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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: 1153
Structure type: monomer
The structure is contained in the following publication(s):
- Article ID: 352
Poirot E, Zhang X, Whittaker NF, Kovác P "Syntheses of the L-manno and some other analogs of the terminal determinants of the O-PS of Vibrio cholerae O:1" -
Carbohydrate Research 330(1) (2001) 7-20
Analogs of the methyl α-glycosides of the terminal residues of the O-specific polysaccharides (O-PS) of Vibrio cholerae O:1, serotype Inaba and Ogawa, have been prepared as probes to study their interaction with anti V. cholerae O:1 antibodies. They differ from the termini of the respective O-PSs in anomeric or absolute configuration of perosamine, position of the O-methyl group in D-perosamine, and nature of the N-acyl side chain.
terminal, O-polysaccharide, Vibrio, determinant, Vibrio cholerae
NCBI PubMed ID: 11217964Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: kpn@helix.nih.gov
Institutions: National Institutes of Health, Building 8, Room B1A24, Bethesda, MD 20892-0815, USA
Methods: chemical methods
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10. Compound ID: 1158
Structure type: monomer
The structure is contained in the following publication(s):
- Article ID: 352
Poirot E, Zhang X, Whittaker NF, Kovác P "Syntheses of the L-manno and some other analogs of the terminal determinants of the O-PS of Vibrio cholerae O:1" -
Carbohydrate Research 330(1) (2001) 7-20
Analogs of the methyl α-glycosides of the terminal residues of the O-specific polysaccharides (O-PS) of Vibrio cholerae O:1, serotype Inaba and Ogawa, have been prepared as probes to study their interaction with anti V. cholerae O:1 antibodies. They differ from the termini of the respective O-PSs in anomeric or absolute configuration of perosamine, position of the O-methyl group in D-perosamine, and nature of the N-acyl side chain.
terminal, O-polysaccharide, Vibrio, determinant, Vibrio cholerae
NCBI PubMed ID: 11217964Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: kpn@helix.nih.gov
Institutions: National Institutes of Health, Building 8, Room B1A24, Bethesda, MD 20892-0815, USA
Methods: chemical methods
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11. Compound ID: 1470
|
GroA-(2--P--4)--b-D-ManpNAc-(1-4)-+
|
a-D-Glcp-(1-6)-+ |
| |
{{{-b-D-Galp-(1-4)-b-D-ManpNAc-(1-3)-}}}/n=21/-a-L-Rhap-(1-3)-a-L-Rhap-(1-3)-a-L-Rhap-(1-3)-b-D-Galp-(1-7)-Tyr |
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Structure type: oligomer
Compound class: S-layer glycoprotein
Contained glycoepitopes: IEDB_136044,IEDB_136105,IEDB_137472,IEDB_141794,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_190606,IEDB_225177,IEDB_885813,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: 468
Schäffer C, Messner P "Surface-layer glycoproteins: an example for the diversity of bacterial glycosylation with promising impacts on nanobiotechnology" -
Glycobiology 14(8) (2004) 31R-42R
Bacterial cell surface layers, referred to simply as S-layers, have been described for all major phylogenetic groups of bacteria, which may indicate their pivotal role for a bacterium in its natural habitat. They have the unique ability to assemble into two-dimensional crystalline arrays that completely cover the bacterial cells. Glycosylation represents the most frequent modification of S-layer proteins. S-layer glycoproteins constitute a class of glycoconjugates first isolated in the mid-1970s, but S-layer glycoprotein research is still being regarded as an 'exotic field of glycobiology,' possibly because of its 'noneukaryotic' character. Extensive work over the past 30 years provided evidence of an enormous diversity of S-layer glycoproteins that have been created in nature over 3 billion years of prokaryotic evolution. These glycoconjugates are substantially different from eukaryotic glycoproteins, with regard to both composition and structure; nevertheless, some general structural concepts may be deduced. The awareness of the high application potential of S-layer glycoproteins, especially in combination with their intrinsic cell surface display feature, in the field of modern nanobiotechnology as a base for glycoengineering has recently led to the investigation of the S-layer protein glycosylation process at the molecular level, which has lagged behind the structural studies due to the lack of suitable molecular tools. From that work an even more interesting picture of this class of glycoconjugates is emerging. The availability of purified enzymes from S-layer glycan biosynthesis pathways exhibiting increased stabilities and/or rare sugar specificities in conjunction with preliminary genomic data on S-layer glycan biosynthesis clusters will pave the way for the rational design of S-layer neoglycoproteins.
LPS, bacterial glycosylation, genomic glycosylation loci, glycan diversity, glycoengineering, S-layer nanoglycobiology
NCBI PubMed ID: 15044388Publication DOI: 10.1093/glycob/cwh064Journal NLM ID: 9104124Publisher: IRL Press at Oxford University Press
Correspondence: paul.messner@boka.ac.at
Institutions: Center for NanoBiotechnology, University of Applied Life Sciences and Natural Resources, Gregor-Mendel-Strasse 33, A-1180 Wien, Austria
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12. 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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13. Compound ID: 4224
Structure type: monomer
Compound class: O-polysaccharide
The structure is contained in the following publication(s):
- Article ID: 1576
Vinogradov E, Caroff M "Structure of the Bordetella trematum LPS O-chain subunit" -
FEBS Letters 579(1) (2005) 18-24
Analysis of the O-chain subunit of the lipopolysaccharide (LPS, endotoxin) isolated from Bordetella trematum, a recently identified human pathogen, was undertaken. The polysaccharide (PS) moiety was shown to contain only two O-chain subunits, which differed in the anomeric bond of their first sugar. A trisaccharide fragment resulting from the cleavage of a FucNAc glycosidic bond was isolated after treatment of the PS with anhydrous HF. Nitrous deamination of the LPS led to the release of the following heptasaccharide corresponding to two trisaccharide subunits linked to an anhydromannitol residue. β-ManNAc3NAmA-(1-4)-β-ManNAc3NAmA-(1-3)-α-FucNAc-(1-4)-β-ManN Ac3NAmA-(1-4)-β-ManNAc3NAmA-(1-3)-β-FucNAc-(1-6)-2,5-anhManol
Lipopolysaccharide, LPS, structure, human, polysaccharide, trisaccharide, analysis, linked, Research, Bordetella, endotoxin, biological, sugar, release, O-chain, treatment, fragment, pathogen, deamination, heptasaccharide, cleavage, anomeric, HF, glycosidic bond
NCBI PubMed ID: 15620685Publication DOI: 10.1016/j.febslet.2004.11.040Journal NLM ID: 0155157Publisher: Elsevier
Institutions: Institute for Biological Sciences, National Research Council, 100 Sussex Dr., Ottawa, ON, Canada K1A 0R6
Methods: NMR, HF solvolysis, TLC, MS, nitrous deamination
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14. Compound ID: 4225
Structure type: monomer
Compound class: O-polysaccharide
The structure is contained in the following publication(s):
- Article ID: 1576
Vinogradov E, Caroff M "Structure of the Bordetella trematum LPS O-chain subunit" -
FEBS Letters 579(1) (2005) 18-24
Analysis of the O-chain subunit of the lipopolysaccharide (LPS, endotoxin) isolated from Bordetella trematum, a recently identified human pathogen, was undertaken. The polysaccharide (PS) moiety was shown to contain only two O-chain subunits, which differed in the anomeric bond of their first sugar. A trisaccharide fragment resulting from the cleavage of a FucNAc glycosidic bond was isolated after treatment of the PS with anhydrous HF. Nitrous deamination of the LPS led to the release of the following heptasaccharide corresponding to two trisaccharide subunits linked to an anhydromannitol residue. β-ManNAc3NAmA-(1-4)-β-ManNAc3NAmA-(1-3)-α-FucNAc-(1-4)-β-ManN Ac3NAmA-(1-4)-β-ManNAc3NAmA-(1-3)-β-FucNAc-(1-6)-2,5-anhManol
Lipopolysaccharide, LPS, structure, human, polysaccharide, trisaccharide, analysis, linked, Research, Bordetella, endotoxin, biological, sugar, release, O-chain, treatment, fragment, pathogen, deamination, heptasaccharide, cleavage, anomeric, HF, glycosidic bond
NCBI PubMed ID: 15620685Publication DOI: 10.1016/j.febslet.2004.11.040Journal NLM ID: 0155157Publisher: Elsevier
Institutions: Institute for Biological Sciences, National Research Council, 100 Sussex Dr., Ottawa, ON, Canada K1A 0R6
Methods: NMR, HF solvolysis, TLC, MS, nitrous deamination
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15. Compound ID: 4698
Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
The structure is contained in the following publication(s):
- Article ID: 1778
Knirel YA, Kochetkov NK "The structure of lipopolysaccharides of gram-negative bacteria. III. The structure of O-antigens: A review" -
Biochemistry (Moscow) 59(12) (1994) 1325-1383
This review summarizes data on the composition and structure of the O-antigens, the polysaccharide chains of the outer-membrane lipopolysaccharides (LPS) of Gram-negative bacteria defining the immunospecificity of these microbial cells. Special reference is given to some structural features of the O-antigens, such as the presence of unique monosaccharides and noncarbohydrate components, masked regularity, and the occurrence in one microorganism of LPS with structurally different polysaccharide chains. Antigenic relationships between microorganisms belonging to different taxonomic groups are discussed.
structure, O-antigen, chemical composition, bacterial lipopolysaccharides, Salmonella livingstone C1
NCBI PubMed ID: 7533007Journal NLM ID: 0376536Publisher: Nauka/Interperiodica
Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
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