Found 21 structures.
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1. Compound ID: 390
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a-D-Glcp-(1-3)-+ a-D-Glcp-(1-4)-+
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a-D-Glcp6Me-(1-4)-a-D-Glcp6Me-(1-4)-a-D-Glcp6Me-(1-4)-a-D-Glcp6Me-(1-4)-a-D-Glcp6Me-(1-4)-a-D-Glcp6Me-(1-4)-a-D-Glcp6Me-(1-4)-a-D-Glcp6Me-(1-4)-a-D-Glcp6Me-(1-4)-a-D-Glcp6Me-(1-4)-a-D-Glcp6Me-(1-4)-a-D-Glcp-(1-3)-a-D-Glcp-(1-2)-L-GroA |
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Structure type: oligomer
Trivial name: methyl glucose lipopolysaccharide
Contained glycoepitopes: IEDB_140629,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_420417,IEDB_420418,IEDB_420421,IEDB_857742,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 127
Tuffal G, Ponthus C, Picard C, Rivière M, Puzo G "Structural elucidation of novel methylglucose-containing polysaccharides from Mycobacterium xenopi" -
European Journal of Biochemistry 233 (1995) 377-383
The structures of methylglucose-containing polysaccharides (MeGlc PS) from Mycobacterium xenopi were investigated using high-pH anion-exchange chromatography and liquid secondary-ion mass spectrometry. We report the structure of two novel MeGlc PS, referred to as A and B. MeGlc PS A is composed of 16 D-glucopyranose residues, 11 of which are methylated, and MeGlc PS B contains 15 D-glucopyranose residues, 10 of which are methylated. The main structural feature of both MeGlc PS A and B, compared to the previously described structures, is the absence of the tetrasaccharide non-reducing end 3-O-Me-D-Glcp-[α(1→4)-D-Glcp]3. The MeGlc PS A structure is similar to the synthetic polysaccharide [Saier, M. H. & Ballou, C. E. (1968) J. Biol. Chem. 243, 992-1005], having a lower affinity for fatty acids than the MeGlc PS of Mycobacterium smegmatis [Kiho, T. & Ballou, C. E. (1988) Biochemistry 27, 5824-5828]. Thus, the occurrence of MeGlc PS A and the consequences on the regulation of fatty acid synthetase I activity involved in the biosynthesis of fatty acids, precursors of mycolic acid biosynthesis, is discussed.
mass spectrometry, Mycobacterium, polymethylglucose polysaccharide, high-pH anion-exchange chromatography, fatty acid complex
NCBI PubMed ID: 7588770Journal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Institutions: Laboratoire de Pharmacologie et de Toxicologie Fondamentales du Centre National de la Recherche Scientifique, Toulouse, France, Sanofi Recherche, Toulouse, France.
Methods: NMR, HPAEC, LSI-MS, LSI-MS/MS
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2. Compound ID: 391
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b-D-Glcp-(1-3)-+ b-D-Glcp-(1-3)-+
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a-D-Glcp3Me-(1-4)-a-D-Glcp-(1-4)-a-D-Glcp-(1-4)-a-D-Glcp-(1-4)-a-D-Glcp6Me-(1-4)-a-D-Glcp6Me-(1-4)-a-D-Glcp6Me-(1-4)-a-D-Glcp6Me-(1-4)-a-D-Glcp6Me-(1-4)-a-D-Glcp6Me-(1-4)-a-D-Glcp6Me-(1-4)-a-D-Glcp6Me-(1-4)-a-D-Glcp6Me-(1-4)-a-D-Glcp6Me-(1-4)-a-D-Glcp-(1-4)-a-D-Glcp-(1-4)-a-D-Glcp-(1-6)-b-D-Glcp-(1-2)-L-GroA |
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Structure type: oligomer
Contained glycoepitopes: IEDB_140629,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_153543,IEDB_420417,IEDB_420418,IEDB_420421,IEDB_857742,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 128
Tuffal G, Albigot R, Rivière M, Puzo G "Newly found 2-N-acetyl-2,6-dideoxy-b-glucopyranose containing methyl glucose polysaccharides in M. bovis BCG: revised structure of the mycobacterial methyl glucose lipopolysaccharides" -
Glycobiology 8(7) (1998) 675-684
The specific mycobacterial methyl polysaccharides 3- O -methyl mannose polysaccharide (MMP) and the 6- O -methyl glucose lipopolysaccharides (MGLPs) were shown to modulate the fatty acid biosynthesis by the mycobacterial fatty acid synthetase I (FAS I). This activity is attributed to their fatty acid complexing properties allowing the release of the neo synthesized fatty acyl chain from the enzyme and probably their transport in the cell. To elucidate, at a molecular level, the mechanism of this unusual kind of polysaccharide-lipid biological interaction, we first analyzed, by mass spectrometry and proton nuclear magnetic resonance (1H NMR) spectroscopy, the structure of the polysaccharidic backbone (MGPs) of the MGLPs from Mycobacterium bovis BCG. This work reveals that this strain produces a new kind of MGP containing an unusual monosaccharide never described in the mycobacterial genus: a 2- N -acetyl-2,6-dideoxy-β-glucopyranosyl. In addition,1H NMR data afforded evidence for the revision of three glycosidic linkages described previously. These modifications affect mainly the reducing end tetrasaccharide and have great consequences on the previously proposed molecular model of the MGP.
NMR, lipopolysaccharides, 2-acetamido-2, Mycobacterium, 6-dideoxyglucose, 2-N-acetyl-b-quinovosamine, methyl glucose, 2-N-acetyl-β-quinovosamine
NCBI PubMed ID: 9621108Publication DOI: 10.1093/glycob/8.7.675Journal NLM ID: 9104124Publisher: IRL Press at Oxford University Press
Institutions: Institut de Pharmacologie et de Biologie Structurale du Centre National de la Recherche Scientifique, 205 Route de Narbonne, 31077 Toulouse Cedex, France
Methods: NMR-2D, NMR, LSI-MS
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3. Compound ID: 436
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L-GroA-(1-2)-+
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-3)-b-D-Glcp6(50%)Ac-(1-4)-b-D-GlcpA-(1-4)-b-D-Glcp-(1-4)-a-L-Rhap-(1- |
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Structure type: polymer chemical repeating unit
Trivial name: gellan, gellan gum
Compound class: CPS, EPS
Contained glycoepitopes: IEDB_115136,IEDB_136105,IEDB_140630,IEDB_142488,IEDB_146664,IEDB_189517,IEDB_225177,IEDB_423153,IEDB_885823,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 162
Videira P, Fialho A, Geremia RA, Breton C, Sá-Correia I "Biochemical characterization of the b-1,4-glucuronosyltransferase GelK in the gellan gum-producing strain Sphingomonas paucimobilis ATCC 31461" -
Biochemical Journal 358(2) (2001) 457-464
Biosynthesis of bacterial polysaccharide-repeat units proceeds by sequential transfer of sugars, from the appropriate sugar donor to an activated lipid carrier, by committed glycosyltransferases (GTs). Few studies on the mechanism of action for this type of GT are available. Sphingomonas paucimobilis A.T.C.C. 31461 produces the industrially important polysaccharide gellan gum. We have cloned the gelK gene from S. paucimobilis A.T.C.C. 31461. GelK belongs to family 1 of the GT classification [Campbell, Davies, Bulone, Henrissat (1997) Biochem. J. 326, 929-939]. Sequence similarity studies suggest that GelK consists of two protein modules corresponding to the -NH(2) and -CO(2)H halves, the latter possibly harbouring the GT activity. The gelK gene and the open reading frames coding for the -NH(2) (GelK(NH2)) and -CO(2)H (GelK(COOH)) halves were overexpressed in Escherichia coli. GelK and GelK(NH2) were present in both the soluble and membrane fractions of E. coli, whereas GelK(COOH) was only present in the soluble fraction. GelK catalysed the transfer of [(14)C]glucuronic acid from UDP-[(14)C]glucuronic acid into a glycolipid extracted from S. paucimobilis or E. coli, even in the presence of EDTA, and the radioactive sugar was released from the glycolipid by β-1,4-glucuronidase. GelK was not able to use synthetic glucosyl derivatives as acceptors, indicating that the PP(i)-lipid moiety is needed for enzymic activity. Recombinant GelK(NH2) and GelK(COOH) did not show detectable activity. Based on the biochemical characteristics of GelK and on sequence similarities with N-acetylglucosaminyltransferase, we propose that GT families 1 and 28 form a superfamily.
strain, characterization, Sphingomonas, Sphingomonas paucimobilis, exopolysaccharide, biochemical, bioinformatics, conserved amino acids, gellan, N-acetylglucosaminyltransferase, secondary structure prediction
NCBI PubMed ID: 11513745Journal NLM ID: 2984726RPublisher: London, UK : Published by Portland Press on behalf of the Biochemical Society
Correspondence: roberto.geremia@ujf-grenoble.fr
Institutions: Centra de Engenharia Bioldgica e Quimica, Instituto Superior Tecnico, Av. Rovisco Pais, 1049-001 Lisboa, Portugal, Plasticite et Expression des Genomes Microbiens, Universite Joseph Fourier and Centre National de la Recherche Scientifique FRE 2383, Bat. CERMO, 460 Rue de la Piscine, 38041 Grenoble cedex 9, France, Centre de Recherches sur les Macromolecules Vegetales, CNRS, BP 53X, 38041 Grenoble, France., Centre de Recherches sur les Macromolecules Vegetales, CNRS, BP 53X, 38041 Grenoble, France
Methods: genetic methods, biochemical methods
- Article ID: 1291
Yamazaki M, Thorne L, Mikolajczak M, Armentrout RW, Pollock TJ "Linkage of genes essential for synthesis of a polysaccharide capsule in Sphingomonas strain S88" -
Journal of Bacteriology 178 (1996) 2676-2687
Several structurally related capsular polysaccharides that are secreted by members of the genus Sphingomonas are being developed as aqueous rheological control agents for diverse industrial and food applications. They include gellan (S-60), welan (S-130), rhamsan (S-194), S-657, S-88, S-198, S-7, and NW-11. We refer to these polysaccharides as sphingans, after the genus name. This paper characterizes the first gene cluster isolated from a Sphingomonas species (S88) that is required for capsule synthesis. Overlapping DNA segments which spanned about 50 kbp of S88 DNA restored the synthesis of sphingan S-88 in capsule-negative mutants. The mutations were mapped into functional complementation groups, and the contiguous nucleotide sequence for the 29-kbp cluster was determined. The genetic complementation map and the DNA sequences were interpreted as an extended multicistronic locus containing genes essential for the assembly and secretion of polysaccharide S-88. Many of the deduced amino acid sequences were similar to gene products from other polysaccharide-secreting bacteria such as Rhizobium meliloti (succinoglycan), Xanthomonas campestris (xanthan gum), and Salmonella enterica (O antigen). The S88 locus contained a four-gene operon for the biosynthesis of dTDP-L-rhamnose, an essential precursor for the sphingans. Unexpectedly, there were also two genes for secretion of a lytic or toxin-like protein nested within the polysaccharide cluster. The conservation and linkage of genes that code for a defensive capsule and genes for secretion of an offensive lysin or toxin suggest a heretofore unknown pathogenic life history for Sphingomonas strain S88
biosynthesis, synthesis, gene, strain, polysaccharide, Sphingomonas, linkage, capsule
NCBI PubMed ID: 8626338Journal NLM ID: 2985120RPublisher: American Society for Microbiology
Institutions: Shin-Etsu Bio, Inc., San Diego, California 92121, USA
- Article ID: 1484
Sletmoen M, Maurstad G, Sikorski P, Paulsen BS, Stokke BT "Characterisation of bacterial polysaccharides: steps towards single-molecular studies" -
Carbohydrate Research 338(23) (2003) 2459-2475
Techniques used in studies of polysaccharides, including chemical composition, linkage pattern, and higher order structures are in constant development. They provide information necessary for understanding of the polysaccharide properties and functions. Here, recent advancements in studies of the polysaccharides at the single-molecule level are highlighted. Over the last few years, single-molecule techniques such as force spectroscopy have improved in sensitivity and can today be used to detect forces in the pN range. In addition, these techniques can be used to investigate properties of single molecules close to physiological conditions. The challenges in the interpretation of the observations are aided by control experiments using well-characterised polysaccharides and by data provided by complementary methods. This field is expected to have increasing impact on the further advancement of the molecular understanding of the role of polysaccharides in various biological processes such as recognition and cell adhesion.
X-ray fibre diffraction, AFM, TEM, Force spectroscopy, Single-molecules
NCBI PubMed ID: 14670709Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: bjorn.stokke@phys.ntnu.no
Institutions: Biophysics and Medical Technology, Department of Physics, The Norwegian University of Science and Technology, NTNU, NO-7491 Trondheim, Norway, Department of Pharmacognosy, School of Pharmacy, University of Oslo, P.O. Box 1068 Blindern, NO-0316 Oslo, Norway
- Article ID: 1647
Saksouk N, Pelosi L, Colin-Morel P, Boumedienne M, Abdian PL, Geremia RA "The capsular polysaccharide biosynthesis of Streptococcus pneumoniae serotype 8: functional identification of the glycosyltransferase WciS (Cap8H)" -
Biochemical Journal (2005) 63-72
CPS (capsular polysaccharide) is a major virulence factor in Streptococcus pneumoniae. Biosynthesis of CPS RU (repeat unit) proceeds by sequential transfer of sugar residues from the appropriate sugar donor to an activated lipid carrier by committed GTs (glycosyltransferases). While the nucleotide sequence of many cps loci is already known, the real substrate specificity of the hypothetical GTs, as well as the sequence of sugar addition is unclear. In the present paper, we report the biochemical characterization of one α-Galactosyltransferase, WciS (Cap8H), a member of GT family 4. This enzyme is implicated in the tetrasaccharide RU biosynthetic pathway of Strep. pneumoniae CPS 8 ([→4)-α-D-Glcp-(1→4)-α-D-Galp-(1→4)-β-D-GlcAp-(1→4)-β-D-Glcp-(1→]n). Expression of WciS-His6 in Escherichia coli BL21 (DE3) strains or BL21 (DE3)/∆galU strain resulted in synthesis of a 39 kDa membrane-associated protein identified by N-terminal sequencing and recognized by anti-His6-tag antibody. This protein was capable of adding a galactose residue cellobiuronic acid [β-D-GlcAp-(1→4)-D-Glcp]-pyrophosphate-polyprenol from UDP-Gal. The newly added galactose residue is removed by α-galactosidase, indicating that WciS is a retaining GT. Our results suggest that WciS catalyses the addition of the third sugar residue of the CPS 8 RU. The recombinant WciS-His6 was solubilized and purified as a soluble multimer, opening the way for structural studies.
Streptococcus pneumoniae, capsular polysaccharide, glycosyltransferase, galactosyltransferase, virulence factor, WciS
NCBI PubMed ID: 15766331Journal NLM ID: 2984726RPublisher: London, UK : Published by Portland Press on behalf of the Biochemical Society
Correspondence: rf.elbonerg-fju@aimereg.otrebor)
Institutions: Laboratoire Adaptation et Pathogenie des Micro-organismes, CNRS UMR 5163, Batiment Jean Roget, Faculte de Medecine Pharmacie, La Tronche, France
Methods: biochemical methods
- Article ID: 4322
Jia W, Zhang J, Jiang Y, Zheng Z, Zhan X, Lin C "Structure of oligosaccharide F21 derived from exopolysaccharide WL-26 produced by Sphingomonas sp. ATCC 31555" -
Carbohydrate Polymers 90(1) (2012) 60-66
Mild hydrolysis of Sphingomonas sp. ATCC 31555 polysaccharide WL-26 afforded a new oligosaccharide, F21. Structural resolution based on sugar and methylation analyses as well as NMR data revealed the oligosaccharide to have the following structure: (formula: see text).
NMR, oligosaccharide, structure, chemistry, carbohydrate, polymer, Sphingomonas, exopolysaccharide, PAGE, biotechnology, Polymers, China, structure characterization, oligosaccharide F21, partial acid hydrolysis
Publication DOI: 10.1016/j.carbpol.2012.04.061Journal NLM ID: 8307156Publisher: Elsevier
Correspondence: X.-B. Zhan
Institutions: Key Laboratory of Carbohydrate Chemistry and Biotechnology, School of Biotechnology, Jiangnan University, Wuxi, China
Methods: 13C NMR, 1H NMR, methylation, NMR-2D, partial acid hydrolysis, GC-MS, sugar analysis, mild acid hydrolysis, HPLC, HPAEC-PAD
- Article ID: 4606
Prajapati VD, Jani GK, Zala BS, Khutliwala TA "An insight into the emerging exopolysaccharide gellan gum as a novel polymer" -
Carbohydrate Polymers 93(2) (2013) 670-678
The microbial exopolysaccharides are water-soluble polymers secreted by microorganisms during fermentation. The biopolymer gellan gum is a relatively recent addition to the family of microbial polysaccharides that is gaining much importance in food, pharmaceutical and chemical industries due to its novel properties. It is commercially produced by C.P. Kelco in Japan and the USA. This article presents a critical review of the available information on the gum synthesized by Sphingomonas paucimobilis with special emphasis on its fermentative production. Factors affecting the fermentative production of gellan gum and problems associated with mass transfer have been addressed. Classification and trade names of gellan gum has been specified. Characteristics of gellan gum with respect to its structure, physicochemical properties are discussed. An attempt has also been made to review the current and potential applications of gellan gum in food, pharmaceutical and other industries.
Sphingomonas paucimobilis, Gellan gum, fermentative production
NCBI PubMed ID: 23499110Publication DOI: 10.1016/j.carbpol.2013.01.030Journal NLM ID: 8307156Publisher: Elsevier
Correspondence: vippra2000@yahoo.com
Institutions: Department of Pharmaceutics, S.S.R. College of Pharmacy, Saily-Silvassa Road, Saily, Silvassa, U.T. of Dadra and Nagar Haveli 396 230, India
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4. Compound ID: 476
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a-D-Glcp-(1-3)-+ a-D-Glcp-(1-4)-+
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a-D-Glcp6Me-(1-4)-a-D-Glcp6Me-(1-4)-a-D-Glcp6Me-(1-4)-a-D-Glcp6Me-(1-4)-a-D-Glcp6Me-(1-4)-a-D-Glcp6Me-(1-4)-a-D-Glcp6Me-(1-4)-a-D-Glcp6Me-(1-4)-a-D-Glcp6Me-(1-4)-a-D-Glcp6Me-(1-4)-a-D-Glcp-(1-3)-a-D-Glcp-(1-2)-L-GroA |
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Structure type: oligomer
Trivial name: methyl glucose lipopolysaccharide
Contained glycoepitopes: IEDB_140629,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_420417,IEDB_420418,IEDB_420421,IEDB_857742,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 127
Tuffal G, Ponthus C, Picard C, Rivière M, Puzo G "Structural elucidation of novel methylglucose-containing polysaccharides from Mycobacterium xenopi" -
European Journal of Biochemistry 233 (1995) 377-383
The structures of methylglucose-containing polysaccharides (MeGlc PS) from Mycobacterium xenopi were investigated using high-pH anion-exchange chromatography and liquid secondary-ion mass spectrometry. We report the structure of two novel MeGlc PS, referred to as A and B. MeGlc PS A is composed of 16 D-glucopyranose residues, 11 of which are methylated, and MeGlc PS B contains 15 D-glucopyranose residues, 10 of which are methylated. The main structural feature of both MeGlc PS A and B, compared to the previously described structures, is the absence of the tetrasaccharide non-reducing end 3-O-Me-D-Glcp-[α(1→4)-D-Glcp]3. The MeGlc PS A structure is similar to the synthetic polysaccharide [Saier, M. H. & Ballou, C. E. (1968) J. Biol. Chem. 243, 992-1005], having a lower affinity for fatty acids than the MeGlc PS of Mycobacterium smegmatis [Kiho, T. & Ballou, C. E. (1988) Biochemistry 27, 5824-5828]. Thus, the occurrence of MeGlc PS A and the consequences on the regulation of fatty acid synthetase I activity involved in the biosynthesis of fatty acids, precursors of mycolic acid biosynthesis, is discussed.
mass spectrometry, Mycobacterium, polymethylglucose polysaccharide, high-pH anion-exchange chromatography, fatty acid complex
NCBI PubMed ID: 7588770Journal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Institutions: Laboratoire de Pharmacologie et de Toxicologie Fondamentales du Centre National de la Recherche Scientifique, Toulouse, France, Sanofi Recherche, Toulouse, France.
Methods: NMR, HPAEC, LSI-MS, LSI-MS/MS
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5. Compound ID: 522
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b-D-Glcp-(1-3)-+ b-D-Glcp-(1-3)-+
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a-D-Glcp3Me-(1-4)-a-D-Glcp-(1-4)-a-D-Glcp-(1-4)-a-D-Glcp-(1-4)-a-D-Glcp6Me-(1-4)-a-D-Glcp6Me-(1-4)-a-D-Glcp6Me-(1-4)-a-D-Glcp6Me-(1-4)-a-D-Glcp6Me-(1-4)-a-D-Glcp6Me-(1-4)-a-D-Glcp6Me-(1-4)-a-D-Glcp6Me-(1-4)-a-D-Glcp6Me-(1-4)-a-D-Glcp6Me-(1-4)-a-D-Glcp6Me-(1-4)-a-D-Glcp6Me-(1-4)-a-D-Glcp-(1-6)-b-D-Glcp-(1-2)-L-GroA |
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Structure type: oligomer
Contained glycoepitopes: IEDB_140629,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_153543,IEDB_420417,IEDB_420418,IEDB_420421,IEDB_857742,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 128
Tuffal G, Albigot R, Rivière M, Puzo G "Newly found 2-N-acetyl-2,6-dideoxy-b-glucopyranose containing methyl glucose polysaccharides in M. bovis BCG: revised structure of the mycobacterial methyl glucose lipopolysaccharides" -
Glycobiology 8(7) (1998) 675-684
The specific mycobacterial methyl polysaccharides 3- O -methyl mannose polysaccharide (MMP) and the 6- O -methyl glucose lipopolysaccharides (MGLPs) were shown to modulate the fatty acid biosynthesis by the mycobacterial fatty acid synthetase I (FAS I). This activity is attributed to their fatty acid complexing properties allowing the release of the neo synthesized fatty acyl chain from the enzyme and probably their transport in the cell. To elucidate, at a molecular level, the mechanism of this unusual kind of polysaccharide-lipid biological interaction, we first analyzed, by mass spectrometry and proton nuclear magnetic resonance (1H NMR) spectroscopy, the structure of the polysaccharidic backbone (MGPs) of the MGLPs from Mycobacterium bovis BCG. This work reveals that this strain produces a new kind of MGP containing an unusual monosaccharide never described in the mycobacterial genus: a 2- N -acetyl-2,6-dideoxy-β-glucopyranosyl. In addition,1H NMR data afforded evidence for the revision of three glycosidic linkages described previously. These modifications affect mainly the reducing end tetrasaccharide and have great consequences on the previously proposed molecular model of the MGP.
NMR, lipopolysaccharides, 2-acetamido-2, Mycobacterium, 6-dideoxyglucose, 2-N-acetyl-b-quinovosamine, methyl glucose, 2-N-acetyl-β-quinovosamine
NCBI PubMed ID: 9621108Publication DOI: 10.1093/glycob/8.7.675Journal NLM ID: 9104124Publisher: IRL Press at Oxford University Press
Institutions: Institut de Pharmacologie et de Biologie Structurale du Centre National de la Recherche Scientifique, 205 Route de Narbonne, 31077 Toulouse Cedex, France
Methods: NMR-2D, NMR, LSI-MS
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6. Compound ID: 523
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b-D-Glcp-(1-3)-+
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a-D-Glcp3Me-(1-4)-a-D-Glcp-(1-4)-a-D-Glcp-(1-4)-a-D-Glcp-(1-4)-a-D-Glcp6Me-(1-4)-a-D-Glcp6Me-(1-4)-a-D-Glcp6Me-(1-4)-a-D-Glcp6Me-(1-4)-a-D-Glcp6Me-(1-4)-a-D-Glcp6Me-(1-4)-a-D-Glcp6Me-(1-4)-a-D-Glcp6Me-(1-4)-a-D-Glcp6Me-(1-4)-a-D-Glcp6Me-(1-4)-a-D-Glcp6Me-(1-4)-a-D-Glcp6Me-(1-4)-a-D-Glcp-(1-6)-b-D-Glcp-(1-2)-L-GroA |
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Structure type: oligomer
Contained glycoepitopes: IEDB_140629,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_153543,IEDB_420417,IEDB_420418,IEDB_420421,IEDB_857742,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 128
Tuffal G, Albigot R, Rivière M, Puzo G "Newly found 2-N-acetyl-2,6-dideoxy-b-glucopyranose containing methyl glucose polysaccharides in M. bovis BCG: revised structure of the mycobacterial methyl glucose lipopolysaccharides" -
Glycobiology 8(7) (1998) 675-684
The specific mycobacterial methyl polysaccharides 3- O -methyl mannose polysaccharide (MMP) and the 6- O -methyl glucose lipopolysaccharides (MGLPs) were shown to modulate the fatty acid biosynthesis by the mycobacterial fatty acid synthetase I (FAS I). This activity is attributed to their fatty acid complexing properties allowing the release of the neo synthesized fatty acyl chain from the enzyme and probably their transport in the cell. To elucidate, at a molecular level, the mechanism of this unusual kind of polysaccharide-lipid biological interaction, we first analyzed, by mass spectrometry and proton nuclear magnetic resonance (1H NMR) spectroscopy, the structure of the polysaccharidic backbone (MGPs) of the MGLPs from Mycobacterium bovis BCG. This work reveals that this strain produces a new kind of MGP containing an unusual monosaccharide never described in the mycobacterial genus: a 2- N -acetyl-2,6-dideoxy-β-glucopyranosyl. In addition,1H NMR data afforded evidence for the revision of three glycosidic linkages described previously. These modifications affect mainly the reducing end tetrasaccharide and have great consequences on the previously proposed molecular model of the MGP.
NMR, lipopolysaccharides, 2-acetamido-2, Mycobacterium, 6-dideoxyglucose, 2-N-acetyl-b-quinovosamine, methyl glucose, 2-N-acetyl-β-quinovosamine
NCBI PubMed ID: 9621108Publication DOI: 10.1093/glycob/8.7.675Journal NLM ID: 9104124Publisher: IRL Press at Oxford University Press
Institutions: Institut de Pharmacologie et de Biologie Structurale du Centre National de la Recherche Scientifique, 205 Route de Narbonne, 31077 Toulouse Cedex, France
Methods: NMR-2D, NMR, LSI-MS
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7. Compound ID: 524
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b-D-Glcp-(1-3)-+ b-D-Glcp-(1-3)-+
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a-D-Glcp3Me-(1-4)-a-D-Glcp-(1-4)-a-D-Glcp-(1-4)-a-D-Glcp-(1-4)-a-D-Glcp6Me-(1-4)-a-D-Glcp6Me-(1-4)-a-D-Glcp6Me-(1-4)-a-D-Glcp6Me-(1-4)-a-D-Glcp6Me-(1-4)-a-D-Glcp6Me-(1-4)-a-D-Glcp6Me-(1-4)-a-D-Glcp6Me-(1-4)-a-D-Glcp6Me-(1-4)-a-D-Glcp6Me-(1-4)-a-D-Glcp6Me-(1-4)-a-D-Glcp-(1-4)-a-D-Glcp-(1-6)-b-D-Glcp-(1-2)-L-GroA |
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Structure type: oligomer
Contained glycoepitopes: IEDB_140629,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_153543,IEDB_420417,IEDB_420418,IEDB_420421,IEDB_857742,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 128
Tuffal G, Albigot R, Rivière M, Puzo G "Newly found 2-N-acetyl-2,6-dideoxy-b-glucopyranose containing methyl glucose polysaccharides in M. bovis BCG: revised structure of the mycobacterial methyl glucose lipopolysaccharides" -
Glycobiology 8(7) (1998) 675-684
The specific mycobacterial methyl polysaccharides 3- O -methyl mannose polysaccharide (MMP) and the 6- O -methyl glucose lipopolysaccharides (MGLPs) were shown to modulate the fatty acid biosynthesis by the mycobacterial fatty acid synthetase I (FAS I). This activity is attributed to their fatty acid complexing properties allowing the release of the neo synthesized fatty acyl chain from the enzyme and probably their transport in the cell. To elucidate, at a molecular level, the mechanism of this unusual kind of polysaccharide-lipid biological interaction, we first analyzed, by mass spectrometry and proton nuclear magnetic resonance (1H NMR) spectroscopy, the structure of the polysaccharidic backbone (MGPs) of the MGLPs from Mycobacterium bovis BCG. This work reveals that this strain produces a new kind of MGP containing an unusual monosaccharide never described in the mycobacterial genus: a 2- N -acetyl-2,6-dideoxy-β-glucopyranosyl. In addition,1H NMR data afforded evidence for the revision of three glycosidic linkages described previously. These modifications affect mainly the reducing end tetrasaccharide and have great consequences on the previously proposed molecular model of the MGP.
NMR, lipopolysaccharides, 2-acetamido-2, Mycobacterium, 6-dideoxyglucose, 2-N-acetyl-b-quinovosamine, methyl glucose, 2-N-acetyl-β-quinovosamine
NCBI PubMed ID: 9621108Publication DOI: 10.1093/glycob/8.7.675Journal NLM ID: 9104124Publisher: IRL Press at Oxford University Press
Institutions: Institut de Pharmacologie et de Biologie Structurale du Centre National de la Recherche Scientifique, 205 Route de Narbonne, 31077 Toulouse Cedex, France
Methods: NMR-2D, NMR, LSI-MS
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8. Compound ID: 525
|
b-D-Glcp-(1-3)-+ b-D-QuipNAc-(1-3)-+
| |
a-D-Glcp3Me-(1-4)-a-D-Glcp-(1-4)-a-D-Glcp-(1-4)-a-D-Glcp-(1-4)-a-D-Glcp6Me-(1-4)-a-D-Glcp6Me-(1-4)-a-D-Glcp6Me-(1-4)-a-D-Glcp6Me-(1-4)-a-D-Glcp6Me-(1-4)-a-D-Glcp6Me-(1-4)-a-D-Glcp6Me-(1-4)-a-D-Glcp6Me-(1-4)-a-D-Glcp6Me-(1-4)-a-D-Glcp6Me-(1-4)-a-D-Glcp6Me-(1-4)-a-D-Glcp-(1-4)-a-D-Glcp-(1-6)-b-D-Glcp-(1-2)-L-GroA |
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Structure type: oligomer
Contained glycoepitopes: IEDB_140629,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_153543,IEDB_420417,IEDB_420418,IEDB_420421,IEDB_857742,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 128
Tuffal G, Albigot R, Rivière M, Puzo G "Newly found 2-N-acetyl-2,6-dideoxy-b-glucopyranose containing methyl glucose polysaccharides in M. bovis BCG: revised structure of the mycobacterial methyl glucose lipopolysaccharides" -
Glycobiology 8(7) (1998) 675-684
The specific mycobacterial methyl polysaccharides 3- O -methyl mannose polysaccharide (MMP) and the 6- O -methyl glucose lipopolysaccharides (MGLPs) were shown to modulate the fatty acid biosynthesis by the mycobacterial fatty acid synthetase I (FAS I). This activity is attributed to their fatty acid complexing properties allowing the release of the neo synthesized fatty acyl chain from the enzyme and probably their transport in the cell. To elucidate, at a molecular level, the mechanism of this unusual kind of polysaccharide-lipid biological interaction, we first analyzed, by mass spectrometry and proton nuclear magnetic resonance (1H NMR) spectroscopy, the structure of the polysaccharidic backbone (MGPs) of the MGLPs from Mycobacterium bovis BCG. This work reveals that this strain produces a new kind of MGP containing an unusual monosaccharide never described in the mycobacterial genus: a 2- N -acetyl-2,6-dideoxy-β-glucopyranosyl. In addition,1H NMR data afforded evidence for the revision of three glycosidic linkages described previously. These modifications affect mainly the reducing end tetrasaccharide and have great consequences on the previously proposed molecular model of the MGP.
NMR, lipopolysaccharides, 2-acetamido-2, Mycobacterium, 6-dideoxyglucose, 2-N-acetyl-b-quinovosamine, methyl glucose, 2-N-acetyl-β-quinovosamine
NCBI PubMed ID: 9621108Publication DOI: 10.1093/glycob/8.7.675Journal NLM ID: 9104124Publisher: IRL Press at Oxford University Press
Institutions: Institut de Pharmacologie et de Biologie Structurale du Centre National de la Recherche Scientifique, 205 Route de Narbonne, 31077 Toulouse Cedex, France
Methods: NMR-2D, NMR, LSI-MS
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9. Compound ID: 3963
Structure type: polymer chemical repeating unit
The structure is contained in the following publication(s):
- Article ID: 1468
Knirel YA, Kocharova NA, Bystrova OV, Katzenellenbogen E, Gamian A "Structures and serology of the O-specific polysaccharides of bacteria of the genus Citrobacter" -
Archivum Immunologiae et Therapiae Experimentalis 50(6) (2002) 379-391
The review presents the structures of the O-specific polysaccharides (O-antigens) of the lipopolysaccharides isolated from over 25 Citrobacter strains, which represent different species and serogroups. The correlation between O-antigen structure and immunospecificity as well as numerous cross-reactions between Citrobacter and other enterobacterial species are discussed.
Lipopolysaccharide, structure, O-antigen, O-specific polysaccharide, serology, Citrobacter, immunospecificity
NCBI PubMed ID: 12546064Journal NLM ID: 0114365Publisher: Basel, Boston: Birkhaüser
Correspondence: knirel@ioc.ac.ru
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
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10. Compound ID: 5327
|
L-GroA-(1-2)-+
|
-4)-a-L-Rhap-(1-3)-b-D-Glcp6Ac-(1-4)-b-D-GlcpA-(1-4)-b-D-Glcp-(1- |
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Structure type: polymer chemical repeating unit
Trivial name: gellan
Compound class: EPS
Contained glycoepitopes: IEDB_115136,IEDB_136105,IEDB_140630,IEDB_142488,IEDB_146664,IEDB_189517,IEDB_225177,IEDB_423153,IEDB_885823,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 2204
Chandrasekaran R, Radha A, Thailambal VG "Roles of potassium ions, acetyl and L-glyceryl groups in native gellan double helix: an X-ray study" -
Carbohydrate Research 224 (1992) 1-17
Native gellan, the natural form of the polysaccharide excreted by the bacterium Pseudomonas elodea, has a tetrasaccharide repeating unit that contains L-glycerol and acetate ester groups, and forms only weak and elastic gels. Based on X-ray diffraction data from well oriented and polycrystalline fibers of its potassium salt, the crystal structure of native gellan, including ions and water, has been determined and refined to a final R-value of 0.17. The molecule forms of a half-staggered, parallel, double helix of pitch 5.68 nm which is stabilized by hydrogen bonds involving the hydroxymethyl groups in one chain and both carboxylate and glyceryl groups in other. Two molecules are packed in an antiparallel fashion in a trigonal unit cell of side a = 1.65 nm. Although the gross molecular morphology and packing arrangements are isomorphous with those observed in the crystal structure of potassium gellan, which is devoid of any substitutions, native gellan exhibits exceptional changes in its ion binding characteristics with respect to gellan. In particular, the L-glyceryl groups do not allow the gellan-like coordinated interactions of the ions and the carbohydrate groups, within and between double helices, which are necessary for strong gelation. These results at the molecular level explain, for the first time, the differences in the behavior of the polymer with and without substitutions.
NCBI PubMed ID: 1591755Publication DOI: 10.1016/0008-6215(92)84088-aJournal NLM ID: 0043535Publisher: Elsevier
Institutions: Whistler Center for Carbohydrate Research, Purdue University, West Lafayette, IN 47907
Methods: X-ray
- Article ID: 5791
Knirel YA, Van Calsteren M "Bacterial exopolysaccharides" -
Book: Comprehensive Glycoscience: From Chemistry to Systems Biology. Reference Module in Chemistry, Molecular Sciences and Chemical Engineering (2021) 1-75
Bacterial extracellular polysaccharides are known as a cell-bound capsule, a sheath, or a slime, which is excreted into the environment. They play an important role in virulence of medical bacteria and plant-to-symbiont interaction and are used for serotyping of bacteria and production of vaccines. Some exopolysaccharides have commercial applications in industry, and claims of health benefits have been documented for an increasing number of them. Exopolysaccharides have diverse composition and structure, and some contain sugar and non-sugar components that are found in bacterial carbohydrates only. The present article provides an updated collection of the data on exopolysaccharides of various classes of gram-negative and gram-positive bacteria reported until the end of 2019. When known, biosynthesis pathways of exopolysaccharides are treated in a summary manner. References are made to structure and biosynthesis relatedness between exopolysaccharides of different bacterial taxa as well as between bacterial polysaccharides and mammalian glycosaminoglycans.
polysaccharide structure, Gram-negative bacteria, capsule, Biofilm, polysaccharide biosynthesis, gram-positive bacteria, Monosaccharide composition, Bacterial exopolysaccharide, non-sugar component
Publication DOI: 10.1016/B978-0-12-819475-1.00005-5Publisher: Elsevier
Correspondence: marie-rose.vancalsteren@canada.ca; yknirel@gmail.com
Editors: Barchi J, Kamerling H
Institutions: N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Saint-Hyacinthe Research and Development Centre, Agriculture and Agri-Food Canada, Saint-Hyacinthe, QC, Canada
- Article ID: 6146
Sun X, Zhang J "Bacterial exopolysaccharides: Chemical structures, gene clusters and genetic engineering" -
International Journal of Biological Macromolecules 173 (2021) 481-490
In recent decades, the composition, structure, biosynthesis, and function of bacterial extracellular polysaccharides (EPS) have been extensively studied. EPS are synthesized through different biosynthetic pathways. The genes responsible for EPS synthesis are usually clustered on the genome or large plasmids of bacteria. Generally, different EPS synthesis gene clusters direct the synthesis of EPS with different chemical structures and biological activities. A better understanding of the gene functions involved in EPS biosynthesis is critical for the production of EPS with special biological activities. Genetic engineering methods are usually used to study EPS synthesis related genes. This review organizes the available information on EPS, including their structures, synthesis of related genes, and highlights the research progress of modifying EPS gene clusters through gene-editing methods.
genetic engineering, gene clusters, bacterial extracellular polysaccharides
Publication DOI: 10.1016/j.ijbiomac.2021.01.139Journal NLM ID: 7909578Publisher: Butterworth-Heinemann
Correspondence: jfzhang@mail.njust.edu.cn
Institutions: Center for Molecular Metabolism, Nanjing University of Science & Technology, Nanjing, China
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11. Compound ID: 5484
Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
The structure is contained in the following publication(s):
- Article ID: 2317
Kocharova NA, Knirel YA, Shashkov AS, Kochetkov NK, Kholodkova EV, Stanislavsky ES "The structure of the O-specific polysaccharide of Citrobacter freundii O32, a partially O-acetylated homopolymer of 3,6-dideoxy-3-(L-glyceroylamino)-a-D-galactopyranose" -
Carbohydrate Research 264 (1994) 123-128
no abstract
Lipopolysaccharide, O-antigen, NMR spectroscopy, Enteric bacteria
Publication DOI: 10.1016/0008-6215(94)00144-8Journal NLM ID: 0043535Publisher: Elsevier
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospekt 47,Moscow,Russian Federation, I.I. Mechnikov Institute of Vaccines and Sera, per. Mechnikova 5a,Moscow,Russian Federation
- Article ID: 6049
Di Lorenzo F, Duda KA, Lanzetta R, Silipo A, De Castro C, Molinaro A "A Journey from Structure to Function of Bacterial Lipopolysaccharides" -
Chemical Reviews (2021)
Lipopolysaccharide (LPS) is a crucial constituent of the outer membrane of most Gram-negative bacteria, playing a fundamental role in the protection of bacteria from environmental stress factors, in drug resistance, in pathogenesis, and in symbiosis. During the last decades, LPS has been thoroughly dissected, and massive information on this fascinating biomolecule is now available. In this Review, we will give the reader a third millennium update of the current knowledge of LPS with key information on the inherent peculiar carbohydrate chemistry due to often puzzling sugar residues that are uniquely found on it. Then, we will drive the reader through the complex and multifarious immunological outcomes that any given LPS can raise, which is strictly dependent on its chemical structure. Further, we will argue about issues that still remain unresolved and that would represent the immediate future of LPS research. It is critical to address these points to complete our notions on LPS chemistry, functions, and roles, in turn leading to innovative ways to manipulate the processes involving such a still controversial and intriguing biomolecule.
Lipopolysaccharide, LPS, structure, Pathogenesis, carbohydrate, function, gram negative bacteria
NCBI PubMed ID: 34286971Publication DOI: 10.1021/acs.chemrev.0c01321Journal NLM ID: 2985134RPublisher: Chem Rev
Correspondence: Antonio Molinaro
Institutions: Department of Chemical Sciences, University of Naples Federico II, via Cinthia 4, 80126 Naples, Italy, Task Force on Microbiome Studies, University of Naples Federico II, Via Cinthia 4, 80126 Naples, Italy, Research Center Borstel Leibniz Lung Center, Parkallee 4a, 23845 Borstel, Germany, Department of Agricultural Sciences, University of Naples Federico II, Via Universita 96, 80055 Portici, Naples, Italy, Department of Chemistry, School of Science, Osaka University, 1-1 Osaka University Machikaneyama, Toyonaka, Osaka 560-0043, Japan
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12. Compound ID: 6545
|
b-D-Galp-(1-3)-+
|
30%L-GroA-(1-2)-+ |
| |
-3)-a-L-Rhap-(1-4)-b-D-Glcp-(1- |
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Structure type: polymer chemical repeating unit
Compound class: CPS
Contained glycoepitopes: IEDB_136044,IEDB_136105,IEDB_137472,IEDB_141794,IEDB_142488,IEDB_146664,IEDB_190606,IEDB_225177,IEDB_885823,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 2960
Grimmecke HD, Knirel YA, Kiesel B, Voges M, Rietschel ET "Structure of the Acetobacter methanolicus MB 129 capsular polysaccharide, and of oligosaccharides resulting from degradation by bacteriophage Acm7" -
Carbohydrate Research 259 (1994) 45-58
The capsular polysaccharide of Acetobacter methanolicus MB 129 consists of D-Glc, D-Gal, L-Rha, and L-glyceric acid in the molar ratios 1:1:1:0.3. Periodate oxidation, methylation analysis, solvolysis with HF, and detailed 1H and 13C NMR analysis resulted in the structure of the repeating unit shown below. [formula: see text] Bacteriophage Acm7-associated end-α-L-rhamnopyranoside hydrolase depolymerizes the CPS even in the presence of the O-acyl group, to give the respective hexa-, nona-, and dodeca-saccharides.
NCBI PubMed ID: 8039190Journal NLM ID: 0043535Publisher: Elsevier
Institutions: Forschungsinstitut Borstel, Institut fur Experimentelle Biologie und Medizin, Borstel, Germany
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13. Compound ID: 8749
|
EtN-(1--P--7)--+
|
L-gro-a-D-manHepp-(1-2)-L-gro-a-D-manHepp-(1-3)-+ | EtN-(1--P--8)--+
| | |
L-GroA-(1-7)-b-Psep5Ac-(2-6)-b-D-Glcp-(1-4)-D-gro-a-D-manHepp-(1-5)-4,7anhKdo
|
EtN-(1--P--2)--+ |
Show graphically |
Structure type: oligomer
Compound class: core oligosaccharide
Contained glycoepitopes: IEDB_120354,IEDB_123890,IEDB_142488,IEDB_146664,IEDB_2189046,IEDB_2189047,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 3797
Vinogradov E, Wilde C, Anderson EM, Nakhamchik A, Lam JS, Rowe-Magnus DA "Structure of the lipopolysaccharide core of Vibrio vulnificus type strain 27562" -
Carbohydrate Research 344(4) (2009) 484-490
The structure of the lipopolysaccharide core of Vibrio vulnificus type strain 27562 is presented. LPS hydrolysis gave two oligosaccharides, OS-1 and OS-2, as well as lipid A. NMR spectroscopic data corresponded to the presence of one Kdo residue, one β-glucopyranose, three heptoses, one glyceric acid, one acetate, three PEtN, and one 5,7-diacylamido-3,5,7,9-tetradeoxynonulosonic acid residue (pseudaminic acid, Pse) in OS1. OS2 differed form OS 1 by the absence of glyceric acid, acetate, and Pse residues. Lipid A was analyzed for fatty acid composition and the following fatty acids were found: C14:0, C12:0-3OH, C16:0, C16:1, C14:0-3OH, C18:0, C18:1 in a ratio of 1:3:3:1:2.5:0.6:0.8.
Lipopolysaccharide, structure, core, Vibrio vulnificus
NCBI PubMed ID: 19185290Publication DOI: 10.1016/j.carres.2008.12.017Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: D.A. Rowe-Magnus
Institutions: Institute for Biological Sciences, National Research Council, 100 Sussex Dr., Ottawa, Ont., Canada K1A 0R6, Department of Molecular and Cellular Biology, University of Guelph, 488 Gordon Street, New Science Complex, Guelph, ON, Canada N1G 2W1, Division of Clinical Integrative Biology, Sunnybrook Health Sciences Centre, 2075 Bayview Avenue, S1-26A, Toronto, Ontario, Canada M4N 3N5, Department of Laboratory Medicine and Pathobiology, Faculty of Medicine, University of Toronto, Toronto, Canada
Methods: 13C NMR, 1H NMR, methylation, NMR-2D, GC-MS, sugar analysis, dephosphorylation, 31P NMR, ESI-MS, mild acid hydrolysis, alkaline degradation, GC, NMR-1D, immunoblotting, PAGE, N-acetylation, partial de-O-acylation
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14. Compound ID: 8751
|
L-gro-a-D-manHepp-(1-2)-L-gro-a-D-manHepp-(1-3)-+
|
L-GroA-(1-7)-b-Psep5Ac-(2-6)-b-D-Glcp-(1-4)-D-gro-a-D-manHepp-(1-5)-Kdop |
Show graphically |
Structure type: oligomer
Compound class: core oligosaccharide
Contained glycoepitopes: IEDB_130650,IEDB_142488,IEDB_146664,IEDB_2189046,IEDB_2189047,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 3797
Vinogradov E, Wilde C, Anderson EM, Nakhamchik A, Lam JS, Rowe-Magnus DA "Structure of the lipopolysaccharide core of Vibrio vulnificus type strain 27562" -
Carbohydrate Research 344(4) (2009) 484-490
The structure of the lipopolysaccharide core of Vibrio vulnificus type strain 27562 is presented. LPS hydrolysis gave two oligosaccharides, OS-1 and OS-2, as well as lipid A. NMR spectroscopic data corresponded to the presence of one Kdo residue, one β-glucopyranose, three heptoses, one glyceric acid, one acetate, three PEtN, and one 5,7-diacylamido-3,5,7,9-tetradeoxynonulosonic acid residue (pseudaminic acid, Pse) in OS1. OS2 differed form OS 1 by the absence of glyceric acid, acetate, and Pse residues. Lipid A was analyzed for fatty acid composition and the following fatty acids were found: C14:0, C12:0-3OH, C16:0, C16:1, C14:0-3OH, C18:0, C18:1 in a ratio of 1:3:3:1:2.5:0.6:0.8.
Lipopolysaccharide, structure, core, Vibrio vulnificus
NCBI PubMed ID: 19185290Publication DOI: 10.1016/j.carres.2008.12.017Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: D.A. Rowe-Magnus
Institutions: Institute for Biological Sciences, National Research Council, 100 Sussex Dr., Ottawa, Ont., Canada K1A 0R6, Department of Molecular and Cellular Biology, University of Guelph, 488 Gordon Street, New Science Complex, Guelph, ON, Canada N1G 2W1, Division of Clinical Integrative Biology, Sunnybrook Health Sciences Centre, 2075 Bayview Avenue, S1-26A, Toronto, Ontario, Canada M4N 3N5, Department of Laboratory Medicine and Pathobiology, Faculty of Medicine, University of Toronto, Toronto, Canada
Methods: 13C NMR, 1H NMR, methylation, NMR-2D, GC-MS, sugar analysis, dephosphorylation, 31P NMR, ESI-MS, mild acid hydrolysis, alkaline degradation, GC, NMR-1D, immunoblotting, PAGE, N-acetylation, partial de-O-acylation
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15. Compound ID: 8756
|
EtN-(1--P--7)--+
|
L-gro-a-D-manHepp-(1-2)-L-gro-a-D-manHepp-(1-3)-+ | P-4)-+ LIP-(?-2)-+ LIP-(?-2)-+
| | | | |
L-GroA-(1-7)-b-Psep5Ac-(2-6)-b-D-Glcp-(1-4)-D-gro-a-D-manHepp-(1-5)-Kdop-(2-6)-b-D-GlcpN-(1-6)-a-D-GlcpN-(1-P
| | |
EtN-(1--P--2)--+ P-8)-+ P-4)-+ |
Show graphically |
Structure type: oligomer
Compound class: core oligosaccharide
Contained glycoepitopes: IEDB_120354,IEDB_123890,IEDB_130650,IEDB_135394,IEDB_137777,IEDB_140956,IEDB_141807,IEDB_142488,IEDB_146664,IEDB_151531,IEDB_2189046,IEDB_2189047,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 3797
Vinogradov E, Wilde C, Anderson EM, Nakhamchik A, Lam JS, Rowe-Magnus DA "Structure of the lipopolysaccharide core of Vibrio vulnificus type strain 27562" -
Carbohydrate Research 344(4) (2009) 484-490
The structure of the lipopolysaccharide core of Vibrio vulnificus type strain 27562 is presented. LPS hydrolysis gave two oligosaccharides, OS-1 and OS-2, as well as lipid A. NMR spectroscopic data corresponded to the presence of one Kdo residue, one β-glucopyranose, three heptoses, one glyceric acid, one acetate, three PEtN, and one 5,7-diacylamido-3,5,7,9-tetradeoxynonulosonic acid residue (pseudaminic acid, Pse) in OS1. OS2 differed form OS 1 by the absence of glyceric acid, acetate, and Pse residues. Lipid A was analyzed for fatty acid composition and the following fatty acids were found: C14:0, C12:0-3OH, C16:0, C16:1, C14:0-3OH, C18:0, C18:1 in a ratio of 1:3:3:1:2.5:0.6:0.8.
Lipopolysaccharide, structure, core, Vibrio vulnificus
NCBI PubMed ID: 19185290Publication DOI: 10.1016/j.carres.2008.12.017Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: D.A. Rowe-Magnus
Institutions: Institute for Biological Sciences, National Research Council, 100 Sussex Dr., Ottawa, Ont., Canada K1A 0R6, Department of Molecular and Cellular Biology, University of Guelph, 488 Gordon Street, New Science Complex, Guelph, ON, Canada N1G 2W1, Division of Clinical Integrative Biology, Sunnybrook Health Sciences Centre, 2075 Bayview Avenue, S1-26A, Toronto, Ontario, Canada M4N 3N5, Department of Laboratory Medicine and Pathobiology, Faculty of Medicine, University of Toronto, Toronto, Canada
Methods: 13C NMR, 1H NMR, methylation, NMR-2D, GC-MS, sugar analysis, dephosphorylation, 31P NMR, ESI-MS, mild acid hydrolysis, alkaline degradation, GC, NMR-1D, immunoblotting, PAGE, N-acetylation, partial de-O-acylation
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