Found 74 structures.
Displayed structures from 1 to 15
Next 15 structure(s)
Expand all compounds
Collapse all compounds
Show all as text (SweetDB notation)
Show all graphically (SNFG notation)
1. Compound ID: 367
|
a-D-Quip3NAc2Ac4Ac-(1-2)-+
|
-4)-a-L-Rhap-(1-4)-b-D-GlcpA-(1-3)-b-D-GlcpNAc-(1-3)-b-L-Rhap-(1- |
Show graphically |
Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_115136,IEDB_135813,IEDB_136105,IEDB_137340,IEDB_140630,IEDB_141807,IEDB_151527,IEDB_151531,IEDB_225177,IEDB_423153,IEDB_885823
The structure is contained in the following publication(s):
- Article ID: 112
Toukach FV, Bartodziejska B, Senchenkova SN, Wykrota M, Shashkov AS, Rozalski A, Knirel YA "Structure of a new acidic O-antigen of Proteus vulgaris O22 containing O-acetylated 3-acetamido-3,6-dideoxy-D-glucose" -
Carbohydrate Research 318(1-4) (1999) 146-153
The acidic O-specific polysaccharide of Proteus vulgaris O22 was studied using 1H and 13C NMR spectroscopy, including 2D COSY, TOCSY, NOESY, and H-detected 1H, 13C heteronuclear multiple-quantum coherence (HMQC) experiments, and the following structure for the branched pentasaccharide repeating unit was established: [sequence: see text] where Qui3NAc is 3-acetamido-3,6-dideoxyglucose, O-acetylation of QuiNAc at position 4 is stoichiometric and at position 2 nonstoichiometric. Serological relationships of P. vulgaris O22 with some other Proteus strains were substantiated on the level of the O-antigen structures.
Lipopolysaccharide, O-antigen, O-specific polysaccharide, O-acetylation, Proteus vulgaris, 3-Acetamido-3, 6-dideoxy-d-glucose
NCBI PubMed ID: 10515053Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: knirel@ioc.ac.ru
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospekt 47, R-117913 Moscow, Russian Federation, Institute of Microbiology and Immunology, University of Lodz, Banacha 12/16, PL-90-237 Lodz, Poland.
Methods: 13C NMR, 1H NMR, NMR-2D, methylation, NMR, serological methods
- Article ID: 1466
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
Expand this compound
Collapse this compound
2. Compound ID: 449
|
a-D-Quip3NAc-(1-2)-+
|
-3)-b-D-GlcpNAc-(1-3)-b-L-Rhap-(1-4)-a-L-Rhap-(1-4)-b-D-GlcpA-(1- |
Show graphically |
Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide
Contained glycoepitopes: IEDB_115136,IEDB_135813,IEDB_136105,IEDB_137340,IEDB_140630,IEDB_141807,IEDB_151527,IEDB_151531,IEDB_225177,IEDB_423153,IEDB_885823
The structure is contained in the following publication(s):
- Article ID: 112
Toukach FV, Bartodziejska B, Senchenkova SN, Wykrota M, Shashkov AS, Rozalski A, Knirel YA "Structure of a new acidic O-antigen of Proteus vulgaris O22 containing O-acetylated 3-acetamido-3,6-dideoxy-D-glucose" -
Carbohydrate Research 318(1-4) (1999) 146-153
The acidic O-specific polysaccharide of Proteus vulgaris O22 was studied using 1H and 13C NMR spectroscopy, including 2D COSY, TOCSY, NOESY, and H-detected 1H, 13C heteronuclear multiple-quantum coherence (HMQC) experiments, and the following structure for the branched pentasaccharide repeating unit was established: [sequence: see text] where Qui3NAc is 3-acetamido-3,6-dideoxyglucose, O-acetylation of QuiNAc at position 4 is stoichiometric and at position 2 nonstoichiometric. Serological relationships of P. vulgaris O22 with some other Proteus strains were substantiated on the level of the O-antigen structures.
Lipopolysaccharide, O-antigen, O-specific polysaccharide, O-acetylation, Proteus vulgaris, 3-Acetamido-3, 6-dideoxy-d-glucose
NCBI PubMed ID: 10515053Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: knirel@ioc.ac.ru
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospekt 47, R-117913 Moscow, Russian Federation, Institute of Microbiology and Immunology, University of Lodz, Banacha 12/16, PL-90-237 Lodz, Poland.
Methods: 13C NMR, 1H NMR, NMR-2D, methylation, NMR, serological methods
Expand this compound
Collapse this compound
3. Compound ID: 1330
|
a-L-Rhap-(1-3)-+
|
-2)-a-D-Galp-(1-4)-b-D-Manp-(1-3)-b-D-Manp-(1-4)-b-D-GlcpA-(1-3)-b-D-GlcpNAc-(1- |
Show graphically |
Structure type: polymer chemical repeating unit
Aglycon: core
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_115136,IEDB_135813,IEDB_136105,IEDB_136906,IEDB_137340,IEDB_137472,IEDB_137485,IEDB_140630,IEDB_141794,IEDB_141807,IEDB_144983,IEDB_151527,IEDB_151528,IEDB_151531,IEDB_152206,IEDB_190606,IEDB_225177,IEDB_423153,IEDB_885823,IEDB_983930,SB_44,SB_7,SB_72
The structure is contained in the following publication(s):
- Article ID: 415
Wang L, Qu WJ, Reeves PR "Sequence analysis of four Shigella boydii O-antigen loci: Implication for Escherichia coli and Shigella relationships" -
Infection and Immunity 69(11) (2001) 6923-6930
Shigella strains are in reality clones of Escherichia coli and are believed to have emerged relatively recently (G. M. Pupo, R. Lan, and P. R. Reeves, Proc. Natl. Acad. Sci. USA 97:10567-10572, 2000). There are 33 O-antigen forms in these Shigella clones, of which 12 are identical to O antigens of other E. coli strains. We sequenced O-antigen gene clusters from Shigella boydii serotypes 4, 5, 6, and 9 and also studied the O53- and O79-antigen gene clusters of E. coli, encoding O antigens identical to those of S. boydii serotype 4 and S. boydii serotype 5, respectively. In both cases the S. boydii and E. coli O-antigen gene clusters have the same genes and organization. The clusters of both S. boydii 6 and S. boydii 9 O antigens have atypical features, with a functional insertion sequence and a wzx gene located in the orientation opposite to that of all other genes in S. boydii serotype 9 and an rmlC gene located away from other rml genes in S. boydii serotype 6. Sequences of O-antigen gene clusters from another three Shigella clones have been published, and two of them also have abnormal structures, with either the entire cluster or one gene being located on a plasmid in Shigella sonnei or Shigella dysenteriae, respectively. It appears that a high proportion of clusters coding for O antigens specific to Shigella clones have atypical features, perhaps indicating recent formation of these gene clusters.
Sequence Analysis, O-antigen, Escherichia, Escherichia coli, Shigella, implication, Shigella boydii
NCBI PubMed ID: 11598067Journal NLM ID: 0246127Publisher: American Society for Microbiology
Correspondence: reeves@angis.org.au
Institutions: Department of Microbiology, The University of Sydney, Sydney, New South Wales 2006, Australia
Expand this compound
Collapse this compound
4. Compound ID: 1631
|
R-3HOBut-(1-3)-+ Gly-(2-6)-+
| |
-4)-a-D-Quip3N-(1-4)-b-D-Galp-(1-4)-b-D-GlcpNAc-(1-4)-b-D-GlcpA-(1-3)-b-D-GlcpNAc-(1- |
Show graphically |
Structure type: suggested polymer biological repeating unit
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_115136,IEDB_130646,IEDB_135813,IEDB_136044,IEDB_137340,IEDB_137472,IEDB_140108,IEDB_140122,IEDB_140630,IEDB_141794,IEDB_141807,IEDB_151527,IEDB_151531,IEDB_190606,IEDB_423153,SB_165,SB_166,SB_187,SB_195,SB_30,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 503
Lycknert K, Widmalm G "Dynamics of the Escherichia coli O91 O-antigen polysaccharide in solution as studied by carbon-13 NMR relaxation" -
Biomacromolecules 5(3) (2004) 1015-1020
The dynamics of the O-antigen part of the lipopolysaccharide from the enterohemorrhagic Escherichia coli O91 has been determined in solution using (13)C NMR relaxation measurements at two magnetic field strengths,9.4 and 14.1 T, thereby facilitating the testing of several dynamical models. The biological repeating unit, consisting of five sugar residues and substituents, could be determined by spectral analysis of different (1)H,(13)C correlations and corroborated by the relaxation data. The site specifically (13)C-labeled material was shown to have approximately 10 repeating units with a narrow distribution. A model-free analysis of the relaxation data revealed a complex dynamical behavior where the sugar residues could be described by a global correlation time (tau(m) = 5.4 ns), generalized order parameters (S(2) approximately 0.63), and different correlation times for internal motions related to their position in the repeating unit along the polymer (tau(e) approximately 360-520 ps). One of the sugar residues showed, in addition, a chemical exchange contribution. Furthermore, a substituent on another sugar residue was described by two order parameters (S(f)(2) = 0.51 and S(s)(2) = 0.21). The solution dynamics of the polysaccharide are thus described by highly intricate motions, both in amplitude and time scales. These results are of significance in the general description of polysaccharides surrounding bacterial cell surfaces and in the presentation of antigenic epitopes to the immune system of an invaded host.
Lipopolysaccharide, NMR, chemistry, correlation, Bacterial, host, significance, polysaccharide, O-antigen, repeating unit, analysis, antigenic, polysaccharides, O antigen, cell, polymer, Escherichia, Escherichia coli, epitope, complex, epitopes, dynamics, biological, chemical, sugar, position, surface, time, site, measurement, solution, relaxation, distribution, exchange, organic, antigenic epitopes, behavior, biological repeating unit, chemical exchange, enterohemorrhagic, immune, immune system, internal motion, model, models, motion, order, presentation
NCBI PubMed ID: 15132695Journal NLM ID: 100892849Publisher: Washington, DC: American Chemical Society
Institutions: Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, Stockholm, Sweden
Methods: NMR, MD simulations
- Article ID: 750
Kjellberg A, Weintraub A, Widmalm G "Structural determination and biosynthetic studies of the O-antigenic polysaccharide from the enterohemorrhagic Escherichia coli O91 using 13C-enrichment and NMR spectroscopy" -
Biochemistry 38(38) (1999) 12205-12211
The structure of the O-antigenic polysaccharide from the enterohemorrhagic Escherichia coli O91 has been determined using primarily NMR spectroscopy on the (13)C-enriched polysaccharide. The O-antigen is composed of pentasaccharide repeating units with the following structure: →4)-β-D-Galp-(1→4)-β-D-GlcpNAc-(1→4)-β-D-GlcpA-6-N-Gly-(1→3)-β-D-GlcpNAc-(1→4)-α-D-Quip-3-N-[(R)-3-hydroxy butyra mido]-(1→. The bacterium was grown with D-[UL-(13)C]glucose in the medium which resulted in an overall degree of labeling of approximately 65% in the sugar residues and approximately 50% in the N-acyl substituents, indicating some metabolic dilution in the latter. The (13)C-enrichment of the polysaccharide proved valuable since NMR assignments could be made on the basis of (13)C, (13)C-connectivity in uniformly labeled residues. The biosynthesis of the (R)-3-hydroxybutyramido substituent via C(2) fragments was identified by NMR spectroscopy. The (R)-configuration at C3 is in accord with fatty acid biosynthesis. Additional cultures with specifically labeled D-[1-(13)C]glucose or D-[6-(13)C]glucose corroborated the direct incorporation of glucose as the building block for the hexose skeletons in the polysaccharide and the biosynthesis of acyl substituents occurring via the triose pool followed by decarboxylation to give acetyl building blocks labeled with (13)C at the methyl group.
NMR, biosynthetic, structural, polysaccharide, antigenic, Escherichia, Escherichia coli, determination, O-antigenic, O-antigenic polysaccharide, structural determination, NMR spectroscopy, spectroscopy, enterohemorrhagic
NCBI PubMed ID: 10493787Journal NLM ID: 0370623Publisher: American Chemical Society
Institutions: Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, Stockholm, Sweden
Methods: NMR
- Article ID: 3196
Stenutz R, Weintraub A, Widmalm G "The structures of Escherichia coli O-polysaccharide antigens" -
FEMS Microbiology Reviews 30(3) (2006) 382-403
Escherichia coli is usually a non-pathogenic member of the human colonic flora. However, certain strains have acquired virulence factors and may cause a variety of infections in humans and in animals. There are three clinical syndromes caused by E. coli: (i) sepsis/meningitis; (ii) urinary tract infection and (iii) diarrhoea. Furthermore the E. coli causing diarrhoea is divided into different 'pathotypes' depending on the type of disease, i.e. (i) enterotoxigenic; (ii) enteropathogenic; (iii) enteroinvasive; (iv) enterohaemorrhagic; (v) enteroaggregative and (vi) diffusely adherent. The serotyping of E. coli based on the somatic (O), flagellar (H) and capsular polysaccharide antigens (K) is used in epidemiology. The different antigens may be unique for a particular serogroup or antigenic determinants may be shared, resulting in cross-reactions with other serogroups of E. coli or even with other members of the family Enterobacteriacea. To establish the uniqueness of a particular serogroup or to identify the presence of common epitopes, a database of the structures of O-antigenic polysaccharides has been created. The E. coli database (ECODAB) contains structures, nuclear magnetic resonance chemical shifts and to some extent cross-reactivity relationships. All fields are searchable. A ranking is produced based on similarity, which facilitates rapid identification of strains that are difficult to serotype (if known) based on classical agglutinating methods. In addition, results pertinent to the biosynthesis of the repeating units of O-antigens are discussed. The ECODAB is accessible to the scientific community at http://www.casper.organ.su.se/ECODAB/
NMR, structure, serotype, O-antigen, Enterobacteriacea, database
NCBI PubMed ID: 16594963Publication DOI: 10.1111/j.1574-6976.2006.00016.xJournal NLM ID: 8902526Publisher: Oxford University Press
Correspondence: andrej.weintraub@ki.se
Institutions: Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, Stockholm, Sweden
- Article ID: 4674
Fontana C, Kovacs H, Widmalm G "NMR structure analysis of uniformly C-labeled carbohydrates" -
Journal of Biomolecular NMR 56(2) (2014) 95-110
In this study, a set of nuclear magnetic resonance experiments, some of them commonly used in the study of 13C-labeled proteins and/or nucleic acids, is applied for the structure determination of uniformly 13C-enriched carbohydrates. Two model substances were employed: one compound of low molecular weight [(UL-13C)-sucrose, 342 Da] and one compound of medium molecular weight (13C-enriched O-antigenic polysaccharide isolated from Escherichia coli O142, ~10 kDa). The first step in this approach involves the assignment of the carbon resonances in each monosaccharide spin system using the anomeric carbon signal as the starting point. The 13C resonances are traced using 13C-13C correlations from homonuclear experiments, such as (H)CC-CT-COSY, (H)CC-NOESY, CC-CT-TOCSY and/or virtually decoupled (H)CC-TOCSY. Based on the assignment of the 13C resonances, the 1H chemical shifts are derived in a straightforward manner using one-bond 1H-13C correlations from heteronuclear experiments (HC-CT-HSQC). In order to avoid the 1 J CC splitting of the 13C resonances and to improve the resolution, either constant-time (CT) in the indirect dimension or virtual decoupling in the direct dimension were used. The monosaccharide sequence and linkage positions in oligosaccharides were determined using either 13C or 1H detected experiments, namely CC-CT-COSY, band-selective (H)CC-TOCSY, HC-CT-HSQC-NOESY or long-range HC-CT-HSQC. However, due to the short T2 relaxation time associated with larger polysaccharides, the sequential information in the O-antigen polysaccharide from E. coli O142 could only be elucidated using the 1H-detected experiments. Exchanging protons of hydroxyl groups and N-acetyl amides in the 13C-enriched polysaccharide were assigned by using HC-H2BC spectra. The assignment of the N-acetyl groups with 15N at natural abundance was completed by using HN-SOFAST-HMQC, HNCA, HNCO and 13C-detected (H)CACO spectra.
NMR, carbohydrates, structure, Escherichia coli, Structure determination, 13C-uniform labeling
NCBI PubMed ID: 24771296Publication DOI: 10.1007/s10858-014-9830-6Journal NLM ID: 9110829Publisher: ESCOM Science Publishers
Correspondence: G. Widmalm
Institutions: Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, Stockholm, Sweden
Methods: 13C NMR, 1H NMR, NMR-2D, 13C-enriched polysaccharide
- Article ID: 5472
Liu B, Furevi A, Perepelov AV, Guo X, Cao H, Wang Q, Reeves PR, Knirel YA, Wang L, Widmalm G "Structure and genetics of Escherichia coli O antigens" -
FEMS Microbiology Reviews 44(6) (2020) 655-683
Escherichia coli includes clonal groups of both commensal and pathogenic strains, with some of the latter causing serious infectious diseases. O antigen variation is current standard in defining strains for taxonomy and epidemiology, providing the basis for many serotyping schemes for Gram-negative bacteria. This review covers the diversity in E. coli O antigen structures and gene clusters, and the genetic basis for the structural diversity. Of the 187 formally defined O antigens, six (O31, O47, O67, O72, O94 and O122) have since been removed and four (O14, O34, O89 and O144) strains do not produce any O antigen. Therefore, structures are presented for 176 of the 181 E. coli O antigens, some of which include subgroups. Most (93%) of these O antigens are synthesized via the Wzx/Wzy pathway, 11 via the ABC transporter pathway, with O20, O57 and O60 still uncharacterized due to failure to find their O antigen gene clusters. Biosynthetic pathways are given for 38 of the 49 sugars found in E. coli O antigens, and several pairs or groups of the E. coli antigens that have related structures show close relationships of the O antigen gene clusters within clades, thereby highlighting the genetic basis of the evolution of diversity.
structure, O antigen, Escherichia coli, gene cluster, serogroup, diversity
NCBI PubMed ID: 31778182Publication DOI: 10.1093/femsre/fuz028Journal NLM ID: 8902526Publisher: Oxford University Press
Correspondence: G. Widmalm
; Lei Wang
Institutions: Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, Stockholm, Sweden, N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Tianjin Key Laboratory of Microbial Functional Genomics, Tianjin, China, The Key Laboratory of Molecular Microbiology and Technology, Ministry of Education, Tianjin, China, School of Molecular and Microbial Bioscience (G08), University of Sydney, Sydney, Australia, TEDA Institute of Biological Sciences and Biotechnology, Nankai University, TEDA, Tianjin, China, Department of Immunology, School of Basic Medical Sciences, Tianjin Medical University, Tianjin, China
Expand this compound
Collapse this compound
5. Compound ID: 1868
|
a-D-GlcpA3(%)Ac4(%)Ac-(1-4)-+
|
-4)-b-D-GlcpA-(1-3)-b-D-GlcpNAc6(%)Ac-(1-6)-b-D-GlcpN3(%)Ac-(1-
|
L-Ala-(1-2)-+ |
Show graphically |
Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_115136,IEDB_135813,IEDB_137340,IEDB_140630,IEDB_141807,IEDB_151527,IEDB_151531,IEDB_423153
The structure is contained in the following publication(s):
- Article ID: 605
Arbatsky NP, Shashkov AS, Widmalm G, Knirel YA, Zych K, Sidorczyk Z "Structure of the O-specific polysaccharide of Proteus penneri strain 25 containing N-(L-alanyl) and multiple O-acetyl groups in a tetrasaccharide repeating unit" -
Carbohydrate Research 298 (1997) 229-235
Based on sugar and methylation analyses, O-deacetylation, Smith degradation, and 1H and 13C NMR spectroscopy, including 2D COSY, 1H-detected 1H,13C heteronuclear single-quantum coherence (HSQC), and 1H-detected 1H,13C heteronuclear multiple-bond connectivity (HMBC) experiments, the following structure of the O-specific polysaccharide of Proteus penneri strain 25 was established: -4)bDGlcpA(1-3)[0.4Ac-6)]bDGlcpNAc(1-6)[0.3Ac-3/4)aDGlcpA(1-4),(0.5Ac-3)]bDGlcpN(L-Ala)(1-, where D-GlcN(L-Ala) is 2-(L-alanylamido)-2-deoxy-D-glucose.
Lipopolysaccharide, structure, O-antigen, Proteus penneri, Bacterial polysaccharide, enterobacteria, 2-(l-Alanylamido)-2-deoxy-d-glucose
NCBI PubMed ID: 9090817Publication DOI: 10.1016/S0008-6215(96)00308-4Journal NLM ID: 0043535Publisher: Elsevier
Institutions: Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, Stockholm, Sweden, N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russian Federation, Institute of Microbiology and Immunology, University of Lodz, Banacha 12/16, 90-237 Lodz, Poland
Methods: NMR-2D, methylation, GLC-MS, sugar analysis, Smith degradation, de-O-acetylation, GPC
- Article ID: 1466
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
Expand this compound
Collapse this compound
6. Compound ID: 1893
|
a-D-Quip3NAc2Ac4Ac-(1-3)-+
|
-3)-b-D-GlcpNAc-(1-2)-b-L-Rhap-(1-4)-a-L-Rhap-(1-4)-b-D-GlcpA-(1- |
Show graphically |
Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_115136,IEDB_135813,IEDB_136105,IEDB_137340,IEDB_140630,IEDB_141807,IEDB_151527,IEDB_151531,IEDB_225177,IEDB_423153,IEDB_885823
The structure is contained in the following publication(s):
- Article ID: 625
Bartodziejska B, Shashkov AS, Babicka D, Grachev AA, Torzewska A, Paramonov NA, Chernyak AY, Rozalski A, Knirel YA "Structural and serological studies on a new acidic O-specific polysaccharide of Proteus vulgaris O32" -
European Journal of Biochemistry 256(2) (1998) 488-493
The following structure of the O-specific polysaccharide chain (O-antigen) of the Proteus vulgaris O32 lipopolysaccharide (LPS) was established by 1H NMR and 13C NMR spectroscopy, including twodimensional NOESY and H-detected 1H,13C heteronuclear multiple-quantum coherence (HMQC) experiments: -2)aLRhap(I)(1-2)aLRhap(II)(1-4)bDGalpA(1-3)[Ac(1-2)]bDGlcpN(1-4)aDGalpA(1-. In addition, an O-acetyl group was detected, which, most probably, is located at position 3 of a part of Rhap(I) residues. Serological studies, using rabbit polyclonal anti-(P. vulgaris O32) serum, homologous and heterologous Proteus O-antigens and related artificial antigens, revealed the importance of an a-D-GalA-associated epitope in manifesting the immunospecificity of P. vulgaris O32 and substantiated serological relationships between the O-antigen studied and those of some other Proteus strains.
Lipopolysaccharide, O-antigen, serological specificity, Proteus vulgaris, bacterial polysaccharide structure
NCBI PubMed ID: 9760190Journal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Correspondence: rozala@biol.uni.lodz.pl
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Institute of Microbiology and Immunology, University of Lodz, Lodz, Poland
Methods: NMR-2D, EIA
- Article ID: 627
Bartodziejska B, Torzewska A, Babicka D, Wykrota M, Rozalski A, Perepelov AV, Toukach FV, Knirel YA "Epitope specificity of polyclonal rabbit antisera against Proteus vulgaris O-antigens" -
Advances in Experimental Medicine and Biology 485 (2000) 243-247
No abstract
virulence, O-antigen, Proteus vulgaris, epitope specificity
NCBI PubMed ID: 11109112Journal NLM ID: 0121103Publisher: Kluwer Academic/Plenum Publishers
Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Department of Immunobiology of Bacteria, Institute of Microbiologyand Immunology, University of Lodz, 90-237 Lodz, Banacha 12/16, Poland
Methods: NMR-2D, DOC-PAGE, Western blotting, passive immunohemolysis (PIH)
- Article ID: 5760
Dobrochaeva K, Khasbiulina N, Shilova N, Antipova N, Obukhova P, Galanina O, Blixt O, Kunz H, Filatov A, Knirel Y, Le Pendu J, Khaidukov S, Bovin N "Specificity of human natural antibodies referred to as anti-Tn" -
Molecular Immunology 120 (2020) 74-82
To understand the role of human natural IgM known as antibodies against the carbohydrate epitope Tn, the antibodies were isolated using GalNAcα-Sepharose affinity chromatography, and their specificity was profiled using microarrays (a glycan array printed with oligosaccharides and bacterial polysaccharides, as well as a glycopeptide array), flow cytometry, and inhibition ELISA. The antibodies bound a restricted number of GalNAcα-terminated oligosaccharides better than the parent monosaccharide, e.g., 6-O-Su-GalNAcα and GalNAcα1-3Galβ1-3(4)GlcNAcβ. The binding with several bacterial polysaccharides that have no structural resemblance to the affinity ligand GalNAcα was quite unexpected. Given that GalNAcα is considered the key fragment of the Tn antigen, it is surprising that these antibodies bind weakly GalNAcα-OSer and do not bind a wide variety of GalNAcα-OSer/Thr-containing mucin glycopeptides. At the same time, we have observed specific binding to cells having Tn-positive glycoproteins containing similar glycopeptide motifs in a conformationally rigid macromolecule. Thus, specific recognition of the Tn antigen apparently requires that the naturally occurring "anti-Tn" IgM recognize a complex epitope comprising the GalNAcα as an essential component and a fairly long amino acid sequence where the amino acids adjacent to GalNAcα do not contact the antibody paratope; i.e., the antibodies recognize a spatial epitope or a molecular pattern rather than a classical continuous sequence. In addition, we have not found any increase in the binding of natural antibodies when GalNAcα residues were clustered. These results may help in further development of anticancer vaccines based on synthetic Tn constructs.
cancer, glycans, natural antibodies, anti-glycan antibodies, Tn antigen
NCBI PubMed ID: 32087569Publication DOI: 10.1016/j.molimm.2020.02.005Journal NLM ID: 7905289Publisher: Elsevier
Correspondence: professorbovin@yandex.ru
Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, 16/10 Miklukho-Maklaya, Moscow, Russian Federation, Semiotik LLC, 16/10 Miklukho-Maklaya, Moscow, Russian Federation, National Medical Research Center for Obstetrics, Gynecology and Perinatology Named after Academician V.I. Kulakov of the Ministry of Healthcare of Russian Federation, Moscow, Russian Federation, National Research University Higher School of Economics, Moscow, Russian Federation, Department of Chemistry, Chemical Biology, University of Copenhagen, Thorvaldsensvej 40, 1871 Frederiksberg C, Denmark, Institut Fur Organische Chemie, Johannes Gutenberg-Universitat Mainz, Duesbergweg 10-14, D-55128, Mainz, Germany, Institute of Immunology, Federal Medical-Biological Agency of Russia, Moscow, Russian Federation, University of Nantes, Inserm, U892 IRT UN, 8 Quai MonCousu, BP70721 Nantes, FR 44007, France
Methods: ELISA, affinity chromatography, flow cytometry analysis, printed glycan array (PGA) analysis, FACS assay
Expand this compound
Collapse this compound
7. Compound ID: 1955
|
a-D-GlcpA-(1-4)-+
|
-4)-b-D-GlcpA-(1-3)-b-D-GlcpNAc-(1-6)-b-D-GlcpN-(1-
|
L-Ala-(1-2)-+ |
Show graphically |
Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_115136,IEDB_135813,IEDB_137340,IEDB_140630,IEDB_141807,IEDB_151527,IEDB_151531,IEDB_423153
The structure is contained in the following publication(s):
- Article ID: 605
Arbatsky NP, Shashkov AS, Widmalm G, Knirel YA, Zych K, Sidorczyk Z "Structure of the O-specific polysaccharide of Proteus penneri strain 25 containing N-(L-alanyl) and multiple O-acetyl groups in a tetrasaccharide repeating unit" -
Carbohydrate Research 298 (1997) 229-235
Based on sugar and methylation analyses, O-deacetylation, Smith degradation, and 1H and 13C NMR spectroscopy, including 2D COSY, 1H-detected 1H,13C heteronuclear single-quantum coherence (HSQC), and 1H-detected 1H,13C heteronuclear multiple-bond connectivity (HMBC) experiments, the following structure of the O-specific polysaccharide of Proteus penneri strain 25 was established: -4)bDGlcpA(1-3)[0.4Ac-6)]bDGlcpNAc(1-6)[0.3Ac-3/4)aDGlcpA(1-4),(0.5Ac-3)]bDGlcpN(L-Ala)(1-, where D-GlcN(L-Ala) is 2-(L-alanylamido)-2-deoxy-D-glucose.
Lipopolysaccharide, structure, O-antigen, Proteus penneri, Bacterial polysaccharide, enterobacteria, 2-(l-Alanylamido)-2-deoxy-d-glucose
NCBI PubMed ID: 9090817Publication DOI: 10.1016/S0008-6215(96)00308-4Journal NLM ID: 0043535Publisher: Elsevier
Institutions: Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, Stockholm, Sweden, N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russian Federation, Institute of Microbiology and Immunology, University of Lodz, Banacha 12/16, 90-237 Lodz, Poland
Methods: NMR-2D, methylation, GLC-MS, sugar analysis, Smith degradation, de-O-acetylation, 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
Expand this compound
Collapse this compound
8. Compound ID: 2067
|
b-D-GlcpNAc-(1-4)-b-D-GlcpA-(1-3)-b-D-GlcpNAc-(1-4)-b-D-GlcpA-(1-3)-b-D-GlcpNAc-(1--/4-methoxyphenyl/ |
Show graphically |
Structure type: oligomer
Aglycon: 4-methoxyphenyl
Contained glycoepitopes: IEDB_115136,IEDB_135813,IEDB_137340,IEDB_140630,IEDB_141807,IEDB_151527,IEDB_151531,IEDB_423153
The structure is contained in the following publication(s):
- Article ID: 673
Halkes KM, Slagnek TM, Hyppönen TK, Kruiskamp PH, Ogawa T, Kamerling JP, Vliegenthart JFG "Synthesis of hyaluronic-acid-related oligosaccharides and analogues, as their 4-methoxyphenyl glycosides, having N-acetyl-b-D-glucosamine at the reducing end" -
Carbohydrate Research 309 (1998) 161-174
To contribute to the possibilities to study the ability of oligosaccharide fragments of hyaluronic acid to induce angiogenesis, several hyaluronic-acid-related oligosaccharides and their 6-O-sulfated analogues were synthesised as their 4-methoxyphenyl glycosides having 2-acetamido-2-deoxy-D-glucopyranose at the reducing end. In all syntheses described, the D-glucopyranosyluronic acid residue was obtained by oxidation at C-6 of a corresponding D-glucopyranosyl residue after construction of the oligosaccharide backbone, using pyridinium dichromate and acetic anhydride.
oxidation, hyaluronic acid oligosaccharides, hyaluronic acid sulfated analogues
NCBI PubMed ID: 9741075Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: kame@boc.chem.uu.nl
Institutions: Bijvoet Center, Department of Bio-Organic Chemistry, Utrecht University, Utrecht, The Netherlands, Agrotechnological Research Institute (ATO-DLO), Wageningen, The Netherlands, TheInstitute of Physical andChemical Research(RIKEN),Wako-shi,Hirosawa 2-1, Saitama, 350-01, Japan
Expand this compound
Collapse this compound
9. Compound ID: 2145
|
b-D-GlcpA-(1-3)-b-D-GlcpNAc-(1-4)-b-D-GlcpA-(1-3)-b-D-GlcpNAc-(1-4)-b-D-GlcpA-(1-3)-b-D-GlcpNAc-(1--/4-methoxyphenyl/ |
Show graphically |
Structure type: oligomer
Aglycon: 4-methoxyphenyl
Contained glycoepitopes: IEDB_115136,IEDB_135813,IEDB_137340,IEDB_140630,IEDB_141807,IEDB_151527,IEDB_151531,IEDB_231709,IEDB_423153
The structure is contained in the following publication(s):
- Article ID: 673
Halkes KM, Slagnek TM, Hyppönen TK, Kruiskamp PH, Ogawa T, Kamerling JP, Vliegenthart JFG "Synthesis of hyaluronic-acid-related oligosaccharides and analogues, as their 4-methoxyphenyl glycosides, having N-acetyl-b-D-glucosamine at the reducing end" -
Carbohydrate Research 309 (1998) 161-174
To contribute to the possibilities to study the ability of oligosaccharide fragments of hyaluronic acid to induce angiogenesis, several hyaluronic-acid-related oligosaccharides and their 6-O-sulfated analogues were synthesised as their 4-methoxyphenyl glycosides having 2-acetamido-2-deoxy-D-glucopyranose at the reducing end. In all syntheses described, the D-glucopyranosyluronic acid residue was obtained by oxidation at C-6 of a corresponding D-glucopyranosyl residue after construction of the oligosaccharide backbone, using pyridinium dichromate and acetic anhydride.
oxidation, hyaluronic acid oligosaccharides, hyaluronic acid sulfated analogues
NCBI PubMed ID: 9741075Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: kame@boc.chem.uu.nl
Institutions: Bijvoet Center, Department of Bio-Organic Chemistry, Utrecht University, Utrecht, The Netherlands, Agrotechnological Research Institute (ATO-DLO), Wageningen, The Netherlands, TheInstitute of Physical andChemical Research(RIKEN),Wako-shi,Hirosawa 2-1, Saitama, 350-01, Japan
Expand this compound
Collapse this compound
10. Compound ID: 2146
|
a-L-4dthrHexp4enA-(1-3)-b-D-GlcpNAc-(1-4)-b-D-GlcpA-(1-3)-b-D-GlcpNAc-(1-4)-b-D-GlcpA-(1-3)-b-D-GlcpNAc-(1--/4-methoxyphenyl/ |
Show graphically |
Structure type: oligomer
Aglycon: 4-methoxyphenyl
Contained glycoepitopes: IEDB_115136,IEDB_135813,IEDB_137340,IEDB_140630,IEDB_141807,IEDB_151527,IEDB_151531,IEDB_423153
The structure is contained in the following publication(s):
- Article ID: 673
Halkes KM, Slagnek TM, Hyppönen TK, Kruiskamp PH, Ogawa T, Kamerling JP, Vliegenthart JFG "Synthesis of hyaluronic-acid-related oligosaccharides and analogues, as their 4-methoxyphenyl glycosides, having N-acetyl-b-D-glucosamine at the reducing end" -
Carbohydrate Research 309 (1998) 161-174
To contribute to the possibilities to study the ability of oligosaccharide fragments of hyaluronic acid to induce angiogenesis, several hyaluronic-acid-related oligosaccharides and their 6-O-sulfated analogues were synthesised as their 4-methoxyphenyl glycosides having 2-acetamido-2-deoxy-D-glucopyranose at the reducing end. In all syntheses described, the D-glucopyranosyluronic acid residue was obtained by oxidation at C-6 of a corresponding D-glucopyranosyl residue after construction of the oligosaccharide backbone, using pyridinium dichromate and acetic anhydride.
oxidation, hyaluronic acid oligosaccharides, hyaluronic acid sulfated analogues
NCBI PubMed ID: 9741075Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: kame@boc.chem.uu.nl
Institutions: Bijvoet Center, Department of Bio-Organic Chemistry, Utrecht University, Utrecht, The Netherlands, Agrotechnological Research Institute (ATO-DLO), Wageningen, The Netherlands, TheInstitute of Physical andChemical Research(RIKEN),Wako-shi,Hirosawa 2-1, Saitama, 350-01, Japan
Expand this compound
Collapse this compound
11. Compound ID: 2147
|
b-D-GlcpA-(1-3)-b-D-GlcpNAc-(1-4)-b-D-GlcpA-(1-3)-b-D-GlcpNAc-(1-4)-b-D-GlcpA-(1-3)-b-D-GlcpNAc-(1-7)-4HOBz4Me |
Show graphically |
Structure type: oligomer
Contained glycoepitopes: IEDB_115136,IEDB_135813,IEDB_137340,IEDB_140630,IEDB_141807,IEDB_151527,IEDB_151531,IEDB_231709,IEDB_423153
The structure is contained in the following publication(s):
- Article ID: 673
Halkes KM, Slagnek TM, Hyppönen TK, Kruiskamp PH, Ogawa T, Kamerling JP, Vliegenthart JFG "Synthesis of hyaluronic-acid-related oligosaccharides and analogues, as their 4-methoxyphenyl glycosides, having N-acetyl-b-D-glucosamine at the reducing end" -
Carbohydrate Research 309 (1998) 161-174
To contribute to the possibilities to study the ability of oligosaccharide fragments of hyaluronic acid to induce angiogenesis, several hyaluronic-acid-related oligosaccharides and their 6-O-sulfated analogues were synthesised as their 4-methoxyphenyl glycosides having 2-acetamido-2-deoxy-D-glucopyranose at the reducing end. In all syntheses described, the D-glucopyranosyluronic acid residue was obtained by oxidation at C-6 of a corresponding D-glucopyranosyl residue after construction of the oligosaccharide backbone, using pyridinium dichromate and acetic anhydride.
oxidation, hyaluronic acid oligosaccharides, hyaluronic acid sulfated analogues
NCBI PubMed ID: 9741075Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: kame@boc.chem.uu.nl
Institutions: Bijvoet Center, Department of Bio-Organic Chemistry, Utrecht University, Utrecht, The Netherlands, Agrotechnological Research Institute (ATO-DLO), Wageningen, The Netherlands, TheInstitute of Physical andChemical Research(RIKEN),Wako-shi,Hirosawa 2-1, Saitama, 350-01, Japan
Expand this compound
Collapse this compound
12. Compound ID: 2204
|
-4)-b-D-Glcp-(1-3)-b-D-GalpNAc-(1-4)-b-D-GlcpA-(1-3)-b-D-GlcpNAc-(1-2)-a-D-Galp-(1-3)-b-D-Manp-(1- |
Show graphically |
Structure type: polymer chemical repeating unit
Compound class: CPS
Contained glycoepitopes: IEDB_115136,IEDB_130648,IEDB_131187,IEDB_135813,IEDB_136906,IEDB_137340,IEDB_137472,IEDB_137473,IEDB_137485,IEDB_140630,IEDB_141794,IEDB_141807,IEDB_142488,IEDB_144983,IEDB_146664,IEDB_151527,IEDB_151528,IEDB_151531,IEDB_152206,IEDB_190606,IEDB_423153,IEDB_983930,IEDB_983931,SB_192,SB_44,SB_7,SB_72
The structure is contained in the following publication(s):
- Article ID: 713
Kalelkar S, Glushka J, van Halbeek H, Morris LC, Cherniak R "Structure of the capsular polysaccharide of Clostridium perfringens Hobbs 5 as determiend by NMR spectroscopy" -
Carbohydrate Research 299(3) (1997) 119-128
The complete primary structure of the capsular polysaccharide of Clostridium perfringens Hobbs 5, an anaerobic bacterium implicated in food poisoning, was determined. The polysaccharide was isolated from C. perfringens Hobbs 5 cells, after deproteination, by ethanol precipitation and by ion-exchange chromatography. The polysaccharide was comprised of glucose, galactose, mannose, N-acetylglucosamine, N-acetylgalactosamine, and glucuronic acid, in equimolar ratios. Sequence and linkage assignments of the glycosyl residues were obtained by NMR spectroscopy, specifically by the combination of two-dimensional homonuclear TOCSY and NOESY experiments and heteronuclear (1H, 13C) multiple-quantum coherence (HMQC, HMQC-COSY, HMQC-TOCSY and HMBC) experiments. Thus, the envelope polysaccharide of C. perfringens Hobbs 5 was found to be a polymer composed of a hexasaccharide repeating unit with the following structure: [formula: see text] This structure is novel among bacterial cell-surface polysaccharides, and it is the first of many serotypically distinct capsular polysaccharides of C. perfringens to be described.
NMR, antigen, structure, capsular, polysaccharide, capsular polysaccharide, NMR spectroscopy, spectroscopy, 2D NMR spectroscopy, HMQC, Clostridium, Clostridium perfingens, TOCSY, NOESY
NCBI PubMed ID: 9163894Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: cherniak@gsu.edu
Institutions: Department of Chemistry (LBCS), Georgia State University, Atlanta, GA, USA
Methods: 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
Expand this compound
Collapse this compound
13. Compound ID: 2596
|
a-D-GlcpA-(1-4)-+
|
-4)-b-D-GlcpA-(1-3)-b-D-GlcpNAc-(1-6)-b-D-GlcpN3(50%)Ac-(1-
|
L-Ala-(1-2)-+ |
Show graphically |
Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide
Contained glycoepitopes: IEDB_115136,IEDB_135813,IEDB_137340,IEDB_140630,IEDB_141807,IEDB_151527,IEDB_151531,IEDB_423153
The structure is contained in the following publication(s):
- Article ID: 889
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, polysaccharides, O-specific, O-specific polysaccharide, Proteus, 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
Expand this compound
Collapse this compound
14. Compound ID: 2597
|
/Variants 0/-a-D-GlcpA-(1-4)-+
|
-4)-b-D-GlcpA-(1-3)-b-D-GlcpNAc6(40%)Ac-(1-6)-b-D-GlcpN3(30%)Ac-(1-
|
L-Ala-(1-2)-+
/Variants 0/ is:
50%Ac-4)-
OR (exclusively)
50%Ac-3)- |
Show graphically |
Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide
Contained glycoepitopes: IEDB_115136,IEDB_135813,IEDB_137340,IEDB_140630,IEDB_141807,IEDB_151527,IEDB_151531,IEDB_423153
The structure is contained in the following publication(s):
- Article ID: 889
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, polysaccharides, O-specific, O-specific polysaccharide, Proteus, 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
Expand this compound
Collapse this compound
15. Compound ID: 2676
|
GroN-(2-6)-+
|
-2)-b-D-GalpA3(30%)Ac4(50%)Ac-(1-3)-a-D-GalpNAc-(1-4)-b-D-GlcpA-(1-3)-b-D-GlcpNAc-(1- |
Show graphically |
Structure type: suggested polymer biological repeating unit
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_115136,IEDB_130648,IEDB_135813,IEDB_137340,IEDB_137473,IEDB_1391961,IEDB_140630,IEDB_141584,IEDB_141807,IEDB_151527,IEDB_151531,IEDB_423153,IEDB_885822
The structure is contained in the following publication(s):
- Article ID: 913
Landersjo C, Weintraub A, Widmalm G "Structure determination of the O-antigen polysaccharide from the enterovasive Escherichia coli (EIEC) O143 by component analysis and NMR spectroscopy" -
Carbohydrate Research 291 (1996) 209-216
no abstract
Lipopolysaccharide, NMR, LPS, structure, strain, structural, polysaccharide, O-antigen, analysis, O antigen, Escherichia, Escherichia coli, determination, NMR spectroscopy, uronic acid, spectroscopy, component, Structure determination, 2-amino-1, 3-propanediol
NCBI PubMed ID: 8864232Publication DOI: 10.1016/S0008-6215(96)00168-1Journal NLM ID: 0043535Publisher: Elsevier
Institutions: Department of Organic Chemisto, Arrhenius Laboratoo, Stockholm University, Stockholm, Sweden, Karolinska Institute, Department of Immunology, Microbiology Pathology and Infectious Diseases, Diuision of Clinical Bacteriology, Huddinge Unit,ersity Hospital, S- 141 86 Huddinge, Sweden
Methods: NMR-2D, NMR, sugar analysis, de-O-acetylation, determination of absolute configuration
Expand this compound
Collapse this compound
Next 15 structure(s)
Total list of structure IDs on all result pages of the current query:
Total list of corresponding CSDB IDs (record IDs):
Execution: 7 sec