Found 27 structures.
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1. Compound ID: 1182
Structure type: polymer chemical repeating unit
Compound class: CPS, O-polysaccharide
Contained glycoepitopes: IEDB_136906,IEDB_137472,IEDB_141794,IEDB_149136,IEDB_151528,IEDB_190606,SB_7
The structure is contained in the following publication(s):
- Article ID: 363
Rodríguez-Carvajal MA, Gonzalez L, Bernabé M, Espinosa JF, Espartero JL, Tejero-Mateo P, Gil-Serrano A, Jiménez-Barbero J "Studies on the solution conformation and dynamics of the trisaccharide repeating unit of the KPS from Sinorhizobium fredii SVQ293" -
Journal of Carbohydrate Chemistry 18(8) (1999) 891-903
The conformational behaviour of the major trisaccharide repeating unit (a-D-Galp-(1→2)-b-D-Ribf-(1→9)-a-5-O-Me-Kdnp-) of the polysaccharide from Sinorhizobium fredii SVQ293, a mutant derivative has been analysed by NMR spectroscopy and extensive molecular dynamics simulations. The results obtained indicate that the five-membered ring adopts and almost unique conformation as do the pyranose rings. The Ribj-(1→9)-a-5-O-Me-Kdnp linkage may adopt a variety of conformations while the a-D-Galp-(1→2)-b-D-Ribf- also populates an extended surface of the F/T map. Two 10 ns MD simulations using the GB/SA continuum solvent model for water and the MM3* force field provides a population distribution of conformers which satisfactorily agrees with the experimental NMR data for both the glycosidic linkages and the hydroxymethyl groups.
conformation, polysaccharide, dynamics, 3-deoxy-D-glycero-D-galacto-nonulosonic acid, Sinorhizobium, trisaccharide repeating unit
Publication DOI: 10.1080/07328309908544042Journal NLM ID: 8218151Publisher: Marcel Dekker
Institutions: Instituto Quimica Organica, CSIC, Juan de la Cierva 3, 28006 Madrid, Departamento Quimica Organica, Facultad Quimica, Univ. Senilla, 41071-Spain
Methods: NMR, MD simulations
- Article ID: 645
Gil-Serrano AM, Rodríguez-Carvajal MA, Tejero-Mateo P, Espartero JL, Thomas-Oates J, Ruiz-Sainz JE, Buendía-Clavería AM "Structural determination of a 5-O-methyl-deaminated neuraminic acid (Kdn)-containing polysaccharide isolated from Sinorhizobium fredii" -
Biochemical Journal 334(3) (1998) 585-594
The structure of a polysaccharide from Sinorhizobium fredii SVQ293, a thiamine auxotrophic mutant of S. fredii HH103, has been determined. This polysaccharide was isolated following the protocol for lipopolysaccharide extraction. On the basis of monosaccharide analysis, methylation analysis, fast atom bombardment MS, collision-induced dissociation tandem MS, one-dimensional 1H and 13C NMR and two-dimensional NMR experiments, the structure was shown to consist of the following trisaccharide repeating unit →2)-α-D-Galp-(1→2)-β-D-Ribf-(1→9)-α-5-O-Me-Kdnp-(2→, in which Kdn stands for deaminated neuraminic acid; 25% of the Kdn residues are not methylated. The structure of this polysaccharide is novel and this is the first report of the presence of Kdn in a rhizobial polysaccharide, as well as being the first structure described containing 5-O-Me-Kdn. This Kdn-containing polysaccharide is not present in the wild-type strain HH103, which produces a 3-deoxy-d-manno-2-octulosonic acid (Kdo)-rich polysaccharide. We conclude that it is likely that the appearance of this new Kdn-containing polysaccharide is a consequence of the mutation.
structural, polysaccharide, determination, structural determination, acid, neuraminic acid, Sinorhizobium
NCBI PubMed ID: 9729466Publication DOI: 10.1042/bj3340585Journal NLM ID: 2984726RPublisher: London, UK : Published by Portland Press on behalf of the Biochemical Society
Correspondence: agil@cica.es
Institutions: Departamento de Qu approximately imica Organica, Facultad de Qu approximately imica, Universidad de Sevilla, 41071-Sevilla, Spain
Methods: methylation, NMR-2D, FAB-MS, partial acid hydrolysis, NMR
- Article ID: 4050
Knirel YA, Shevelev SD, Perepelov AV "Higher aldulosonic acids: components of bacterial glycans" -
Mendeleev Communications 21(4) (2011) 173-182
Recent data on the natural occurrence, chemistry, and biochemistry of C8 and C9 aldulosonic acids (3-deoxy-d-manno-oct-2-ulosonic acid, sialic acids, N-acyl derivatives of 5,7-diamino-3,5,7,9-tetradeoxynon-2-ulosonic acids, and some others) as well as on the structures and biological significance of bacterial glycans containing these higher acidic monosaccharides are summarized.
structure, Bacterial, glycan, aldulosonic acid, higher acidic monosaccharides, sialic acids
Publication DOI: 10.1016/j.mencom.2011.07.001Journal NLM ID: 9425965Publisher: Moscow: Academy of Sciences of the USSR; Cambridge,UK : Royal Society of Chemistry
Correspondence: knirel@ioc.ac.ru
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
- 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
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2. Compound ID: 1183
Structure type: oligomer
Compound class: O-polysaccharide
Contained glycoepitopes: IEDB_136906,IEDB_137472,IEDB_141794,IEDB_149136,IEDB_151528,IEDB_190606,SB_7
The structure is contained in the following publication(s):
- Article ID: 363
Rodríguez-Carvajal MA, Gonzalez L, Bernabé M, Espinosa JF, Espartero JL, Tejero-Mateo P, Gil-Serrano A, Jiménez-Barbero J "Studies on the solution conformation and dynamics of the trisaccharide repeating unit of the KPS from Sinorhizobium fredii SVQ293" -
Journal of Carbohydrate Chemistry 18(8) (1999) 891-903
The conformational behaviour of the major trisaccharide repeating unit (a-D-Galp-(1→2)-b-D-Ribf-(1→9)-a-5-O-Me-Kdnp-) of the polysaccharide from Sinorhizobium fredii SVQ293, a mutant derivative has been analysed by NMR spectroscopy and extensive molecular dynamics simulations. The results obtained indicate that the five-membered ring adopts and almost unique conformation as do the pyranose rings. The Ribj-(1→9)-a-5-O-Me-Kdnp linkage may adopt a variety of conformations while the a-D-Galp-(1→2)-b-D-Ribf- also populates an extended surface of the F/T map. Two 10 ns MD simulations using the GB/SA continuum solvent model for water and the MM3* force field provides a population distribution of conformers which satisfactorily agrees with the experimental NMR data for both the glycosidic linkages and the hydroxymethyl groups.
conformation, polysaccharide, dynamics, 3-deoxy-D-glycero-D-galacto-nonulosonic acid, Sinorhizobium, trisaccharide repeating unit
Publication DOI: 10.1080/07328309908544042Journal NLM ID: 8218151Publisher: Marcel Dekker
Institutions: Instituto Quimica Organica, CSIC, Juan de la Cierva 3, 28006 Madrid, Departamento Quimica Organica, Facultad Quimica, Univ. Senilla, 41071-Spain
Methods: NMR, MD simulations
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3. Compound ID: 1200
Structure type: polymer chemical repeating unit
Compound class: cell wall polysaccharide
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 374
Shashkov AS, Streshinskaya GM, Kosmachevskaya LN, Evtushenko LI, Naumova IB "A polymer of 8-O-glucosylated 2-keto-3-deoxy-D-glycero-D-galacto-nonulosonic acid (Kdn) in the cell wall of Streptomyces sp. VKM Ac-2090" -
Mendeleev Communications 10(5) (2000) 167-168
The title polymer of Kdn was detected in biological object for the first time.
cell wall, homopolymer, Kdn, Streptomyces
Publication DOI: 10.1070/MC2000v010n05ABEH001338Journal NLM ID: 9425965Publisher: Moscow: Academy of Sciences of the USSR; Cambridge,UK : Royal Society of Chemistry
Correspondence: shash@ioc.ac.ru
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Department of Biology, M.V. Lomonosov Moscow State University, 119899 Moscow, Russian Federation, Institute of Biochemistry and Physiology of Microorganisms, Russian Academy of Sciences, 142292 Pushchimo, Moscow Region, Russian Federation
Methods: NMR-2D, NMR
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4. Compound ID: 1253
|
a-Kdnp-(2-1)-Subst
Subst = 4-methylumbelliferone = SMILES O=C1C=C(C)C2=C(O1)C={1}C(O)C=C2 |
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Structure type: monomer
The structure is contained in the following publication(s):
- Article ID: 395
Terada T, Kitajima K, Inoue S, Wilson JC, Norton AK, Kong DCM, Thomson RJ, Von Itzstein M, Inoue Y "Catalysis by a new sialidase, deaminoneuraminic acid residue-cleaving enzyme (KDNase Sm), initially forms a less stable a-anomer of 3-deoxy-D-glycero-D-galacto-nonulosonic acid and is strongly inhibited by the transition state analogue, 2-deoxy-2,3-didehydro-D-glycero-D-galacto-2-nonulopyranosonic acid, but not by 2-deoxy-2,3-didehydro-N-acetylneuraminic acid" -
Journal of Biological Chemistry 272(9) (1997) 5452-5456
Deaminoneuraminic acid residue-cleaving enzyme (KDNase Sm) is a new sialidase that has been induced and purified from Sphingobacterium multivorum. Catalysis by this new sialidase has been studied by enzyme kinetics and 1H NMR spectroscopy. Vmax/Km values determined for synthetic and natural substrates of KDNase Sm reveal that 4-methylumbelliferyl-KDN (KDNα2MeUmb, Vmax/Km = 0.033 min-1) is the best substrate for this sialidase, presumably because of its good leaving group properties. The transition state analogue, 2, 3-didehydro-2,3-dideoxy-D-galacto-D-glycero-nonulosonic acid, is a strong competitive inhibitor of KDNase Sm (Ki = 7.7 microM versus Km = 42 microM for KDNα2MeUmb). 2-Deoxy-2, 3-didehydro-N-acetylneuraminic acid and 2-deoxy-2, 3-didehydro-N-glycolylneuraminic acid are known to be strong competitive inhibitors for bacterial sialidases such as Arthrobacter ureafaciens sialidase; however, KDNase Sm activity is not significantly inhibited by these compounds. This observation suggests that the hydroxyl group at C-5 is important for recognition of the inhibitor by the enzyme. Reversible addition of water molecule (or hydroxide ion) to the reactive sialosyl cation, presumably formed at the catalytic site of KDNase Sm, eventually gives rise to two different adducts, the α- and β-anomers of free 3-deoxy-D-glycero-D-galacto-nonulosonic acid. 1H NMR spectroscopic studies clearly demonstrate that the thermodynamically less stable α-form is preferentially formed as the first product of the cleavage reaction and that isomerization rapidly follows, leading to an equilibrium mixture of the two isomers, the beta-isomer being the major species at equilibrium. Therefore, we propose that KDNase Sm catalysis proceeds via a mechanism common to the known exosialidases, but the recognition of the substituent at C-5 by the enzyme differs.
2, enzyme, 3-deoxy-D-glycero-D-galacto-nonulosonic acid, N-acetylneuraminic acid, Kdn, 3-didehhydro, desialylation, sialidase, transition state
NCBI PubMed ID: 9038146Journal NLM ID: 2985121RPublisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
Correspondence: syinoue@gate.sinica.edu.tw
Institutions: Department of Biophysics and Biochemistry, Graduate School of Science, University of Tokyo, Hongo-7, Tokyo 113, Japan, Institute of Biological Chemistry, Academia Sinica, Nankang, Taipei 115, Taiwan, the Department of Medicinal Chemistry, Victorian College of Pharmacy, Monash University, Parkville, 3052 Victoria, Australia
Methods: NMR
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5. Compound ID: 1255
Structure type: oligomer
The structure is contained in the following publication(s):
- Article ID: 395
Terada T, Kitajima K, Inoue S, Wilson JC, Norton AK, Kong DCM, Thomson RJ, Von Itzstein M, Inoue Y "Catalysis by a new sialidase, deaminoneuraminic acid residue-cleaving enzyme (KDNase Sm), initially forms a less stable a-anomer of 3-deoxy-D-glycero-D-galacto-nonulosonic acid and is strongly inhibited by the transition state analogue, 2-deoxy-2,3-didehydro-D-glycero-D-galacto-2-nonulopyranosonic acid, but not by 2-deoxy-2,3-didehydro-N-acetylneuraminic acid" -
Journal of Biological Chemistry 272(9) (1997) 5452-5456
Deaminoneuraminic acid residue-cleaving enzyme (KDNase Sm) is a new sialidase that has been induced and purified from Sphingobacterium multivorum. Catalysis by this new sialidase has been studied by enzyme kinetics and 1H NMR spectroscopy. Vmax/Km values determined for synthetic and natural substrates of KDNase Sm reveal that 4-methylumbelliferyl-KDN (KDNα2MeUmb, Vmax/Km = 0.033 min-1) is the best substrate for this sialidase, presumably because of its good leaving group properties. The transition state analogue, 2, 3-didehydro-2,3-dideoxy-D-galacto-D-glycero-nonulosonic acid, is a strong competitive inhibitor of KDNase Sm (Ki = 7.7 microM versus Km = 42 microM for KDNα2MeUmb). 2-Deoxy-2, 3-didehydro-N-acetylneuraminic acid and 2-deoxy-2, 3-didehydro-N-glycolylneuraminic acid are known to be strong competitive inhibitors for bacterial sialidases such as Arthrobacter ureafaciens sialidase; however, KDNase Sm activity is not significantly inhibited by these compounds. This observation suggests that the hydroxyl group at C-5 is important for recognition of the inhibitor by the enzyme. Reversible addition of water molecule (or hydroxide ion) to the reactive sialosyl cation, presumably formed at the catalytic site of KDNase Sm, eventually gives rise to two different adducts, the α- and β-anomers of free 3-deoxy-D-glycero-D-galacto-nonulosonic acid. 1H NMR spectroscopic studies clearly demonstrate that the thermodynamically less stable α-form is preferentially formed as the first product of the cleavage reaction and that isomerization rapidly follows, leading to an equilibrium mixture of the two isomers, the beta-isomer being the major species at equilibrium. Therefore, we propose that KDNase Sm catalysis proceeds via a mechanism common to the known exosialidases, but the recognition of the substituent at C-5 by the enzyme differs.
2, enzyme, 3-deoxy-D-glycero-D-galacto-nonulosonic acid, N-acetylneuraminic acid, Kdn, 3-didehhydro, desialylation, sialidase, transition state
NCBI PubMed ID: 9038146Journal NLM ID: 2985121RPublisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
Correspondence: syinoue@gate.sinica.edu.tw
Institutions: Department of Biophysics and Biochemistry, Graduate School of Science, University of Tokyo, Hongo-7, Tokyo 113, Japan, Institute of Biological Chemistry, Academia Sinica, Nankang, Taipei 115, Taiwan, the Department of Medicinal Chemistry, Victorian College of Pharmacy, Monash University, Parkville, 3052 Victoria, Australia
Methods: NMR
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6. Compound ID: 1256
Structure type: oligomer
Contained glycoepitopes: IEDB_136044,IEDB_137472,IEDB_141794,IEDB_142487,IEDB_142488,IEDB_144998,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: 395
Terada T, Kitajima K, Inoue S, Wilson JC, Norton AK, Kong DCM, Thomson RJ, Von Itzstein M, Inoue Y "Catalysis by a new sialidase, deaminoneuraminic acid residue-cleaving enzyme (KDNase Sm), initially forms a less stable a-anomer of 3-deoxy-D-glycero-D-galacto-nonulosonic acid and is strongly inhibited by the transition state analogue, 2-deoxy-2,3-didehydro-D-glycero-D-galacto-2-nonulopyranosonic acid, but not by 2-deoxy-2,3-didehydro-N-acetylneuraminic acid" -
Journal of Biological Chemistry 272(9) (1997) 5452-5456
Deaminoneuraminic acid residue-cleaving enzyme (KDNase Sm) is a new sialidase that has been induced and purified from Sphingobacterium multivorum. Catalysis by this new sialidase has been studied by enzyme kinetics and 1H NMR spectroscopy. Vmax/Km values determined for synthetic and natural substrates of KDNase Sm reveal that 4-methylumbelliferyl-KDN (KDNα2MeUmb, Vmax/Km = 0.033 min-1) is the best substrate for this sialidase, presumably because of its good leaving group properties. The transition state analogue, 2, 3-didehydro-2,3-dideoxy-D-galacto-D-glycero-nonulosonic acid, is a strong competitive inhibitor of KDNase Sm (Ki = 7.7 microM versus Km = 42 microM for KDNα2MeUmb). 2-Deoxy-2, 3-didehydro-N-acetylneuraminic acid and 2-deoxy-2, 3-didehydro-N-glycolylneuraminic acid are known to be strong competitive inhibitors for bacterial sialidases such as Arthrobacter ureafaciens sialidase; however, KDNase Sm activity is not significantly inhibited by these compounds. This observation suggests that the hydroxyl group at C-5 is important for recognition of the inhibitor by the enzyme. Reversible addition of water molecule (or hydroxide ion) to the reactive sialosyl cation, presumably formed at the catalytic site of KDNase Sm, eventually gives rise to two different adducts, the α- and β-anomers of free 3-deoxy-D-glycero-D-galacto-nonulosonic acid. 1H NMR spectroscopic studies clearly demonstrate that the thermodynamically less stable α-form is preferentially formed as the first product of the cleavage reaction and that isomerization rapidly follows, leading to an equilibrium mixture of the two isomers, the beta-isomer being the major species at equilibrium. Therefore, we propose that KDNase Sm catalysis proceeds via a mechanism common to the known exosialidases, but the recognition of the substituent at C-5 by the enzyme differs.
2, enzyme, 3-deoxy-D-glycero-D-galacto-nonulosonic acid, N-acetylneuraminic acid, Kdn, 3-didehhydro, desialylation, sialidase, transition state
NCBI PubMed ID: 9038146Journal NLM ID: 2985121RPublisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
Correspondence: syinoue@gate.sinica.edu.tw
Institutions: Department of Biophysics and Biochemistry, Graduate School of Science, University of Tokyo, Hongo-7, Tokyo 113, Japan, Institute of Biological Chemistry, Academia Sinica, Nankang, Taipei 115, Taiwan, the Department of Medicinal Chemistry, Victorian College of Pharmacy, Monash University, Parkville, 3052 Victoria, Australia
Methods: NMR
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7. Compound ID: 2129
Structure type: oligomer
Contained glycoepitopes: IEDB_136906,IEDB_137472,IEDB_141794,IEDB_149136,IEDB_151528,IEDB_190606,SB_7
The structure is contained in the following publication(s):
- Article ID: 645
Gil-Serrano AM, Rodríguez-Carvajal MA, Tejero-Mateo P, Espartero JL, Thomas-Oates J, Ruiz-Sainz JE, Buendía-Clavería AM "Structural determination of a 5-O-methyl-deaminated neuraminic acid (Kdn)-containing polysaccharide isolated from Sinorhizobium fredii" -
Biochemical Journal 334(3) (1998) 585-594
The structure of a polysaccharide from Sinorhizobium fredii SVQ293, a thiamine auxotrophic mutant of S. fredii HH103, has been determined. This polysaccharide was isolated following the protocol for lipopolysaccharide extraction. On the basis of monosaccharide analysis, methylation analysis, fast atom bombardment MS, collision-induced dissociation tandem MS, one-dimensional 1H and 13C NMR and two-dimensional NMR experiments, the structure was shown to consist of the following trisaccharide repeating unit →2)-α-D-Galp-(1→2)-β-D-Ribf-(1→9)-α-5-O-Me-Kdnp-(2→, in which Kdn stands for deaminated neuraminic acid; 25% of the Kdn residues are not methylated. The structure of this polysaccharide is novel and this is the first report of the presence of Kdn in a rhizobial polysaccharide, as well as being the first structure described containing 5-O-Me-Kdn. This Kdn-containing polysaccharide is not present in the wild-type strain HH103, which produces a 3-deoxy-d-manno-2-octulosonic acid (Kdo)-rich polysaccharide. We conclude that it is likely that the appearance of this new Kdn-containing polysaccharide is a consequence of the mutation.
structural, polysaccharide, determination, structural determination, acid, neuraminic acid, Sinorhizobium
NCBI PubMed ID: 9729466Publication DOI: 10.1042/bj3340585Journal NLM ID: 2984726RPublisher: London, UK : Published by Portland Press on behalf of the Biochemical Society
Correspondence: agil@cica.es
Institutions: Departamento de Qu approximately imica Organica, Facultad de Qu approximately imica, Universidad de Sevilla, 41071-Sevilla, Spain
Methods: methylation, NMR-2D, FAB-MS, partial acid hydrolysis, NMR
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8. Compound ID: 3336
Structure type: oligomer
Contained glycoepitopes: IEDB_136044,IEDB_137472,IEDB_141794,IEDB_190606,SB_165,SB_166,SB_187,SB_195,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 1230
Shashkov AS, Tul'skaya EM, Evtushenko LI, Denisenko VA, Ivanyuk VG, Stomakhin AA, Naumova IB, Stackebrandt E "Cell wall anionic polymers of Streptomyces sp. MB-8, the causative agent of potato scab" -
Carbohydrate Research 337(21-23) (2002) 2255-2261
The cell wall of Streptomyces sp. MB-8 contains a major teichoic acid, viz., 1,3-poly(glycerol phosphate) substituted with N-acetyl-α-D-glucosamine (the degree of substitution is 60%), a minor teichoic acid, viz., non-substituted poly(glycerol phosphate), and a family of Kdn (3-deoxy-D-glycero-D-galacto-non-2-ulopyranosonic acid)-containing oligomers of the following general structure: [carbohydrate structure: see text]. The composition of the oligomers was established using MALDI-TOF mass spectroscopy. The present study provides the second example of the identification of Kdn as a component of cell wall polymers of streptomycetes, which are the causative agents of potato scab.
NMR spectroscopy, teichoic acids, Kdn, Streptomyces, MALDI-TOF MS, 3-O-methylgalactose
NCBI PubMed ID: 12433490Publication DOI: 10.1016/s0008-6215(02)00188-xJournal NLM ID: 0043535Publisher: Elsevier
Correspondence: shash@ioc.ac.ru
Institutions: N.D.Zelinsky Institute of Organic Chemistry,Russian Academy of Sciences,Moscow,Russia, Institute of Biochemistry and Physiology of Microorganisms, Russian Academy of Sciences, Pushchino, Moscow Region, 142292, Russia, Belarussian Research Institute for Potato Growing, 2a Kovaleva St., Samokhvalovitchi, Minsk Region 223013, Belarus, B.A. Engelhardt Institute of Molecular Biology, Russian Academy of Science, Moscow, Russia, DSMZ-Deutsche Sammlung von Mikroorganismen und Zellkulturen GmbH, Mascheroder Weg 1b, D-38124 Braunschweig, Germany
Methods: NMR
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9. Compound ID: 4901
|
a-Kdnp-(2-4)-+
|
-3)-b-D-Glcp-(1-2)-a-D-GlcpA3Ac-(1-3)-a-D-Manp-(1-3)-a-D-Glcp-(1- |
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Structure type: polymer chemical repeating unit
Compound class: CPS
Contained glycoepitopes: IEDB_115136,IEDB_130701,IEDB_140630,IEDB_142488,IEDB_144983,IEDB_144998,IEDB_146664,IEDB_152206,IEDB_153755,IEDB_983930,IEDB_983931,SB_192,SB_44,SB_67,SB_72
The structure is contained in the following publication(s):
- Article ID: 1867
Knirel YA, Mamontova VA, Kocharova NA, Shashkov AS, Solov'eva TF, Kochetkov NK "Structure of the capsular polysaccharide of Klebsiella ozaenae K4 containing a 3-deoxynonulosonic acid" -
Bioorganicheskaya Khimia = Bioorganic Chemistry [Russian] 14(11) (1988) 1583-1585
3-Deoxy-D-glycero-D-galacto-nonulosonic acid was identified as a component of the Klebsiella ozaenae K4 capsular polysaccharide. On the basis of methylation, complete and partial acid hydrolyses, Smith degradation, and NMR analysis including computer-assisted 13C NMR evaluation, the following structure of the polysaccharide has been established.
NCBI PubMed ID: 3240330Journal NLM ID: 7804941Publisher: Moskva: Nauka
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Academy of Sciences of the USSR, Moscow, Russia
Methods: 13C NMR
- Article ID: 2139
Knirel YA, Kocharova NA, Shashkov AS, Kochetkov NK, Mamontova VA, Solov'eva TF "The structure of the capsular polysaccharide of Klebsiella ozaenae serotype K4 containing 3-deoxy-D-glycero-D-galacto-nonulosonic acid" -
Carbohydrate Research 188 (1989) 145-155
The acidic capsular polysaccharide from the museum strain 2211 of Klebsiella ozaenae serotype K4 is built up of pentasaccharide repeating-units that contain residues of D-glucose, D-mannose, D-glucuronic acid, and 3-deoxy-D-glycero-D-galacto-nonulosonic acid (Kdn) in the ratios 2:1:1:1, as well as an O-acetyl group. The last-named sugar, which is reported in bacterial polysaccharides for the first time, was identified as the methyl (methyl 3-deoxynonulopyranosid)onate obtained by methanolysis of the polysaccharide. On the basis of the results of partial acid hydrolysis, Smith degradation, and computer-assisted 13C-n.m.r. analysis, it was concluded that the capsular polysaccharide has the following structure: (formula see text)
NCBI PubMed ID: 2776127Publication DOI: 10.1016/0008-6215(89)84067-4Journal NLM ID: 0043535Publisher: Elsevier
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Academy of Sciences of the USSR, Moscow, Russia
Methods: 13C NMR, 1H NMR, methylation, GLC-MS, gel filtration, partial acid hydrolysis, sugar analysis, GLC, Smith degradation
- Article ID: 4050
Knirel YA, Shevelev SD, Perepelov AV "Higher aldulosonic acids: components of bacterial glycans" -
Mendeleev Communications 21(4) (2011) 173-182
Recent data on the natural occurrence, chemistry, and biochemistry of C8 and C9 aldulosonic acids (3-deoxy-d-manno-oct-2-ulosonic acid, sialic acids, N-acyl derivatives of 5,7-diamino-3,5,7,9-tetradeoxynon-2-ulosonic acids, and some others) as well as on the structures and biological significance of bacterial glycans containing these higher acidic monosaccharides are summarized.
structure, Bacterial, glycan, aldulosonic acid, higher acidic monosaccharides, sialic acids
Publication DOI: 10.1016/j.mencom.2011.07.001Journal NLM ID: 9425965Publisher: Moscow: Academy of Sciences of the USSR; Cambridge,UK : Royal Society of Chemistry
Correspondence: knirel@ioc.ac.ru
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
- 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
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10. Compound ID: 9652
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b-D-Galp3(%)Me-(1-9)-+
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b-D-Galp3(%)Me-(1-9)-a-Kdnp-(2-4)-b-Kdnp |
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Structure type: oligomer
Trivial name: teichulosonic acid
Compound class: cell wall polysaccharide
Contained glycoepitopes: IEDB_136044,IEDB_137472,IEDB_141794,IEDB_190606,SB_165,SB_166,SB_187,SB_195,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 4050
Knirel YA, Shevelev SD, Perepelov AV "Higher aldulosonic acids: components of bacterial glycans" -
Mendeleev Communications 21(4) (2011) 173-182
Recent data on the natural occurrence, chemistry, and biochemistry of C8 and C9 aldulosonic acids (3-deoxy-d-manno-oct-2-ulosonic acid, sialic acids, N-acyl derivatives of 5,7-diamino-3,5,7,9-tetradeoxynon-2-ulosonic acids, and some others) as well as on the structures and biological significance of bacterial glycans containing these higher acidic monosaccharides are summarized.
structure, Bacterial, glycan, aldulosonic acid, higher acidic monosaccharides, sialic acids
Publication DOI: 10.1016/j.mencom.2011.07.001Journal NLM ID: 9425965Publisher: Moscow: Academy of Sciences of the USSR; Cambridge,UK : Royal Society of Chemistry
Correspondence: knirel@ioc.ac.ru
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
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11. Compound ID: 9886
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b-D-Galp3(33%)Me-(1-9)-+
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b-D-Galp3(33%)Me-(1-9)-a-Kdnp-(2-4)-b-Kdnp |
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Structure type: oligomer
Compound class: teichulosonic acid
Contained glycoepitopes: IEDB_136044,IEDB_137472,IEDB_141794,IEDB_190606,SB_165,SB_166,SB_187,SB_195,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 4122
Tul'skaya EM, Shashkov AS, Streshinskaia GM, Senchenkova SN, Potekhina NV, Kozlova YI, Evtushenko LI "Teichuronic and teichulosonic acids of actinomycetes" -
Biochemistry (Moscow) 76(7) (2011) 736-744
The subject of the present review is the structural diversity and abundance of cell wall teichuronic and teichulosonic acids of representatives of the order Actinomycetales. Recently found teichulosonic acids are a new class of natural glycopolymers with ald-2-ulosonic acid residues: Kdn (3-deoxy-D-glycero-D-galacto-non-2-ulosonic acid) or di-N-acyl derivatives of Pse (5,7-diamino-3,5,7,9-tetradeoxy-L-glycero-L-manno-non-2-ulosonic or pseudaminic acid) as the obligatory component. The structures of teichuronic and teichulosonic acids are presented. Data are summarized on the occurrence of the glycopolymers of different nature in the cell wall of the studied actinomycetes. The biological role of the glycopolymers and their possible taxonomic implication are discussed. The comprehensive tables given in the Supplement show (13)C NMR spectroscopic data of teichuronic and teichulosonic acids obtained by the authors.
NMR spectroscopy, cell wall, teichuronic acid, actinomycetes, teichulosonic acid
NCBI PubMed ID: 21999534Publication DOI: 10.1134/S0006297911070030Journal NLM ID: 0376536Publisher: Nauka/Interperiodica
Correspondence: em_tulskaya@mail.ru
Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, All-Russian Collection of Microorganisms (VKM), Skryabin Institute of Biochemistry and Physiology of Microorganisms, Russian Academy of Sciences, Pushchino, Russia, Lomonosov Moscow State University, Russia, Biological Faculty, Lomonosov Moscow State University, Moscow, Russia
Methods: NMR, ESI-MS, MALDI-TOF MS
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12. Compound ID: 10807
Structure type: oligomer
Compound class: polysaccharide
Contained glycoepitopes: IEDB_136044,IEDB_137472,IEDB_141794,IEDB_190606,SB_165,SB_166,SB_187,SB_195,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 4391
Shashkov AS, Ostash BE, Fedorenko VA, Streshinskaya GM, Tul'skaya EM, Senchenkova SN, Baryshnikova LM, Evtushenko LI "Novel teichulosonic acid from cell wall of Streptomyces coelicolor M145" -
Carbohydrate Research 359 (2012) 70-75
The cell wall of Streptomyces coelicolor M145, a prototrophic plasmidless (SCP1(-) SCP2(-)) variant of strain S. coelicolor A3(2) contains the main glycopolymer represented by Kdn-containing teichulosonic acid with unusual structure which has not been described so far: [structure: see text]. The minor polymer was found to be a poly(diglycosyl 1-phosphate) with the following repeating unit: -6)-α-Galp-(1→6)-α-GlcpNAc-(1-P-. The structures of both glycopolymers were established by using a combination of chemical and NMR spectroscopic methods.
NMR spectroscopy, cell wall, Streptomyces, teichulosonic acid, glycosyl 1-phosphate polymer
NCBI PubMed ID: 22925767Publication DOI: 10.1016/j.carres.2012.05.018Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: G.M. Streshinskaya
Institutions: School of Biology, M. V. Lomonosov Moscow State University, Moscow, Russian Federation, N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospect, 47, Moscow, Russian Federation, All-Russian Collection of Microorganisms (VKM), G. K. Skryabin Institute of Biochemistry and Physiology of Microorganisms, Russian Academy of Sciences, Pushchino, Russia, Ivan Franko National University of Lviv, Department of Genetics and Biotechnology, Lviv 79005, Ukraine
Methods: 13C NMR, 1H NMR, NMR-2D, sugar analysis, 31P NMR, acid hydrolysis, GLC, paper chromatography, NMR-1D, paper electrophoresis
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13. Compound ID: 10808
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b-D-Galp-(1-9)-+ a-D-GlcpNAc-(1-4)-+
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a-D-GlcpNAc-(1-4)-a-Kdnp-(2-6)-b-D-Galp-(1-9)-b-Kdn |
Show graphically |
Structure type: oligomer
Compound class: cell wall polysaccharide
Contained glycoepitopes: IEDB_136044,IEDB_137340,IEDB_137472,IEDB_141794,IEDB_141807,IEDB_151531,IEDB_190606,SB_165,SB_166,SB_187,SB_195,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 4391
Shashkov AS, Ostash BE, Fedorenko VA, Streshinskaya GM, Tul'skaya EM, Senchenkova SN, Baryshnikova LM, Evtushenko LI "Novel teichulosonic acid from cell wall of Streptomyces coelicolor M145" -
Carbohydrate Research 359 (2012) 70-75
The cell wall of Streptomyces coelicolor M145, a prototrophic plasmidless (SCP1(-) SCP2(-)) variant of strain S. coelicolor A3(2) contains the main glycopolymer represented by Kdn-containing teichulosonic acid with unusual structure which has not been described so far: [structure: see text]. The minor polymer was found to be a poly(diglycosyl 1-phosphate) with the following repeating unit: -6)-α-Galp-(1→6)-α-GlcpNAc-(1-P-. The structures of both glycopolymers were established by using a combination of chemical and NMR spectroscopic methods.
NMR spectroscopy, cell wall, Streptomyces, teichulosonic acid, glycosyl 1-phosphate polymer
NCBI PubMed ID: 22925767Publication DOI: 10.1016/j.carres.2012.05.018Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: G.M. Streshinskaya
Institutions: School of Biology, M. V. Lomonosov Moscow State University, Moscow, Russian Federation, N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospect, 47, Moscow, Russian Federation, All-Russian Collection of Microorganisms (VKM), G. K. Skryabin Institute of Biochemistry and Physiology of Microorganisms, Russian Academy of Sciences, Pushchino, Russia, Ivan Franko National University of Lviv, Department of Genetics and Biotechnology, Lviv 79005, Ukraine
Methods: 13C NMR, 1H NMR, NMR-2D, sugar analysis, 31P NMR, acid hydrolysis, GLC, paper chromatography, NMR-1D, paper electrophoresis
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14. Compound ID: 10809
Structure type: oligomer
Compound class: cell wall polysaccharide
Contained glycoepitopes: IEDB_136044,IEDB_137472,IEDB_141794,IEDB_190606,SB_165,SB_166,SB_187,SB_195,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 4391
Shashkov AS, Ostash BE, Fedorenko VA, Streshinskaya GM, Tul'skaya EM, Senchenkova SN, Baryshnikova LM, Evtushenko LI "Novel teichulosonic acid from cell wall of Streptomyces coelicolor M145" -
Carbohydrate Research 359 (2012) 70-75
The cell wall of Streptomyces coelicolor M145, a prototrophic plasmidless (SCP1(-) SCP2(-)) variant of strain S. coelicolor A3(2) contains the main glycopolymer represented by Kdn-containing teichulosonic acid with unusual structure which has not been described so far: [structure: see text]. The minor polymer was found to be a poly(diglycosyl 1-phosphate) with the following repeating unit: -6)-α-Galp-(1→6)-α-GlcpNAc-(1-P-. The structures of both glycopolymers were established by using a combination of chemical and NMR spectroscopic methods.
NMR spectroscopy, cell wall, Streptomyces, teichulosonic acid, glycosyl 1-phosphate polymer
NCBI PubMed ID: 22925767Publication DOI: 10.1016/j.carres.2012.05.018Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: G.M. Streshinskaya
Institutions: School of Biology, M. V. Lomonosov Moscow State University, Moscow, Russian Federation, N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospect, 47, Moscow, Russian Federation, All-Russian Collection of Microorganisms (VKM), G. K. Skryabin Institute of Biochemistry and Physiology of Microorganisms, Russian Academy of Sciences, Pushchino, Russia, Ivan Franko National University of Lviv, Department of Genetics and Biotechnology, Lviv 79005, Ukraine
Methods: 13C NMR, 1H NMR, NMR-2D, sugar analysis, 31P NMR, acid hydrolysis, GLC, paper chromatography, NMR-1D, paper electrophoresis
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15. Compound ID: 10810
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/Variants 1/-+ /Variants 0/-+
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b-D-Galp-(1-9)-a-Kdnp-(2-6)-Subst-(2-6)-b-D-Galp-(1-9)-b-Kdn
/Variants 0/ is:
a-D-GlcpNAc-(1-4)-
OR (exclusively)
Me-4)-
/Variants 1/ is:
a-D-GlcpNAc-(1-4)-
OR (exclusively)
Me-4)-
Subst = teichulosonic acid (ID 28628, ID 31082) |
Show graphically |
Structure type: oligomer
Compound class: teichulosonic acid
Contained glycoepitopes: IEDB_136044,IEDB_137340,IEDB_137472,IEDB_141794,IEDB_141807,IEDB_151531,IEDB_190606,SB_165,SB_166,SB_187,SB_195,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 4391
Shashkov AS, Ostash BE, Fedorenko VA, Streshinskaya GM, Tul'skaya EM, Senchenkova SN, Baryshnikova LM, Evtushenko LI "Novel teichulosonic acid from cell wall of Streptomyces coelicolor M145" -
Carbohydrate Research 359 (2012) 70-75
The cell wall of Streptomyces coelicolor M145, a prototrophic plasmidless (SCP1(-) SCP2(-)) variant of strain S. coelicolor A3(2) contains the main glycopolymer represented by Kdn-containing teichulosonic acid with unusual structure which has not been described so far: [structure: see text]. The minor polymer was found to be a poly(diglycosyl 1-phosphate) with the following repeating unit: -6)-α-Galp-(1→6)-α-GlcpNAc-(1-P-. The structures of both glycopolymers were established by using a combination of chemical and NMR spectroscopic methods.
NMR spectroscopy, cell wall, Streptomyces, teichulosonic acid, glycosyl 1-phosphate polymer
NCBI PubMed ID: 22925767Publication DOI: 10.1016/j.carres.2012.05.018Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: G.M. Streshinskaya
Institutions: School of Biology, M. V. Lomonosov Moscow State University, Moscow, Russian Federation, N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospect, 47, Moscow, Russian Federation, All-Russian Collection of Microorganisms (VKM), G. K. Skryabin Institute of Biochemistry and Physiology of Microorganisms, Russian Academy of Sciences, Pushchino, Russia, Ivan Franko National University of Lviv, Department of Genetics and Biotechnology, Lviv 79005, Ukraine
Methods: 13C NMR, 1H NMR, NMR-2D, sugar analysis, 31P NMR, acid hydrolysis, GLC, paper chromatography, NMR-1D, paper electrophoresis
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