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1. Compound ID: 336
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R-3HOBut-(1-2)-+ a-D-Glcp-(1-6)-+
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-6)-a-D-GlcpN3(30%)Ac-(1-4)-a-D-GalpNAc-(1-3)-b-D-GalpNAc-(1-2)-a-D-Glcp-(1-P- |
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Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_130648,IEDB_137473,IEDB_1391961,IEDB_141582,IEDB_141584,IEDB_141807,IEDB_142488,IEDB_144998,IEDB_145002,IEDB_146664,IEDB_151531,IEDB_153207,IEDB_885822,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 94
Gamian A, Katzenellenbogen E, Romanowska E, Grosskurth H, Dabrowski J "Reinvestigation of the O-specific polysaccharides of Hafnia alvei lipopolysaccharides isolated from strains ATCC 13337 and 1187" -
Carbohydrate Research 307(1-2) (1998) 173-176
The structure of the O-specific polysaccharides of the lipopolysaccharides produced by Hafnia alvei strains ATCC 13337 and 1187 was reinvestigated. The position of phosphate group in the repeating units of the polysaccharides was established with the aid of 1H detected, 31P edited NMR spectra. According to the results obtained, the polysaccharides are teichoic acid-like polymers with the repeating units of the following structure: [formula: see text] where Acyl = D-3-hydroxylbutyryl, and 3-O-acetylation was approximately 30%
Lipopolysaccharide, O-specific polysaccharide, Hafnia alvei
NCBI PubMed ID: 9658571Publication DOI: 10.1016/S0008-6215(98)00035-4Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: gamian@immuno.iitd.pan.wroc.pl
Institutions: Ludwik Hirszfeld Institute of Immunology and Experimental Therapy, Wroclaw, Poland
Methods: NMR-2D, methylation, FAB-MS, NMR, sugar analysis, Smith degradation
- Article ID: 3364
Nikolaev AV, Botvinko IV, Ross AJ "Natural phosphoglycans containing glycosyl phosphate units: structural diversity and chemical synthesis" -
Carbohydrate Research 342(3-4) (2007) 297-344
An anomeric phosphodiester linkage formed by a glycosyl phosphate unit and a hydroxyl group of another monosaccharide is found in many glycopolymers of the outer membrane in bacteria (e.g., capsular polysaccharides and lipopolysaccharides), yeasts and protozoa. The polymers (phosphoglycans) composed of glycosyl phosphate (or oligoglycosyl phosphate) repeating units could be chemically classified as poly(glycosyl phosphates). Their importance as immunologically active components of the cell wall and/or capsule of numerous microorganisms upholds the need to develop routes for the chemical preparation of these biopolymers. In this paper, we (1) present a review of the primary structures (known to date) of natural phosphoglycans from various sources, which contain glycosyl phosphate units, and (2) discuss different approaches and recent achievements in the synthesis of glycosyl phosphosaccharides and poly(glycosyl phosphates).
synthesis, structure, polysaccharides, Phosphoglycans, Anomeric phosphodiesters
NCBI PubMed ID: 17092493Publication DOI: 10.1016/j.carres.2006.10.006Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: a.v.nikolaev@dundee.ac.uk
Institutions: College of Life Sciences, Division of Biological Chemistry and Molecular Microbiology, University of Dundee, Dundee DD1 5EH, UK.
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2. Compound ID: 337
|
R-3HOBut-(1-2)-+
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-2)-a-D-Glcp-(1--P--6)--a-D-GlcpN-(1-4)-a-D-GalpNAc-(1-3)-b-D-GalpNAc-(1- |
Show graphically |
Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_130648,IEDB_137473,IEDB_1391961,IEDB_141582,IEDB_141584,IEDB_141807,IEDB_142488,IEDB_144998,IEDB_145002,IEDB_146664,IEDB_151531,IEDB_153207,IEDB_885822,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 94
Gamian A, Katzenellenbogen E, Romanowska E, Grosskurth H, Dabrowski J "Reinvestigation of the O-specific polysaccharides of Hafnia alvei lipopolysaccharides isolated from strains ATCC 13337 and 1187" -
Carbohydrate Research 307(1-2) (1998) 173-176
The structure of the O-specific polysaccharides of the lipopolysaccharides produced by Hafnia alvei strains ATCC 13337 and 1187 was reinvestigated. The position of phosphate group in the repeating units of the polysaccharides was established with the aid of 1H detected, 31P edited NMR spectra. According to the results obtained, the polysaccharides are teichoic acid-like polymers with the repeating units of the following structure: [formula: see text] where Acyl = D-3-hydroxylbutyryl, and 3-O-acetylation was approximately 30%
Lipopolysaccharide, O-specific polysaccharide, Hafnia alvei
NCBI PubMed ID: 9658571Publication DOI: 10.1016/S0008-6215(98)00035-4Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: gamian@immuno.iitd.pan.wroc.pl
Institutions: Ludwik Hirszfeld Institute of Immunology and Experimental Therapy, Wroclaw, Poland
Methods: NMR-2D, methylation, FAB-MS, NMR, sugar analysis, Smith degradation
- Article ID: 3364
Nikolaev AV, Botvinko IV, Ross AJ "Natural phosphoglycans containing glycosyl phosphate units: structural diversity and chemical synthesis" -
Carbohydrate Research 342(3-4) (2007) 297-344
An anomeric phosphodiester linkage formed by a glycosyl phosphate unit and a hydroxyl group of another monosaccharide is found in many glycopolymers of the outer membrane in bacteria (e.g., capsular polysaccharides and lipopolysaccharides), yeasts and protozoa. The polymers (phosphoglycans) composed of glycosyl phosphate (or oligoglycosyl phosphate) repeating units could be chemically classified as poly(glycosyl phosphates). Their importance as immunologically active components of the cell wall and/or capsule of numerous microorganisms upholds the need to develop routes for the chemical preparation of these biopolymers. In this paper, we (1) present a review of the primary structures (known to date) of natural phosphoglycans from various sources, which contain glycosyl phosphate units, and (2) discuss different approaches and recent achievements in the synthesis of glycosyl phosphosaccharides and poly(glycosyl phosphates).
synthesis, structure, polysaccharides, Phosphoglycans, Anomeric phosphodiesters
NCBI PubMed ID: 17092493Publication DOI: 10.1016/j.carres.2006.10.006Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: a.v.nikolaev@dundee.ac.uk
Institutions: College of Life Sciences, Division of Biological Chemistry and Molecular Microbiology, University of Dundee, Dundee DD1 5EH, UK.
- Article ID: 3485
Katzenellenbogen E, Kocharova NA, Korzeniowska-Kowal A, Gamian A, Bogulska M, Szostko B, Shashkov AS, Knirel YA "Immunochemical studies of the lipopolysaccharides of Hafnia alvei PCM 1219 and other strains with the O-antigens containing D-glucose 1-phosphate and 2-deoxy-2-[(R)-3-hydroxybutyramido]-D-glucose" -
Archivum Immunologiae et Therapiae Experimentalis 56(5) (2008) 347-352
INTRODUCTION: Hafnia alveiis the only species of the genus Hafnia, which belongs to the family of Enterobacteriaceae. These Gram-negative bacteria are commonly distributed in the natural environment and are often the cause of human opportunistic infections. Their lipopolysaccharides (LPSs) are important surface antigens which are responsible for the serological specificity and numerous cross-reactions with other enterobacterial genera. So far, 29 different O-polysaccharide (OPS, O-antigen) structures in Hafnias LPSs have been established and for some of them the molecular basis of the serological activity has been elucidated. MATERIALS AND METHODS: OPS from H. alvei strain PCM 1219 was obtained by mild acid hydrolysis of the LPS followed by gel permeation chromatography of carbohydrate material on Sephadex G-50 column. The polysaccharide structure was determined using chemical methods as well as (13)C NMR and (1)H NMR spectroscopy. For serological studies, SDS-PAGE, immunoblotting, and passive hemagglutination tests were used. RESULTS: The serological studies revealed a cross-reactivity of the LPSs of H. alvei PCM 1219 and a group of H. alvei strains with an O-antigen containing D-glucose 1-phosphate and [(R)-3-hydroxybutyramido]-D-glucose. The following structure of the OPS was established: where Acyl stands for (R)-3-hydroxybutyryl and the degree of O-acetylation is ~70%. The structure of the core oligosaccharide was found to be typical of the genus Hafnia. CONCLUSIONS: Based on the OPS structure and serological results it was concluded that H. alvei strain PCM 1219 should be classified in the same serogroup as the H. alvei type strain ATCC 13337 and five other strains containing D-glucose 1-phosphate and 2-deoxy-2-[(R)-3-hydroxybutyramido]-D-glucose in their O-antigens.
O-antigen, Hafnia alvei, enterobacteria, bacterial polysaccharide structure, Serological cross-reactivity
NCBI PubMed ID: 18836891Journal NLM ID: 0114365Publisher: Basel, Boston: Birkhaüser
Correspondence: katzenel@iitd.pan.wroc.pl
Institutions: Institute of Immunology and Experimental Therapy, Polish Academy of Sciences, Weigla 12, 53-114, Wroclaw, Poland
Methods: 13C NMR, 1H NMR, NMR-2D, methylation, GLC-MS, GC-MS, SDS-PAGE, sugar analysis, acid hydrolysis, serological methods
- Article ID: 4328
Knirel YA "Structure of O-antigens" -
Book: Bacterial lipopolysaccharides: Structure, chemical synthesis, biogenesis and interaction with host cells (2011) Chapter 3, 41-115
The lipopolysaccharide (LPS) is the major constituent of the outer leaflet of the outer membrane of Gram-negative bacteria. Its lipid A moiety is embedded in the membrane and serves as an anchor for the rest of the LPS molecule. The outermost repetitive glycan region of the LPS is linked to the lipid A through a core oligosaccharide (OS), and is designated as the O-specific polysaccharide (O-polysaccharide, OPS) or O-antigen. The O-antigen is the most variable portion of the LPS and provides serological specificity, which is used for bacterial serotyping. The OPS also provides protection to the microorganisms from host defenses such as complement mediated killing and phagocytosis, and is involved in interactions of bacteria with plants and bacteriophages. Studies of the OPSs ranging from the elucidation of their chemical structures and conformations to their biological and physico-chemical properties help improving classification schemes of Gram-negative bacteria. Furthermore, these studies contributed to a better understanding of the mechanisms of pathogenesis of infectious diseases, as well as provided information to develop novel vaccines and diagnostic reagents.
Lipopolysaccharide, synthesis, lipopolysaccharides, structure, Bacterial, host, O-antigen, O antigen, cell, O antigens, O-antigens, chemical, interaction, cells, PDF, chemical synthesis, biogenesis
Publication DOI: 10.1007/978-3-7091-0733-1_3Publisher: Springer
Correspondence: knirel@ioc.ac.ru
Editors: Knirel YA, Valvano MA
Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
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3. Compound ID: 930
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S-3HOBut-(1-2)-+
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-2)-a-D-Glcp-(1--P--6)--a-D-GlcpN-(1-4)-a-D-GalpNAc-(1-3)-b-D-GalpNAc-(1- |
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Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide
Contained glycoepitopes: IEDB_130648,IEDB_137473,IEDB_1391961,IEDB_141582,IEDB_141584,IEDB_141807,IEDB_142488,IEDB_144998,IEDB_145002,IEDB_146664,IEDB_151531,IEDB_153207,IEDB_885822,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 269
Jankowski S, Rowinski S, Cisowska A, Gamian A "The sensitivity of Hafnia alvei strains to the bactericidal effect of serum" -
FEMS Immunology and Medical Microbiology 13(1) (1996) 59-64
Most Hafnia alvei strains are sensitive to the bactericidal action of normal bovine serum (NBS) as well as to a serum in which the alternative pathway of complement activation has been thermally blocked. Introduction of polysaccharides (PS) to NBS lowers the bactericidal effect. In a serum in which the alternative pathway of complement activation is blocked, PS completely cancels the bacterial effect.
strain, polysaccharide, Hafnia alvei, Hafnia, sensitivity, serum, bactericidal, effect, serum killing
NCBI PubMed ID: 8821399Journal NLM ID: 9315554Publisher: Elsevier
Institutions: Department of Microbiology, Academy of Medicine, Chalubinskiego 4, 50-368 Wroclaw, Poland, Ludwik Hirschfeld Institute of Immunology and Experimental Therapy, Polish Academy of Sciences, Czerska 6, 53-114 Wroclaw, Poland.
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4. Compound ID: 983
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S-3HOBut-(1-2)-+
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-2)-a-D-Glcp-(1--P--6)--a-D-GlcpN3(30%)Ac-(1-4)-a-D-GalpNAc6Ac-(1-3)-b-D-GalpNAc-(1- |
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Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_130648,IEDB_137473,IEDB_1391961,IEDB_141582,IEDB_141584,IEDB_141807,IEDB_142488,IEDB_144998,IEDB_145002,IEDB_146664,IEDB_151531,IEDB_153207,IEDB_885822,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 269
Jankowski S, Rowinski S, Cisowska A, Gamian A "The sensitivity of Hafnia alvei strains to the bactericidal effect of serum" -
FEMS Immunology and Medical Microbiology 13(1) (1996) 59-64
Most Hafnia alvei strains are sensitive to the bactericidal action of normal bovine serum (NBS) as well as to a serum in which the alternative pathway of complement activation has been thermally blocked. Introduction of polysaccharides (PS) to NBS lowers the bactericidal effect. In a serum in which the alternative pathway of complement activation is blocked, PS completely cancels the bacterial effect.
strain, polysaccharide, Hafnia alvei, Hafnia, sensitivity, serum, bactericidal, effect, serum killing
NCBI PubMed ID: 8821399Journal NLM ID: 9315554Publisher: Elsevier
Institutions: Department of Microbiology, Academy of Medicine, Chalubinskiego 4, 50-368 Wroclaw, Poland, Ludwik Hirschfeld Institute of Immunology and Experimental Therapy, Polish Academy of Sciences, Czerska 6, 53-114 Wroclaw, Poland.
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5. Compound ID: 1505
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-3)-a-L-FucpNAc-(1-4)-a-D-Glcp6(70%)Ac-(1--P--4)--a-D-Glcp-(1-3)-a-L-FucpNAc-(1-3)-a-D-GlcpNAc-(1- |
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Structure type: suggested polymer biological repeating unit
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_141807,IEDB_142488,IEDB_144998,IEDB_145002,IEDB_146664,IEDB_151531,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 481
Guo H, Feng L, Tao J, Zhang C, Wang L "Identification of Escherichia coli O172 O-antigen gene cluster and development of a serogroup-specific PCR assay" -
Journal of Applied Microbiology 97(1) (2004) 181-190
Abstract h. guo, l. feng, j. tao, c. zhang and l. wang. 2004.Aim: To characterize the locus for O-antigen biosynthesis from Escherichia coli O172 type strain and to develop a rapid, specific and sensitive PCR-based method for identification and detection of E. coli O172. Methods and Results: DNA of O-antigen gene cluster of E. coli O172 was amplified by long-range PCR method using primers based on housekeeping genes galF and gnd Shot gun bank was constructed and high quality sequencing was performed. The putative genes for synthesis of UDP-FucNAc, O-unit flippase, O-antigen polymerase and glycosyltransferases were assigned by the homology search. The evolutionary relationship between O-antigen gene clusters of E. coli O172 and E. coli O26 is shown by sequence comparison. Genes specific to E. coli O172 strains were identified by PCR assays using primers based on genes for O-unit flippase, O-antigen polymerase and glycosyltransferases. The specificity of PCR assays was tested using all E. coli and Shigella O-antigen type strains, as well as 24 clinical E. coli isolates. The sensitivity of PCR assays was determined, and the detection limits were 1 pg microl(-1) chromosomal DNA, 0.2 CFU g(-1) pork and 0.2 CFU ml(-1) water. The total time required from beginning to end of the procedure was within 16 h. Conclusion: The O-antigen gene cluster of E. coli O172 was identified and PCR assays based on O-antigen specific genes showed high specificity and sensitivity. Significance and Impact of the Study: An O-antigen gene cluster was identified by sequencing. The specific genes were determined for E. coli O172. The sensitivity of O-antigen specific PCR assay was tested. Although Shiga toxin-producing O172 strains were not yet isolated from clinical specimens, they may emerge as pathogens
Molecular typing, Escherichia coli O172, O-antigen gene cluster, specific genes, STEC
NCBI PubMed ID: 15186455Journal NLM ID: 9706280Publisher: Oxford: Blackwell Publishing for the Society for Applied Bacteriology
Correspondence: wanglei@nankai.edu.cn
Institutions: TEDA School of Biological Sciences and Biotechnology, Tianjin State Laboratory of Microbial Functional Genomics, Nankai University, TEDA, Tianjin, China
- Article ID: 3355
Perepelov AV, Bartodziejska B, Shashkov AS, Wykrota M, Knirel YA, Rozalski A "Structure of a glucosyl phosphate-containing O-polysaccharide of Proteus vulgaris O42" -
Carbohydrate Research 342(18) (2007) 2826-2831
An O-polysaccharide was isolated by mild acid degradation of the lipopolysaccharide of Proteus vulgaris O42 and studied by sugar and methylation analyses along with 1H, 13C and 31P NMR spectroscopy. The following structure of the polysaccharide having a linear pentasaccharide phosphate repeating unit was established:
Lipopolysaccharide, O-antigen, NMR spectroscopy, Proteus vulgaris, bacterial polysaccharide structure, Glucosyl phosphate
NCBI PubMed ID: 17936254Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: perepel@ioc.ac.ru
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia,Department of Immunobiology of Bacteria, Institute of Microbiology and Immunology, Lodz, Poland
Methods: 13C NMR, 1H NMR, NMR-2D, methylation, GLC-MS, chemical analysis, 31P NMR, GLC, mild acid hydrolysis, NMR-1D, serological methods, alkaline hydrolysis
- Article ID: 3364
Nikolaev AV, Botvinko IV, Ross AJ "Natural phosphoglycans containing glycosyl phosphate units: structural diversity and chemical synthesis" -
Carbohydrate Research 342(3-4) (2007) 297-344
An anomeric phosphodiester linkage formed by a glycosyl phosphate unit and a hydroxyl group of another monosaccharide is found in many glycopolymers of the outer membrane in bacteria (e.g., capsular polysaccharides and lipopolysaccharides), yeasts and protozoa. The polymers (phosphoglycans) composed of glycosyl phosphate (or oligoglycosyl phosphate) repeating units could be chemically classified as poly(glycosyl phosphates). Their importance as immunologically active components of the cell wall and/or capsule of numerous microorganisms upholds the need to develop routes for the chemical preparation of these biopolymers. In this paper, we (1) present a review of the primary structures (known to date) of natural phosphoglycans from various sources, which contain glycosyl phosphate units, and (2) discuss different approaches and recent achievements in the synthesis of glycosyl phosphosaccharides and poly(glycosyl phosphates).
synthesis, structure, polysaccharides, Phosphoglycans, Anomeric phosphodiesters
NCBI PubMed ID: 17092493Publication DOI: 10.1016/j.carres.2006.10.006Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: a.v.nikolaev@dundee.ac.uk
Institutions: College of Life Sciences, Division of Biological Chemistry and Molecular Microbiology, University of Dundee, Dundee DD1 5EH, UK.
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6. Compound ID: 1784
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-4)-a-D-GlcpNAc6(15%)Ac-(1-3)-a-L-QuipNAc-(1-3)-a-D-GlcpNAc-(1-3)-a-L-QuipNAc-(1-4)-a-D-Glcp-(1-P- |
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Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_141807,IEDB_142488,IEDB_144998,IEDB_145002,IEDB_146664,IEDB_151531,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 560
Feng L, Senchenkova SN, Yang J, Shashkov AS, Tao J, Guo H, Zhao G, Knirel YA, Reeves P, Wang L "Structural and genetic characterization of the Shigella boydii type 13 O-antigen" -
Journal of Bacteriology 186(2) (2004) 383-392
Shigella is an important human pathogen. It is generally agreed that Shigella and Escherichia coli constitute a single species; the only exception is Shigella boydii type 13, which is more distantly related to E. coli and other Shigella forms and seems to represent another species. This gives S. boydii type 13 an important status in evolution. O antigen is the polysaccharide part of the lipopolysaccharide in the outer membrane of gram-negative bacteria and plays an important role in pathogenicity. The chemical structure and genetic organization of the S. boydii type 13 O antigen were investigated. The O polysaccharide was found to be acid labile owing to the presence of a glycosyl phosphate linkage in the main chain. The structure of the linear pentasaccharide phosphate repeating unit (O unit) was established by nuclear magnetic resonance spectroscopy, including two-dimensional COSY, TOCSY, ROESY, and H-detected 1H, 13C and 1H, 31P HMQC experiments, along with chemical methods. The O antigen gene cluster of S. boydii type 13 was located and sequenced. Genes for synthesis of UDP-2-acetamido-2,6-dideoxy-L-glucose and genes that encode putative sugar transferases, O unit flippase, and O antigen polymerase were identified. Seven genes were found to be specific to S. boydii type 13. The S. boydii type 13 O antigen gene cluster has higher levels of sequence similarity with Vibrio cholerae gene clusters and may be evolutionarily related to these gene clusters.
genetic, structure, gene, O-antigen, Shigella, Shigella boydii
NCBI PubMed ID: 14702307Journal NLM ID: 2985120RPublisher: American Society for Microbiology
Correspondence: wanglei@nankai.edu.cn
Institutions: College of Life Sciences, Nankai University, Tianjin 300071, People's Republic of China
Methods: 13C NMR, 1H NMR, NMR-2D, methylation, PCR, DNA sequencing, sugar analysis, ESI-MS, GLC
- Article ID: 3364
Nikolaev AV, Botvinko IV, Ross AJ "Natural phosphoglycans containing glycosyl phosphate units: structural diversity and chemical synthesis" -
Carbohydrate Research 342(3-4) (2007) 297-344
An anomeric phosphodiester linkage formed by a glycosyl phosphate unit and a hydroxyl group of another monosaccharide is found in many glycopolymers of the outer membrane in bacteria (e.g., capsular polysaccharides and lipopolysaccharides), yeasts and protozoa. The polymers (phosphoglycans) composed of glycosyl phosphate (or oligoglycosyl phosphate) repeating units could be chemically classified as poly(glycosyl phosphates). Their importance as immunologically active components of the cell wall and/or capsule of numerous microorganisms upholds the need to develop routes for the chemical preparation of these biopolymers. In this paper, we (1) present a review of the primary structures (known to date) of natural phosphoglycans from various sources, which contain glycosyl phosphate units, and (2) discuss different approaches and recent achievements in the synthesis of glycosyl phosphosaccharides and poly(glycosyl phosphates).
synthesis, structure, polysaccharides, Phosphoglycans, Anomeric phosphodiesters
NCBI PubMed ID: 17092493Publication DOI: 10.1016/j.carres.2006.10.006Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: a.v.nikolaev@dundee.ac.uk
Institutions: College of Life Sciences, Division of Biological Chemistry and Molecular Microbiology, University of Dundee, Dundee DD1 5EH, UK.
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7. Compound ID: 1891
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-6)-b-D-Galp-(1-6)-b-D-Galp-(1-6)-b-D-Galf-(1-3)-b-D-Glcp-(1-6)-b-D-Galf-(1-6)-a-D-Galp-(1-6)-a-D-Glcp-(1-P- |
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Structure type: polymer chemical repeating unit
Trivial name: poly(glycosyl phosphate)
Contained glycoepitopes: IEDB_136044,IEDB_136095,IEDB_136906,IEDB_137472,IEDB_140529,IEDB_141794,IEDB_142488,IEDB_144998,IEDB_145002,IEDB_146664,IEDB_151528,IEDB_153201,IEDB_156493,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: 632
Bergstrom N, Jansson P, Kilian M, Sorensen UBS, Sorensen UB "Structures of two cell wall-associated polysaccharides of a Streptococcus mitis biovar 1 strain. A unique teichoic acid-like polysaccharide and the group O antigen which is a C-polysaccharide in common with pneumococci" -
European Journal of Biochemistry 267 (2000) 7147-7157
The cell wall of Streptococcus mitis biovar 1 strain SK137 contains the C-polysaccharide known as the common antigen of a closely related species Streptococcus pneumoniae, and a teichoic acid-like polysaccharide with a unique structure. The two polysaccharides are different entities and could be partially separated by gel chromatography. The structures of the two polysaccharides were determined by chemical methods and by NMR spectroscopy. The teichoic acid-like polymer has a heptasaccharide phosphate repeating unit with the following structure: -6)bDGalp(1-6)bDGalp(1-6)bDGalf(1-3)bDGlcp(1-6)bDGalf(1-6)aDGalp(1-6)aDGlcp(1-P- The structure neither contains ribitol nor glycerol phosphate as classical teichoic acids do, thus we have used the expression teichoic acid-like for this polysaccharide. The following structure of the C-polysaccharide repeating unit was established: -6)bDGlcp(1-3)aAATp(1-4)[Cho(1-P-6)]aDGalpNAc(1-3)[Cho(1-P-6)]aDGalpNAc(1-1)Rib-ol(5-P- where AAT is 2-acetamido-4-amino-2,4,6-trideoxy-D-galactose. It has a carbohydrate backbone identical to that of one of the two structures of C-polysaccharide previously identified in S. pneumoniae. C-polysaccharide of S. mitis is characterized by the presence, in each repeating unit, of two residues of phosphocholine and both galactosamine residues in the N-acetylated form. Immunochemical analysis showed that C-polysaccharide constitutes the Lancefield group O antigen. Studies using mAbs directed against the backbone and against the phosphocholine moiety of the C-polysaccharide revealed several different patterns of these epitopes among 95 S. mitis and Streptococcus oralis strains tested and the exclusive presence of the group O antigen in the majority of S. mitis biovar 1 strains.
antigen, structure, common, strain, polysaccharide, Streptococcus, O-antigen, polysaccharides, O antigen, cell, group, form, common antigen, Phosphocholine, biovar, pneumococcal, C-polysaccharide, C polysaccharide, choline, teichoic acid-like
NCBI PubMed ID: 11106426Publication DOI: 10.1046/j.1432-1327.2000.01821.x-i2Journal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Correspondence: pererik.jansson@kfcmail.hs.sll.se
Institutions: Clinical Research Centre, Analytical Unit, Karolinska Institute, Huddinge Hospital, Novum, Huddinge, Sweden, Department of Medical Microbiology and Immunology, University of Aarhus, Denmark
Methods: MAb studies
- Article ID: 3364
Nikolaev AV, Botvinko IV, Ross AJ "Natural phosphoglycans containing glycosyl phosphate units: structural diversity and chemical synthesis" -
Carbohydrate Research 342(3-4) (2007) 297-344
An anomeric phosphodiester linkage formed by a glycosyl phosphate unit and a hydroxyl group of another monosaccharide is found in many glycopolymers of the outer membrane in bacteria (e.g., capsular polysaccharides and lipopolysaccharides), yeasts and protozoa. The polymers (phosphoglycans) composed of glycosyl phosphate (or oligoglycosyl phosphate) repeating units could be chemically classified as poly(glycosyl phosphates). Their importance as immunologically active components of the cell wall and/or capsule of numerous microorganisms upholds the need to develop routes for the chemical preparation of these biopolymers. In this paper, we (1) present a review of the primary structures (known to date) of natural phosphoglycans from various sources, which contain glycosyl phosphate units, and (2) discuss different approaches and recent achievements in the synthesis of glycosyl phosphosaccharides and poly(glycosyl phosphates).
synthesis, structure, polysaccharides, Phosphoglycans, Anomeric phosphodiesters
NCBI PubMed ID: 17092493Publication DOI: 10.1016/j.carres.2006.10.006Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: a.v.nikolaev@dundee.ac.uk
Institutions: College of Life Sciences, Division of Biological Chemistry and Molecular Microbiology, University of Dundee, Dundee DD1 5EH, UK.
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8. Compound ID: 1897
|
a-D-Glcp-(1-6)-+
|
-6)-a-D-GlcpNAc-(1-4)-a-D-GalpNAc-(1-3)-b-D-GalpNAc-(1-2)-a-D-Glcp-(1-P- |
Show graphically |
Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_130648,IEDB_137473,IEDB_1391961,IEDB_141582,IEDB_141584,IEDB_141807,IEDB_142488,IEDB_144998,IEDB_145002,IEDB_146664,IEDB_151531,IEDB_153207,IEDB_885822,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 628
Bartodziejska B, Toukach FV, Vinogradov EV, Senchenkova SN, Shashkov AS, Ziolkowski A, Czaja J, Perry MB, Knirel YA, Rozalski A "Structural and serological studies of two related O-specific polysaccharides of Proteus vulgaris O21 and Proteus mirabilis O48 having oligosaccharide-phosphate repeating units" -
European Journal of Biochemistry 267 (2000) 6888-6896
The O-specific polysaccharide chains (O-antigens) of the lipopolysaccharides (LPSs) of Proteus mirabilis O48 and Proteus vulgaris O21 were found to have tetrasaccharide and pentasaccharide repeating units, respectively, interlinked by a glycosidic phosphate. Polysaccharides and an oligosaccharide were derived from the LPSs by various degradation procedures and studied by 1H and 13C NMR spectroscopy, including 2D COSY, TOCSY, NOESY, H-detected 1H,13C and 1H,31P HMQC experiments. The following related structures of the repeating units of the O-antigens were established (top: Proteus mirabilis O48; bottom: Proteus vulgaris O21). The O-specific polysaccharide of P. vulgaris O21 has the same structure as that of Hafnia allvei 744 and PCM1194 [Petersson C., Jachymek, W., Klonowska, A., Lugowski, C., Niedziela, T. & Kenne, L. (1997) Eur. J. Biochem., 245, 668-675], except that the GlcN residue carries the N-acetyl rather than the N-[(R)-3-hydroxybutyryl] group. Serological investigations confirmed the close relatedness of the Proteus and Hafnia O-antigens studied.
Lipopolysaccharide, NMR, O-antigen, O-specific polysaccharide, Proteus, Proteus mirabilis, Proteus vulgaris, 3-Acetamido-3, 6-dideoxy-d-glucose, Serological cross-reactivity
NCBI PubMed ID: 11082201Publication DOI: 10.1046/j.1432-1033.2000.01793.xJournal 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 for Biological Sciences, National Research Council, Ottawa, Ontario, Canada, L. Hirszfeld Institute of Immunology and Experimental Therapy, Polish Academy of Sciences, Wroclaw, Poland, Department of Immunobiology of Bacteria, Institute of Microbiology and Immunology, University of Lodz, Poland
Methods: NMR-2D, EIA, ESI-MS, GLC, alkaline degradation, deamination, acid degradation, passive hemolysis test(PHT)
- Article ID: 3364
Nikolaev AV, Botvinko IV, Ross AJ "Natural phosphoglycans containing glycosyl phosphate units: structural diversity and chemical synthesis" -
Carbohydrate Research 342(3-4) (2007) 297-344
An anomeric phosphodiester linkage formed by a glycosyl phosphate unit and a hydroxyl group of another monosaccharide is found in many glycopolymers of the outer membrane in bacteria (e.g., capsular polysaccharides and lipopolysaccharides), yeasts and protozoa. The polymers (phosphoglycans) composed of glycosyl phosphate (or oligoglycosyl phosphate) repeating units could be chemically classified as poly(glycosyl phosphates). Their importance as immunologically active components of the cell wall and/or capsule of numerous microorganisms upholds the need to develop routes for the chemical preparation of these biopolymers. In this paper, we (1) present a review of the primary structures (known to date) of natural phosphoglycans from various sources, which contain glycosyl phosphate units, and (2) discuss different approaches and recent achievements in the synthesis of glycosyl phosphosaccharides and poly(glycosyl phosphates).
synthesis, structure, polysaccharides, Phosphoglycans, Anomeric phosphodiesters
NCBI PubMed ID: 17092493Publication DOI: 10.1016/j.carres.2006.10.006Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: a.v.nikolaev@dundee.ac.uk
Institutions: College of Life Sciences, Division of Biological Chemistry and Molecular Microbiology, University of Dundee, Dundee DD1 5EH, UK.
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9. Compound ID: 2228
|
-3)-b-D-Quip4NAc-(1-3)-a-D-6dTalp4Ac-(1-3)-a-L-Fucp-(1-6)-a-D-Glcp-(1--P--3)--a-D-GlcpNAc-(1- |
Show graphically |
Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide
Contained glycoepitopes: IEDB_136045,IEDB_141807,IEDB_142488,IEDB_142489,IEDB_144562,IEDB_144998,IEDB_145002,IEDB_146664,IEDB_151531,IEDB_152214,IEDB_174333,IEDB_983931,SB_192,SB_86
The structure is contained in the following publication(s):
- Article ID: 728
Katzenellenbogen E, Kocharova NA, Zatonsky GV, Bogulska M, Witkowska D, Shashkov AS, Romanowska E, Knirel YA "Structure of the O-specific polysaccharide of Hafnia alvei strain 23 having an oligosaccharide-phosphate repeating unit" -
Journal of Carbohydrate Chemistry 18(5) (1999) 545-558
Lipopolysaccharide (LPS) of Hafnia alvei 23 has an acid-labile O-specific polysaccharide (OPS) with a pentasaccharide-phosphate repeating unit containing D-Glc1P, D-GlcNAc, L-Fuc, 6-deoxy-D-talose (D-6dTal), 4-acetamido-4,6-dideoxy-D-glucose (D-Qui4NAc), and an O-acetyl group. A partially degraded OPS was obtained by hydrolysis of LPS with 0.25 M sodium acetate in aqueous 0.5% acetic acid. Fractionation of LPS on Sephadex G-200 in DOC buffer allowed isolation of long-chain LPS species which, together with OPS, were studied by methylation analysis, chemical degradations (O-deacetylation, dephosphorylation with 48% hydrofluoric acid, Smith degradation), and 1H and 13C NMR spectroscopy, including 2D COSY, TOCSY, NOESY, and H-detected 1H,13C heteronuclear single-quantum coherence (HSQC) experiments. The following structure of the repeating unit of OPS was established: [structure: see text].
Lipopolysaccharide, structure, O-specific polysaccharide, Hafnia alvei
Journal NLM ID: 8218151Publisher: Marcel Dekker
Correspondence: knirel@ioc.ac.ru
Institutions: L.Hirszfeld Institute of Immunology and Experimental Therapy, Wroclaw, Poland
Methods: NMR
- Article ID: 4328
Knirel YA "Structure of O-antigens" -
Book: Bacterial lipopolysaccharides: Structure, chemical synthesis, biogenesis and interaction with host cells (2011) Chapter 3, 41-115
The lipopolysaccharide (LPS) is the major constituent of the outer leaflet of the outer membrane of Gram-negative bacteria. Its lipid A moiety is embedded in the membrane and serves as an anchor for the rest of the LPS molecule. The outermost repetitive glycan region of the LPS is linked to the lipid A through a core oligosaccharide (OS), and is designated as the O-specific polysaccharide (O-polysaccharide, OPS) or O-antigen. The O-antigen is the most variable portion of the LPS and provides serological specificity, which is used for bacterial serotyping. The OPS also provides protection to the microorganisms from host defenses such as complement mediated killing and phagocytosis, and is involved in interactions of bacteria with plants and bacteriophages. Studies of the OPSs ranging from the elucidation of their chemical structures and conformations to their biological and physico-chemical properties help improving classification schemes of Gram-negative bacteria. Furthermore, these studies contributed to a better understanding of the mechanisms of pathogenesis of infectious diseases, as well as provided information to develop novel vaccines and diagnostic reagents.
Lipopolysaccharide, synthesis, lipopolysaccharides, structure, Bacterial, host, O-antigen, O antigen, cell, O antigens, O-antigens, chemical, interaction, cells, PDF, chemical synthesis, biogenesis
Publication DOI: 10.1007/978-3-7091-0733-1_3Publisher: Springer
Correspondence: knirel@ioc.ac.ru
Editors: Knirel YA, Valvano MA
Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
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10. Compound ID: 2680
|
-3)-a-L-FucpNAc-(1-4)-a-D-Glcp6Ac-(1--P--4)--a-D-Glcp-(1-3)-a-L-FucpNAc-(1-3)-a-D-GlcpNAc-(1- |
Show graphically |
Structure type: suggested polymer biological repeating unit
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_141807,IEDB_142488,IEDB_144998,IEDB_145002,IEDB_146664,IEDB_151531,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 916
Landersjo C, Weintraub A, Widmalm G "Structural analysis of the O-antigen polysaccharide from the Shiga toxin-producing Escherichia coli O172" -
European Journal of Biochemistry 268(8) (2001) 2239-2245
The structure of the O-antigen polysaccharide from Escherichia coli O172 has been determined. In combination with sugar analysis, NMR spectroscopy shows that the polysaccharide is composed of pentasaccharide repeating units. Sequential information was obtained by mass spectrometry and two-dimensional NMR techniques. An O-acetyl group was present as 0.7 equivalent per repeating unit. Treatment of the O-deacetylated polysaccharide with aqueous 48% hydrofluoric acid rendered cleavage of the phosphodiester in the backbone of the polymer and the pentasaccharide isolated after gel permeation chromatography was structurally characterized. Subsequent NMR experiments on polymeric materials revealed the structure of the repeating unit of the O-polysaccharide from E. coli O172 as: →P-4)-α-D-Glcp-(1→3)-α-L-FucpNAc-(1→3)-α-D-GlcpNAc-(1→3)-α-L-FucpNAc-(1→4)-α-D-Glcp6Ac-(1→.
structural, polysaccharide, O-antigen, analysis, structural analysis, O antigen, Escherichia, Escherichia coli
NCBI PubMed ID: 11298740Journal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Correspondence: G. Widmalm
Institutions: Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, Sweden, Karolinska Institute, Department of Microbiology, Pathology and Immunology, Division of Clinical Bacteriology, Huddinge University Hospital, Sweden
Methods: NMR-2D, NMR, HF solvolysis, sugar analysis, de-O-acetylation
- 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: 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
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11. Compound ID: 2719
|
a-L-Fucp-(1-4)-+
|
-3)-a-D-Glcp-(1--P--6)--a-D-Glcp-(1-2)-b-D-Glcp-(1-3)-b-D-GlcpNAc-(1- |
Show graphically |
Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_135813,IEDB_136045,IEDB_137340,IEDB_141807,IEDB_142488,IEDB_142489,IEDB_144562,IEDB_144998,IEDB_144999,IEDB_145002,IEDB_146664,IEDB_151531,IEDB_152214,IEDB_174333,IEDB_241118,IEDB_983931,SB_192,SB_86
The structure is contained in the following publication(s):
- Article ID: 941
Linnerborg M, Weintraub A, Widmalm G "Structural studies of the O-antigen polysaccharide from the enteroinvasive Escherichia coli O173" -
Carbohydrate Research 320(3-4) (1999) 200-208
The structure of the O-antigen polysaccharide (PS) from Escherichia coli O173 has been investigated. Sugar and methylation analyses, electrospray ionisation mass spectrometry together with 1H, 31P and 13C NMR spectroscopy were the main methods used. The structure of the pentasaccharide repeating unit of the PS was found to be: [see structure in text]. By treatment with 48% HF the phosphoric diester linkage was cleaved together with the glycosidic linkage of the fucosyl group, rendering a tetrasaccharide with the structure: a-D-Glcp-(1→2)-b-D-Glcp-(1→3)-b-D-GlcpNAc-(1→3)-D-Glc.
structural, polysaccharide, O-antigen, O antigen, Escherichia, Escherichia coli, structural studies
NCBI PubMed ID: 10573858Publication DOI: 10.1016/S0008-6215(99)00142-1Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: G. Widmalm
Institutions: Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, S- 106 91 Stockholm, Sweden, Karolinska Institute, Department of Immunology, Microbiology, Pathology and Infectious Diseases, Division of Clinical and Oral Bacteriology, Huddinge University Hospital, S- 141 86 Huddinge, Sweden
Methods: 13C NMR, 1H NMR, NMR-2D, methylation, HF solvolysis, sugar analysis, 31P NMR, ESI-MS
- Article ID: 1547
Olsson U, Lycknert K, Stenutz R, Weintraub A, Widmalm G "Structural analysis of the O-antigen polysaccharide from Escherichia coli O152" -
Carbohydrate Research 340(1) (2005) 167-171
The structure of the O-antigen polysaccharide (PS) from Escherichia coli O152 has been determined. Component analysis together with (1)H, (13)C and (31)P NMR spectroscopy were used to elucidate the structure. Inter-residue correlations were determined by (1)H,(31)P COSY, (1)H,(1)H NOESY and (1)H,(13)C heteronuclear multiple-bond correlation experiments. The PS is composed of pentasaccharide repeating units with the following structure: The structure is similar to that of the O-antigen polysaccharide from E. coli O173. The cross-reactivity between E. coli O152 and E. coli O3 may be explained by structural similarities in the branching region of their O-antigen polysaccharides
NMR, structure, chemistry, correlation, structural, polysaccharide, O-antigen, repeating unit, analysis, polysaccharides, structural analysis, O antigen, Escherichia, Escherichia coli, NMR spectroscopy, region, spectroscopy, pentasaccharide, component, similarity, cross-reactivity, crossreactivity, organic, NOESY, COSY, heteronuclear
NCBI PubMed ID: 15620681Publication DOI: 10.1016/j.carres.2004.11.008Journal NLM ID: 0043535Publisher: Elsevier
Institutions: Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, Stockholm, Sweden, Karolinska Institute, Department of Laboratory Medicine, Division of Clinical Bacteriology, F-82 Karolinska University Hospital, Huddinge Stockholm, Sweden
Methods: NMR, composition analysis
- 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: 3364
Nikolaev AV, Botvinko IV, Ross AJ "Natural phosphoglycans containing glycosyl phosphate units: structural diversity and chemical synthesis" -
Carbohydrate Research 342(3-4) (2007) 297-344
An anomeric phosphodiester linkage formed by a glycosyl phosphate unit and a hydroxyl group of another monosaccharide is found in many glycopolymers of the outer membrane in bacteria (e.g., capsular polysaccharides and lipopolysaccharides), yeasts and protozoa. The polymers (phosphoglycans) composed of glycosyl phosphate (or oligoglycosyl phosphate) repeating units could be chemically classified as poly(glycosyl phosphates). Their importance as immunologically active components of the cell wall and/or capsule of numerous microorganisms upholds the need to develop routes for the chemical preparation of these biopolymers. In this paper, we (1) present a review of the primary structures (known to date) of natural phosphoglycans from various sources, which contain glycosyl phosphate units, and (2) discuss different approaches and recent achievements in the synthesis of glycosyl phosphosaccharides and poly(glycosyl phosphates).
synthesis, structure, polysaccharides, Phosphoglycans, Anomeric phosphodiesters
NCBI PubMed ID: 17092493Publication DOI: 10.1016/j.carres.2006.10.006Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: a.v.nikolaev@dundee.ac.uk
Institutions: College of Life Sciences, Division of Biological Chemistry and Molecular Microbiology, University of Dundee, Dundee DD1 5EH, UK.
- 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
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12. Compound ID: 3054
|
a-D-Glcp-(1-6)-+
|
R-3HOBut-(1-3)-+ |
| |
-6)-a-D-GlcpN-(1-4)-a-D-GalpNAc-(1-3)-b-D-GalpNAc-(1-2)-a-D-Glcp-(1-P- |
Show graphically |
Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide
Contained glycoepitopes: IEDB_130648,IEDB_137473,IEDB_1391961,IEDB_141582,IEDB_141584,IEDB_141807,IEDB_142488,IEDB_144998,IEDB_145002,IEDB_146664,IEDB_151531,IEDB_153207,IEDB_885822,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 1104
Petersson C, Jachymek W, Klonowska A, Lugowski C, Niedziela T, Kenne L "Structural studies of the O-specific chains of Hafnia alvei strains 744, PCM1194 and PCM1210 lipopolysaccharides" -
European Journal of Biochemistry 245(3) (1997) 668-675
The structures of the O-specific chains of the Hafnia alvei strain 744 and PCMstrains 1194 and 1210 lipopolysaccharides have been investigated. Methylation analysis, dephosphorylation, NMR spectroscopy, matrix-assisted laser-desorption ionisation time-of-flight mass spectrometry and fast-atom-bombardment mass spectrometry were the principal methods used. It was concluded that the polysaccharides of strains 744 and PCM1194 are composed of the same pentasaccharide repeating unit having the following structure: [structure in text] and that the polysaccharide of strain PCM1210 is composed of a pentasaccharide repeating unit having the following structure: [structure in text].
Lipopolysaccharide, lipopolysaccharides, LPS, strain, structural, O-antigen, chain, O-specific, Hafnia alvei, structural studies, Hafnia, phosphodiester
NCBI PubMed ID: 9183004Publication DOI: 10.1111/j.1432-1033.1997.00668.xJournal 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, L. Hirzfeld Institute of Immunology and Experimental Therapy, Polish Academy of Science, Wroclaw, Poland
Methods: NMR-2D, methylation, NMR, dephosphorylation, MALDI-MS
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13. Compound ID: 3776
|
3HOMyr-(1-2)-+
|
P-4)-+ |
| |
3HOMyr-(1-2)-+ | |
| | |
a-Kdop-(2-4)-a-Kdop-(2-6)-b-D-Glcp-(1-6)-a-D-Glcp-(1-P
| |
3HOMyr-(1-3)-+ |
|
3HOMyr-(1-3)-+ |
Show graphically |
Structure type: oligomer
Trivial name: Kdo2-lipid IVA
Compound class: lipid A
Contained glycoepitopes: IEDB_130650,IEDB_130659,IEDB_141806,IEDB_142488,IEDB_144998,IEDB_145002,IEDB_146664,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 1437
Basu SS, Karbarz MJ, Raetz CR "Expression cloning and characterization of the C28 acyltransferase of lipid A biosynthesis in Rhizobium leguminosarum" -
Journal of Biological Chemistry 277(32) (2002) 28959-28971
An unusual feature of lipid A from plant endosymbionts of the Rhizobiaceae family is the presence of a 27-hydroxyoctacosanoic acid (C28) moiety. An enzyme that incorporates this acyl chain is present in extracts of Rhizobium leguminosarum, Rhizobium etli, and Sinorhizobium meliloti but not Escherichia coli. The enzyme transfers 27- hydroxyoctacosanate from a specialized acyl carrier protein (AcpXL) to the precursor Kdo2 ((3-deoxy-d-manno-octulosonic acid)2)-lipid IV(A). We now report the identification of five hybrid cosmids that direct the overexpression of this activity by screening approximately 4000 lysates of individual colonies of an R. leguminosarum 3841 genomic DNA library in the host strain S. meliloti 1021. In these heterologous constructs, both the C28 acyltransferase and C28-AcpXL are overproduced. Sequencing of a 9-kb insert from cosmid pSSB-1, which is also present in the other cosmids, shows that acpXL and the lipid A acyltransferase gene (lpxXL) are close to each other but not contiguous. Nine other open reading frames around lpxXL were also sequenced. Four of them encode orthologues of fatty acid and/or polyketide biosynthetic enzymes. AcpXL purified from S. meliloti expressing pSSB-1 is fully acylated, mainly with 27-hydroxyoctacosanoate. Expression of lpxXL in E. coli behind a T7 promoter results in overproduction in vitro of the expected R. leguminosarum acyltransferase, which is C28-AcpXL-dependent and utilizes (3-deoxy-d-manno-octulosonic acid)2-lipid IV(A) as the acceptor. These findings confirm that lpxXL is the structural gene for the C28 acyltransferase. LpxXL is distantly related to the lauroyltransferase (LpxL) of E. coli lipid A biosynthesis, but highly significant LpxXL orthologues are present in Agrobacterium tumefaciens, Brucella melitensis, and all sequenced strains of Rhizobium, consistent with the occurrence of long secondary acyl chains in the lipid A molecules of these organisms
biosynthesis, structure, cloning, lipid A, sequencing, Rhizobium leguminosarum, acyltransferase
NCBI PubMed ID: 12019272Publication DOI: 10.1074/jbc.M204525200Journal NLM ID: 2985121RPublisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
Correspondence: raetz@biochem.duke.edu
Institutions: Department of Biochemistry, Duke University Medical Center, Durham, North Carolina 27710, USA
Methods: SDS-PAGE, DNA techniques, acid hydrolysis, genetic methods, biochemical methods, HPLC, enzyme assay, FPLC, bioinformatic analysis
- Article ID: 4030
Hankins JV, Madsen JA, Giles DK, Childers BM, Klose KE, Brodbelt JS, Trent MS "Elucidation of a novel Vibrio cholerae lipid A secondary hydroxy-acyltransferase and its role in innate immune recognition" -
Molecular Microbiology 81(5) (2011) 1313-1329
Similar to most Gram-negative bacteria, the outer leaflet of the outer membrane of Vibrio cholerae is comprised of lipopolysaccharide. Previous reports have proposed that V. cholerae serogroups O1 and O139 synthesize structurally different lipid A domains, which anchor lipopolysaccharide within the outer membrane. In the current study, intact lipid A species of V. cholerae O1 and O139 were analysed by mass spectrometry. We demonstrate that V. cholerae serogroups associated with human disease synthesize a similar asymmetrical hexa-acylated lipid A species, bearing a myristate (C14:0) and 3-hydroxylaurate (3-OH C12:0) at the 2'- and 3'-positions respectively. A previous report from our laboratory characterized the V. cholerae LpxL homologue Vc0213, which transfers a C14:0 to the 2'-position of the glucosamine disaccharide. Our current findings identify V. cholerae Vc0212 as a novel lipid A secondary hydroxy-acyltransferase, termed LpxN, responsible for transferring the 3-hydroxylaurate (3-OH C12:0) to the V. cholerae lipid A domain. Importantly, the presence of a 3-hydroxyl group on the 3'-linked secondary acyl chain was found to promote antimicrobial peptide resistance in V. cholerae; however, this functional group was not required for activation of the innate immune response.
Lipopolysaccharide, lipid A, mass spectrometry, Vibrio cholerae
NCBI PubMed ID: 21752109Journal NLM ID: 8712028Publisher: Blackwell Publishing
Correspondence: strent@mail.utexas.edu
Institutions: Department of Biochemistry and Molecular Biology, Georgia Health Sciences University, Augusta, GA 30912, USA, Department of Chemistry and Biochemistry, Section of Molecular Genetics and Microbiology, The Institute of Cellular and Molecular Biology, The University of Texas at Austin, Austin, TX 78712, USA, South Texas Center for Emerging Infectious Diseases and Department of Biology, The University of Texas at San Antonio, San Antonio, TX 78249, USA
Methods: GC-MS, DNA techniques, GC, MALDI-TOF MS, genetic methods, CID-MS
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14. Compound ID: 3777
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3HOMyr-(1-2)-+
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P-4)-+ |
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a-Kdop-(2-4)-a-Kdop-(2-6)-+ | |
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27HOMon-(1-3)-3HOMyr-(1-2)-b-D-Glcp-(1-6)-a-D-Glcp-(1-P
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3HOMyr-(1-3)-+ |
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3HOMyr-(1-3)-+ |
Show graphically |
Structure type: oligomer
Compound class: lipid A
Contained glycoepitopes: IEDB_130650,IEDB_130659,IEDB_141806,IEDB_142488,IEDB_144998,IEDB_145002,IEDB_146664,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 1437
Basu SS, Karbarz MJ, Raetz CR "Expression cloning and characterization of the C28 acyltransferase of lipid A biosynthesis in Rhizobium leguminosarum" -
Journal of Biological Chemistry 277(32) (2002) 28959-28971
An unusual feature of lipid A from plant endosymbionts of the Rhizobiaceae family is the presence of a 27-hydroxyoctacosanoic acid (C28) moiety. An enzyme that incorporates this acyl chain is present in extracts of Rhizobium leguminosarum, Rhizobium etli, and Sinorhizobium meliloti but not Escherichia coli. The enzyme transfers 27- hydroxyoctacosanate from a specialized acyl carrier protein (AcpXL) to the precursor Kdo2 ((3-deoxy-d-manno-octulosonic acid)2)-lipid IV(A). We now report the identification of five hybrid cosmids that direct the overexpression of this activity by screening approximately 4000 lysates of individual colonies of an R. leguminosarum 3841 genomic DNA library in the host strain S. meliloti 1021. In these heterologous constructs, both the C28 acyltransferase and C28-AcpXL are overproduced. Sequencing of a 9-kb insert from cosmid pSSB-1, which is also present in the other cosmids, shows that acpXL and the lipid A acyltransferase gene (lpxXL) are close to each other but not contiguous. Nine other open reading frames around lpxXL were also sequenced. Four of them encode orthologues of fatty acid and/or polyketide biosynthetic enzymes. AcpXL purified from S. meliloti expressing pSSB-1 is fully acylated, mainly with 27-hydroxyoctacosanoate. Expression of lpxXL in E. coli behind a T7 promoter results in overproduction in vitro of the expected R. leguminosarum acyltransferase, which is C28-AcpXL-dependent and utilizes (3-deoxy-d-manno-octulosonic acid)2-lipid IV(A) as the acceptor. These findings confirm that lpxXL is the structural gene for the C28 acyltransferase. LpxXL is distantly related to the lauroyltransferase (LpxL) of E. coli lipid A biosynthesis, but highly significant LpxXL orthologues are present in Agrobacterium tumefaciens, Brucella melitensis, and all sequenced strains of Rhizobium, consistent with the occurrence of long secondary acyl chains in the lipid A molecules of these organisms
biosynthesis, structure, cloning, lipid A, sequencing, Rhizobium leguminosarum, acyltransferase
NCBI PubMed ID: 12019272Publication DOI: 10.1074/jbc.M204525200Journal NLM ID: 2985121RPublisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
Correspondence: raetz@biochem.duke.edu
Institutions: Department of Biochemistry, Duke University Medical Center, Durham, North Carolina 27710, USA
Methods: SDS-PAGE, DNA techniques, acid hydrolysis, genetic methods, biochemical methods, HPLC, enzyme assay, FPLC, bioinformatic analysis
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15. Compound ID: 3868
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Lau-(1-3)-3HOLau-(1-2)-+
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P-4)-+ |
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3HOLau-(1-3)-+ | |
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Dco-(1-3)-3HOLau-(1-2)-b-D-Glcp-(1-6)-a-D-Glcp-(1---P---P---1)-EtN
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Subst-(2-6)-+ |
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Dco-(1-3)-3HOLau-(1-3)-+
Subst = core oligosaccharide |
Show graphically |
Structure type: oligomer
Compound class: lipid A
Contained glycoepitopes: IEDB_120354,IEDB_141806,IEDB_142488,IEDB_144998,IEDB_145002,IEDB_146664,IEDB_534864,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 1457
Holme T, Rahman M, Jansson PE, Widmalm G "The lipopolysaccharide of Moraxella catarrhalis - Structural relationships and antigenic properties" -
European Journal of Biochemistry 265(2) (1999) 524-529
Moraxella catarrhalis has recently been shown to be both widespread and pathogenic, in contrast to previous reports. Several factors have been suggested as virulence factors, lipopolysaccharide (LPS) being one. Recent studies have shown the LPS to be without the O-chain, i.e. the polysaccharide part, and to have specific structural features corresponding to each of the three serogroups, A, B and C. The structures resemble in many respects those present in other Gram-negative nonenteric bacteria, with a galabiosyl element as a prominent common denominator. The presence of such common structures suggests that the LPS of these bacteria might be a part of a mechanism of survival for bacteria colonizing the human host.
NMR, antigen, structure, monoclonal antibodies, Cross Reactions, Moraxella catarrhalis
NCBI PubMed ID: 10504382Publication DOI: 10.1046/j.1432-1327.1999.00731.xJournal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Correspondence: pererik.jansson@kfcmail.hs.sll.se
Institutions: Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, Sweden, International Centre for Diarrhoeal Disease Research, Dhaka, Bangladesh, Microbiology and Tumor Biology Center, Karolinska Institute, Stockholm, Sweden, Clinical Research Centre, Analytical Unit, Karolinska Institute, Huddinge Hospital, Novum, Huddinge, Sweden
Methods: acid hydrolysis, HPAEC
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