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1. Compound ID: 189
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a-L-Rhap-(1-3)-a-D-Galp-(1-3)-b-D-GlcpNAc-(1-4)-+ a-L-Rhap-(1-3)-+
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a-L-Rhap-(1-3)-a-D-Galp-(1-3)-b-D-Glcp2Ac-(1-4)-a-L-Rhap-(1-2)-a-L-Rhap-(1-2)-a-L-Rhap-(1-1)-D-Glc-ol |
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Structure type: oligomer
Contained glycoepitopes: IEDB_114708,IEDB_133754,IEDB_135813,IEDB_136105,IEDB_136906,IEDB_137340,IEDB_137472,IEDB_141794,IEDB_141807,IEDB_142488,IEDB_144825,IEDB_144826,IEDB_146664,IEDB_151528,IEDB_151531,IEDB_190606,IEDB_225177,IEDB_885823,IEDB_983931,SB_192,SB_61,SB_7
The structure is contained in the following publication(s):
- Article ID: 43
Deng LY, Kasper DL, Krick TP, Wessels MR "Characterization of the linkage between the type III capsular polysaccharide and the bacterial cell wall of group B Streptococcus" -
Journal of Biological Chemistry 275(11) (2000) 7497-7504
The capsular polysaccharide of group B Streptococcus is a key virulence factor and an important target for protective immune responses. Until now, the nature of the attachment between the capsular polysaccharide and the bacterial cell has been poorly defined. We isolated insoluble cell wall fragments from lysates of type III group B Streptococcus and showed that the complexes contained both capsular polysaccharide and group B carbohydrate covalently bound to peptidoglycan. Treatment with the endo-N-acetylmuramidase mutanolysin released soluble complexes of capsular polysaccharide linked to group B carbohydrate by peptidoglycan fragments. Capsular polysaccharide could be enzymatically cleaved from group B carbohydrate by treatment of the soluble complexes with β-N-acetylglucosaminidase, which catalyzes hydrolysis of the β-D-GlcNAc(1→4)β-D-MurNAc subunit produced by mutanolysin digestion of peptidoglycan. Evidence from gas chromatography/mass spectrometry and (31)P NMR analysis of the separated polysaccharides supports a model of the group B Streptococcus cell surface in which the group B carbohydrate and the capsular polysaccharide are independently linked to the glycan backbone of cell wall peptidoglycan; group B carbohydrate is linked to N-acetylmuramic acid, and capsular polysaccharide is linked via a phosphodiester bond and an oligosaccharide linker to N-acetylglucosamine
polysaccharide, Streptococcus, capsular polysaccharide, type, group B Streptococcus, cell wall, linkage
NCBI PubMed ID: 10713053Publication DOI: 10.1074/jbc.275.11.7497Journal NLM ID: 2985121RPublisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
Correspondence: mwessels@channing.harvard.edu
Institutions: Channing Laboratory, Brigham and Women's Hospital, Harvard Medical School, Boston, Massachusetts 02115, USA
Methods: enzymatic degradation
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2. Compound ID: 190
|
a-L-Rhap-(1-2)-+ a-L-Rhap-(1-3)-+
| |
a-L-Rhap-(1-3)-a-D-Galp-(1-3)-b-D-GlcpNAc-(1-4)-a-L-Rhap-(1-2)-a-L-Rhap-(1-1)-D-Glc-ol |
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Structure type: oligomer
Compound class: CPS
Contained glycoepitopes: IEDB_114708,IEDB_133754,IEDB_135813,IEDB_136105,IEDB_136906,IEDB_137340,IEDB_137472,IEDB_141794,IEDB_141807,IEDB_144825,IEDB_144826,IEDB_151528,IEDB_151531,IEDB_190606,IEDB_225177,IEDB_885823,SB_7
The structure is contained in the following publication(s):
- Article ID: 43
Deng LY, Kasper DL, Krick TP, Wessels MR "Characterization of the linkage between the type III capsular polysaccharide and the bacterial cell wall of group B Streptococcus" -
Journal of Biological Chemistry 275(11) (2000) 7497-7504
The capsular polysaccharide of group B Streptococcus is a key virulence factor and an important target for protective immune responses. Until now, the nature of the attachment between the capsular polysaccharide and the bacterial cell has been poorly defined. We isolated insoluble cell wall fragments from lysates of type III group B Streptococcus and showed that the complexes contained both capsular polysaccharide and group B carbohydrate covalently bound to peptidoglycan. Treatment with the endo-N-acetylmuramidase mutanolysin released soluble complexes of capsular polysaccharide linked to group B carbohydrate by peptidoglycan fragments. Capsular polysaccharide could be enzymatically cleaved from group B carbohydrate by treatment of the soluble complexes with β-N-acetylglucosaminidase, which catalyzes hydrolysis of the β-D-GlcNAc(1→4)β-D-MurNAc subunit produced by mutanolysin digestion of peptidoglycan. Evidence from gas chromatography/mass spectrometry and (31)P NMR analysis of the separated polysaccharides supports a model of the group B Streptococcus cell surface in which the group B carbohydrate and the capsular polysaccharide are independently linked to the glycan backbone of cell wall peptidoglycan; group B carbohydrate is linked to N-acetylmuramic acid, and capsular polysaccharide is linked via a phosphodiester bond and an oligosaccharide linker to N-acetylglucosamine
polysaccharide, Streptococcus, capsular polysaccharide, type, group B Streptococcus, cell wall, linkage
NCBI PubMed ID: 10713053Publication DOI: 10.1074/jbc.275.11.7497Journal NLM ID: 2985121RPublisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
Correspondence: mwessels@channing.harvard.edu
Institutions: Channing Laboratory, Brigham and Women's Hospital, Harvard Medical School, Boston, Massachusetts 02115, USA
Methods: enzymatic degradation
- Article ID: 1752
Michon F, Katzenellenbogen E, Kasper DL, Jennings HJ "Structure of the complex group-specific polysaccharide of Group B Streptococcus" -
Biochemistry 26 (1987) 476-486
The group-specific antigen was isolated from a type Ia group B streptococcal strain and is a complex polysaccharide composed of α-L-rhamnopyranosyl, α-D-galactopyranosyl, 2-acetamido-2-deoxy-β-D-glucopyranosyl, D-glucitol, and phosphate residues. The complexity of the group B polysaccharide antigen is evident from the fact that when depolymerized by basic hydrolysis it yielded three structurally related, but nevertheless significantly different, oligosaccharides. These oligosaccharides were obtained in different molar quantities as their monophosphate esters. This evidence strongly suggests that they are linked by phosphodiester bonds in the original group B antigen. If these oligosaccharides are in fact randomly situated throughout the linear polysaccharide, then this type of heterogeneous repeating unit is unusual for a polysaccharide of bacterial origin. However, this structural arrangement of the oligosaccharides has yet to be unambiguously established because the alternate explanation of there being three different polysaccharides in the group B antigen cannot be discounted in the evidence presented here. The oligosaccharides were enzymatically dephosphorylated, and the structures of two of the three oligosaccharides are (formula: see text) Despite their structural differences, the two oligosaccharides are related by the smaller being an integral part of the larger. In the structural analysis of the group B antigen, methylation analysis, periodate oxidation, nuclear magnetic resonance (NMR) spectroscopy, mass spectrometry, fast atom bombardment mass spectrometry, and various specific chemical and enzymatic degradations were the principal methods used. Of particular interest was the use of an α-rhamnosidase to selectively degrade the larger oligosaccharide. This facilitated the assignment of signals in its 1H and 13C NMR spectra.
NCBI PubMed ID: 3548820Journal NLM ID: 0370623Publisher: American Chemical Society
Institutions: Division of Biological Sciences, National Research Council of Canada, Ottawa, Ontario, Canada K1A OR6
Methods: 13C NMR, 1H NMR
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3. Compound ID: 191
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a-L-Rhap-(1-3)-+
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a-L-Rhap-(1-2)-a-L-Rhap-(1-2)-a-L-Rhap-(1-1)-D-Glc-ol |
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Structure type: oligomer
Compound class: CPS
Contained glycoepitopes: IEDB_114708,IEDB_133754,IEDB_136105,IEDB_144825,IEDB_225177,IEDB_885823
The structure is contained in the following publication(s):
- Article ID: 43
Deng LY, Kasper DL, Krick TP, Wessels MR "Characterization of the linkage between the type III capsular polysaccharide and the bacterial cell wall of group B Streptococcus" -
Journal of Biological Chemistry 275(11) (2000) 7497-7504
The capsular polysaccharide of group B Streptococcus is a key virulence factor and an important target for protective immune responses. Until now, the nature of the attachment between the capsular polysaccharide and the bacterial cell has been poorly defined. We isolated insoluble cell wall fragments from lysates of type III group B Streptococcus and showed that the complexes contained both capsular polysaccharide and group B carbohydrate covalently bound to peptidoglycan. Treatment with the endo-N-acetylmuramidase mutanolysin released soluble complexes of capsular polysaccharide linked to group B carbohydrate by peptidoglycan fragments. Capsular polysaccharide could be enzymatically cleaved from group B carbohydrate by treatment of the soluble complexes with β-N-acetylglucosaminidase, which catalyzes hydrolysis of the β-D-GlcNAc(1→4)β-D-MurNAc subunit produced by mutanolysin digestion of peptidoglycan. Evidence from gas chromatography/mass spectrometry and (31)P NMR analysis of the separated polysaccharides supports a model of the group B Streptococcus cell surface in which the group B carbohydrate and the capsular polysaccharide are independently linked to the glycan backbone of cell wall peptidoglycan; group B carbohydrate is linked to N-acetylmuramic acid, and capsular polysaccharide is linked via a phosphodiester bond and an oligosaccharide linker to N-acetylglucosamine
polysaccharide, Streptococcus, capsular polysaccharide, type, group B Streptococcus, cell wall, linkage
NCBI PubMed ID: 10713053Publication DOI: 10.1074/jbc.275.11.7497Journal NLM ID: 2985121RPublisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
Correspondence: mwessels@channing.harvard.edu
Institutions: Channing Laboratory, Brigham and Women's Hospital, Harvard Medical School, Boston, Massachusetts 02115, USA
Methods: enzymatic degradation
- Article ID: 1752
Michon F, Katzenellenbogen E, Kasper DL, Jennings HJ "Structure of the complex group-specific polysaccharide of Group B Streptococcus" -
Biochemistry 26 (1987) 476-486
The group-specific antigen was isolated from a type Ia group B streptococcal strain and is a complex polysaccharide composed of α-L-rhamnopyranosyl, α-D-galactopyranosyl, 2-acetamido-2-deoxy-β-D-glucopyranosyl, D-glucitol, and phosphate residues. The complexity of the group B polysaccharide antigen is evident from the fact that when depolymerized by basic hydrolysis it yielded three structurally related, but nevertheless significantly different, oligosaccharides. These oligosaccharides were obtained in different molar quantities as their monophosphate esters. This evidence strongly suggests that they are linked by phosphodiester bonds in the original group B antigen. If these oligosaccharides are in fact randomly situated throughout the linear polysaccharide, then this type of heterogeneous repeating unit is unusual for a polysaccharide of bacterial origin. However, this structural arrangement of the oligosaccharides has yet to be unambiguously established because the alternate explanation of there being three different polysaccharides in the group B antigen cannot be discounted in the evidence presented here. The oligosaccharides were enzymatically dephosphorylated, and the structures of two of the three oligosaccharides are (formula: see text) Despite their structural differences, the two oligosaccharides are related by the smaller being an integral part of the larger. In the structural analysis of the group B antigen, methylation analysis, periodate oxidation, nuclear magnetic resonance (NMR) spectroscopy, mass spectrometry, fast atom bombardment mass spectrometry, and various specific chemical and enzymatic degradations were the principal methods used. Of particular interest was the use of an α-rhamnosidase to selectively degrade the larger oligosaccharide. This facilitated the assignment of signals in its 1H and 13C NMR spectra.
NCBI PubMed ID: 3548820Journal NLM ID: 0370623Publisher: American Chemical Society
Institutions: Division of Biological Sciences, National Research Council of Canada, Ottawa, Ontario, Canada K1A OR6
Methods: 13C NMR, 1H NMR
- Article ID: 1755
Michon F, Brisson JR, Dell A, Kasper DL, Jennings HJ "Multiantennary group-specific polysaccharide of group B Streptococcus" -
Biochemistry 27 (1988) 5341-5351
The group-specific antigen of group B Streptococcus is composed of four different oligosaccharide units of Mw 766 (III), 1277 (II), 1462 (IV), and 1788 (I). The major constituent sugars of the oligosaccharides are α-L-rhamnopyranose, α-D-galactopyranose, 2-acetamido-2-deoxy-β-D-glucopyranosyl, and D-glucitol except that III does not contain α-D-galactopyranosyl or 2-acetamido-2-deoxy-β-D-glucopyranosyl residues and IV contains no D-glucitol but has one additional β-L-rhamnopyranosyl residue. The structures of II and III have been previously elucidated [Michon, F., Katzenellenbogen, E., Kasper, D. L., & Jennings, H. J. (1987) Biochemistry 26, 476-486]. In the group B antigen all the oligosaccharides are linked by one type of phosphodiester bond from O6 of the D-glucitol residue of one oligosaccharide to O6 of the α-D-galactopyranosyl residue of the next to form a complex and highly branched multiantennary structure. However, despite the heterogeneous nature of its component oligosaccharides, some order has been identified in the biosynthesis of the group B antigen from chemical and enzymatic sequence studies. Because III lacks an α-D-galactopyranosyl residue but has a D-glucitol residue, it is situated at the reducing terminus of all the branches of the group B antigen where it is always adjacent to a II moiety. Conversely, IV has an α-D-galactopyranosyl residue but has no D-glucitol and is therefore located at the reducing terminus of the group B antigen where it probably functions as a linker molecule between the group B polysaccharide and the cell wall peptidoglycan of the group B streptococcal organisms. Oligosaccharide I contains two α-D-galactopyranosyl residues and one D-glucitol residue and thus constitutes the branch point in the group B antigen, whereas II contains one of each of the above residues and therefore is situated in linear interchain positions. The group B antigen is highly branched and probably has a unique multiantennary structure.
NCBI PubMed ID: 3048399Journal NLM ID: 0370623Publisher: American Chemical Society
Institutions: Division of Biological Sciences, National Research Council of Canada, Ottawa, Ontario
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4. Compound ID: 243
Structure type: oligomer
Compound class: EPS
Contained glycoepitopes: IEDB_114708,IEDB_136044,IEDB_137472,IEDB_141794,IEDB_190606,IEDB_922721,SB_165,SB_166,SB_187,SB_195,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 63
Faber EJ, Kamerling JP, Vliegenthart JFG "Structure of the extracellular polysaccharide produced by Lactobacillus delbrueckii subsp bulgaricus 291" -
Carbohydrate Research 331(2) (2001) 183-194
The lactic acid bacterium Lactobacillus delbrueckii subsp. bulgaricus 291, when grown in skimmed milk, produced 80 mg/L exopolysaccharide with an average molecular mass of 1.4 x 10(3) kDa. Monosaccharide analysis, methylation analysis, MS, and 1D/2D NMR (1H and 13C) studies performed on the native polysaccharide, and on oligosaccharides obtained from a mild acid hydrolysate of the native polysaccharide, showed the polysaccharide to consist of branched pentasaccharide repeating units with the following structure: [structure: see text].
structural analysis, exopolysaccharide, Lactobacillus delbrueckii subsp. bulgaicus
NCBI PubMed ID: 11322732Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: kame@boc.chem.uu.nl
Institutions: Department of Bio-Organic Chemistry, Bijvoet Center, Utrecht University, Utrecht, The Netherlands
Methods: NMR-2D, methylation, NMR, sugar analysis, acid hydrolysis, MS
- Article ID: 4102
Roslund MU, Sawen E, Landstrom J, Ronnols J, Jonsson KH, Lundborg M, Svensson MV, Widmalm G "Complete 1H and 13C NMR chemical shift assignments of mono-, di-, and trisaccharides as basis for NMR chemical shift predictions of polysaccharides using the computer program casper" -
Carbohydrate Research 346(11) (2011) 1311-1319
The computer program casper uses (1)H and (13)C NMR chemical shift data of mono- to trisaccharides for the prediction of chemical shifts of oligo- and polysaccharides. In order to improve the quality of these predictions the (1)H and (13)C, as well as (31)P when applicable, NMR chemical shifts of 30 mono-, di-, and trisaccharides were assigned. The reducing sugars gave two distinct sets of NMR resonances due to the α- and β-anomeric forms. In total 35 (1)H and (13)C NMR chemical shift data sets were obtained from the oligosaccharides. One- and two-dimensional NMR experiments were used for the chemical shift assignments and special techniques were employed in some cases such as 2D (1)H,(13)C-HSQC Hadamard Transform methodology which was acquired approximately 45 times faster than a regular t(1) incremented (1)H,(13)C-HSQC experiment and a 1D (1)H,(1)H-CSSF-TOCSY experiment which was able to distinguish spin-systems in which the target protons were only 3.3Hz apart. The (1)H NMR chemical shifts were subsequently refined using total line-shape analysis with the PERCH NMR software. The acquired NMR data were then utilized in the casper program (http://www.casper.organ.su.se/casper/) for NMR chemical shift predictions of the O-antigen polysaccharides from Klebsiella O5, Shigella flexneri serotype X, and Salmonella arizonae O62. The data were compared to experimental data of the polysaccharides from the two former strains and the lipopolysaccharide of the latter strain showing excellent agreement between predicted and experimental (1)H and (13)C NMR chemical shifts.
Lipopolysaccharide, chemical shift prediction, chemical shift filter, Hadamard matrix
NCBI PubMed ID: 21621752Publication DOI: 10.1016/j.carres.2011.04.033Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: G. Widmalm
Institutions: Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, Stockholm, Sweden
Methods: 13C NMR, 1H NMR, NMR-2D, 31P NMR, NMR-1D, computer analysis with CASPER
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5. Compound ID: 244
Structure type: oligomer
Compound class: EPS
Contained glycoepitopes: IEDB_114708,IEDB_142488,IEDB_146664,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 63
Faber EJ, Kamerling JP, Vliegenthart JFG "Structure of the extracellular polysaccharide produced by Lactobacillus delbrueckii subsp bulgaricus 291" -
Carbohydrate Research 331(2) (2001) 183-194
The lactic acid bacterium Lactobacillus delbrueckii subsp. bulgaricus 291, when grown in skimmed milk, produced 80 mg/L exopolysaccharide with an average molecular mass of 1.4 x 10(3) kDa. Monosaccharide analysis, methylation analysis, MS, and 1D/2D NMR (1H and 13C) studies performed on the native polysaccharide, and on oligosaccharides obtained from a mild acid hydrolysate of the native polysaccharide, showed the polysaccharide to consist of branched pentasaccharide repeating units with the following structure: [structure: see text].
structural analysis, exopolysaccharide, Lactobacillus delbrueckii subsp. bulgaicus
NCBI PubMed ID: 11322732Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: kame@boc.chem.uu.nl
Institutions: Department of Bio-Organic Chemistry, Bijvoet Center, Utrecht University, Utrecht, The Netherlands
Methods: NMR-2D, methylation, NMR, sugar analysis, acid hydrolysis, MS
- Article ID: 1146
Robijn GW, Thomas JR, Haas H, van den Berg DJC, Kamerling JP, Vliegenthart JFG "The structure of the exopolysaccharide produced by Lactobacillus helveticus 766" -
Carbohydrate Research 276(1) (1995) 137-154
The exopolysaccharide produced by Lactobacillus helveticus 766 in skimmed milk was found to be composed of D-glucose and D-galactose in a molar ratio of 2:1. Linkage analysis and 1D/2D NMR studies (1H and 13C) performed on the native polysaccharide, and on oligosaccharides obtained from a partial acid hydrolysate, showed the polysaccharide to consist of hexasaccharide repeating units with the following structure: [formula: see text]
NMR, structure, exopolysaccharide, Lactobacillus, lactic acid bacterium, D-glucose, D-galactose, milk, lactic acid bacteria;lactobacillus helveticus;exopolysaccharide structure
NCBI PubMed ID: 8536251Publication DOI: 10.1016/0008-6215(95)00171-OJournal NLM ID: 0043535Publisher: Elsevier
Institutions: Bijvoet Center, Department of Bio-Organic Chemistry, Utrecht University, Utrecht, The Netherlands, Unilever Research Laboratory Vlaardingen, P.O. Box 114, NL-3130 AC, Vlaardingen, The Netherlands
Methods: 13C NMR, 1H NMR, NMR-2D, methylation, GLC-MS, FAB-MS, partial acid hydrolysis, sugar analysis, dephosphorylation, GLC, anion-exchange chromatography, de-O-acetylation
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6. Compound ID: 245
Structure type: oligomer
Compound class: EPS
Contained glycoepitopes: IEDB_114708,IEDB_142488,IEDB_146664,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 63
Faber EJ, Kamerling JP, Vliegenthart JFG "Structure of the extracellular polysaccharide produced by Lactobacillus delbrueckii subsp bulgaricus 291" -
Carbohydrate Research 331(2) (2001) 183-194
The lactic acid bacterium Lactobacillus delbrueckii subsp. bulgaricus 291, when grown in skimmed milk, produced 80 mg/L exopolysaccharide with an average molecular mass of 1.4 x 10(3) kDa. Monosaccharide analysis, methylation analysis, MS, and 1D/2D NMR (1H and 13C) studies performed on the native polysaccharide, and on oligosaccharides obtained from a mild acid hydrolysate of the native polysaccharide, showed the polysaccharide to consist of branched pentasaccharide repeating units with the following structure: [structure: see text].
structural analysis, exopolysaccharide, Lactobacillus delbrueckii subsp. bulgaicus
NCBI PubMed ID: 11322732Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: kame@boc.chem.uu.nl
Institutions: Department of Bio-Organic Chemistry, Bijvoet Center, Utrecht University, Utrecht, The Netherlands
Methods: NMR-2D, methylation, NMR, sugar analysis, acid hydrolysis, MS
- Article ID: 1146
Robijn GW, Thomas JR, Haas H, van den Berg DJC, Kamerling JP, Vliegenthart JFG "The structure of the exopolysaccharide produced by Lactobacillus helveticus 766" -
Carbohydrate Research 276(1) (1995) 137-154
The exopolysaccharide produced by Lactobacillus helveticus 766 in skimmed milk was found to be composed of D-glucose and D-galactose in a molar ratio of 2:1. Linkage analysis and 1D/2D NMR studies (1H and 13C) performed on the native polysaccharide, and on oligosaccharides obtained from a partial acid hydrolysate, showed the polysaccharide to consist of hexasaccharide repeating units with the following structure: [formula: see text]
NMR, structure, exopolysaccharide, Lactobacillus, lactic acid bacterium, D-glucose, D-galactose, milk, lactic acid bacteria;lactobacillus helveticus;exopolysaccharide structure
NCBI PubMed ID: 8536251Publication DOI: 10.1016/0008-6215(95)00171-OJournal NLM ID: 0043535Publisher: Elsevier
Institutions: Bijvoet Center, Department of Bio-Organic Chemistry, Utrecht University, Utrecht, The Netherlands, Unilever Research Laboratory Vlaardingen, P.O. Box 114, NL-3130 AC, Vlaardingen, The Netherlands
Methods: 13C NMR, 1H NMR, NMR-2D, methylation, GLC-MS, FAB-MS, partial acid hydrolysis, sugar analysis, dephosphorylation, GLC, anion-exchange chromatography, de-O-acetylation
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7. Compound ID: 246
Structure type: oligomer
Compound class: EPS
Contained glycoepitopes: IEDB_114708,IEDB_136044,IEDB_137472,IEDB_141794,IEDB_142487,IEDB_142488,IEDB_146664,IEDB_190606,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_6,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 63
Faber EJ, Kamerling JP, Vliegenthart JFG "Structure of the extracellular polysaccharide produced by Lactobacillus delbrueckii subsp bulgaricus 291" -
Carbohydrate Research 331(2) (2001) 183-194
The lactic acid bacterium Lactobacillus delbrueckii subsp. bulgaricus 291, when grown in skimmed milk, produced 80 mg/L exopolysaccharide with an average molecular mass of 1.4 x 10(3) kDa. Monosaccharide analysis, methylation analysis, MS, and 1D/2D NMR (1H and 13C) studies performed on the native polysaccharide, and on oligosaccharides obtained from a mild acid hydrolysate of the native polysaccharide, showed the polysaccharide to consist of branched pentasaccharide repeating units with the following structure: [structure: see text].
structural analysis, exopolysaccharide, Lactobacillus delbrueckii subsp. bulgaicus
NCBI PubMed ID: 11322732Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: kame@boc.chem.uu.nl
Institutions: Department of Bio-Organic Chemistry, Bijvoet Center, Utrecht University, Utrecht, The Netherlands
Methods: NMR-2D, methylation, NMR, sugar analysis, acid hydrolysis, MS
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8. Compound ID: 591
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Subst-(?-6)-+
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-3)-D-Glc-ol-(6--P--5)--b-D-Galf-(1-3)-a-D-Galp-(1-2)-a-L-Rhap-(1-3)-a-D-Manp-(1-
Subst = N-(2-hydroxyethyl)-2-aminoethylphosphonic acid = SMILES O{1}P(CCNC{5}CO)(O)=O |
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Structure type: polymer chemical repeating unit
; 50000-150000
Compound class: CPS
Contained glycoepitopes: IEDB_114708,IEDB_130701,IEDB_136095,IEDB_136105,IEDB_136906,IEDB_137472,IEDB_141794,IEDB_144983,IEDB_151528,IEDB_152206,IEDB_190606,IEDB_225177,IEDB_885823,IEDB_983930,SB_44,SB_67,SB_7,SB_72
The structure is contained in the following publication(s):
- Article ID: 176
Vinogradov E, Egbosimba EE, Perry MB, Lam JS, Forsberg CW "Structural analysis of the carbohydrate components of the outer membrane of the lipopolysaccharide-lacking cellulolytic ruminal bacterium Fibrobacter succinogenes S85" -
European Journal of Biochemistry 268(12) (2001) 3566-3576
The polysaccharides from the outer membrane of the Gram-negative ruminal bacterium Fibrobacter succinogenes were isolated by phenol/water extraction and separated by size-exclusion chromatography in the presence of deoxycholate detergent into a lower-molecular-mass fraction designated 'glycolipid' and a high-molecular-mass 'capsular polysaccharide' fraction. Both fractions lacked typical lipopolysaccharide components including 2-keto-3-deoxyoctulosonic acid and 3-hydroxy fatty acids. Carbohydrate components of these fractions were represented by two polysaccharides and one oligosaccharide (possibly glycolipid) with the following structures: : : where HEAEP is N-(2-hydroxyethyl)-2-aminoethylphosphonic acid, found for the first time in natural compounds. The polysaccharides contained pentadecanoic acid and anteisopentadecanoic acid, possibly present as the acyl components. All constituent monosaccharides except L-rhamnose had a D- configuration. In addition to having a structural role in the outer membrane, these polysaccharides may provide protection for this lipopolysaccharide-less bacterium in the highly competitive ruminal environment, as phosphonic acids covalently linked to membrane polymers have in the past been attributed the function of stabilizing membranes in the presence of phosphatases and lipases.
NMR, structure, polysaccharide, Fibrobacter succinogenes, glycolipid
NCBI PubMed ID: 11422388Journal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Correspondence: evguenii.vinogradov@nrc.ca
Institutions: Institute for Biological Sciences, National Research Council, Ottawa, ON, Canada
Methods: 13C NMR, 1H NMR, NMR-2D, 31P NMR
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9. Compound ID: 594
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Subst-(?-6)-+
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P-5)-b-D-Galf-(1-3)-a-D-Galp-(1-2)-a-L-Rhap-(1-3)-a-D-Manp-(1-3)-D-Glc-ol
Subst = N-(2-hydroxyethyl)-2-aminoethylphosphonic acid = SMILES O{1}P(CCNC{5}CO)(O)=O |
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Structure type: oligomer
Compound class: CPS
Contained glycoepitopes: IEDB_114708,IEDB_130701,IEDB_136095,IEDB_136105,IEDB_136906,IEDB_137472,IEDB_141794,IEDB_144983,IEDB_151528,IEDB_152206,IEDB_190606,IEDB_225177,IEDB_885823,IEDB_983930,SB_44,SB_67,SB_7,SB_72
The structure is contained in the following publication(s):
- Article ID: 176
Vinogradov E, Egbosimba EE, Perry MB, Lam JS, Forsberg CW "Structural analysis of the carbohydrate components of the outer membrane of the lipopolysaccharide-lacking cellulolytic ruminal bacterium Fibrobacter succinogenes S85" -
European Journal of Biochemistry 268(12) (2001) 3566-3576
The polysaccharides from the outer membrane of the Gram-negative ruminal bacterium Fibrobacter succinogenes were isolated by phenol/water extraction and separated by size-exclusion chromatography in the presence of deoxycholate detergent into a lower-molecular-mass fraction designated 'glycolipid' and a high-molecular-mass 'capsular polysaccharide' fraction. Both fractions lacked typical lipopolysaccharide components including 2-keto-3-deoxyoctulosonic acid and 3-hydroxy fatty acids. Carbohydrate components of these fractions were represented by two polysaccharides and one oligosaccharide (possibly glycolipid) with the following structures: : : where HEAEP is N-(2-hydroxyethyl)-2-aminoethylphosphonic acid, found for the first time in natural compounds. The polysaccharides contained pentadecanoic acid and anteisopentadecanoic acid, possibly present as the acyl components. All constituent monosaccharides except L-rhamnose had a D- configuration. In addition to having a structural role in the outer membrane, these polysaccharides may provide protection for this lipopolysaccharide-less bacterium in the highly competitive ruminal environment, as phosphonic acids covalently linked to membrane polymers have in the past been attributed the function of stabilizing membranes in the presence of phosphatases and lipases.
NMR, structure, polysaccharide, Fibrobacter succinogenes, glycolipid
NCBI PubMed ID: 11422388Journal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Correspondence: evguenii.vinogradov@nrc.ca
Institutions: Institute for Biological Sciences, National Research Council, Ottawa, ON, Canada
Methods: 13C NMR, 1H NMR, NMR-2D, 31P NMR
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10. Compound ID: 595
|
Subst-(?-6)-+
|
P-6)-b-D-Galf-(1-3)-a-D-Galp-(1-2)-a-L-Rhap-(1-3)-a-D-Manp-(1-3)-D-Glc-ol
Subst = N-(2-hydroxyethyl)-2-aminoethylphosphonic acid = SMILES O{1}P(CCNC{5}CO)(O)=O |
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Structure type: oligomer
Compound class: CPS
Contained glycoepitopes: IEDB_114708,IEDB_130701,IEDB_136095,IEDB_136105,IEDB_136906,IEDB_137472,IEDB_141794,IEDB_144983,IEDB_151528,IEDB_152206,IEDB_190606,IEDB_225177,IEDB_885823,IEDB_983930,SB_44,SB_67,SB_7,SB_72
The structure is contained in the following publication(s):
- Article ID: 176
Vinogradov E, Egbosimba EE, Perry MB, Lam JS, Forsberg CW "Structural analysis of the carbohydrate components of the outer membrane of the lipopolysaccharide-lacking cellulolytic ruminal bacterium Fibrobacter succinogenes S85" -
European Journal of Biochemistry 268(12) (2001) 3566-3576
The polysaccharides from the outer membrane of the Gram-negative ruminal bacterium Fibrobacter succinogenes were isolated by phenol/water extraction and separated by size-exclusion chromatography in the presence of deoxycholate detergent into a lower-molecular-mass fraction designated 'glycolipid' and a high-molecular-mass 'capsular polysaccharide' fraction. Both fractions lacked typical lipopolysaccharide components including 2-keto-3-deoxyoctulosonic acid and 3-hydroxy fatty acids. Carbohydrate components of these fractions were represented by two polysaccharides and one oligosaccharide (possibly glycolipid) with the following structures: : : where HEAEP is N-(2-hydroxyethyl)-2-aminoethylphosphonic acid, found for the first time in natural compounds. The polysaccharides contained pentadecanoic acid and anteisopentadecanoic acid, possibly present as the acyl components. All constituent monosaccharides except L-rhamnose had a D- configuration. In addition to having a structural role in the outer membrane, these polysaccharides may provide protection for this lipopolysaccharide-less bacterium in the highly competitive ruminal environment, as phosphonic acids covalently linked to membrane polymers have in the past been attributed the function of stabilizing membranes in the presence of phosphatases and lipases.
NMR, structure, polysaccharide, Fibrobacter succinogenes, glycolipid
NCBI PubMed ID: 11422388Journal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Correspondence: evguenii.vinogradov@nrc.ca
Institutions: Institute for Biological Sciences, National Research Council, Ottawa, ON, Canada
Methods: 13C NMR, 1H NMR, NMR-2D, 31P NMR
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11. Compound ID: 596
|
Subst-(?-6)-+
|
b-D-Galf-(1-3)-a-D-Galp-(1-2)-a-L-Rhap-(1-3)-a-D-Manp-(1-3)-D-Glc-ol
Subst = N-(2-hydroxyethyl)-2-aminoethylphosphonic acid = SMILES O{1}P(CCNC{5}CO)(O)=O |
Show graphically |
Structure type: oligomer
Compound class: CPS
Contained glycoepitopes: IEDB_114708,IEDB_130701,IEDB_136095,IEDB_136105,IEDB_136906,IEDB_137472,IEDB_141794,IEDB_144983,IEDB_151528,IEDB_152206,IEDB_190606,IEDB_225177,IEDB_885823,IEDB_983930,SB_44,SB_67,SB_7,SB_72
The structure is contained in the following publication(s):
- Article ID: 176
Vinogradov E, Egbosimba EE, Perry MB, Lam JS, Forsberg CW "Structural analysis of the carbohydrate components of the outer membrane of the lipopolysaccharide-lacking cellulolytic ruminal bacterium Fibrobacter succinogenes S85" -
European Journal of Biochemistry 268(12) (2001) 3566-3576
The polysaccharides from the outer membrane of the Gram-negative ruminal bacterium Fibrobacter succinogenes were isolated by phenol/water extraction and separated by size-exclusion chromatography in the presence of deoxycholate detergent into a lower-molecular-mass fraction designated 'glycolipid' and a high-molecular-mass 'capsular polysaccharide' fraction. Both fractions lacked typical lipopolysaccharide components including 2-keto-3-deoxyoctulosonic acid and 3-hydroxy fatty acids. Carbohydrate components of these fractions were represented by two polysaccharides and one oligosaccharide (possibly glycolipid) with the following structures: : : where HEAEP is N-(2-hydroxyethyl)-2-aminoethylphosphonic acid, found for the first time in natural compounds. The polysaccharides contained pentadecanoic acid and anteisopentadecanoic acid, possibly present as the acyl components. All constituent monosaccharides except L-rhamnose had a D- configuration. In addition to having a structural role in the outer membrane, these polysaccharides may provide protection for this lipopolysaccharide-less bacterium in the highly competitive ruminal environment, as phosphonic acids covalently linked to membrane polymers have in the past been attributed the function of stabilizing membranes in the presence of phosphatases and lipases.
NMR, structure, polysaccharide, Fibrobacter succinogenes, glycolipid
NCBI PubMed ID: 11422388Journal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Correspondence: evguenii.vinogradov@nrc.ca
Institutions: Institute for Biological Sciences, National Research Council, Ottawa, ON, Canada
Methods: 13C NMR, 1H NMR, NMR-2D, 31P NMR
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12. Compound ID: 598
Structure type: oligomer
Compound class: CPS
Contained glycoepitopes: IEDB_114708,IEDB_130701,IEDB_136105,IEDB_136906,IEDB_137472,IEDB_141794,IEDB_144983,IEDB_151528,IEDB_152206,IEDB_190606,IEDB_225177,IEDB_885823,IEDB_983930,SB_44,SB_67,SB_7,SB_72
The structure is contained in the following publication(s):
- Article ID: 176
Vinogradov E, Egbosimba EE, Perry MB, Lam JS, Forsberg CW "Structural analysis of the carbohydrate components of the outer membrane of the lipopolysaccharide-lacking cellulolytic ruminal bacterium Fibrobacter succinogenes S85" -
European Journal of Biochemistry 268(12) (2001) 3566-3576
The polysaccharides from the outer membrane of the Gram-negative ruminal bacterium Fibrobacter succinogenes were isolated by phenol/water extraction and separated by size-exclusion chromatography in the presence of deoxycholate detergent into a lower-molecular-mass fraction designated 'glycolipid' and a high-molecular-mass 'capsular polysaccharide' fraction. Both fractions lacked typical lipopolysaccharide components including 2-keto-3-deoxyoctulosonic acid and 3-hydroxy fatty acids. Carbohydrate components of these fractions were represented by two polysaccharides and one oligosaccharide (possibly glycolipid) with the following structures: : : where HEAEP is N-(2-hydroxyethyl)-2-aminoethylphosphonic acid, found for the first time in natural compounds. The polysaccharides contained pentadecanoic acid and anteisopentadecanoic acid, possibly present as the acyl components. All constituent monosaccharides except L-rhamnose had a D- configuration. In addition to having a structural role in the outer membrane, these polysaccharides may provide protection for this lipopolysaccharide-less bacterium in the highly competitive ruminal environment, as phosphonic acids covalently linked to membrane polymers have in the past been attributed the function of stabilizing membranes in the presence of phosphatases and lipases.
NMR, structure, polysaccharide, Fibrobacter succinogenes, glycolipid
NCBI PubMed ID: 11422388Journal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Correspondence: evguenii.vinogradov@nrc.ca
Institutions: Institute for Biological Sciences, National Research Council, Ottawa, ON, Canada
Methods: 13C NMR, 1H NMR, NMR-2D, 31P NMR
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13. Compound ID: 599
|
b-D-Galf-(1-3)-a-D-Galp-(1-2)-a-L-Rhap-(1-3)-a-D-Manp-(1-3)-D-Glc-ol |
Show graphically |
Structure type: oligomer
Compound class: CPS
Contained glycoepitopes: IEDB_114708,IEDB_130701,IEDB_136095,IEDB_136105,IEDB_136906,IEDB_137472,IEDB_141794,IEDB_144983,IEDB_151528,IEDB_152206,IEDB_190606,IEDB_225177,IEDB_885823,IEDB_983930,SB_44,SB_67,SB_7,SB_72
The structure is contained in the following publication(s):
- Article ID: 176
Vinogradov E, Egbosimba EE, Perry MB, Lam JS, Forsberg CW "Structural analysis of the carbohydrate components of the outer membrane of the lipopolysaccharide-lacking cellulolytic ruminal bacterium Fibrobacter succinogenes S85" -
European Journal of Biochemistry 268(12) (2001) 3566-3576
The polysaccharides from the outer membrane of the Gram-negative ruminal bacterium Fibrobacter succinogenes were isolated by phenol/water extraction and separated by size-exclusion chromatography in the presence of deoxycholate detergent into a lower-molecular-mass fraction designated 'glycolipid' and a high-molecular-mass 'capsular polysaccharide' fraction. Both fractions lacked typical lipopolysaccharide components including 2-keto-3-deoxyoctulosonic acid and 3-hydroxy fatty acids. Carbohydrate components of these fractions were represented by two polysaccharides and one oligosaccharide (possibly glycolipid) with the following structures: : : where HEAEP is N-(2-hydroxyethyl)-2-aminoethylphosphonic acid, found for the first time in natural compounds. The polysaccharides contained pentadecanoic acid and anteisopentadecanoic acid, possibly present as the acyl components. All constituent monosaccharides except L-rhamnose had a D- configuration. In addition to having a structural role in the outer membrane, these polysaccharides may provide protection for this lipopolysaccharide-less bacterium in the highly competitive ruminal environment, as phosphonic acids covalently linked to membrane polymers have in the past been attributed the function of stabilizing membranes in the presence of phosphatases and lipases.
NMR, structure, polysaccharide, Fibrobacter succinogenes, glycolipid
NCBI PubMed ID: 11422388Journal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Correspondence: evguenii.vinogradov@nrc.ca
Institutions: Institute for Biological Sciences, National Research Council, Ottawa, ON, Canada
Methods: 13C NMR, 1H NMR, NMR-2D, 31P NMR
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14. Compound ID: 742
|
a-D-Glcp-(1-6)-a-D-Glcp-(1-6)-b-D-Glcp-(1-4)-a-D-Glcp-(1-5)-a-Kop-(2-6)-b-D-GlcpN-(1-6)-D-Glc-ol |
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Structure type: oligomer
Compound class: core oligosaccharide
Contained glycoepitopes: IEDB_114708,IEDB_135609,IEDB_137340,IEDB_141807,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_151531,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 195
Vinogradov EV, Müller-Loennies S, Petersen BO, Meshkov S, Thomas-Oates JE, Holst O, Brade H "Structural investigation of the lipopolysaccharide from Acinetobacter haemolyticus strain NCTC 10305 (ATCC 17906, DNA group 4)" -
European Journal of Biochemistry 247(1) (1997) 82-90
The structure of the lipopolysaccharide (LPS) from Acinetobacer haemolyticus strain NCTC 10305 (DNA group 4) was elucidated by means of analytical chemistry, NMR spectroscopy and fast-atom-bombardment mass spectrometry. Several oligosaccharides were obtained after deacylation or successive de-O-acylation, dephosphorylation, reduction, and de-N-acylation of LPS. In the major fraction of the LPS, the core is attached to the lipid A through D-glycero-D-talo-2-octulopyranosonic acid (Ko), whereas in a minor fraction (<20%) Ko is replaced by 3-deoxy-D-manno-octulopyranosonic acid (Kdo). The structures of the phosphorylated carbohydrate backbones of these LPS fractions are [see formula in text] with Dha = 3-deoxy-D-lyxo-2-heptulosaric acid, Sug = sugar and is Ko in a major fraction and Kdo in a minor fraction. All sugar residues have the D-configuration and are present in the pyranose form. Mass spectrometry of de-O-acylated LPS revealed the presence of and additional hexose residue in minor amounts, the position and nature of which could not be identified.
Lipopolysaccharide, NMR, structure, Acinetobacter, core-lipid A region
NCBI PubMed ID: 9249012Journal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Institutions: Department of Chemistry, Carlsberg Laboratory, Copenhagen, Denmark, Division of Medical and Microbiology, Center for Medicine and Biosciences, Research Center Borstel, Germany, Insitute of Chemical Physics, Russian Academy of Sciences, Moscow, Russia, Department of Mass Spectrometry, Bijvoet Center for Biomolecular Research, Universiteit Utrecht, The Netherlands
Methods: NMR-2D, FAB-MS, NMR, analytical methods
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15. Compound ID: 1611
Structure type: monomer
Compound class: O-polysaccharide
Contained glycoepitopes: IEDB_114708,IEDB_120354,IEDB_123890
The structure is contained in the following publication(s):
- Article ID: 498
Kocharova NA, Senchenkova SN, Kondakova AN, Gremyakov AI, Zatonsky GV, Shashkov AS, Knirel YA, Kochetkov NK "D- And L-aspartic acids: new non-sugar components of bacterial polysaccharides" -
Biochemistry (Moscow) 69(1) (2004) 103-107
For the first time in bacterial polysaccharides, residues of D- and L-aspartic acids were identified as N-acyl substituents of 4-amino-4,6-dideoxy-D-glucose in the O-antigens of enterobacteria of the genera Providencia and Proteus.
Lipopolysaccharide, NMR, LPS, structure, Bacterial, structural, polysaccharide, O-antigen, polysaccharides, O antigen, acidic, acidic polysaccharide, acid, phosphate, bacteria, O-specific, O-specific polysaccharide, Providencia, Proteus, Proteus mirabilis, serological, Ethanolamine phosphate, Bacterial polysaccharide, component, bacterial polysaccharides, amino acid, PDF, aspartic acid, N-linked, Acids
NCBI PubMed ID: 14972025Journal NLM ID: 0376536Publisher: Nauka/Interperiodica
Correspondence: knirel@ioc.ac.ru
Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
Methods: NMR-2D, methylation, NMR, HF solvolysis, ESI-MS, Smith degradation, triflic acid solvolysis
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