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1. Compound ID: 56
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b-D-Galp-(1-4)-b-D-GlcpNAc-(1-6)-+
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b-D-Galp-(1-3)-b-D-GlcpNAc-(1-3)-D-Gal |
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Structure type: oligomer
Contained glycoepitopes: IEDB_130646,IEDB_135813,IEDB_136044,IEDB_136095,IEDB_136906,IEDB_137340,IEDB_137472,IEDB_1391962,IEDB_140108,IEDB_140122,IEDB_141794,IEDB_141807,IEDB_142078,IEDB_143794,IEDB_150899,IEDB_151528,IEDB_151531,IEDB_153529,IEDB_157001,IEDB_158533,IEDB_190606,SB_137,SB_156,SB_165,SB_166,SB_173,SB_187,SB_195,SB_29,SB_30,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 17
Blixt O, Van Die I, Norberg T, van den Eijnden DH "High-level expression of the Neisseria meningitidis lgtA gene in Escherichia coli and characterization of the encoded N-acetylglucosaminyltransferase as a useful catalyst in the synthesis of GlcNAcb1→3Gal and GalNAcb1-3Gal linkages" -
Glycobiology 9(10) (1999) 1061-1071
We have expressed the Neisseria meningitidis lgtA gene at a high level in Escherichia coli. The encoded β-N-acetylglucosaminyltransferase, referred to as LgtA, which in the bacterium is involved in the synthesis of the lacto-N-neo-tetraose structural element of the bacterial lipooligosaccharide, was obtained in an enzymatically highly active form. This glycosyltransferase appeared to be unusual in that it displays a broad acceptor specificity toward both α- and β-galactosides, whether structurally related to N- or O-protein-, or lipid-linked oligosaccharides. Product analysis by one- and two-dimensional 400 MHz 1H- and 13C NMR spectroscopy reveals that LgtA catalyzes the introduction of GlcNAc from UDP-GlcNAc in a β1→3-linkage to accepting Gal residues. The enzyme can thus be characterized as a UDP-GlcNAc:Gal α/β-R β 3-N-acetylglucosaminyltransferase. Although lactose is a highly preferred acceptor substrate the recombinant enzyme also acts efficiently on monomeric and dimeric N-acetyllactosamine revealing its potential value in the synthesis of polylactosaminoglycan structures in enzyme assisted procedures. Furthermore, LgtA shows a high donor promiscuity toward UDP-GalNAc, but not toward other UDP-sugars, and can catalyze the introduction of GalNAc in β1→3-linkage to α- or β-Gal in the acceptor structures at moderate rates. LgtA therefore shows promise to be a useful catalyst in the preparative synthesis of both GlcNAc β1→3 Gal and GalNAc β1→3 Gal linkages.
oligosaccharide, enzyme-assisted-synthesis, recombinant glycosyltransferase, glycosidic linkage, polylactosaminoglycan, recombinant glycosyltrasferase
NCBI PubMed ID: 10521543Publication DOI: 10.1093/glycob/9.10.1061Journal NLM ID: 9104124Publisher: IRL Press at Oxford University Press
Institutions: Department of Chemistry, Swedish University of Agricultural Sciences, Uppsala, Sweden, Department of Medical Chemistry, Vrije Universiteit, Van der Boechorstraat 7, 1081 BT Amsterdam, The Netherlands
Methods: 13C NMR, 1H NMR, NMR-2D, SDS-PAGE, enzyme-assisted synthesis, DNA techniques, glycosyltransferase assays, kinetics assays
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2. Compound ID: 57
Structure type: oligomer
Trivial name: lacto-N-biose
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_135813,IEDB_136044,IEDB_137340,IEDB_137472,IEDB_1391962,IEDB_141794,IEDB_141807,IEDB_142078,IEDB_143794,IEDB_150899,IEDB_151531,IEDB_190606,SB_137,SB_165,SB_166,SB_187,SB_195,SB_29,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 17
Blixt O, Van Die I, Norberg T, van den Eijnden DH "High-level expression of the Neisseria meningitidis lgtA gene in Escherichia coli and characterization of the encoded N-acetylglucosaminyltransferase as a useful catalyst in the synthesis of GlcNAcb1→3Gal and GalNAcb1-3Gal linkages" -
Glycobiology 9(10) (1999) 1061-1071
We have expressed the Neisseria meningitidis lgtA gene at a high level in Escherichia coli. The encoded β-N-acetylglucosaminyltransferase, referred to as LgtA, which in the bacterium is involved in the synthesis of the lacto-N-neo-tetraose structural element of the bacterial lipooligosaccharide, was obtained in an enzymatically highly active form. This glycosyltransferase appeared to be unusual in that it displays a broad acceptor specificity toward both α- and β-galactosides, whether structurally related to N- or O-protein-, or lipid-linked oligosaccharides. Product analysis by one- and two-dimensional 400 MHz 1H- and 13C NMR spectroscopy reveals that LgtA catalyzes the introduction of GlcNAc from UDP-GlcNAc in a β1→3-linkage to accepting Gal residues. The enzyme can thus be characterized as a UDP-GlcNAc:Gal α/β-R β 3-N-acetylglucosaminyltransferase. Although lactose is a highly preferred acceptor substrate the recombinant enzyme also acts efficiently on monomeric and dimeric N-acetyllactosamine revealing its potential value in the synthesis of polylactosaminoglycan structures in enzyme assisted procedures. Furthermore, LgtA shows a high donor promiscuity toward UDP-GalNAc, but not toward other UDP-sugars, and can catalyze the introduction of GalNAc in β1→3-linkage to α- or β-Gal in the acceptor structures at moderate rates. LgtA therefore shows promise to be a useful catalyst in the preparative synthesis of both GlcNAc β1→3 Gal and GalNAc β1→3 Gal linkages.
oligosaccharide, enzyme-assisted-synthesis, recombinant glycosyltransferase, glycosidic linkage, polylactosaminoglycan, recombinant glycosyltrasferase
NCBI PubMed ID: 10521543Publication DOI: 10.1093/glycob/9.10.1061Journal NLM ID: 9104124Publisher: IRL Press at Oxford University Press
Institutions: Department of Chemistry, Swedish University of Agricultural Sciences, Uppsala, Sweden, Department of Medical Chemistry, Vrije Universiteit, Van der Boechorstraat 7, 1081 BT Amsterdam, The Netherlands
Methods: 13C NMR, 1H NMR, NMR-2D, SDS-PAGE, enzyme-assisted synthesis, DNA techniques, glycosyltransferase assays, kinetics assays
- Article ID: 5119
Naumenko OI, Guo X, Senchenkova SN, Geng P, Perepelov AV, Shashkov AS, Liu B, Knirel YA "Structure and gene cluster of the O-antigen of Escherichia coli O54" -
Carbohydrate Research 462 (2018) 34-38
Mild acid hydrolysis of the lipopolysaccharide of Escherichia coli O54 afforded an O-polysaccharide, which was studied by sugar analysis, solvolysis with anhydrous trifluoroacetic acid, and 1H and 13C NMR spectroscopy. Solvolysis cleaved predominantly the linkage of β-d-Ribf and, to a lesser extent, that of β-d-GlcpNAc, whereas the other linkages, including the linkage of α-l-Rhap, were stable under selected conditions (40 °C, 5 h). The following structure of the O-polysaccharide was established: →4)-α-d-GalpA-(1 → 2)-α-l-Rhap-(1 → 2)-β-d-Ribf-(1 → 4)-β-d-Galp-(1 → 3)-β-d-GlcpNAc-(1→ The O-antigen gene cluster of E. coli O54 was analyzed and found to be consistent in general with the O-polysaccharide structure established but there were two exceptions: i) in the cluster, there were genes for phosphoserine phosphatase and serine transferase, which have no apparent role in the O-polysaccharide synthesis, and ii) no ribofuranosyltransferase gene was present in the cluster. Both uncommon features are shared by some other enteric bacteria.
O-antigen, Escherichia coli, O-polysaccharide, bacterial polysaccharide structure, O-antigen gene cluster
NCBI PubMed ID: 29660546Publication DOI: 10.1016/j.carres.2018.04.001Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: A.V. Perepelov
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Higher Chemical College of the Russian Academy of Sciences, D. I. Mendeleev University of Chemical Technology of Russia, Moscow, Russia, TEDA Institute of Biological Sciences and Biotechnology, Nankai University, Tianjin, 300457, China, Russian Federation, School of Basic Medical Sciences, Tianjin Medical University, Heping District, Tianjin, 300070, PR China
Methods: 13C NMR, 1H NMR, NMR-2D, sugar analysis, ESI-MS, GLC, GPC, acetylation, delipidation, function analysis of gene clusters, solvolysis with trifluoroacetic acid
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3. Compound ID: 58
Structure type: oligomer
Aglycon: (CH2)2NHC(O)OCH2Ph
Contained glycoepitopes: IEDB_135813,IEDB_136044,IEDB_137340,IEDB_137472,IEDB_1391962,IEDB_141794,IEDB_141807,IEDB_142078,IEDB_143794,IEDB_150899,IEDB_151531,IEDB_190606,SB_137,SB_165,SB_166,SB_187,SB_195,SB_29,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 17
Blixt O, Van Die I, Norberg T, van den Eijnden DH "High-level expression of the Neisseria meningitidis lgtA gene in Escherichia coli and characterization of the encoded N-acetylglucosaminyltransferase as a useful catalyst in the synthesis of GlcNAcb1→3Gal and GalNAcb1-3Gal linkages" -
Glycobiology 9(10) (1999) 1061-1071
We have expressed the Neisseria meningitidis lgtA gene at a high level in Escherichia coli. The encoded β-N-acetylglucosaminyltransferase, referred to as LgtA, which in the bacterium is involved in the synthesis of the lacto-N-neo-tetraose structural element of the bacterial lipooligosaccharide, was obtained in an enzymatically highly active form. This glycosyltransferase appeared to be unusual in that it displays a broad acceptor specificity toward both α- and β-galactosides, whether structurally related to N- or O-protein-, or lipid-linked oligosaccharides. Product analysis by one- and two-dimensional 400 MHz 1H- and 13C NMR spectroscopy reveals that LgtA catalyzes the introduction of GlcNAc from UDP-GlcNAc in a β1→3-linkage to accepting Gal residues. The enzyme can thus be characterized as a UDP-GlcNAc:Gal α/β-R β 3-N-acetylglucosaminyltransferase. Although lactose is a highly preferred acceptor substrate the recombinant enzyme also acts efficiently on monomeric and dimeric N-acetyllactosamine revealing its potential value in the synthesis of polylactosaminoglycan structures in enzyme assisted procedures. Furthermore, LgtA shows a high donor promiscuity toward UDP-GalNAc, but not toward other UDP-sugars, and can catalyze the introduction of GalNAc in β1→3-linkage to α- or β-Gal in the acceptor structures at moderate rates. LgtA therefore shows promise to be a useful catalyst in the preparative synthesis of both GlcNAc β1→3 Gal and GalNAc β1→3 Gal linkages.
oligosaccharide, enzyme-assisted-synthesis, recombinant glycosyltransferase, glycosidic linkage, polylactosaminoglycan, recombinant glycosyltrasferase
NCBI PubMed ID: 10521543Publication DOI: 10.1093/glycob/9.10.1061Journal NLM ID: 9104124Publisher: IRL Press at Oxford University Press
Institutions: Department of Chemistry, Swedish University of Agricultural Sciences, Uppsala, Sweden, Department of Medical Chemistry, Vrije Universiteit, Van der Boechorstraat 7, 1081 BT Amsterdam, The Netherlands
Methods: 13C NMR, 1H NMR, NMR-2D, SDS-PAGE, enzyme-assisted synthesis, DNA techniques, glycosyltransferase assays, kinetics assays
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4. Compound ID: 59
Structure type: oligomer
Trivial name: lacto-N-tetraose
Contained glycoepitopes: IEDB_117715,IEDB_135813,IEDB_136044,IEDB_137340,IEDB_137472,IEDB_1391962,IEDB_1391966,IEDB_141794,IEDB_141807,IEDB_142076,IEDB_142078,IEDB_142351,IEDB_142487,IEDB_142488,IEDB_143794,IEDB_144998,IEDB_146664,IEDB_150899,IEDB_151531,IEDB_157001,IEDB_190606,IEDB_983931,SB_137,SB_145,SB_156,SB_165,SB_166,SB_173,SB_174,SB_187,SB_192,SB_195,SB_29,SB_6,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 17
Blixt O, Van Die I, Norberg T, van den Eijnden DH "High-level expression of the Neisseria meningitidis lgtA gene in Escherichia coli and characterization of the encoded N-acetylglucosaminyltransferase as a useful catalyst in the synthesis of GlcNAcb1→3Gal and GalNAcb1-3Gal linkages" -
Glycobiology 9(10) (1999) 1061-1071
We have expressed the Neisseria meningitidis lgtA gene at a high level in Escherichia coli. The encoded β-N-acetylglucosaminyltransferase, referred to as LgtA, which in the bacterium is involved in the synthesis of the lacto-N-neo-tetraose structural element of the bacterial lipooligosaccharide, was obtained in an enzymatically highly active form. This glycosyltransferase appeared to be unusual in that it displays a broad acceptor specificity toward both α- and β-galactosides, whether structurally related to N- or O-protein-, or lipid-linked oligosaccharides. Product analysis by one- and two-dimensional 400 MHz 1H- and 13C NMR spectroscopy reveals that LgtA catalyzes the introduction of GlcNAc from UDP-GlcNAc in a β1→3-linkage to accepting Gal residues. The enzyme can thus be characterized as a UDP-GlcNAc:Gal α/β-R β 3-N-acetylglucosaminyltransferase. Although lactose is a highly preferred acceptor substrate the recombinant enzyme also acts efficiently on monomeric and dimeric N-acetyllactosamine revealing its potential value in the synthesis of polylactosaminoglycan structures in enzyme assisted procedures. Furthermore, LgtA shows a high donor promiscuity toward UDP-GalNAc, but not toward other UDP-sugars, and can catalyze the introduction of GalNAc in β1→3-linkage to α- or β-Gal in the acceptor structures at moderate rates. LgtA therefore shows promise to be a useful catalyst in the preparative synthesis of both GlcNAc β1→3 Gal and GalNAc β1→3 Gal linkages.
oligosaccharide, enzyme-assisted-synthesis, recombinant glycosyltransferase, glycosidic linkage, polylactosaminoglycan, recombinant glycosyltrasferase
NCBI PubMed ID: 10521543Publication DOI: 10.1093/glycob/9.10.1061Journal NLM ID: 9104124Publisher: IRL Press at Oxford University Press
Institutions: Department of Chemistry, Swedish University of Agricultural Sciences, Uppsala, Sweden, Department of Medical Chemistry, Vrije Universiteit, Van der Boechorstraat 7, 1081 BT Amsterdam, The Netherlands
Methods: 13C NMR, 1H NMR, NMR-2D, SDS-PAGE, enzyme-assisted synthesis, DNA techniques, glycosyltransferase assays, kinetics assays
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5. Compound ID: 60
Structure type: oligomer
Trivial name: Lewisa, Lewis a
Contained glycoepitopes: IEDB_130653,IEDB_135813,IEDB_136044,IEDB_136045,IEDB_137340,IEDB_137472,IEDB_1391962,IEDB_141794,IEDB_141807,IEDB_142078,IEDB_142489,IEDB_143794,IEDB_144562,IEDB_149556,IEDB_150899,IEDB_151531,IEDB_152214,IEDB_174333,IEDB_190606,IEDB_423096,IEDB_461723,SB_137,SB_155,SB_165,SB_166,SB_187,SB_195,SB_29,SB_7,SB_86,SB_88
The structure is contained in the following publication(s):
- Article ID: 17
Blixt O, Van Die I, Norberg T, van den Eijnden DH "High-level expression of the Neisseria meningitidis lgtA gene in Escherichia coli and characterization of the encoded N-acetylglucosaminyltransferase as a useful catalyst in the synthesis of GlcNAcb1→3Gal and GalNAcb1-3Gal linkages" -
Glycobiology 9(10) (1999) 1061-1071
We have expressed the Neisseria meningitidis lgtA gene at a high level in Escherichia coli. The encoded β-N-acetylglucosaminyltransferase, referred to as LgtA, which in the bacterium is involved in the synthesis of the lacto-N-neo-tetraose structural element of the bacterial lipooligosaccharide, was obtained in an enzymatically highly active form. This glycosyltransferase appeared to be unusual in that it displays a broad acceptor specificity toward both α- and β-galactosides, whether structurally related to N- or O-protein-, or lipid-linked oligosaccharides. Product analysis by one- and two-dimensional 400 MHz 1H- and 13C NMR spectroscopy reveals that LgtA catalyzes the introduction of GlcNAc from UDP-GlcNAc in a β1→3-linkage to accepting Gal residues. The enzyme can thus be characterized as a UDP-GlcNAc:Gal α/β-R β 3-N-acetylglucosaminyltransferase. Although lactose is a highly preferred acceptor substrate the recombinant enzyme also acts efficiently on monomeric and dimeric N-acetyllactosamine revealing its potential value in the synthesis of polylactosaminoglycan structures in enzyme assisted procedures. Furthermore, LgtA shows a high donor promiscuity toward UDP-GalNAc, but not toward other UDP-sugars, and can catalyze the introduction of GalNAc in β1→3-linkage to α- or β-Gal in the acceptor structures at moderate rates. LgtA therefore shows promise to be a useful catalyst in the preparative synthesis of both GlcNAc β1→3 Gal and GalNAc β1→3 Gal linkages.
oligosaccharide, enzyme-assisted-synthesis, recombinant glycosyltransferase, glycosidic linkage, polylactosaminoglycan, recombinant glycosyltrasferase
NCBI PubMed ID: 10521543Publication DOI: 10.1093/glycob/9.10.1061Journal NLM ID: 9104124Publisher: IRL Press at Oxford University Press
Institutions: Department of Chemistry, Swedish University of Agricultural Sciences, Uppsala, Sweden, Department of Medical Chemistry, Vrije Universiteit, Van der Boechorstraat 7, 1081 BT Amsterdam, The Netherlands
Methods: 13C NMR, 1H NMR, NMR-2D, SDS-PAGE, enzyme-assisted synthesis, DNA techniques, glycosyltransferase assays, kinetics assays
- Article ID: 231
Feizi T "Progress in deciphering the information content of the 'glycome' - a crescendo in the closing years of the millennium" -
Glycoconjugate Journal 17(7-9) (2000) 553-565
The closing years of the second millennium have been uplifting for carbohydrate biology. Optimism that oligosaccharide sequences are bearers of crucial biological information has been borne out by the constellation of efforts of carbohydrate chemists, biochemists, immunochemists, and cell- and molecular biologists. The direct involvement of specific oligosaccharide sequences in protein targeting and folding, and in mechanisms of infection, inflammation and immunity is now unquestioned. With the emergence of families of proteins with carbohydrate-binding activities, assignments of information content for defined oligosaccharide sequences will become more common, but the pinpointing and elucidation of the bioactive domains on oligosaccharides will continue to pose challenges even to the most experienced carbohydrate biologists. The neoglycolipid technology incorporates some of the key requirements for this challenge: namely the resolution of complex glycan mixtures, and ligand binding coupled with sequence determination by mass spectrometry.
monoclonal antibodies, mass spectrometry, blood group antigen, carbohydrate ligands, differentiation antigens, embryonic development, galectins, inflammation, leukocyte adhesion, neoglycolipids, oligosaccharide ligands, oligosaccharid probes, selectins
NCBI PubMed ID: 11421348Journal NLM ID: 8603310Publisher: Kluwer Academic Publishers
Correspondence: t.feizi@ic.ac.uk
Institutions: The Glycosciences Laboratory, Imperial College School of Medicine, Harrow, United Kingdom
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6. Compound ID: 311
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a-D-Glcp-(1-4)-+ Cho-(1--P--4)--+
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-6)-b-D-Glcp-(1-3)-b-D-Galp-(1-3)-b-D-GlcpNAc-(1-3)-a-D-GlcpNAc-(1-P- |
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Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_115009,IEDB_116046,IEDB_135813,IEDB_136044,IEDB_137340,IEDB_137472,IEDB_1391962,IEDB_140624,IEDB_140629,IEDB_141794,IEDB_141807,IEDB_142078,IEDB_142488,IEDB_143794,IEDB_144998,IEDB_146664,IEDB_150077,IEDB_150899,IEDB_151531,IEDB_190606,IEDB_241118,IEDB_423115,IEDB_983931,SB_137,SB_165,SB_166,SB_187,SB_192,SB_195,SB_29,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 83
Fudala R, Kondakova AN, Bednarska K, Senchenkova SN, Shashkov AS, Knirel YA, Zähringer U, Kaca W "Structure and serological characterization of the O-antigen of Proteus mirabilis O18 with a phosphocholine-containing oligosaccharide phosphate repeating unit" -
Carbohydrate Research 338(18) (2003) 1835-1842
A phosphorylated, choline-containing polysaccharide was obtained by O-deacylation of the lipopolysaccharide (LPS) of Proteus mirabilis O18 by treatment with aqueous 12% ammonia, whereas hydrolysis with dilute acetic acid resulted in depolymerisation of the polysaccharide chain by the glycosyl phosphate linkage. Treatment of the O-deacylated LPS with aqueous 48% hydrofluoric acid cleaved the glycosyl phosphate group but, unexpectedly, did not affect the choline phosphate group. The polysaccharide and the derived oligosaccharides were studied by NMR spectroscopy, including 2D 1H,1H COSY, TOCSY, ROESY, 1H,13C HMQC and HMQC-TOSCY experiments, along with chemical methods, and the following structure of the pentasaccharide phosphate repeating unit was established: [carbohydrate structure in text] Where ChoP=Phosphocoline Immunochemical studies of the LPS, O-deacylated LPS and partially dephosphorylated pentasaccharide using rabbit polyclonal anti-P. mirabilis O18 serum showed the importance of the glycosyl phosphate group in manifesting the serological specificity of the O18-antigen
Lipopolysaccharide, O-polysaccharide, Proteus mirabilis, Glycosyl phosphate, Phosphocholine
NCBI PubMed ID: 12932366Publication DOI: 10.1016/S0008-6215(03)00274-XJournal NLM ID: 0043535Publisher: Elsevier
Correspondence: wkaca@cmiwpan.lodz.pl
Institutions: Institute of Microbiology and Immunology, University of Lodz, 90-237 Lodz, Poland
Methods: methylation, NMR-2D, NMR, sugar analysis, MS
- Article ID: 541
Kondakova AN, Fudala R, Bednarska K, Senchenkova SN, Knirel YA, Kaca W "Structure of the neutral O-polysaccharide and biological activities of the lipopolysaccharide of Proteus mirabilis O20" -
Carbohydrate Research 339(3) (2004) 623-628
Mild acid degradation of the lipopolysaccharide (LPS) of Proteus mirabilis O20 resulted in depolymerisation of the O-polysaccharide to give a repeating-unit pentasaccharide. A polysaccharide was obtained by O-deacylation of the LPS followed by nitrous acid deamination. The derived pentasaccharide and polysaccharide were studied by NMR spectroscopy, including 2D 1H,1H COSY, TOCSY, ROESY, 1H,13C HMQC and HMQC-TOSCY experiments, along with chemical methods, and the following structure of the repeating unit of the O-polysaccharide was established: [Carbohydrate structure: see text]. As opposite to most other P. mirabilis O-polysaccharides studied, that of P. mirabilis O20 is neutral. A week serological cross-reactivity was observed between anti-P. mirabilis O20 serum and LPS of a number of Proteus serogroups with known O-polysaccharide structure. The ability of LPS of P. mirabilis O20 to activate the serine protease cascade was tested in Limulus amoebocyte lysate and in human blood plasma and compared with that of P. mirabilis O14a,14c having an acidic O-polysaccharide. The LPS of P. mirabilis O20 was found to be less active in both assays than the LPS of P. mirabilis O14a,14c and, therefore, the structurally variable O-polysaccharide may influenced the biological activity of the conserved lipid A moiety of the LPS.
Lipopolysaccharide, Proteus mirabilis, O-Polysaccharide structure, Serological cross-reactivity, Blood serum
NCBI PubMed ID: 15013399Publication DOI: 10.1016/j.carres.2003.11.016Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: rafalfu@wp.pl
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Institute of Microbiology and Immunology, University of Lodz,90-237 Lodz, Poland, Center for Medical Biology and Microbiology, Polish Academy of Sciences,93-232 Lodz, Poland, Institute of Microbiology, Swietokrzyska Academy, Kielce 25-406, Poland
Methods: methylation, NMR-2D, NMR, sugar analysis
- Article ID: 3365
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: 4043
Kaca W, Glenska J, Lechowicz L, Grabowski S, Brauner A, Kwinkowski M "Serotyping of Proteus mirabilis clinical strains based on lipopolysaccharide O-polysaccharide and core oligosaccharide structures" -
Biochemistry (Moscow) 76(7) (2011) 851-861
The aim of this work was to serotype Proteus mirabilis urinary tract infection (UTI) strains based on chemically defined O-antigens with the use of two clinical collections from Sweden and Poland consisting of 99 and 24 UTI strains, respectively. A simple two-step serotyping scheme was proposed using enzyme immunoassay with heat-stable surface antigens of Proteus cells and immunoblotting with isolated lipopolysaccharides (LPSs). Using polyclonal anti-P. mirabilis rabbit antisera, 50 Swedish and 8 Polish strains were classified into serogroups O10, O38, O36, O30, O17, O23, O9, O40, O49, O27, O5, O13, O24, O14, and O33. From the Swedish strains, 10 belonged to serogroup O10 and five to each of serogroups O38, O36, and O9. Therefore, none of the O-serogroups was predominant. The majority of the serotyped clinical strains possess acidic O-antigens containing uronic acids and various acidic non-carbohydrate substituents. In immunoblotting, antisera cross-reacted with both O-antigen and core of LPSs. The core region of 19 LPSs bound a single serum, and that of 12 LPSs bound more than two sera. Following bioinformatic analysis of the available sequences, a molecular approach to the prediction of Proteus core oligosaccharide structures was proposed. The identification of the core type of P. mirabilis R110, derived from a serogroup O3 wild strain, using restriction fragments length polymorphism analysis of galacturonic acid transferase is shown as an example. In summary, the most frequent O-serogroups among P. mirabilis UTI stains were identified. The diversity of serological reactions of LPSs is useful for serotyping of P. mirabilis clinical isolates. A possible role of the acidic components of O-antigens in UTI is discussed.
Lipopolysaccharide, O-antigen, Proteus mirabilis, serology, serotyping, glycosyl transferas
NCBI PubMed ID: 21999547Publication DOI: 10.1134/S0006297911070169Journal NLM ID: 0376536Publisher: Nauka/Interperiodica
Correspondence: wieslaw.kaca@ujk.edu.pl
Institutions: Department of Microbiology, Institute of Biology, Jan Kochanowski University, Kielce, Poland
Methods: PCR, SDS-PAGE, EIA, serological methods, immunoblotting, bioinformatic analysis
- Article ID: 4830
Young NM, Foote SJ, Wakarchuk WW "Review of phosphocholine substituents on bacterial pathogen glycans: synthesis, structures and interactions with host proteins" -
Molecular Immunology 56(4) (2013) 563-573
Among the non-carbohydrate components of glycans, the addition of phosphocholine (ChoP) to the glycans of pathogens occurs more rarely than acetylation or methylation, but it has far more potent biological consequences. These arise from ChoP's multiple interactions with host proteins, which are important at all stages of the infection process. These stages include initial adherence to cells, encountering the host's innate immune system and then the adaptive immune system. Thus, in the initial stages of an infection, ChoP groups are an asset to the pathogen, but they can turn into a disadvantage subsequently. In this review, we have focussed on structural aspects of these phenomena. We describe the biosynthesis of the ChoP modification, the structures of the pathogen glycans known to carry ChoP groups and the host proteins that recognize ChoP.
Haemophilus influenzae, Streptococcus pneumoniae, Phosphocholine, 4, 2-acetamido-4-amino-2, 6-trideoxyhexose, C-reactive protein, choline phosphate, ChoP, lipotechoic acid, LTA
NCBI PubMed ID: 23911414Publication DOI: 10.1016/j.molimm.2013.05.237Journal NLM ID: 7905289Publisher: Elsevier
Correspondence: martin.young@nrc-cnrc.gc.ca; wwakarchuk@ryerson.ca
Institutions: Human Health Therapeutics, National Research Council of Canada, 100 Sussex Drive, Ottawa, Ontario, Canada K1A 0R6, Department of Chemistry and Biology, Ryerson University, 350 Victoria Street, Toronto, Ontario, Canada M5B 2K3
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7. Compound ID: 312
|
Cho-(1--P--4)--+
|
a-D-Glcp-(1-4)-b-D-Glcp-(1-3)-b-D-Galp-(1-3)-b-D-GlcpNAc-(1-3)-D-GlcNAc-ol |
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Structure type: oligomer
Compound class: O-polysaccharide
Contained glycoepitopes: IEDB_115009,IEDB_116046,IEDB_135813,IEDB_136044,IEDB_137340,IEDB_137472,IEDB_1391962,IEDB_140624,IEDB_140629,IEDB_141794,IEDB_141807,IEDB_142078,IEDB_142488,IEDB_143794,IEDB_144998,IEDB_146664,IEDB_150899,IEDB_151531,IEDB_190606,IEDB_423115,IEDB_983931,SB_137,SB_165,SB_166,SB_187,SB_192,SB_195,SB_29,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 83
Fudala R, Kondakova AN, Bednarska K, Senchenkova SN, Shashkov AS, Knirel YA, Zähringer U, Kaca W "Structure and serological characterization of the O-antigen of Proteus mirabilis O18 with a phosphocholine-containing oligosaccharide phosphate repeating unit" -
Carbohydrate Research 338(18) (2003) 1835-1842
A phosphorylated, choline-containing polysaccharide was obtained by O-deacylation of the lipopolysaccharide (LPS) of Proteus mirabilis O18 by treatment with aqueous 12% ammonia, whereas hydrolysis with dilute acetic acid resulted in depolymerisation of the polysaccharide chain by the glycosyl phosphate linkage. Treatment of the O-deacylated LPS with aqueous 48% hydrofluoric acid cleaved the glycosyl phosphate group but, unexpectedly, did not affect the choline phosphate group. The polysaccharide and the derived oligosaccharides were studied by NMR spectroscopy, including 2D 1H,1H COSY, TOCSY, ROESY, 1H,13C HMQC and HMQC-TOSCY experiments, along with chemical methods, and the following structure of the pentasaccharide phosphate repeating unit was established: [carbohydrate structure in text] Where ChoP=Phosphocoline Immunochemical studies of the LPS, O-deacylated LPS and partially dephosphorylated pentasaccharide using rabbit polyclonal anti-P. mirabilis O18 serum showed the importance of the glycosyl phosphate group in manifesting the serological specificity of the O18-antigen
Lipopolysaccharide, O-polysaccharide, Proteus mirabilis, Glycosyl phosphate, Phosphocholine
NCBI PubMed ID: 12932366Publication DOI: 10.1016/S0008-6215(03)00274-XJournal NLM ID: 0043535Publisher: Elsevier
Correspondence: wkaca@cmiwpan.lodz.pl
Institutions: Institute of Microbiology and Immunology, University of Lodz, 90-237 Lodz, Poland
Methods: methylation, NMR-2D, NMR, sugar analysis, MS
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8. Compound ID: 313
|
P-6)-+ Cho-(1--P--4)--+
| |
a-D-Glcp-(1-4)-b-D-Glcp-(1-3)-b-D-Galp-(1-3)-b-D-GlcpNAc-(1-3)-D-GlcNAc |
Show graphically |
Structure type: oligomer
Compound class: O-polysaccharide
Contained glycoepitopes: IEDB_115009,IEDB_116046,IEDB_135813,IEDB_136044,IEDB_137340,IEDB_137472,IEDB_1391962,IEDB_140624,IEDB_140629,IEDB_141794,IEDB_141807,IEDB_142078,IEDB_142488,IEDB_143794,IEDB_144998,IEDB_146664,IEDB_150899,IEDB_151531,IEDB_190606,IEDB_241118,IEDB_423115,IEDB_983931,SB_137,SB_165,SB_166,SB_187,SB_192,SB_195,SB_29,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 83
Fudala R, Kondakova AN, Bednarska K, Senchenkova SN, Shashkov AS, Knirel YA, Zähringer U, Kaca W "Structure and serological characterization of the O-antigen of Proteus mirabilis O18 with a phosphocholine-containing oligosaccharide phosphate repeating unit" -
Carbohydrate Research 338(18) (2003) 1835-1842
A phosphorylated, choline-containing polysaccharide was obtained by O-deacylation of the lipopolysaccharide (LPS) of Proteus mirabilis O18 by treatment with aqueous 12% ammonia, whereas hydrolysis with dilute acetic acid resulted in depolymerisation of the polysaccharide chain by the glycosyl phosphate linkage. Treatment of the O-deacylated LPS with aqueous 48% hydrofluoric acid cleaved the glycosyl phosphate group but, unexpectedly, did not affect the choline phosphate group. The polysaccharide and the derived oligosaccharides were studied by NMR spectroscopy, including 2D 1H,1H COSY, TOCSY, ROESY, 1H,13C HMQC and HMQC-TOSCY experiments, along with chemical methods, and the following structure of the pentasaccharide phosphate repeating unit was established: [carbohydrate structure in text] Where ChoP=Phosphocoline Immunochemical studies of the LPS, O-deacylated LPS and partially dephosphorylated pentasaccharide using rabbit polyclonal anti-P. mirabilis O18 serum showed the importance of the glycosyl phosphate group in manifesting the serological specificity of the O18-antigen
Lipopolysaccharide, O-polysaccharide, Proteus mirabilis, Glycosyl phosphate, Phosphocholine
NCBI PubMed ID: 12932366Publication DOI: 10.1016/S0008-6215(03)00274-XJournal NLM ID: 0043535Publisher: Elsevier
Correspondence: wkaca@cmiwpan.lodz.pl
Institutions: Institute of Microbiology and Immunology, University of Lodz, 90-237 Lodz, Poland
Methods: methylation, NMR-2D, NMR, sugar analysis, MS
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9. Compound ID: 332
|
a-L-Rhap-(1-3)-+
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-3)-b-D-GlcpNAc-(1-4)-b-D-GlcpA-(1-2)-a-D-Manp-(1-4)-b-D-Galp-(1- |
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Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_115136,IEDB_130701,IEDB_135813,IEDB_136044,IEDB_136105,IEDB_137340,IEDB_137472,IEDB_1391962,IEDB_140630,IEDB_141794,IEDB_141807,IEDB_142078,IEDB_143794,IEDB_144983,IEDB_150899,IEDB_151531,IEDB_152206,IEDB_190606,IEDB_225177,IEDB_423153,IEDB_885823,IEDB_983930,SB_137,SB_165,SB_166,SB_187,SB_195,SB_29,SB_44,SB_67,SB_7,SB_72,SB_88
The structure is contained in the following publication(s):
- Article ID: 94
Gamian A, Katzenellenbogen E, Romanowska E, Fernandez JMG, Pedersen C, Ulrich J, Defaye J "Structure of the Hafnia alvei strain PCM 1188 O-specific polysaccharide" -
Carbohydrate Research 277 (1995) 245-255
The lipopolysaccharide was extracted from cells of Hafnia alvei PCM 1188 strain and, after mild acid hydrolysis, the O-specific polysaccharide isolated and characterized. On the basis of sugar and methylation analysis, FAB mass spectrometry and NMR spectroscopy of the polysaccharide and oligosaccharides obtained after Smith degradation, or solvolysis with anhydrous hydrogen fluoride, the repeating unit of the O-specific polysaccharide was shown to be the pentasaccharide: [formula: see text]
LPS, O-antigen, endotoxin, Hafnia alvei
NCBI PubMed ID: 8556734Publication DOI: 10.1016/0008-6215(95)00200-DJournal NLM ID: 0043535Publisher: Elsevier
Correspondence: gamian@immuno.iitd.pan.wroc.pl
Institutions: Ludwik Hirszfeld Institute of Immunology and Experimental Therapy, Wroclaw, Poland, Universidad de Sevillia, Departamento de Quimica Organica, Facultad de Quimica, Sevillie, Spain, The Technical University of Denmark, Institute of Organic Chemistry, Lyngby, Denmark, CNRS and CEA, Institut de Biologie Structurale, Grenoble, France, CNRS and CEA, Departament de Recherche Fondamentale sur la Matiere Condensee, Grenoble, France
Methods: methylation, NMR-2D, FAB-MS, NMR, HF solvolysis, sugar analysis, Smith degradation
- Article ID: 1834
L'vov VL, Lapina EB, Belaya OF, Pluzhnikova GN, Shashkov AS, Dmitriev BA "Somatic antigens of Shigella and Escherichia coli. Structure elucidation of O-specific polysaccharide from Shigella boydii, type 12,and investigation of its serological properties in comparison with O-specific polysaccharide from E. coli 07" -
Bioorganicheskaya Khimia = Bioorganic Chemistry [Russian] 12(9) (1986) 1240-1252
The structure of the O-specific polysaccharide of the somatic antigen (lipopolysaccharide) of Shigella boydii, type 12, was established by 1H- and 13C-NMR, methylation analysis and partial acid hydrolysis methods. The polysaccharide consists of pentasaccharide repeating units of the following structure: (formula; see text) The amount of O-acetyl groups was far less than stoichiometric, only about 2 for 3-4 repeating units. Nevertheless, the results of serological studies revealed 3-O-acetyl-α-L-rhamnose residue to be the major immunodominant group. In spite of the presence of similar trisaccharide fragments, the lipopolysaccharide and polysaccharide from Shigella boydii type 12 gave no crossreaction with lipopolysaccharide and polysaccharide from Escherichia coli 07. The possible reasons of the absence of serological relatedness between the Sh. boydii, type 12, and E. coli 07 cells were discussed.
NCBI PubMed ID: 2430583Journal NLM ID: 7804941Publisher: Moskva: Nauka
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Academy of Sciences of the USSR, Moscow, Russia
Methods: 13C NMR, 1H NMR
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10. Compound ID: 333
Structure type: oligomer
Compound class: O-polysaccharide
Contained glycoepitopes: IEDB_115136,IEDB_130701,IEDB_135813,IEDB_136044,IEDB_137340,IEDB_137472,IEDB_1391962,IEDB_140630,IEDB_141794,IEDB_141807,IEDB_142078,IEDB_143794,IEDB_144983,IEDB_150899,IEDB_151531,IEDB_152206,IEDB_190606,IEDB_423153,IEDB_983930,SB_137,SB_165,SB_166,SB_187,SB_195,SB_29,SB_44,SB_67,SB_7,SB_72,SB_88
The structure is contained in the following publication(s):
- Article ID: 94
Gamian A, Katzenellenbogen E, Romanowska E, Fernandez JMG, Pedersen C, Ulrich J, Defaye J "Structure of the Hafnia alvei strain PCM 1188 O-specific polysaccharide" -
Carbohydrate Research 277 (1995) 245-255
The lipopolysaccharide was extracted from cells of Hafnia alvei PCM 1188 strain and, after mild acid hydrolysis, the O-specific polysaccharide isolated and characterized. On the basis of sugar and methylation analysis, FAB mass spectrometry and NMR spectroscopy of the polysaccharide and oligosaccharides obtained after Smith degradation, or solvolysis with anhydrous hydrogen fluoride, the repeating unit of the O-specific polysaccharide was shown to be the pentasaccharide: [formula: see text]
LPS, O-antigen, endotoxin, Hafnia alvei
NCBI PubMed ID: 8556734Publication DOI: 10.1016/0008-6215(95)00200-DJournal NLM ID: 0043535Publisher: Elsevier
Correspondence: gamian@immuno.iitd.pan.wroc.pl
Institutions: Ludwik Hirszfeld Institute of Immunology and Experimental Therapy, Wroclaw, Poland, Universidad de Sevillia, Departamento de Quimica Organica, Facultad de Quimica, Sevillie, Spain, The Technical University of Denmark, Institute of Organic Chemistry, Lyngby, Denmark, CNRS and CEA, Institut de Biologie Structurale, Grenoble, France, CNRS and CEA, Departament de Recherche Fondamentale sur la Matiere Condensee, Grenoble, France
Methods: methylation, NMR-2D, FAB-MS, NMR, HF solvolysis, sugar analysis, Smith degradation
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11. Compound ID: 335
|
b-D-GlcpNAc-(1-4)-b-D-GlcpA-(1-2)-a-D-Manp-(1-4)-b-D-Galp-(1-3)-b-D-GlcpNAc-(1-4)-b-D-GlcpA-(1-2)-a-D-Manp |
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Structure type: oligomer
Compound class: O-polysaccharide
Contained glycoepitopes: IEDB_115136,IEDB_130701,IEDB_135813,IEDB_136044,IEDB_137340,IEDB_137472,IEDB_1391962,IEDB_140630,IEDB_141794,IEDB_141807,IEDB_142078,IEDB_143794,IEDB_144983,IEDB_150899,IEDB_151531,IEDB_152206,IEDB_190606,IEDB_423153,IEDB_983930,SB_137,SB_165,SB_166,SB_187,SB_195,SB_29,SB_44,SB_67,SB_7,SB_72,SB_88
The structure is contained in the following publication(s):
- Article ID: 94
Gamian A, Katzenellenbogen E, Romanowska E, Fernandez JMG, Pedersen C, Ulrich J, Defaye J "Structure of the Hafnia alvei strain PCM 1188 O-specific polysaccharide" -
Carbohydrate Research 277 (1995) 245-255
The lipopolysaccharide was extracted from cells of Hafnia alvei PCM 1188 strain and, after mild acid hydrolysis, the O-specific polysaccharide isolated and characterized. On the basis of sugar and methylation analysis, FAB mass spectrometry and NMR spectroscopy of the polysaccharide and oligosaccharides obtained after Smith degradation, or solvolysis with anhydrous hydrogen fluoride, the repeating unit of the O-specific polysaccharide was shown to be the pentasaccharide: [formula: see text]
LPS, O-antigen, endotoxin, Hafnia alvei
NCBI PubMed ID: 8556734Publication DOI: 10.1016/0008-6215(95)00200-DJournal NLM ID: 0043535Publisher: Elsevier
Correspondence: gamian@immuno.iitd.pan.wroc.pl
Institutions: Ludwik Hirszfeld Institute of Immunology and Experimental Therapy, Wroclaw, Poland, Universidad de Sevillia, Departamento de Quimica Organica, Facultad de Quimica, Sevillie, Spain, The Technical University of Denmark, Institute of Organic Chemistry, Lyngby, Denmark, CNRS and CEA, Institut de Biologie Structurale, Grenoble, France, CNRS and CEA, Departament de Recherche Fondamentale sur la Matiere Condensee, Grenoble, France
Methods: methylation, NMR-2D, FAB-MS, NMR, HF solvolysis, sugar analysis, Smith degradation
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12. Compound ID: 336
|
b-D-Galp-(1-3)-b-D-GlcpNAc-(1-4)-b-D-GlcpA-(1-2)-a-D-Manp-(1-4)-b-D-Galp-(1-3)-b-D-GlcpNAc-(1-4)-b-D-GlcpA-(1-2)-D-Man |
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Structure type: oligomer
Compound class: O-polysaccharide
Contained glycoepitopes: IEDB_115136,IEDB_130701,IEDB_135813,IEDB_136044,IEDB_137340,IEDB_137472,IEDB_137485,IEDB_1391962,IEDB_140630,IEDB_141794,IEDB_141807,IEDB_142078,IEDB_143794,IEDB_144983,IEDB_150899,IEDB_151531,IEDB_152206,IEDB_190606,IEDB_423153,IEDB_983930,SB_137,SB_165,SB_166,SB_187,SB_195,SB_29,SB_44,SB_67,SB_7,SB_72,SB_88
The structure is contained in the following publication(s):
- Article ID: 94
Gamian A, Katzenellenbogen E, Romanowska E, Fernandez JMG, Pedersen C, Ulrich J, Defaye J "Structure of the Hafnia alvei strain PCM 1188 O-specific polysaccharide" -
Carbohydrate Research 277 (1995) 245-255
The lipopolysaccharide was extracted from cells of Hafnia alvei PCM 1188 strain and, after mild acid hydrolysis, the O-specific polysaccharide isolated and characterized. On the basis of sugar and methylation analysis, FAB mass spectrometry and NMR spectroscopy of the polysaccharide and oligosaccharides obtained after Smith degradation, or solvolysis with anhydrous hydrogen fluoride, the repeating unit of the O-specific polysaccharide was shown to be the pentasaccharide: [formula: see text]
LPS, O-antigen, endotoxin, Hafnia alvei
NCBI PubMed ID: 8556734Publication DOI: 10.1016/0008-6215(95)00200-DJournal NLM ID: 0043535Publisher: Elsevier
Correspondence: gamian@immuno.iitd.pan.wroc.pl
Institutions: Ludwik Hirszfeld Institute of Immunology and Experimental Therapy, Wroclaw, Poland, Universidad de Sevillia, Departamento de Quimica Organica, Facultad de Quimica, Sevillie, Spain, The Technical University of Denmark, Institute of Organic Chemistry, Lyngby, Denmark, CNRS and CEA, Institut de Biologie Structurale, Grenoble, France, CNRS and CEA, Departament de Recherche Fondamentale sur la Matiere Condensee, Grenoble, France
Methods: methylation, NMR-2D, FAB-MS, NMR, HF solvolysis, sugar analysis, Smith degradation
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13. Compound ID: 352
|
a-L-Fucp-(1-2)-+
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a-D-GalpNAc-(1-3)-b-D-Galp-(1-3)-b-D-GlcpNAc |
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Structure type: fragment of a bigger structure
Trivial name: monofucosyl A type 1 histo-blood group epitope
Compound class: core oligosaccharide
Contained glycoepitopes: IEDB_130648,IEDB_130652,IEDB_135813,IEDB_136044,IEDB_136045,IEDB_137340,IEDB_137472,IEDB_137473,IEDB_1391961,IEDB_1391962,IEDB_140124,IEDB_141584,IEDB_141794,IEDB_141807,IEDB_142078,IEDB_142489,IEDB_143794,IEDB_144562,IEDB_149554,IEDB_149568,IEDB_150899,IEDB_150948,IEDB_151531,IEDB_152213,IEDB_152214,IEDB_152218,IEDB_153205,IEDB_153223,IEDB_153536,IEDB_153553,IEDB_153554,IEDB_174039,IEDB_174333,IEDB_190606,IEDB_461709,IEDB_461712,IEDB_461719,IEDB_885822,SB_100,SB_137,SB_149,SB_154,SB_165,SB_166,SB_187,SB_195,SB_29,SB_7,SB_86,SB_88
The structure is contained in the following publication(s):
- Article ID: 100
Therisod H, Monteiro MA, Perry MB, Caroff M "Helicobacter mustelae lipid A structure differs from that of Helicobacter pylori" -
FEBS Letters 499(1-2) (2001) 1-5
The lipid A structure of the Gram-negative bacterium Helicobacter mustelae, a ferret gastric pathogen responsible for the onset of gastric diseases in its host, was investigated. Two variant lipid A structures were found in the same strain. One structure contained a bisphosphorylated β-(1→6)-linked D-glucosamine backbone disaccharide with hydroxytetradecanoic acid in amide linkages. Unlike the structure described for the lipid A of the related human Helicobacter pylori gastric pathogen, which contains a C1 phosphate moiety, this lipid A presented phosphate groups at both the C1 and C4' positions, and contained no octadecanoyl fatty acid, which is present in H. pylori. The second lipid A structure had a different fatty acid composition in that 3-OH C(16) replaced most of the amide-linked 3-OH C(14).
structure, lipid A, endotoxin, Helicobacter mustelae, Helicobacter pylori
NCBI PubMed ID: 11418100Publication DOI: 10.1016/S0014-5793(01)02496-6Journal NLM ID: 0155157Publisher: Elsevier
Correspondence: martine.caroff@bbmpc.u-psud.fr
Institutions: Equipe Endotoxines, UMR 8619 du Centre National de la Recherche Scientifique, Biochimie, Université de Paris-Sud, Orsay, France, Institute for Biological Sciences, National Research Council of Canada, Ottawa, ON, Canada
Methods: 13C NMR, 1H NMR, NMR-2D, GC-MS, de-O-acylation, TLC, 31P NMR, GC, MALDI-TOF MS, composition analysis, PD-MS, NMR-1D
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14. Compound ID: 550
|
R-CetEtN-(1--P--6)--+
|
-3)-a-D-Galp-(1-6)-b-D-Glcp-(1-3)-b-D-Galp-(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_136044,IEDB_136906,IEDB_137340,IEDB_137472,IEDB_1391962,IEDB_140529,IEDB_141794,IEDB_141807,IEDB_142078,IEDB_142488,IEDB_143794,IEDB_146664,IEDB_150899,IEDB_151528,IEDB_151531,IEDB_167069,IEDB_190606,IEDB_983931,SB_137,SB_156,SB_165,SB_166,SB_173,SB_187,SB_192,SB_195,SB_29,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 114
Toukach FV, Shashkov AS "Computer-assisted structural analysis of regular glycopolymers on the basis of 13C NMR data" -
Carbohydrate Research 335(2) (2001) 101-104
A computer-assisted approach to the prediction of the primary structures of regular glycopolymers is described. The analysis is based on comparing the calculated 13C NMR spectra of all the possible structures of the repeating unit (for the given monomeric composition) to an experimental 13C NMR spectrum. The spectra generation is based on the spectral database containing information on the 13C chemical shifts of monomers, di- and trimeric fragments. If the required data are missing from this database, the special database for average glycosylation effects is used. The analysis reveals those structures with the calculated 13C NMR spectrum most close to observed. The structures of repeating units of any topology containing up to six residues linked by glycosidic, amidic or phospho-diester bridges can be predicted. Unambiguous selection of the proper structure from the output list of possible structures may require additional experimental data. Testing the created program and databases on bacterial polysaccharides and their derivatives containing up to three non-sugar residues (alditols, amino acids, phosphate groups etc.) per repeating unit revealed the good convergence of prediction with independently obtained structural data.
NMR, structural, analysis, structural analysis, 13C NMR, calculation, computer, glycopolymer, regular
NCBI PubMed ID: 11567641Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: tou@cacr.ioc.ac.ru
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospect 47, 117913 Moscow, Russian Federation.
Methods: NMR simulation
- Article ID: 494
Torzewska A, Kocharova NA, Maszewska A, Knirel YA, Rozalski A "Serological characterization of the O-specific polysaccharide of Providencia alcalifaciens O23" -
Archivum Immunologiae et Therapiae Experimentalis 52(1) (2004) 43-49
INTRODUCTION: The genus Providencia belongs to the Enterobacteriaceae family and currently consists of five species: P. alcalifaciens, P. heimbachae, P. rettgerii, P. rustigianii and P. stuartii. The serological classification scheme of P. alcalifaciens, P. rustigianii and P. stuartii includes 63 O-serogroups and 30 H-serogroups. The O-antigenic specificity is defined by the structure of the O-antigen (O-specific polysaccharide--OPS), a part of the lipopolysaccharide (LPS, endotoxin), one of the major components of the outer membrane of gram-negative bacteria and an important virulence factor of these bacteria. Among the bacteria of the Enterobacteriaceae family, the genus Providencia is one of the least studied in respect to its LPS structure and antigenic specificity. Studies of the chemical structures and the serological specificity of the O-antigens aim at the elucidation of the molecular basis of the serological classification of Providencia sp. MATERIALS AND METHODS: LPS and alkali-treated LPS of P. alcalifaciens O23 and serologically related P. rustigianii O14, P. mirabilis O13 and P. myxofaciens as well as O-antiserum against P. alcalifaciens O23 were used. Serological characterization of P. alcalifaciens O23 O-specific polysaccharide was done by use enzyme immunosorbent assay (EIA), passive hemolysis test (PHT) as well as by inhibition and sodium deoxycholate polyacrylamide gel electrophoresis (DOC-PAGE) of LPS and Western blot. RESULTS AND CONCLUSIONS: The OPS of P. alcalifaciens, O23, contains an N-(D-glucuronoyl)-N-[(R)-1-carboxyethyl]-L-lysine residue (GlcAAlaLys). The LPS of P. alcalifaciens, O23, and other LPSs containing AlaLys from Providencia and Proteus strains were tested with rabbit anti-P. alcalifiaciens O23 serum. The serological data showed that a GlcAAlaLys-associated epitope plays a role as an antigenic determinant in the P. alcalifaciens O23 OPS and revealed the particular importance of glucuronic acid and the carboxyethyl group for the binding of O23-specific antibodies.
Lipopolysaccharide, structure, characterization, polysaccharide, O-antigen, O-specific, O-specific polysaccharide, Providencia, Providencia alcalifaciens, serological, O-serogroups, Ne-[(R)-1-carboxyethyl]-L-lysine
NCBI PubMed ID: 15053232Journal NLM ID: 0114365Publisher: Basel, Boston: Birkhaüser
Correspondence: rozala@biol.uni.lodz.pl
Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Institute of Microbiology and Immunology, University of Lodz, Lodz, Poland
- Article ID: 1467
Knirel YA, Kaca W, Rozalski A, Sidorczyk Z "Structure of the O-antigenic polysaccharides of Proteus bacteria" -
Polish Journal of Chemistry 73 (1999) 895-907
Data on the composition and structure of the O-specific polysaccharides (O-antigens) of the lipopolysaccharides of the genus Proteus are summarized and discussed as the molecular basis for serotyping of these medically important bacteria.
structure, O-antigen, Proteus, Bacterial polysaccharide, epitope specificity
Journal NLM ID: 7901356WWW link: http://www.ichf.edu.pl/pjch/pj-1999/pj0699.htm#0895Publisher: Państwowe Wydawnictwo Naukowe
Correspondence: knirel@ioc.ac.ru
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences,Leninsky Prospekt 47, Moscow, Russia, Institute of Microbiology and Immunology, University of Łódź, Banacha 12/16, 90-237 Łódź, Poland, Center of Microbiology and Virology, Polish Academy of Sciences, Lodowa 106, 93-232 Łódź, Poland
- Article ID: 1873
Vinogradov EV, Kaca W, Shashkov AS, Pietrasik D, Rozalski A, Knirel YA, Kochetkov NK "Structure of Proteus mirabilis O3 O-specific polysaccharide containing N-(2-hydroxyethyl)-D-alanine" -
Bioorganicheskaya Khimia = Bioorganic Chemistry [Russian] 15 (1989) 1431-1434
O-Specific polysaccharide, obtained by mild acid degradation of the Proteus mirabilis 03 lipopolysaccharide, was dephosphorylated with 48% HF to give a linear polysaccharide and an amino acid, N-(2-hydroxyethyl)-D-alanine. The structure of the polysaccharide was determined by methylation, the Smith degradation and computer-assisted analysis of the 13C NMR spectra of original and dephosphorylated polymers and oligomers. The structure of the amino acid was elucidated by using 1H and 13C NMR spectroscopy and mass spectrometry (applied to the acetylated methyl ester derivative), optical rotation and CD spectrum data and comparison with the synthetic sample. The repeating unit of P. mirabilis 03 O-specific polysaccharide is shown to have the following structure: (formula: see text)
NCBI PubMed ID: 2483615Journal NLM ID: 7804941Publisher: Moskva: Nauka
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Academy of Sciences of the USSR, Moscow, Russia
Methods: 13C NMR, 1H NMR, methylation, Smith degradation, HF treatment
- Article ID: 2423
Vinogradov EV, Kaca W, Shashkov AS, Krajewska-Pietrasik D, Rozalski A, Knirel YA, Kochetkov NK "The structure of Proteus mirabilis O3 O-specific polysaccharide containing N-(2-hydroxyethyl)-D-alanine" -
European Journal of Biochemistry 188 (1990) 645-651
O-Specific polysaccharide was obtained by mild acid degradation of Proteus mirabilis O3 lipopolysaccharide. The polysaccharide was dephosphorylated with 48% HF to give a linear polysaccharide and an amino acid, N-(2-hydroxyethyl)-D-alanine. The structure of the polysaccharide was determined by methylation, Smith degradation and computer-assisted analysis of the 13C-NMR spectra of original and dephosphorylated polymers and oligomers. The structure of the amino acid was investigated by using 1H and 13C-NMR spectroscopy and mass spectrometry (applied to the acetylated methyl ester derivative). Its absolute configuration was established by comparison of the optical rotation value and CD spectrum of the natural and synthetic product. On the basis of the data obtained, it was concluded that the repeating unit of P. mirabilis O3 O-specific polysaccharide has the following structure: (formula; see text) Removal of the amino acid phosphate substituent significantly decreased serological activity of the O-specific polysaccharide, thus showing the immunodominant role of this group. Serological cross-reactions between P. mirabilis O3 and O27 were demonstrated and tentatively substantiated.
NCBI PubMed ID: 2185017Journal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Academy of Sciences of the USSR, Moscow, Russia
Methods: 13C NMR
- Article ID: 2684
Knirel YA, Vinogradov EV, Shashkov AS, Sidorczyk Z, Rozalski A, Radziejewska-Lebrecht I, Kaca W "Structural study of O-specific polysaccharides of Proteus" -
Journal of Carbohydrate Chemistry 12 (1993) 379-414
Proteus bacteria are important human opportunistic pathogens which frequently cause urinary tract infections. According to Bergey's Manual of Systematic Bacteriology,1 this genus includes three species: P. mirabilis, P. vulgaris, and P. myxofaciens. A novel species of P. penneri has been recently proposed2,3 for strains formerly called P. vulgaris biogroup I. Proteus is an antigenically heterogeneous group of bacteria, and this is mainly associated with diverse composition and structures of O-specific polysaccharide chains of outer-membrane lipopolysaccharides (O-antigens). The Kauffman-Perch serological classification4 of P. mirabilis and P. vulgaris includes 49 O-serogroups. However, a number of S-strains remain unclassified,5 including strains of P. penneri.
Publication DOI: 10.1080/07328309308019396Journal NLM ID: 8218151Publisher: Marcel Dekker
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky pr. 47, Moscow, B-334, Russia
Methods: 13C NMR, NMR
- Article ID: 3724
Kwinkowski M, Grabowski S, Konieczna I, Nazarenko EL, Kaca W "The cross-reactivity of Shewanella fidelis lipopolysaccharide with anti-Proteus antibodies" -
Polish Journal of Microbiology 58(3) (2009) 275-278
The serological cross-reactivity between lipopolysaccharides (LPS) of S. fidelis KMM3582(T) and rabbit anti-O P. mirabilis antibodies was tested. Using ELISA and Western blot cross-reactivity between S. fidelis LPS and antisera against P. mirabilis O14, O3 LPSs was found. The observed cross-reaction may suggest that anti-P. mirabilis S1959 (O3) antibodies may bind to the internal part of S. fidelis O-polysaccharides. A weak interaction between S. fidelis LPS and antiserum against P. mirabilis O13 in Western blot suggests that the absolute configuration of non-sugar 'AlaLys' component (N(ε)-[(S)-l-carboxyethyl]-N(α)-(D-galacturonoyl)-L-lysine) may influence the affinity of antibodies for S. fidelis LPS.
lipopolysaccharides, Proteus mirabilis, cross-reactivity, Shewanella fidelis
NCBI PubMed ID: 19899622Journal NLM ID: 101229003Publisher: Polskie Towarzystwo Mikrobiologow
Correspondence: marek.kwinkowski@ujk.edu.pl
Institutions: Department of Microbiology, Institute of Biology, Jan Kochanowski University, Kielce, Poland
Methods: ELISA, serological methods
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15. Compound ID: 556
Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide
Contained glycoepitopes: IEDB_135813,IEDB_136044,IEDB_137340,IEDB_137472,IEDB_1391962,IEDB_141794,IEDB_141807,IEDB_142078,IEDB_143794,IEDB_150899,IEDB_151531,IEDB_153212,IEDB_190606,SB_137,SB_165,SB_166,SB_173,SB_187,SB_195,SB_29,SB_7,SB_74,SB_85,SB_88
The structure is contained in the following publication(s):
- Article ID: 114
Toukach FV, Shashkov AS "Computer-assisted structural analysis of regular glycopolymers on the basis of 13C NMR data" -
Carbohydrate Research 335(2) (2001) 101-104
A computer-assisted approach to the prediction of the primary structures of regular glycopolymers is described. The analysis is based on comparing the calculated 13C NMR spectra of all the possible structures of the repeating unit (for the given monomeric composition) to an experimental 13C NMR spectrum. The spectra generation is based on the spectral database containing information on the 13C chemical shifts of monomers, di- and trimeric fragments. If the required data are missing from this database, the special database for average glycosylation effects is used. The analysis reveals those structures with the calculated 13C NMR spectrum most close to observed. The structures of repeating units of any topology containing up to six residues linked by glycosidic, amidic or phospho-diester bridges can be predicted. Unambiguous selection of the proper structure from the output list of possible structures may require additional experimental data. Testing the created program and databases on bacterial polysaccharides and their derivatives containing up to three non-sugar residues (alditols, amino acids, phosphate groups etc.) per repeating unit revealed the good convergence of prediction with independently obtained structural data.
NMR, structural, analysis, structural analysis, 13C NMR, calculation, computer, glycopolymer, regular
NCBI PubMed ID: 11567641Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: tou@cacr.ioc.ac.ru
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospect 47, 117913 Moscow, Russian Federation.
Methods: NMR simulation
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