine. The structure of the polysaccharide was determined by methylation, Smith degradation and computer-assisted analysis of the 13C-NMR spectra of original and dephosphorylated polymers and oligomers. The structure of the amino acid was investigated by using 1H and 13C-NMR spectroscopy and mass spectrometry (applied to the acetylated methyl ester derivative). Its absolute configuration was established by comparison of the optical rotation value and CD spectrum of the natural and synthetic product. On the basis of the data obtained, it was concluded that the repeating unit of P. mirabilis O3 O-specific polysaccharide has the following structure: (formula; see text) Removal of the amino acid phosphate substituent significantly decreased serological activity of the O-specific polysaccharide, thus showing the immunodominant role of this group. Serological cross-reactions between P. mirabilis O3 and O27 were demonstrated and tentatively substantiated.
NCBI PubMed ID: 2185017Journal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Academy of Sciences of the USSR, Moscow, Russia
Methods: 13C NMR
- Article ID: 2684
Knirel YA, Vinogradov EV, Shashkov AS, Sidorczyk Z, Rozalski A, Radziejewska-Lebrecht I, Kaca W "Structural study of O-specific polysaccharides of Proteus" -
Journal of Carbohydrate Chemistry 12 (1993) 379-414
Proteus bacteria are important human opportunistic pathogens which frequently cause urinary tract infections. According to Bergey's Manual of Systematic Bacteriology,1 this genus includes three species: P. mirabilis, P. vulgaris, and P. myxofaciens. A novel species of P. penneri has been recently proposed2,3 for strains formerly called P. vulgaris biogroup I. Proteus is an antigenically heterogeneous group of bacteria, and this is mainly associated with diverse composition and structures of O-specific polysaccharide chains of outer-membrane lipopolysaccharides (O-antigens). The Kauffman-Perch serological classification4 of P. mirabilis and P. vulgaris includes 49 O-serogroups. However, a number of S-strains remain unclassified,5 including strains of P. penneri.
Publication DOI: 10.1080/07328309308019396Journal NLM ID: 8218151Publisher: Marcel Dekker
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky pr. 47, Moscow, B-334, Russia
Methods: 13C NMR, NMR
- Article ID: 3724
Kwinkowski M, Grabowski S, Konieczna I, Nazarenko EL, Kaca W "The cross-reactivity of Shewanella fidelis lipopolysaccharide with anti-Proteus antibodies" -
Polish Journal of Microbiology 58(3) (2009) 275-278
The serological cross-reactivity between lipopolysaccharides (LPS) of S. fidelis KMM3582(T) and rabbit anti-O P. mirabilis antibodies was tested. Using ELISA and Western blot cross-reactivity between S. fidelis LPS and antisera against P. mirabilis O14, O3 LPSs was found. The observed cross-reaction may suggest that anti-P. mirabilis S1959 (O3) antibodies may bind to the internal part of S. fidelis O-polysaccharides. A weak interaction between S. fidelis LPS and antiserum against P. mirabilis O13 in Western blot suggests that the absolute configuration of non-sugar 'AlaLys' component (N(ε)-[(S)-l-carboxyethyl]-N(α)-(D-galacturonoyl)-L-lysine) may influence the affinity of antibodies for S. fidelis LPS.
lipopolysaccharides, Proteus mirabilis, cross-reactivity, Shewanella fidelis
NCBI PubMed ID: 19899622Journal NLM ID: 101229003Publisher: Polskie Towarzystwo Mikrobiologow
Correspondence: marek.kwinkowski@ujk.edu.pl
Institutions: Department of Microbiology, Institute of Biology, Jan Kochanowski University, Kielce, Poland
Methods: ELISA, serological methods
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4. Compound ID: 552
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b-D-GalpNAc-(1-3)-+
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-6)-b-D-Glcp-(1-3)-b-D-GalpNAc-(1-4)-a-D-Galp-(1- |
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Structure type: polymer chemical repeating unit
Trivial name: O-deacetylated and dephosphorylated polysaccharide (DPS)
Compound class: O-polysaccharide
Contained glycoepitopes: IEDB_130648,IEDB_136906,IEDB_137472,IEDB_137473,IEDB_140529,IEDB_141794,IEDB_142488,IEDB_146664,IEDB_151528,IEDB_167069,IEDB_190606,IEDB_983931,SB_192,SB_21,SB_25,SB_7
The structure is contained in the following publication(s):
- Article ID: 114
Toukach FV, Shashkov AS "Computer-assisted structural analysis of regular glycopolymers on the basis of 13C NMR data" -
Carbohydrate Research 335(2) (2001) 101-104
A computer-assisted approach to the prediction of the primary structures of regular glycopolymers is described. The analysis is based on comparing the calculated 13C NMR spectra of all the possible structures of the repeating unit (for the given monomeric composition) to an experimental 13C NMR spectrum. The spectra generation is based on the spectral database containing information on the 13C chemical shifts of monomers, di- and trimeric fragments. If the required data are missing from this database, the special database for average glycosylation effects is used. The analysis reveals those structures with the calculated 13C NMR spectrum most close to observed. The structures of repeating units of any topology containing up to six residues linked by glycosidic, amidic or phospho-diester bridges can be predicted. Unambiguous selection of the proper structure from the output list of possible structures may require additional experimental data. Testing the created program and databases on bacterial polysaccharides and their derivatives containing up to three non-sugar residues (alditols, amino acids, phosphate groups etc.) per repeating unit revealed the good convergence of prediction with independently obtained structural data.
NMR, structural, analysis, structural analysis, 13C NMR, calculation, computer, glycopolymer, regular
NCBI PubMed ID: 11567641Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: tou@cacr.ioc.ac.ru
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospect 47, 117913 Moscow, Russian Federation.
Methods: NMR simulation
- Article ID: 494
Torzewska A, Kocharova NA, Maszewska A, Knirel YA, Rozalski A "Serological characterization of the O-specific polysaccharide of Providencia alcalifaciens O23" -
Archivum Immunologiae et Therapiae Experimentalis 52(1) (2004) 43-49
INTRODUCTION: The genus Providencia belongs to the Enterobacteriaceae family and currently consists of five species: P. alcalifaciens, P. heimbachae, P. rettgerii, P. rustigianii and P. stuartii. The serological classification scheme of P. alcalifaciens, P. rustigianii and P. stuartii includes 63 O-serogroups and 30 H-serogroups. The O-antigenic specificity is defined by the structure of the O-antigen (O-specific polysaccharide--OPS), a part of the lipopolysaccharide (LPS, endotoxin), one of the major components of the outer membrane of gram-negative bacteria and an important virulence factor of these bacteria. Among the bacteria of the Enterobacteriaceae family, the genus Providencia is one of the least studied in respect to its LPS structure and antigenic specificity. Studies of the chemical structures and the serological specificity of the O-antigens aim at the elucidation of the molecular basis of the serological classification of Providencia sp. MATERIALS AND METHODS: LPS and alkali-treated LPS of P. alcalifaciens O23 and serologically related P. rustigianii O14, P. mirabilis O13 and P. myxofaciens as well as O-antiserum against P. alcalifaciens O23 were used. Serological characterization of P. alcalifaciens O23 O-specific polysaccharide was done by use enzyme immunosorbent assay (EIA), passive hemolysis test (PHT) as well as by inhibition and sodium deoxycholate polyacrylamide gel electrophoresis (DOC-PAGE) of LPS and Western blot. RESULTS AND CONCLUSIONS: The OPS of P. alcalifaciens, O23, contains an N-(D-glucuronoyl)-N-[(R)-1-carboxyethyl]-L-lysine residue (GlcAAlaLys). The LPS of P. alcalifaciens, O23, and other LPSs containing AlaLys from Providencia and Proteus strains were tested with rabbit anti-P. alcalifiaciens O23 serum. The serological data showed that a GlcAAlaLys-associated epitope plays a role as an antigenic determinant in the P. alcalifaciens O23 OPS and revealed the particular importance of glucuronic acid and the carboxyethyl group for the binding of O23-specific antibodies.
Lipopolysaccharide, structure, characterization, polysaccharide, O-antigen, O-specific, O-specific polysaccharide, Providencia, Providencia alcalifaciens, serological, O-serogroups, Ne-[(R)-1-carboxyethyl]-L-lysine
NCBI PubMed ID: 15053232Journal NLM ID: 0114365Publisher: Basel, Boston: Birkhaüser
Correspondence: rozala@biol.uni.lodz.pl
Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Institute of Microbiology and Immunology, University of Lodz, Lodz, Poland
- Article ID: 890
Kondakova AN, Toukach FV, Senchenkova SN, Arbatsky NP, Shashkov AS, Knirel YA, Zych K, Torzewska A, Kolodziejska K, Rozalski A, Sidorczyk Z "New structures of the O-specific polysaccharides of Proteus. Part 2. O-Acetylated polysaccharides" -
Biochemistry (Moscow) 67(2) (2002) 201-211
Structures of five new O-specific polysaccharides of Proteus bacteria were established. Four of them, Proteus penneri 4 (O72), Proteus vulgaris 63/57 (O37), Proteus mirabilis TG 277 (O69), and Proteus penneri 20 (O17), contain O-acetyl groups in non-stoichiometric quantities, and the polysaccharide of P. penneri 1 is structurally related to that of P. penneri 4. The structures were elucidated using NMR spectroscopy, including one dimensional 1H- and 13C-NMR spectroscopy, two-dimensional 1H, 1H correlation (COSY, TOCSY), H-detected 1H, 13C heteronuclear multiple-quantum coherence (HMQC), heteronuclear multiple-bond correlation (HMBC), and nuclear Overhauser effect spectroscopy (NOESY or ROESY), along with chemical methods. The structural data obtained are useful as the chemical basis for the creation of the classification scheme for Proteus strains.
structure, Bacterial, polysaccharide, O-antigen, O-specific, O-specific polysaccharide, Proteus, polysaccharides, O-specific polysaccharides, O-acetyl
Publication DOI: 10.1023/A:1014414030784Journal NLM ID: 0376536Publisher: Nauka/Interperiodica
Correspondence: knirel@ioc.ac.ru
Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
Methods: NMR, de-O-acetylation
- Article ID: 1238
Sidorczyk Z, Toukach FV, Zych K, Drzewiecka D, Arbatsky NP, Shashkov AS, Knirel YA "Structural and serological relatedness of the O-antigens of Proteus penneri 1 and 4 from a novel Proteus serogroup O72" -
European Journal of Biochemistry 269(1) (2002) 358-363
O-specific polysaccharides (O-antigens) of the lipopolysaccharides (LPS) of Proteus penneri strains 1 and 4 were studied using sugar analysis, (1)H and (13)C NMR spectroscopy, including 2D COSY, H-detected (1)H,(13)C HMQC, and rotating-frame NOE spectroscopy (ROESY). The following structures of the tetrasaccharide (strain 1) and pentasaccharide (strain 4) repeating units of the polysaccharides were established: [reaction: see text]. In the polysaccharide of P. penneri strain 4, glycosylation with the lateral Glc residue (75%) and O-acetylation of the lateral GalNAc residue (55%) are nonstoichiometric. This polysaccharide contains also other, minor O-acetyl groups, whose positions were not determined. The structural similarity of the O-specific polysaccharides was consistent with the close serological relatedness of the LPS, which was demonstrated by immunochemical studies with O-antisera against P. penneri 1 and 4. Based on these data, it was proposed to classify P. penneri strains 1 and 4 into a new Proteus serogroup, O72, as two subgroups, O72a and O72a,b, respectively. Serological cross-reactivity of P. penneri 1 O-antiserum with the LPS of P. penneri 40 and 41 was substantiated by the presence of an epitope(s) on the LPS core region shared by all P. penneri strains studied.
Lipopolysaccharide, O-antigen, O-specific polysaccharide, Proteus penneri, O-serogroup
NCBI PubMed ID: 11784330Publication DOI: 10.1046/j.0014-2956.2001.02660.xJournal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Correspondence: zsidor@biol.uni.lodz.pl
Institutions: N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Department of General Microbiology, Institute of Microbiology and Immunology, University of Łodź, Łodź, Poland
Methods: NMR
- Article ID: 3357
Perepelov AV, Liu B, Senchenkova SN, Shevelev SD, Wang W, Shashkov AS, Feng L, Wang L, Knirel YA "The structure of the glycerol phosphate-containing O-specific polysaccharide from Escherichia coli O130" -
Russian Journal of Bioorganic Chemistry 33(1) (2007) 64-68
A phosphorylated O-specific polysaccharide was obtained by mild acidic degradation of the lipopolysaccharide from the enteric bacterium Escherichia coli O130 and characterized by the methods of chemical analysis, including dephosphorylation and 1H and 13C NMR spectroscopy. The polysaccharide was shown to be composed of branched tetrasaccharide repeating units containing two N-acetyl-D-galactosamine residues,D-galactose, D-glucose,and glycerophosphate residues (one of each). The polysaccharide has the following structure, which is unique among the known bacterial polysaccharides:
Escherichia coli, O-specific polysaccharide, teichoic acid, glycerophosphate, structure; NMR spectroscopy
Publication DOI: 10.1134/S1068162007010062Journal NLM ID: 9420101Publisher: Springer Science and Business Media
Correspondence: knirel@ioc.ac.ru
Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia,TEDA School of Biological Sciences and Biotechnology, Nankai University, TEDA, China Tyan-jin Key Laboratory for Microbial Functional Genomics, TEDA College, Nankai University, TEDA, Tyan-jin, China
Methods: 13C NMR, 1H NMR, NMR-2D, HF solvolysis, sugar analysis, 31P NMR, GLC, mild acid hydrolysis, NMR-1D
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5. Compound ID: 575
|
EtN-(1--P--6)--+
|
L-gro-a-D-manHepp-(1-2)-D-gro-a-D-manHepp-(1-2)-+ |
| |
EtN-(1--P--6)--+ | | b-D-Glcp-(1-4)-+ b-L-Arap4N-(1-8)-+
| | | | |
R-3HOBut-(1-3)-a-D-Fucp3N-(1-4)-a-D-Galp-(1-6)-b-D-Glcp-(1-3)-a-D-GalpN-(1-4)-a-D-GalpA-(1-3)-L-gro-a-D-manHepp-(1-3)-L-gro-a-D-manHepp-(1-5)-a-Kdop-(2-6)-b-D-GlcpN-(1-6)-a-D-GlcpN-(1-P
| |
L-gro-a-D-manHepp-(1-7)-+ a-Kdop-(2-4)-+ |
Show graphically |
Structure type: oligomer
Trivial name: core-lipid A region
Contained glycoepitopes: IEDB_120354,IEDB_123890,IEDB_130650,IEDB_130659,IEDB_130670,IEDB_136906,IEDB_137472,IEDB_137473,IEDB_140087,IEDB_140088,IEDB_140090,IEDB_140529,IEDB_141794,IEDB_141807,IEDB_142488,IEDB_146664,IEDB_151528,IEDB_151531,IEDB_167069,IEDB_190606,IEDB_2189046,IEDB_2189047,IEDB_226811,IEDB_983931,SB_192,SB_7
The structure is contained in the following publication(s):
- Article ID: 174
Vinogradov E, Sidorczyk Z "The structure of the core part of Proteus penneri strain 16 lipopolysaccharide" -
Carbohydrate Research 326(3) (2000) 185-193
The structure of the carbohydrate backbone of the lipid A-core region of the lipopolysaccharide (LPS) from Proteus penneri strain 16 was determined using NMR and chemical analysis of the core oligosaccharide, obtained by mild acid hydrolysis of the LPS, and of the products of alkaline deacylation of the LPS: formula [see text]. Incomplete substitution is indicated by bold italics. All sugars are in the pyranose form, α-Hep is the residue of L-glycero-α-D-manno-Hep, α-DD-Hep is the residue of D-glycero-α-D-manno-Hep, Bu is the (R)-3-hydroxybutyryl residue.
Lipopolysaccharide, LPS, structure, core, strain, Proteus, Proteus penneri
NCBI PubMed ID: 10903028Publication DOI: 10.1016/S0008-6215(99)00304-3Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: evguenii.vinogradov@nrc.ca
Institutions: Carlsberg Laboratory, Department of Chemistry. Gamle Carlsberg Vej 10, DK- 2500 Valby, Copenhagen, Denmark, Institute of Microbiology and Immunology, Uni6ersity of Lodz, 90- 237 Lodz, Banacha 12: 16, Poland
Methods: NMR-2D, NMR, chemical analysis
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6. Compound ID: 576
|
EtN-(1--P--6)--+
|
L-gro-a-D-manHepp-(1-2)-D-gro-a-D-manHepp-(1-2)-+ |
| |
EtN-(1--P--6)--+ | | b-D-Glcp-(1-4)-+ b-L-Arap4N-(1-8)-+
| | | | |
R-3HOBut-(1-3)-a-D-Fucp3N-(1-4)-a-D-Galp-(1-6)-b-D-Glcp-(1-3)-a-D-GalpN-(1-4)-a-GalpA-(1-3)-L-gro-a-D-manHepp-(1-3)-L-gro-a-D-manHepp-(1-5)-Kdo
|
L-gro-a-D-manHepp-(1-7)-+ |
Show graphically |
Structure type: oligomer
Trivial name: core-lipid A region
Contained glycoepitopes: IEDB_120354,IEDB_123890,IEDB_130650,IEDB_130670,IEDB_136906,IEDB_137472,IEDB_137473,IEDB_140087,IEDB_140088,IEDB_140090,IEDB_140529,IEDB_141794,IEDB_142488,IEDB_146664,IEDB_151528,IEDB_167069,IEDB_190606,IEDB_2189046,IEDB_2189047,IEDB_226811,IEDB_983931,SB_192,SB_7
The structure is contained in the following publication(s):
- Article ID: 174
Vinogradov E, Sidorczyk Z "The structure of the core part of Proteus penneri strain 16 lipopolysaccharide" -
Carbohydrate Research 326(3) (2000) 185-193
The structure of the carbohydrate backbone of the lipid A-core region of the lipopolysaccharide (LPS) from Proteus penneri strain 16 was determined using NMR and chemical analysis of the core oligosaccharide, obtained by mild acid hydrolysis of the LPS, and of the products of alkaline deacylation of the LPS: formula [see text]. Incomplete substitution is indicated by bold italics. All sugars are in the pyranose form, α-Hep is the residue of L-glycero-α-D-manno-Hep, α-DD-Hep is the residue of D-glycero-α-D-manno-Hep, Bu is the (R)-3-hydroxybutyryl residue.
Lipopolysaccharide, LPS, structure, core, strain, Proteus, Proteus penneri
NCBI PubMed ID: 10903028Publication DOI: 10.1016/S0008-6215(99)00304-3Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: evguenii.vinogradov@nrc.ca
Institutions: Carlsberg Laboratory, Department of Chemistry. Gamle Carlsberg Vej 10, DK- 2500 Valby, Copenhagen, Denmark, Institute of Microbiology and Immunology, Uni6ersity of Lodz, 90- 237 Lodz, Banacha 12: 16, Poland
Methods: NMR-2D, NMR, chemical analysis
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7. Compound ID: 578
|
R-3HOBut-(1-3)-a-D-Fucp3N-(1-4)-a-D-Galp-(1-6)-b-D-Glcp-(1-3)-D-2,5anhTala |
Show graphically |
Structure type: oligomer
Trivial name: core-lipid A region
Contained glycoepitopes: IEDB_136906,IEDB_137472,IEDB_140529,IEDB_141794,IEDB_142488,IEDB_146664,IEDB_151528,IEDB_167069,IEDB_190606,IEDB_983931,SB_192,SB_7
The structure is contained in the following publication(s):
- Article ID: 174
Vinogradov E, Sidorczyk Z "The structure of the core part of Proteus penneri strain 16 lipopolysaccharide" -
Carbohydrate Research 326(3) (2000) 185-193
The structure of the carbohydrate backbone of the lipid A-core region of the lipopolysaccharide (LPS) from Proteus penneri strain 16 was determined using NMR and chemical analysis of the core oligosaccharide, obtained by mild acid hydrolysis of the LPS, and of the products of alkaline deacylation of the LPS: formula [see text]. Incomplete substitution is indicated by bold italics. All sugars are in the pyranose form, α-Hep is the residue of L-glycero-α-D-manno-Hep, α-DD-Hep is the residue of D-glycero-α-D-manno-Hep, Bu is the (R)-3-hydroxybutyryl residue.
Lipopolysaccharide, LPS, structure, core, strain, Proteus, Proteus penneri
NCBI PubMed ID: 10903028Publication DOI: 10.1016/S0008-6215(99)00304-3Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: evguenii.vinogradov@nrc.ca
Institutions: Carlsberg Laboratory, Department of Chemistry. Gamle Carlsberg Vej 10, DK- 2500 Valby, Copenhagen, Denmark, Institute of Microbiology and Immunology, Uni6ersity of Lodz, 90- 237 Lodz, Banacha 12: 16, Poland
Methods: NMR-2D, NMR, chemical analysis
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8. Compound ID: 579
Structure type: oligomer
Trivial name: core-lipid A region
Contained glycoepitopes: IEDB_136906,IEDB_137472,IEDB_140529,IEDB_141794,IEDB_142488,IEDB_146664,IEDB_151528,IEDB_167069,IEDB_190606,IEDB_983931,SB_192,SB_7
The structure is contained in the following publication(s):
- Article ID: 174
Vinogradov E, Sidorczyk Z "The structure of the core part of Proteus penneri strain 16 lipopolysaccharide" -
Carbohydrate Research 326(3) (2000) 185-193
The structure of the carbohydrate backbone of the lipid A-core region of the lipopolysaccharide (LPS) from Proteus penneri strain 16 was determined using NMR and chemical analysis of the core oligosaccharide, obtained by mild acid hydrolysis of the LPS, and of the products of alkaline deacylation of the LPS: formula [see text]. Incomplete substitution is indicated by bold italics. All sugars are in the pyranose form, α-Hep is the residue of L-glycero-α-D-manno-Hep, α-DD-Hep is the residue of D-glycero-α-D-manno-Hep, Bu is the (R)-3-hydroxybutyryl residue.
Lipopolysaccharide, LPS, structure, core, strain, Proteus, Proteus penneri
NCBI PubMed ID: 10903028Publication DOI: 10.1016/S0008-6215(99)00304-3Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: evguenii.vinogradov@nrc.ca
Institutions: Carlsberg Laboratory, Department of Chemistry. Gamle Carlsberg Vej 10, DK- 2500 Valby, Copenhagen, Denmark, Institute of Microbiology and Immunology, Uni6ersity of Lodz, 90- 237 Lodz, Banacha 12: 16, Poland
Methods: NMR-2D, NMR, chemical analysis
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9. Compound ID: 641
|
EtN-(1--P--6)--+
|
D-gro-a-D-manHepp-(1-2)-D-gro-a-D-manHepp-(1-2)-+ |
| |
EtN-(1--P--6)--+ | | b-D-Glcp-(1-4)-+ b-L-Arap4N-(1-8)-+ P-4)-+
| | | | | |
R-3HOBut-(1-3)-a-D-Fucp3N-(1-4)-a-D-Galp-(1-6)-b-D-Glcp-(1-3)-a-D-GalpN-(1-4)-a-D-GalpA-(1-3)-L-gro-a-D-manHepp-(1-3)-L-gro-a-D-manHepp-(1-5)-a-Kdop-(2-6)-b-D-GlcpN-(1-6)-a-D-GlcpN-(1-P
| |
L-gro-a-D-manHepp-(1-7)-+ a-Kdop-(2-4)-+ |
Show graphically |
Structure type: oligomer
Compound class: LOS
Contained glycoepitopes: IEDB_120354,IEDB_123890,IEDB_130650,IEDB_130659,IEDB_130670,IEDB_135394,IEDB_136906,IEDB_137472,IEDB_137473,IEDB_140087,IEDB_140088,IEDB_140090,IEDB_140529,IEDB_141794,IEDB_141807,IEDB_142488,IEDB_146664,IEDB_150908,IEDB_151528,IEDB_151531,IEDB_167069,IEDB_190606,IEDB_2189046,IEDB_2189047,IEDB_226811,IEDB_983931,SB_192,SB_7
The structure is contained in the following publication(s):
- Article ID: 181
Vinogradov E, Sidorczyk Z, Knirel YA "Structure of the lipopolysaccharide core region of the bacteria of the genus Proteus" -
Australian Journal of Chemistry 55(1-2) (2002) 61-67
The lipopolysaccharide (LPS) core structure was studied in seven rough strains of Proteus and 26 smooth strains belonging to various Proteus O-serogroups. All LPSs share a common heptasaccharide fragment, which includes two Kdo, three Hep, one Glc, and one GalA residue. Core structures differ between strains and within each strain in the presence of a variety of additional monosaccharides and non-sugar substituents. In many strains, the LPS includes a cyclic acetal of GalNAc in the open-chain form, which builds up a new type of linkage between monosaccharides. The covalent linkage of aliphatic polyamines, e.g. putrescine and spermidine, to the LPS was confirmed for the first time and the location of the amines at the carboxyl group of a GalA residue established. Analyses revealed peculiar features of the core structure, which are characteristic of P. mirabilis on one hand and P. vulgaris and P. penneri on the other hand.
Lipopolysaccharide, structure, core, carbohydrate, lipopolysaccharide core, bacteria, Proteus, core region, region, genus
Publication DOI: 10.1071/CH01184Journal NLM ID: 0370614Institutions: Institute for Biological Sciences. National Research Council,100 Sussex Drive. Ottawa ON, K1A 0R6, Canada, Department of General Microbiology, Institute of Microbiology and Immunology, University of Lodz, Banacha 12/16, 90-237, Lodz, Poland, N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky pr. 47, Moscow, B-334, Russia
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10. Compound ID: 874
|
a-D-Galp-(1-6)-+
|
-3)-a-D-GalpNAc-(1-3)-b-D-Galp-(1-3)-b-D-Glcp-(1- |
Show graphically |
Structure type: polymer chemical repeating unit
Compound class: CPS, EPS
Contained glycoepitopes: IEDB_130648,IEDB_136044,IEDB_136906,IEDB_137472,IEDB_137473,IEDB_1391961,IEDB_140529,IEDB_141584,IEDB_141794,IEDB_142488,IEDB_146664,IEDB_151528,IEDB_152213,IEDB_153205,IEDB_167069,IEDB_190606,IEDB_885822,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 244
Griffin AM, Morris VJ, Gasso MJ "The cpsABCDE genes involved in polysaccharide production in Streptococcus salivarius ssp thermophilus strain NCBF 2393" -
Gene 183 (1996) 23-27
A 4074-bp EcoRI fragment of Streptococcus salivarius ssp. thermophilus (S. thermophilus) chromosomal DNA containing genes involved in exocellular polysaccharide (EPS) was identified and cloned. The nucleotide sequence of this fragment was determined and found to contain one partial and four complete open reading frames. These were designated cpsA, cpsB, cpsC, cpsD and cpsE and encoded proteins of >130, 243, 230, 246 and 455 amino acids, respectively, that showed homology with the genes of the cps cluster, involved in polysaccharide biosynthesis, in Streptococcus pneumoniae Type 19F. The cpsA gene is predicted to encode a transcriptional regulator, while cpsC anc cpsD are predicted to encode proteins involved in polysaccharide polymerization and export. The cpsE gene is likely to encode the phosphate-prenyl glycosyl-1-phosphate transferase catalyzing the first step in polysaccharide biosynthesis in S. thermophilus. Southern blot analysis revealed that cpsE is found only in polysaccharide producing strains of S. thermophilus.
gene, strain, polysaccharide, Streptococcus, exocellular polysaccharide, production, genetic engineering, lactic acid bacterium, polysaccharide production, ropy strain, Streptococcus salivarius, yoghurt
NCBI PubMed ID: 8996082Journal NLM ID: 7706761Publisher: Amsterdam: Elsevier
Correspondence: annette.griffin@bbsrc.ac.uk
Institutions: Genetic and Mircobiology Department, Institute of Food Research, Norwich Laboratory, Norwich Research Park, Colney, Norwich, NR4 7UA, UK
- Article ID: 1266
Stingele F, Neeser JR, Mollet B "Identification and characterization of the eps (Exopolysaccharide) gene cluster from Streptococcus thermophilus Sfi6" -
Journal of Bacteriology 178(6) (1996) 1680-1690
We report the identification and characterization of the eps gene cluster of Streptococcus thermophilus Sfi6 required for exopolysaccharide (EPS) synthesis. This report is the first genetic work concerning EPS production in a food microorganism. The EPS secreted by this strain consists of the following tetrasaccharide repeating unit: →3)-β-D-Galp-(1→3)-[α-D-Galp-(1→6)]-β-D-D-Galp-(1→3)-α-D-Galp-D-GalpNAc-(1→. The genetic locus The genetic locus was identified by Tn916 mutagenesis in combination with a plate assay to identify Eps mutants. Sequence analysis of the gene region, which was obtained from subclones of a genomic library of Sfi6, revealed a 15.25-kb region encoding 15 open reading frames. EPS expression in the non-EPS-producing heterologous host, Lactococcus lactis MG1363, showed that within the 15.25-kb region, a region with a size of 14.52 kb encoding the 13 genes epsA to epsM was capable of directing EPS synthesis and secretion in this host. Homology searches of the predicted proteins in the Swiss-Prot database revealed high homology (40 to 68+ACU- identity) for epsA, B, C, D, and E and the genes involved in capsule synthesis in Streptococcus pneumoniae and Streptococcus agalactiae. Moderate to low homology (37 to 18+ACU- identity) was detected for epsB, D, F, and H and the genes involved in capsule synthesis in Staphylococcus aureus for epsC, D, and E and the genes involved in exopolysaccharide I (EPSI) synthesis in Rhizobium meliloti for epsC to epsJ and the genes involved in lipopolysaccharide synthesis in members of the Enterobacteriaceae, and finally for eps K and lipB of Neisseria meningitidis. Genes (epsJ, epsL, and epsM) for which the predicted proteins showed little or no homology with proteins in the Swiss-Prot database were shown to be involved in EPS synthesis by single-crossover gene disruption experiments.
gene, characterization, Streptococcus, Streptococcus thermophilus, cluster, gene cluster, exopolysaccharide, identification, EPS
NCBI PubMed ID: 862629Journal NLM ID: 2985120RPublisher: American Society for Microbiology
Correspondence: francesca.stingele+AEA-chlsnr.nestrd.ch
Institutions: Nestle Research Center, Nestec Ltd., Vers-chez-les-Blanc, 1000 Lausanne 26, Switzerland
- Article ID: 2160
Doco T, Wieruszeski JM, Fournet B, Carcano D, Ramos P, Loones A "Structure of an exocellular polysaccharide produced by Streptococcus thermophilus" -
Carbohydrate Research 198 (1990) 313-321
Streptococcus thermophilus strains grown on skimmed milk produced a viscosifying, exocellular, and water-soluble polysaccharide which contains D-glucose, D-galactose, and N-acetyl-D-galactosamine in the ratio of 1:2:1. Methylation analysis identified the glycosidic linkages in the tetrasaccharidic repeating-unit, and Smith degradation and nitrous deamination after N-deacetylation gave the sequence of monosaccharides in the repeating-unit. The anomeric configurations of the sugar residues were determined by oxidation of the peracetylated polysaccharide with chromium trioxide and by 1H- and 13C-n.m.r. spectroscopy. The following structure was assigned to the repeating unit of the polysaccharide, →3)-β-D-Galp-(1→3)-[α-D-Galp-(1→6)]-β-D-Glcp-(1→3)-α-D-GalpNAc-(1→.
NCBI PubMed ID: 2165858Publication DOI: 10.1016/0008-6215(90)84301-aJournal NLM ID: 0043535Publisher: Elsevier
Institutions: Laboratoire de Chimie Biologique de l'Université des Sciences et Techniques de Lille Flandres-Artois, Unité Associée au C.N.R.S. No 217, Villeneuve d'Ascq, France
Methods: 13C NMR, 1H NMR
- Article ID: 3406
Gorska S, Grycko P, Rybka J, Gamian A "Exopolysaccharides of lactic acid bacteria: structure and biosynthesis" -
Postȩpy Higieny i Medycyny Doświadczalnej [Polish] 61 (2007) 805-818
The group of lactic acid bacteria (LABs) includes four genera: Lactobacillus, Leuconostoc, Pediococcus, and Streptococcus. The most characteristic feature of this group of microorganisms is the production of lactic acid as a main product of carbohydrate metabolism. LABs are responsible for the fermentation of alimentary products and they also produce a variety of agents, among them exopolysaccharides (EPSs), which inhibit the growth of pathogenic bacteria. In this article on the different types of EPSs produced by LABs, data concerning their structure and biosynthesis are presented
biosynthesis, structure, Streptococcus, Lactic acid bacteria, exopolysaccharides, Lactococcus, Lactobacillus, Leuconostoc
NCBI PubMed ID: 18097339Journal NLM ID: 0421052Publisher: Warszawa: Panstwowy Zaklad Wydawnictw Lekarskich
Institutions: Laboratorium Mikrobiologii Lekarskiej, Instytut Immunologii i Terapii Doswiadczalnej PAN im. L. Hirszfelda we Wroclawiu
- Article ID: 5067
Birch J, Harðarson HK, Khan S, Van Calsteren MR, Ipsen R, Garrigues C, Almdal K, Hachem MA, Svensson B "Effect of repeat unit structure and molecular mass of lactic acid bacteria hetero-exopolysaccharides on binding to milk proteins" -
Carbohydrate Polymers 177 (2017) 406-414
Interactions of exopolysaccharides and proteins are of great importance in food science, but complicated to analyze and quantify at the molecular level. A surface plasmon resonance procedure was established to characterize binding of seven structure-determined, branched hetero-exopolysaccharides (HePSs) of 0.14-4.9MDa from lactic acid bacteria to different milk proteins (β-casein, κ-casein, native and heat-treated β-lactoglobulin) at pH 4.0-5.0. Maximum binding capacity (RUmax) and apparent affinity (KA,app) were HePS- and protein-dependent and varied for example 10- and 600-fold, respectively, in the complexation with native β-lactoglobulin at pH 4.0. Highest RUmax and KA,app were obtained with heat-treated β-lactoglobulin and β-casein, respectively. Overall, RUmax and KA,app decreased 6- and 20-fold, respectively, with increasing pH from 4.0 to 5.0. KA,app was influenced by ionic strength and temperature, indicating that polar interactions stabilize HePS-protein complexes. HePS size as well as oligosaccharide repeat structure, conferring chain flexibility and hydrogen bonding potential, influence the KA,app.
Binding parameters, Dynamic light scattering (DLS), Hetero-exopolysaccharides (HePSs), Surface plasmon resonance (SPR), β- and κ-casein, β-lactoglobulin
NCBI PubMed ID: 28962786Publication DOI: 10.1016/j.carbpol.2017.08.055Journal NLM ID: 8307156Publisher: Elsevier
Correspondence: B. Svensson
Institutions: Enzyme and Protein Chemistry, Department of Biotechnology and Biomedicine, Technical University of Denmark, Elektrovej, building 375, DK-2800 Kgs. Lyngby, Denmark, Department of Micro- and Nanotechnology, Technical University of Denmark, Produktionstorvet, building 423, DK-2800 Kgs. Lyngby, Denmark, Saint-Hyacinthe Research and Development Centre, Agriculture and Agri-Food Canada, 3600 Casavant Boulevard West, Saint-Hyacinthe, Quebec J2S 8E3, Canada, Department of Food Science, University of Copenhagen, Rolighedsvej 26, DK-1958 Frederiksberg C, Denmark, CED-Discovery, Chr Hansen A/S, DK-2970 Hørsholm, Denmark
Methods: 13C NMR, 1H NMR, gel filtration, sugar analysis, ESI-MS, acid hydrolysis, GC, MS/MS, methanolysis, reduction with NaBD4, acetylation, SPR, protein immobilization, dynamic light scattering
- Article ID: 5075
Pachekrepapol U, Lucey JA, Gong Y, Naran R, Azadi P "Characterization of the chemical structures and physical properties of exopolysaccharides produced by various Streptococcus thermophilus strains" -
Journal of Dairy Science 100(5) (2017) 3424-3435
Exopolysaccharides (EPS) produced by some lactic acid bacteria are often used by the dairy industry to improve the rheological and physical properties of yogurt, but the relationship between their structure and functional effect is still unclear. The EPS from different species, or different strains from the same species, may differ in terms of molar mass, repeating unit structure, and EPS yield during fermentation of milk. This study aimed to characterize the detailed properties of EPS produced from 7 strains of Streptococcus thermophilus, which is one of the key cultures used for yogurt manufacture. Milk was fermented with strains DGCC 7698, DGCC 7710, DGCC 7785, ST-10255y, St-143, STCth-9204, and ST4239. These strains were selected because they have been used in previous studies on yogurt texture, but a complete description of their EPS structural properties has not yet been reported. All strains were fermented under a similar acidification rate by adjusting the level of supplementation with peptone or the inoculation level, which allowed for a comparison of EPS yields under similar growth conditions (reconstituted skim milk at 40°C). The EPS from each strain was isolated and the weight-average molar mass and z-average root mean square radius determined using size-exclusion chromatography multiangle laser light scattering. The monosaccharide composition of EPS was determined using gas chromatography-mass spectrometry, and repeating unit structure was determined using nuclear magnetic resonance spectroscopy. The weight-average molar mass values of EPS ranged from 0.14 to 1.61 × 106 g/mol. All 7 EPS samples were uncharged. The strains ST-10255y and ST4239 had EPS with the same repeating unit structure. The monosaccharide compositions of the various EPS were mainly composed of glucose and galactose, with low levels of rhamnose in the EPS isolated from DGCC 7698, and N-acetylgalactosamine in the EPS from DGCC 7785, ST-10255y, and ST4239. The yields of EPS (measured when fermented milks reached pH 4.6) ranged from 8.0 to 76.4 mg of glucose equivalents/kg. In addition to (free) EPS, some strains were also able to produce capsular polysaccharide (associated with the bacterial cells) when observed with negative staining technique. The results of our study will help the dairy industry to better understand the mechanism by which different strains of Streptococcus thermophilus affect yogurt texture.
Streptococcus thermophilus, exopolysaccharide, acid milk gel, molar mass
NCBI PubMed ID: 28318581Publication DOI: 10.3168/jds.2016-12125Journal NLM ID: 2985126RPublisher: Champaign, IL: American Dairy Science Association
Correspondence: jlucey@cdr.wisc.edu
Institutions: Complex Carbohydrate Research Center, University of Georgia, Athens, USA, Department of Food Science, University of Wisconsin-Madison, Madison, USA, Wisconsin Center for Dairy Research, University of Wisconsin-Madison, Madison, USA
Methods: 13C NMR, 1H NMR, methylation, NMR-2D, GC-MS, sugar analysis, acid hydrolysis, methanolysis, reduction, dialysis, SEC-MALLS
- Article ID: 5196
Pachekrepapol U, Lucey JA, Gong Y, Naran R, Azadi P "Corrigendum to 'Characterization of the chemical structures and physical properties of exopolysaccharides produced by various Streptococcus thermophilus strains' (J. Dairy Sci. 100:3424-3435)" -
Journal of Dairy Science 101(6) (2018) 5686
U. Pachekrepapol, J.A. Lucey, Y. Gong, R. Naran, P. Azadi Characterization of the chemical structures and physical properties of exopolysaccharides produced by various Streptococcus thermophilus strains J. Dairy Sci., 100 (5) (2017), pp. 3424-3435 DOI:10.3168/jds.2016-12125In Figure 2, on page 3431, the structures of some of the exopolysaccharide repeating units were incorrect. The corrected figure is shown below with revised structures for ST-10255y and ST4239, St-143, and STCth-9204 (Figure 2, parts d, e, and f).
structure, Streptococcus, Streptococcus thermophilus, exopolysaccharide
Publication DOI: 10.3168/jds.2018-101-6-5668Journal NLM ID: 2985126RPublisher: Champaign, IL: American Dairy Science Association
Correspondence: jlucey@cdr.wisc.edu
Institutions: Department of Food Science, University of Wisconsin-Madison, Madison, USA, Wisconsin Center for Dairy Research, University of Wisconsin-Madison, Madison, USA, Complex Carbohydrate Research Center, University of Georgia, Athens 30602
- Article ID: 5533
Zhou Y, Cui Y, Qu X "Exopolysaccharides of lactic acid bacteria: Structure, bioactivity and associations: A review" -
Carbohydrate Polymers 207 (2019) 317-332
The ability to exhibit various bioactivities is widespread in exopolysaccharide (EPS) of lactic acid bacteria (LAB), and it has been admittedly associated with large structural variability of these polymers. Exceptional bioactivities such as cholesterol-lowering, immunomodulating, antioxidant, antiviral and anticoagulant effects render these biopolymers vast commercial value for global market and application potentials in medicine sector. Therefore, an elaborate understanding of structure-to-function associations will be prerequisite to search natural and artificial EPSs for new applications in functional food, health and medicine fields. In this review, it is presented a significant overview of the latest advances in the field of EPS from genes to application. This review emphasized in the general biosynthesis pathway together with genetic modules, multiple structures, functions, and respective functional mechanisms of LAB-derived EPSs, and the relationships between their structure and bioactivity, which will help to exploit new bioactive drugs from LAB-derived EPS.
biosynthesis, structure, exopolysaccharide, mechanism, bioactivity, Structure-to-function association
NCBI PubMed ID: 30600013Publication DOI: 10.1016/j.carbpol.2018.11.093Journal NLM ID: 8307156Publisher: Elsevier
Correspondence: Y. Cui
Institutions: Department of Food Science and Engineering, School of Chemistry and Chemical Engineering, Harbin Institute of Technology, Harbin, China, Institute of Microbiology, Heilongjiang Academy of Sciences, Harbin, China
- 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
- Article ID: 5880
De Vuyst L, De Vin F "Exopolysaccharides from Lactic Acid Bacteria" -
Book: Comprehensive Glycoscience: From Chemistry to Systems Biology. Reference Module in Chemistry, Molecular Sciences and Chemical Engineering (2007) 477-519
carbohydrates, Lactic acid bacteria, exopolysaccharides, polysaccharides, glycolipids, glycoproteins, Glycomics
Publication DOI: 10.1016/B978-044451967-2/00129-XPublisher: Elsevier
Correspondence: ldvuyst@vub.ac.be
Editors: Barchi J, Kamerling H
Institutions: Department of Applied Biological Sciences and Engineering, Research Group of Industrial Microbiology and Food Biotechnology, Vrije Universiteit Brussel, Brussels, Belgium
- Article ID: 6033
Birch J, Khan S, Madsen M, Kjeldsen C, Møller MS, Stender EGP, Peters GHJ, Duus J, Kragelund BB, Svensson B "Binding Sites for Oligosaccharide Repeats from Lactic Acid Bacteria Exopolysaccharides on Bovine beta-Lactoglobulin Identified by NMR Spectroscopy" -
ACS Omega 6(13) (2021) 9039-9052
Lactic acid bacterial exopolysaccharides (EPS) are used in the food industry to improve the stability and rheological properties of fermented dairy products. beta-Lactoglobulin (BLG), the dominant whey protein in bovine milk, is well known to bind small molecules such as fatty acids, vitamins, and flavors, and to interact with neutral and anionic polysaccharides used in food and pharmaceuticals. While sparse data are available on the affinity of EPS-milk protein interactions, structural information on BLG-EPS complexes, including the EPS binding sites, is completely lacking. Here, binding sites on BLG variant A (BLGA), for oligosaccharides prepared by mild acid hydrolysis of two EPS produced by Streptococcus thermophilus LY03 and Lactobacillus delbrueckii ssp. bulgaricus CNRZ 1187, respectively, are identified by NMR spectroscopy and supplemented by isothermal titration calorimetry (ITC) and molecular docking of complexes. Evidence of two binding sites (site 1 and site 2) on the surface of BLGA is achieved for both oligosaccharides (LY03-OS and 1187-OS) through NMR chemical shift perturbations, revealing multivalency of BLGA for EPS. The affinities of LY03-OS and 1187-OS for BLGA gave K D values in the mM range obtained by both NMR (pH 2.65) and ITC (pH 4.0). Molecular docking suggested that the BLGA and EPS complexes depend on hydrogen bonds and hydrophobic interactions. The findings provide insights into how BLGA engages structurally different EPS-derived oligosaccharides, which may facilitate the design of BLG-EPS complexation, of relevance for formulation of dairy products and improve understanding of BLGA coacervation.
NMR, Lactic acid bacteria, exopolysaccharide, binding site
NCBI PubMed ID: 33842774Publication DOI: 10.1021/acsomega.1c00060Journal NLM ID: 101691658Publisher: Washington, DC: American Chemical Society
Correspondence: Birthe B. Kragelund
; Birte Svensson
Institutions: Enzyme and Protein Chemistry, Department of Biotechnology and Biomedicine, Technical University of Denmark, Søltofts Plads, Building 224, DK-2800 Kgs. Lyngby, Denmark, NMR Spectroscopy, Department of Chemistry, Technical University of Denmark, Kemitorvet 207, DK-2800 Kgs. Lyngby, Denmark, Biophysical and Biomedicinal Chemistry, Department of Chemistry, Technical University of Denmark, Kemitorvet 206, DK-2800 Kgs. Lyngby, Denmark, Structural Biology and NMR Laboratory, Department of Biology, University of Copenhagen, Ole Maaloes Vej 5, DK-2200 Copenhagen N, Denmark
Methods: 13C NMR, 1H NMR, NMR-2D, TLC, mild acid hydrolysis, MALDI-TOF MS, radiolabeling, HPLC, 15N NMR, cloning, ITC, mutagenesis, molecular docking
- Article ID: 6166
Xu Z, Guo O, Zhang H, Xiong Z, Zhang X, Ai L "Structural characterisation of EPS of Streptococcus thermophilus S-3 and its application in milk fermentation" -
International Journal of Biological Macromolecules 178 (2021) 263-269
The application of Streptococcus thermophilus S-3 into yogurt production was studied and the structural properties of the generated exopolysaccharides (EPS-S3) were characterized. The proposed structure of EPS-S3 was obtained. EPS-S3 contained a high ratio of N-Acetyl-galactosamine with the Mw of 574 kDa, which was higher than that of AR333 (314 kD) leading to higher apparent viscosity. Streptococcus thermophilus strain S-3 was co-cultured with Lactobacillus delbrueckii for yogut production which highly increased the acidifying rate and post-acidification rate. The quality of the co-cultured yogurts in terms of apparent viscosity, syneresis capacity, water holding capacity and rheological properties were much better than that by using Lactobacillus bulgaricus only. The production mechanism of EPS-S3 from gene regulated level was also discussed which is helpful to facilitate the application of Streptococcus thermophilus strain into milk production.
NMR, Streptococcus thermophilus, exopolysaccharides, co-culture
NCBI PubMed ID: 33639187Publication DOI: 10.1016/j.ijbiomac.2021.02.173Journal NLM ID: 7909578Publisher: Butterworth-Heinemann
Correspondence: ailianzhong@163.com
Institutions: Shanghai Engineering Research Center of Food Microbiology, School of Medical Instruments and Food Engineering, University of Shanghai for Science and Technology, Shanghai 200093, China, State Key Laboratory of Dairy Biotechnology, Technology Center Bright Dairy & Food Co., Ltd, Shanghai 200436, China, State Key Laboratory of Food Nutrition and Safety, College of Food Science and Technology, Tianjin University of Science and Technology, Tianjin, China
Methods: 13C NMR, 1H NMR, methylation, NMR-2D, GC-MS, acid hydrolysis, HPLC, function analysis of gene clusters, yogurt production, yogurt quality evaluation
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11. Compound ID: 2452
|
D-Gro-(1--P--3)--+ a-D-Glcp-(1-2)-+
| |
-6)-b-D-Galp-(1-4)-b-D-GalpNAc-(1-4)-b-D-Glcp-(1-3)-b-D-GalpNAc-(1-
|
a-D-Galp-(1-6)-+ |
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Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide
Contained glycoepitopes: IEDB_130648,IEDB_130695,IEDB_136044,IEDB_136906,IEDB_137472,IEDB_137473,IEDB_140529,IEDB_141794,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_151528,IEDB_167069,IEDB_190606,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 837
Jachymek W, Czaja J, Niedziela T, Lugowski C, Kenne L "Structural studies of the O-specific polysaccharide of Hafnia alvei strain PCM1207 lipopolysaccharide" -
European Journal of Biochemistry 266 (1999) 53-61
The structure of the O-specific side-chain of the Hafnia alvei strain PCM1207 lipopolysaccharide (LPS) has been investigated. Methylation analysis, partial acid hydrolysis, matrix-assisted laser-desorption ionization time-of-flight (MALDI-TOF) MS, fast atom bombardment (FAB)-MS/MS and 1H- and 13C NMR spectroscopy were the principal methods used. Glycerol phosphate was identified as a constituent in the polysaccharide and the following structure of a pentasaccharide repeating unit was established: -3)[aDGlcp(1-6),Ac(1-2)]bDGalpN(1-4)[xDGro(1-P-3),Ac(1-2)]bDGalpN(1-3)aDGalp(1-4)bDGalp(1-. The polysaccharide is partially (< 10%) substituted with O-acetyl groups. The lipopolysaccharide was also subjected to high resolution magic angle spinning (HR-MAS) NMR analysis, which showed both the signals of the O-specific polysaccharide as well as several signals from unsubstituted core oligosaccharides. This confirmed the presence of the described structure in the native LPS.
Lipopolysaccharide, O-antigen, Hafnia alvei, MALDI-TOF, MALDI-TOF MS, HR-MAS NMR
NCBI PubMed ID: 10542050Journal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Correspondence: Lennart.Kenne@kemi.slu.se
Institutions: Department of Chemistry, Swedish University of Agricultural Sciences, Uppsala, Sweden, Hirszfeld Institute of Immunology and Experimental Therapy, Wroclaw, Poland
Methods: methylation, NMR-2D, partial acid hydrolysis, ELISA, MALDI-TOF MS, de-O-acetylation, FAB-MS/MS, TEMPO oxidation
- Article ID: 1468
Knirel YA, Kocharova NA, Bystrova OV, Katzenellenbogen E, Gamian A "Structures and serology of the O-specific polysaccharides of bacteria of the genus Citrobacter" -
Archivum Immunologiae et Therapiae Experimentalis 50(6) (2002) 379-391
The review presents the structures of the O-specific polysaccharides (O-antigens) of the lipopolysaccharides isolated from over 25 Citrobacter strains, which represent different species and serogroups. The correlation between O-antigen structure and immunospecificity as well as numerous cross-reactions between Citrobacter and other enterobacterial species are discussed.
Lipopolysaccharide, structure, O-antigen, O-specific polysaccharide, serology, Citrobacter, immunospecificity
NCBI PubMed ID: 12546064Journal NLM ID: 0114365Publisher: Basel, Boston: Birkhaüser
Correspondence: knirel@ioc.ac.ru
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
- Article ID: 3488
Katzenellenbogen E, Kocharova NA, Korzeniowska-Kowal A, Bogulska M, Rybka J, Gamian A, Kachala VV, Shashkov AS, Knirel YA "Structure of the glycerol phosphate-containing O-specific polysaccharide and serological studies on the lipopolysaccharides of Citrobacter werkmanii PCM 1548 and PCM 1549 (serogroup O14)" -
FEMS Immunology and Medical Microbiology 54(2) (2008) 255-262
The O-specific polysaccharide was obtained by mild acid hydrolysis of the lipopolysaccharide of Citrobacter werkmanii PCM 1548 and PCM 1549 (serogroup O14) and found to contain D-glucose, D-glucosamine and glycerol-1-phosphate in molar ratios 2 : 2 : 1. Based on methylation analysis and 1H and 13C nuclear magnetic resonance spectroscopy data, it was established that the O-specific polysaccharides from both strains have the identical branched tetrasaccharide repeating unit with 3,6-disubstituted GlcNAc, followed by 2,4-disubstituted Glc residues carrying at the branching points lateral residues of Glc and GlcNAc at positions 6 and 2, respectively. Glycerol-1-phosphate is linked to position 6 of the chain Glc. All sugars have a beta configuration, except for the side-chain Glc, which is α. Serological studies revealed a close relatedness of the lipopolysaccharides of C. werkmanii PCM 1548 and PCM 1549, both belonging to serogroup O14. In immunoblotting, anti-C. werkmanii PCM 1548 serum showed no cross-reactivity with the O-polysaccharide bands of the lipopolysaccharides of Citrobacter youngae PCM 1550 (serogroup O16) and Hafnia alvei PCM 1207, also containing a lateral glycerol phosphate residue.
Lipopolysaccharide, O-antigen, polysaccharide structure, serological specificity, glycerol phosphate, Citrobacter werkmanii
NCBI PubMed ID: 18811720Journal NLM ID: 9315554Publisher: Elsevier
Correspondence: katzenel@iitd.pan.wroc.pl
Institutions: L. Hirszfeld Institute of Immunology and Experimental Therapy, Polish Academy of Sciences, Wroclaw, Poland
Methods: 13C NMR, 1H NMR, methylation, GLC-MS, NMR-2D, SDS-PAGE, sugar analysis, mild acid hydrolysis, Smith degradation, serological methods
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12. Compound ID: 2595
|
b-D-GalpNAc6(55%)Ac-(1-3)-+
|
75%a-D-Glcp-(1-6)-+ |
| |
-3)-b-D-GalpNAc-(1-4)-a-D-Galp-(1-6)-b-D-Glcp-(1- |
Show graphically |
Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide
Contained glycoepitopes: IEDB_130648,IEDB_136906,IEDB_137472,IEDB_137473,IEDB_140529,IEDB_141794,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_151528,IEDB_167069,IEDB_190606,IEDB_983931,SB_192,SB_21,SB_25,SB_7
The structure is contained in the following publication(s):
- Article ID: 890
Kondakova AN, Toukach FV, Senchenkova SN, Arbatsky NP, Shashkov AS, Knirel YA, Zych K, Torzewska A, Kolodziejska K, Rozalski A, Sidorczyk Z "New structures of the O-specific polysaccharides of Proteus. Part 2. O-Acetylated polysaccharides" -
Biochemistry (Moscow) 67(2) (2002) 201-211
Structures of five new O-specific polysaccharides of Proteus bacteria were established. Four of them, Proteus penneri 4 (O72), Proteus vulgaris 63/57 (O37), Proteus mirabilis TG 277 (O69), and Proteus penneri 20 (O17), contain O-acetyl groups in non-stoichiometric quantities, and the polysaccharide of P. penneri 1 is structurally related to that of P. penneri 4. The structures were elucidated using NMR spectroscopy, including one dimensional 1H- and 13C-NMR spectroscopy, two-dimensional 1H, 1H correlation (COSY, TOCSY), H-detected 1H, 13C heteronuclear multiple-quantum coherence (HMQC), heteronuclear multiple-bond correlation (HMBC), and nuclear Overhauser effect spectroscopy (NOESY or ROESY), along with chemical methods. The structural data obtained are useful as the chemical basis for the creation of the classification scheme for Proteus strains.
structure, Bacterial, polysaccharide, O-antigen, O-specific, O-specific polysaccharide, Proteus, polysaccharides, O-specific polysaccharides, O-acetyl
Publication DOI: 10.1023/A:1014414030784Journal NLM ID: 0376536Publisher: Nauka/Interperiodica
Correspondence: knirel@ioc.ac.ru
Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
Methods: NMR, de-O-acetylation
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13. Compound ID: 2596
|
b-D-GalpNAc-(1-3)-+
|
75%a-D-Glcp-(1-6)-+ |
| |
-3)-b-D-GalpNAc-(1-4)-a-D-Galp6(55%)Ac-(1-6)-b-D-Glcp-(1- |
Show graphically |
Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide
Contained glycoepitopes: IEDB_130648,IEDB_136906,IEDB_137472,IEDB_137473,IEDB_140529,IEDB_141794,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_151528,IEDB_167069,IEDB_190606,IEDB_983931,SB_192,SB_21,SB_25,SB_7
The structure is contained in the following publication(s):
- Article ID: 890
Kondakova AN, Toukach FV, Senchenkova SN, Arbatsky NP, Shashkov AS, Knirel YA, Zych K, Torzewska A, Kolodziejska K, Rozalski A, Sidorczyk Z "New structures of the O-specific polysaccharides of Proteus. Part 2. O-Acetylated polysaccharides" -
Biochemistry (Moscow) 67(2) (2002) 201-211
Structures of five new O-specific polysaccharides of Proteus bacteria were established. Four of them, Proteus penneri 4 (O72), Proteus vulgaris 63/57 (O37), Proteus mirabilis TG 277 (O69), and Proteus penneri 20 (O17), contain O-acetyl groups in non-stoichiometric quantities, and the polysaccharide of P. penneri 1 is structurally related to that of P. penneri 4. The structures were elucidated using NMR spectroscopy, including one dimensional 1H- and 13C-NMR spectroscopy, two-dimensional 1H, 1H correlation (COSY, TOCSY), H-detected 1H, 13C heteronuclear multiple-quantum coherence (HMQC), heteronuclear multiple-bond correlation (HMBC), and nuclear Overhauser effect spectroscopy (NOESY or ROESY), along with chemical methods. The structural data obtained are useful as the chemical basis for the creation of the classification scheme for Proteus strains.
structure, Bacterial, polysaccharide, O-antigen, O-specific, O-specific polysaccharide, Proteus, polysaccharides, O-specific polysaccharides, O-acetyl
Publication DOI: 10.1023/A:1014414030784Journal NLM ID: 0376536Publisher: Nauka/Interperiodica
Correspondence: knirel@ioc.ac.ru
Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
Methods: NMR, de-O-acetylation
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14. Compound ID: 2703
|
b-D-Glcp-(1-2)-+
|
b-D-GlcpA-(1-3)-+ |
| |
-4)-a-D-Galp-(1-6)-b-D-Glcp-(1-3)-b-D-GalpNAc-(1- |
Show graphically |
Structure type: polymer chemical repeating unit
Compound class: K-antigen
Contained glycoepitopes: IEDB_115136,IEDB_130648,IEDB_136906,IEDB_137472,IEDB_137473,IEDB_140529,IEDB_140628,IEDB_140630,IEDB_141794,IEDB_142488,IEDB_146664,IEDB_151528,IEDB_167069,IEDB_190606,IEDB_423153,IEDB_983931,SB_192,SB_25,SB_7
The structure is contained in the following publication(s):
- Article ID: 929
Leslie MR, Parolis H, Parolis LAS "Structural analysis of the capsular antigen of Escherichia coli O8:K41:H11" -
Carbohydrate Research 299(3) (1997) 197-202
The primary structure of the acidic capsular antigen of Escherichia coli O8:K41 :HI 1 was shown by monosaccharide analysis, methylation analysis, and by 1D and 2D 1H and 13C NMR spectroscopy to be composed of branched pentasaccharide repeating units with the structure:[formula: see in the text].
antigen, structural, capsular, analysis, acidic, Escherichia, Escherichia coli, structural analysis
NCBI PubMed ID: 9163898Publication DOI: 10.1016/S0008-6215(97)00002-5Journal NLM ID: 0043535Publisher: Elsevier
Institutions: School of Pharmaceutical Sciences, Rhodes University, Grahamstown 6140, South Africa
Methods: methylation, NMR-2D, NMR, sugar analysis
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15. Compound ID: 2915
|
a-D-Galp-(1-6)-+
|
-3)-a-D-GalpNAc-(1-3)-b-D-Galp-(1-3)-b-D-Glcp-(1- |
Show graphically |
Structure type: polymer chemical repeating unit
; 1370000
Compound class: EPS
Contained glycoepitopes: IEDB_130648,IEDB_136044,IEDB_136906,IEDB_137472,IEDB_137473,IEDB_1391961,IEDB_140529,IEDB_141584,IEDB_141794,IEDB_142488,IEDB_146664,IEDB_151528,IEDB_152213,IEDB_153205,IEDB_167069,IEDB_190606,IEDB_885822,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 1045
Navarini L, Abatangelo A, Bertocchi C, Conti E, Bosco M, Picotti F "Isolation and characterization of the exopolysaccharide produced by Streptococcus thermophilus SFi20" -
International Journal of Biological Macromolecules 28(3) (2001) 219-226
This paper reports isolation, structural characterization and some physico-chemical properties in aqueous solution of the exopolysaccharide (EPS) produced by Streptococcus thermophilus strain SFi20. The yield of the purified EPS was found to be reproducible and close to the average value of 143 mg/l. The chemical structure, previously suggested, has been confirmed on the basis of NMR data. Viscometric, chiro-optical and rheological measurements have been carried out with the aim of characterizing the conformational state of the polysaccharide in aqueous solution. All the data reported indicate that the EPS does not undergo a cooperative conformational transition under the investigated experimental conditions. Furthermore, the viscosity data and the viscoelastic behaviour suggest that the polymer is rather flexible and adopts a random coil conformation in aqueous solution
characterization, Streptococcus thermophilus, exopolysaccharide, isolation
NCBI PubMed ID: 11251229Journal NLM ID: 7909578Publisher: Butterworth-Heinemann
Correspondence: navarini@polytech3.area.trieste.it
Institutions: POLY-tech s.c.a.r.l., AREA Science Park, Padriciano 99, I- 34012 Trieste, Italy.
Methods: NMR, viscosity measurement, rheological measurements, chiro-optical measurements
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