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1. Compound ID: 30
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-3)-b-D-Galp-(1-3)-b-D-Galf5Ac6Ac-(1-3)-b-D-Glcp-(1-6)-b-D-Galf2Ac-(1-1)-D-Man-ol-(6-P- |
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Structure type: polymer chemical repeating unit
Compound class: CPS
Contained glycoepitopes: IEDB_114705,IEDB_136044,IEDB_136095,IEDB_137472,IEDB_141794,IEDB_142488,IEDB_146664,IEDB_190606,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: 11
Beynon LM, Richards JC, Perry MB "Identification of the common antigenic determinant shared by Streptococcus pneumoniae serotypes 35A and 20 capsular polysaccharides - Structural analysis of the Streptococcus pneumoniae serotype 35A capsular polysaccharide" -
European Journal of Biochemistry 250(1) (1997) 163-167
The specific polysaccharide antigen of Streptococcus pneumoniae serotype 35A was shown, by a combination of one- and two-dimensional NMR methods and chemical analyses, to be a high-molecular-mass polymer composed of D-galactose, D-glucose, mannitol, and phosphate (3:1:1:1). The pentasaccharide repeating unit is polymerized through phosphate diester linkages to give the structure, [formula in text] O-Acetyl substituents are present at positions 5 and 6 of the 3)-β-D-Galf residue and at position 2 of the 6)-β-D-Galf residue. The capsular polysaccharides of S. pneumoniae serotypes 20 and 35A both contain the disaccharide unit →3)-β-D-Galf-(1→3)-β-D-Glcp-(1→ which is the probable structural determinant responsible for the serological cross reactivity of the two polysaccharides
structure, Streptococcus pneumoniae, antigenic determinant, capsular polysaccharides
NCBI PubMed ID: 9432005Publication DOI: 10.1111/j.1432-1033.1997.00163.xJournal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Institutions: Institute for Biological Sciences, National Research Council of Canada, Ottawa ON
Methods: FAB-MS, GC-MS, GC-EI-MS, NMR, HF solvolysis, de-O-acylation
- Article ID: 4284
Calix JJ, Saad JS, Brady AM, Nahm MH "Structural characterization of Streptococcus pneumoniae serotype 9A capsule polysaccharide reveals role of glycosyl 6-O-acetyltransferase wcjE in serotype 9V capsule biosynthesis and immunogenicity" -
Journal of Biological Chemistry 287(17) (2012) 13996-14003
The putative capsule O-acetyltransferase gene wcjE is highly conserved across various Streptococcus pneumoniae serotypes, but the role of the gene in capsule biosynthesis and bacterial fitness remains largely unclear. Isolates expressing pneumococcal serotype 9A arise from precursors expressing wcjE-associated serotype 9V through loss-of-function mutation to wcjE. To define the biosynthetic role of 9V wcjE, we characterized the structure and serological properties of serotype 9V and 9A capsule polysaccharide (PS). NMR data revealed that both 9V and 9A PS are composed of an identical pentasaccharide repeat unit, as reported previously. However, in sharp contrast to previous studies on 9A PS being devoid of any O-acetylation, we identified O-acetylation of α-glucuronic acid and α-glucose in 9A PS. In addition, 9V PS also contained -CH(2) O-acetylation of β-N-acetylmannosamine, a modification that disappeared following in vitro recombinatorial deletion of wcjE. We also show that serotyping sera and monoclonal antibodies specific for 9V and 9A bound capsule PS in an O-acetate-dependent manner. Furthermore, IgG and to a lesser extent IgM from human donors immunized with serotype 9V PS displayed stronger binding to 9V compared with 9A PS. We conclude that serotype 9V wcjE mediates 6-O-acetylation of β-N-acetylmannosamine. This PS modification can be selectively targeted by antibodies in immunized individuals, identifying a potential selective advantage for wcjE inactivation and serotype 9A emergence.
structure, capsule polysaccharide, capsule biosynthesis, O-acetyltransferase, Streptococcus pneumoniae 9A, wcjE
NCBI PubMed ID: 22367197Publication DOI: 10.1074/jbc.M112.346924Journal NLM ID: 2985121RPublisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
Correspondence: nahm@uab.edu
Institutions: Department of Microbiology, University of Alabama at Birmingham, Birmingham, Alabama 35294, USA
Methods: 13C NMR, 1H NMR, NMR-2D, GC-MS, sugar analysis, ELISA, de-O-acetylation, NMR-1D, serological methods
- Article ID: 4714
Petersen BO, Meier S, Paulsen BS, Redondo AR, Skovsted IC "Determination of native capsular polysaccharide structures of Streptococcus pneumoniae serotypes 39, 42, and 47F and comparison to genetically or serologically related strains" -
Carbohydrate Research 395 (2014) 38-46
The diversity of capsular polysaccharides of the bacterial pathogen Streptococcus pneumoniae leads to at least 91 different serotypes. While the genetic loci for capsular biosynthesis have been characterized for all serotypes, the determination of resultant polysaccharide structures remains incomplete. Here, we report the chemical structures of the capsular polysaccharides of serotypes 39, 42, and 47F from the genetic cluster 4, and discuss the structures in the context of structures from serologically and genetically related serotypes. Antigenic determinants can be approximated in this manner. The structure of the serotype 39 capsular polysaccharide is and has identical composition to the capsular polysaccharide 10A, but two different linkages. The serotype 42 structure closely resembles the genetically related serotype 35A, which does not contain residue A. The structure of the serotype 47F capsular polysaccharide is somewhat different from a recently determined structure from the same serogroup, while containing a structural motif that is reflected in serotype 35A and 42 capsular polysaccharide structures, thus explaining the cross-reactivity of serotype 47F with the typing serum 35a.
Streptococcus pneumoniae, capsular polysaccharide, Serotypes, serotype 47F, serotype 39, serotype 42
NCBI PubMed ID: 25036733Publication DOI: 10.1016/j.carres.2014.06.018Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: B.O. Petersen
; bp@crc.dk
Institutions: Carlsberg Laboratory, Gamle Carlsberg Vej 10, DK-1799 Copenhagen V, Denmark, Novo Nordisk A/S, Novo Nordisk Park, DK-2760 Malov, Denmark, Department of Chemistry, Technical University of Denmark, Kemitorvet, Building 201, DK-2800 Kgs. Lyngby, Denmark, Farmasøytisk institutt, Sem Sælands vei 3, N-0316 Oslo, Norway, Statens Serum Institut, Artillerivej 5, DK-2300 Copenhagen S, Denmark
Methods: 13C NMR, 1H NMR, NMR-2D, 31P NMR, GC, composition analysis, NMR-1D
- Article ID: 4838
Bush CA, Cisar JO, Yang J "Structures of Capsular Polysaccharide Serotypes 35F and 35C of Streptococcus pneumoniae Determined by Nuclear Magnetic Resonance and Their Relation to Other Cross-Reactive Serotypes" -
Journal of Bacteriology 197(17) (2015) 2762-2769
The structures of Streptococcus pneumoniae capsular polysaccharides (CPSs) are essential for defining the antigenic as well as genetic relationships between CPS serotypes. The four serotypes that comprise CPS serogroup 35 (i.e., types 35F, 35A, 35B, and 35C) are known to cross-react with genetically related type 20, 29, 34, 42, or 47F. While the structures of CPS serotype 35A (CPS35A) and CPS35B are known, those of CPS35F and CPS35C are not. In the present study, the serotypes of CPS35F and CPS35C were characterized by high-resolution heteronuclear magnetic resonance (NMR) spectroscopy and glycosyl composition analyses to reveal the following repeat unit structures: [Formula: see text] where OAc indicates O-acetylated. Importantly, CPS35F, the immunizing serotype for the production of group 35 serum, more closely resembles CPS34 and CPS47F than other members of serogroup 35. Moreover, CPS35C is distinct from either CPS35F or CPS35B but closely related to CPS35A and identical to de-O-acetylated CPS42. The findings provide a comprehensive view of the structural and genetic relations that exist between the members of CPS serogroup 35 and other cross-reactive serotypes. IMPORTANCE: Cross-reactions of diagnostic rabbit antisera with Streptococcus pneumoniae capsular polysaccharide serotypes are generally limited to members of the same serogroup. Exceptions do, however, occur, most notably among a group of nonvaccine serotypes that includes the members of serogroup 35 (i.e., types 35F, 35A, 35B, and 35C) and other genetically related types. The presently determined structures of S. pneumoniae serotypes 35F and 35C complete the structural characterization of serogroup 35 and thereby provide the first comprehensive description of how different members of this serogroup are related to each other and to types 29, 34, 42, and 47F. The structural and genetic features of these serotypes suggest the existence of three distinct capsular polysaccharide subgroups that presumably emerged by immune selection in the human host.
NMR, structure, Streptococcus pneumoniae, capsular polysaccharides, serotyping, cross-reaction, receptor
NCBI PubMed ID: 26055112Publication DOI: 10.1128/JB.00207-15Journal NLM ID: 2985120RPublisher: American Society for Microbiology
Correspondence: yangjh@im.ac.cn
Institutions: Department of Chemistry and Biochemistry, University of Maryland Baltimore County, Baltimore, Maryland, USA, Microbial Receptors Section, Laboratory of Cell and Developmental Biology, National Institutes of Health, Bethesda, Maryland, USA, State Key Laboratory of Mycology, Institute of Microbiology, Chinese Academy of Sciences, Beijing, People's Republic of China
Methods: 13C NMR, 1H NMR, NMR-2D, GC-MS, HF solvolysis, de-O-acetylation, composition analysis, NMR-1D, methanolysis, serological methods, genetic methods
- 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: 31
|
-3)-b-D-Galp-(1-3)-b-D-Galf-(1-3)-b-D-Glcp-(1-6)-b-D-Galf-(1-1)-D-Man-ol-(6-P- |
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Structure type: polymer chemical repeating unit
Compound class: CPS
Contained glycoepitopes: IEDB_114705,IEDB_136044,IEDB_136095,IEDB_137472,IEDB_141794,IEDB_142488,IEDB_146664,IEDB_190606,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: 11
Beynon LM, Richards JC, Perry MB "Identification of the common antigenic determinant shared by Streptococcus pneumoniae serotypes 35A and 20 capsular polysaccharides - Structural analysis of the Streptococcus pneumoniae serotype 35A capsular polysaccharide" -
European Journal of Biochemistry 250(1) (1997) 163-167
The specific polysaccharide antigen of Streptococcus pneumoniae serotype 35A was shown, by a combination of one- and two-dimensional NMR methods and chemical analyses, to be a high-molecular-mass polymer composed of D-galactose, D-glucose, mannitol, and phosphate (3:1:1:1). The pentasaccharide repeating unit is polymerized through phosphate diester linkages to give the structure, [formula in text] O-Acetyl substituents are present at positions 5 and 6 of the 3)-β-D-Galf residue and at position 2 of the 6)-β-D-Galf residue. The capsular polysaccharides of S. pneumoniae serotypes 20 and 35A both contain the disaccharide unit →3)-β-D-Galf-(1→3)-β-D-Glcp-(1→ which is the probable structural determinant responsible for the serological cross reactivity of the two polysaccharides
structure, Streptococcus pneumoniae, antigenic determinant, capsular polysaccharides
NCBI PubMed ID: 9432005Publication DOI: 10.1111/j.1432-1033.1997.00163.xJournal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Institutions: Institute for Biological Sciences, National Research Council of Canada, Ottawa ON
Methods: FAB-MS, GC-MS, GC-EI-MS, NMR, HF solvolysis, de-O-acylation
- Article ID: 6388
Ganaie FA, Saad JS, Lo SW, McGee L, Bentley SD, van Tonder AJ, Hawkins PA, Keenan S, Calix JJ, Nahm MH "Discovery and Characterization of Pneumococcal Serogroup 36 Capsule Subtypes, Serotypes 36A and 36B" -
Journal of Clinical Microbiology 61(4) (2023) e0002423
Streptococcus pneumoniae can produce a wide breadth of antigenically diverse capsule types, a fact that poses a looming threat to the success of vaccines that target pneumococcal polysaccharide (PS) capsule. Yet, many pneumococcal capsule types remain undiscovered and/or uncharacterized. Prior sequence analysis of pneumococcal capsule synthesis (cps) loci suggested the existence of capsule subtypes among isolates identified as "serotype 36" according to conventional capsule typing methods. We discovered these subtypes represent two antigenically similar but distinguishable pneumococcal capsule serotypes, 36A and 36B. Biochemical analysis of their capsule PS structure reveals that both have the shared repeat unit backbone [→5)-α-d-Galf-(1→1)-d-Rib-ol-(5→P→6)-β-d-ManpNAc-(1→4)-β-d-Glcp-(1→] with two branching structures. Both serotypes have a β-d-Galp branch to Ribitol. Serotypes 36A and 36B differ by the presence of a α-d-Glcp-(1→3)-β-d-ManpNAc or α-d-Galp-(1→3)-β-d-ManpNAc branch, respectively. Comparison of the phylogenetically distant serogroup 9 and 36 cps loci, which all encode this distinguishing glycosidic bond, revealed that the incorporation of Glcp (in types 9N and 36A) versus Galp (in types 9A, 9V, 9L, and 36B) is associated with the identity of four amino acids in the cps-encoded glycosyltransferase WcjA. Identifying functional determinants of cps-encoded enzymes and their impact on capsule PS structure is key to improving the resolution and reliability of sequencing-based capsule typing methods and discovering novel capsule variants indistinguishable by conventional serotyping methods.
serotype, Streptococcus pneumoniae, capsular polysaccharide, cps locus typing
NCBI PubMed ID: 36971549Publication DOI: 10.1128/jcm.00024-23Journal NLM ID: 7505564Publisher: American Society for Microbiology
Correspondence: M.H. Nahm
Institutions: Department of Microbiology, University of Alabama at Birmingham, Birmingham, Alabama, USA, Respiratory Diseases Branch, Centers for Disease Control and Prevention, Atlanta, Georgia, USA, Department of Veterinary Medicine, University of Cambridge, Cambridge, United Kingdom, Parasites and Microbes, Wellcome Sanger Institute, Hinxton, Cambridge, United Kingdom, Department of Ophthalmology, University of California, San Francisco, California, USA, Department of Medicine, Division of Pulmonary/Allergy/Critical Care, University of Alabama at Birmingham, Birmingham, Alabama, USA, Hubert Department of Global Health, Rollins School of Public Health, Emory University, Atlanta, Georgia, USA
Methods: 13C NMR, 1H NMR, NMR-2D, PCR, GC-MS, ELISA, 31P NMR, composition analysis, serological methods, genetic methods, serotyping analysis, opsonophagocytic assay, genome sequencing
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3. Compound ID: 3081
Structure type: polymer chemical repeating unit
Compound class: teichoic acid
Contained glycoepitopes: IEDB_114705,IEDB_136105,IEDB_225177,IEDB_885823
The structure is contained in the following publication(s):
- Article ID: 1113
Potekhina NV, Shashkov AS, Evtushenko LI, Senchenkova SN, Naumova IB "A mannitol teichoic acid containing rhamnose and pyruvic acid acetal from the cell wall of Brevibacterium permense VKM Ac-2280" -
Carbohydrate Research 338(23) (2003) 2745-2749
The cell wall of Brevibacterium permense VKM Ac-2280 contains two teichoic acids. The major polymer represents a 1,6-poly(mannitol phosphate) substituted wirh either L-rhamnose (approximately 70%, unit A) or (S)-acetal of pyruvic acid (approximately 30%, unit B) with the overall chain length approximately 10 mannitol phosphate units. [carbohydrate structure: see text] The other polymer is an unsubstituted 1,3-poly(glycerol phosphate). The structures of the polymers were established using chemical degradations and NMR spectroscopy. The data obtained may be helpful in determination of the species-specific status of newly isolated Brevibacterium strains
Poly(mannitol phosphate); Pyruvic acid acetal; L-Rhamnose; Brevibacterium
NCBI PubMed ID: 14670732Journal NLM ID: 0043535Publisher: Elsevier
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, School of Biology, M. V. Lomonosov Moscow State University, Moscow, Russian Federation, Institute of Biochemistry and Physiology of Microorganisms, Russian Academy of Sciences, Pushchino, Moscow Region 142292, Russian Federation
Methods: NMR-2D, NMR, chemical degradation
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4. Compound ID: 3082
Structure type: polymer chemical repeating unit
Compound class: teichoic acid
Contained glycoepitopes: IEDB_114705
The structure is contained in the following publication(s):
- Article ID: 1113
Potekhina NV, Shashkov AS, Evtushenko LI, Senchenkova SN, Naumova IB "A mannitol teichoic acid containing rhamnose and pyruvic acid acetal from the cell wall of Brevibacterium permense VKM Ac-2280" -
Carbohydrate Research 338(23) (2003) 2745-2749
The cell wall of Brevibacterium permense VKM Ac-2280 contains two teichoic acids. The major polymer represents a 1,6-poly(mannitol phosphate) substituted wirh either L-rhamnose (approximately 70%, unit A) or (S)-acetal of pyruvic acid (approximately 30%, unit B) with the overall chain length approximately 10 mannitol phosphate units. [carbohydrate structure: see text] The other polymer is an unsubstituted 1,3-poly(glycerol phosphate). The structures of the polymers were established using chemical degradations and NMR spectroscopy. The data obtained may be helpful in determination of the species-specific status of newly isolated Brevibacterium strains
Poly(mannitol phosphate); Pyruvic acid acetal; L-Rhamnose; Brevibacterium
NCBI PubMed ID: 14670732Journal NLM ID: 0043535Publisher: Elsevier
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, School of Biology, M. V. Lomonosov Moscow State University, Moscow, Russian Federation, Institute of Biochemistry and Physiology of Microorganisms, Russian Academy of Sciences, Pushchino, Moscow Region 142292, Russian Federation
Methods: NMR-2D, NMR, chemical degradation
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5. Compound ID: 3083
Structure type: polymer chemical repeating unit
Compound class: teichoic acid
Contained glycoepitopes: IEDB_114705
The structure is contained in the following publication(s):
- Article ID: 1114
Potekhina NV, Shashkov AS, Evtushenko LI, Gavrish EY, Senchenkova SN, Stomakhin AA, Usov AI, Naumova IB, Stackebrandt E "A novel mannitol teichoic acid with side phosphate groups of Brevibacterium sp. VKM Ac-2118" -
European Journal of Biochemistry 270(22) (2003) 4420-4425
The cell wall of Brevibacterium sp. VKM Ac-2118 isolated from a frozen (mean annual temperature -12 degrees C) late Pliocene layer, 1.8-3 Myr, Kolyma lowland, Russia, contains mannitol teichoic acid with a previously unknown structure. This is 1,6-poly(mannitol phosphate) with the majority of the mannitol residues bearing side phosphate groups at O-4(3). The structure of the polymer was established by chemical methods, NMR spectroscopy, and MALDI-TOF mass spectrometry
NMR, structure, chemistry, cell, group, molecular, polymer, degree, acid, phosphate, NMR spectroscopy, spectrometry, cell wall, chemical, region, mass spectrometry, biochemistry, spectroscopy, method, MALDI-TOF, biology, methods, teichoic acid, organic, physiology, temperature, layer, Brevibacterium, mannitol, molecular biology
NCBI PubMed ID: 14622270Journal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Correspondence: potekchina@hotbox.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, Russia, School of Biology, M. V. Lomonosov Moscow State University, Russia, B. A. Engelhardt Institute of Molecular Biology, Russian Academy of Science, Moscow, Russia, DSMZ-Deutsche Sammlung von Mikroorganismen und Zellkulturen GmbH, Braunschweig, Germany
Methods: NMR, chemical methods, MALDI-TOF MS
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6. Compound ID: 3286
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a-Sugp5Ac-(2-3)-D-Man-ol
Sug = 5-amino-3,5-dideoxy-a-lyxo-nonulopyranosonic (rhodaminic) acid = SMILES O{8}C({7}C([C@@H]1O{2}[C@](C(O)=O)(C{4}[C@@H]({5}[C@@H]1N)O)O)O){9}CO |
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Structure type: oligomer
Contained glycoepitopes: IEDB_114705
The structure is contained in the following publication(s):
- Article ID: 1207
Severn WB, Richards JC "The structure of the specific capsular polysaccharide of Rhodococcus equi serotype 4" -
Carbohydrate Research 320(3-4) (1999) 209-222
The specific capsular polysaccharide produced by Rhodococcus equi serotype 4 was found to be a high-molecular-weight acidic polymer composed of D-glucose, D-mannose, pyruvic acid and a previously unidentified 5-amino-3,5-dideoxynonulosonic (rhodaminic) acid in the proportions 2:1:1:1. Structural analysis, employing a combination of microanalytical methods, nuclear magnetic resonance spectroscopy, and mass spectrometric techniques, established that the polysaccharide consisted of linear repeating tetrasaccharide units having the sequence of residues shown below. In the native polysaccharide, the rhodaminic acid residues were present as their acetamido derivatives (RhoANAc) and carried 1-carboxyethylidene groups that bridged the O-7 and O-9 positions. Treatment of the capsular polysaccharide with dilute acetic acid and/or anhydrous hydrogen fluoride under hydrolytic/solvolytic conditions, resulted in the formation of four different oligosaccharide species. The 1H and 13C NMR resonances of these oligosaccharide fragments and of the native serotype 4 capsular polysaccharides were fully assigned by homo- and heteronuclear chemical shift correlation methods.
structure, capsular polysaccharide, NMR spectroscopy, Rhodococcus equi, Rhodococcus, 5-Amino-3, 5-dideoxynonulosonic acid, Rhodaminic acid
NCBI PubMed ID: 10573859Publication DOI: 10.1016/s0008-6215(99)00138-xJournal NLM ID: 0043535Publisher: Elsevier
Correspondence: severnw@agresearch.cri.nz
Institutions: AgResearch,Wallaceville Animal Research, Centre Hutt, New Zealand
Methods: NMR
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7. Compound ID: 3287
|
Pyr-(2-9:2-7)-a-Sugp-(2-3)-D-Man-ol
Sug = 5-amino-3,5-dideoxy-a-lyxo-nonulopyranosonic (rhodaminic) acid = SMILES O{8}C({7}C([C@@H]1O{2}[C@](C(O)=O)(C{4}[C@@H]({5}[C@@H]1N)O)O)O){9}CO |
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Structure type: oligomer
Contained glycoepitopes: IEDB_114705
The structure is contained in the following publication(s):
- Article ID: 1207
Severn WB, Richards JC "The structure of the specific capsular polysaccharide of Rhodococcus equi serotype 4" -
Carbohydrate Research 320(3-4) (1999) 209-222
The specific capsular polysaccharide produced by Rhodococcus equi serotype 4 was found to be a high-molecular-weight acidic polymer composed of D-glucose, D-mannose, pyruvic acid and a previously unidentified 5-amino-3,5-dideoxynonulosonic (rhodaminic) acid in the proportions 2:1:1:1. Structural analysis, employing a combination of microanalytical methods, nuclear magnetic resonance spectroscopy, and mass spectrometric techniques, established that the polysaccharide consisted of linear repeating tetrasaccharide units having the sequence of residues shown below. In the native polysaccharide, the rhodaminic acid residues were present as their acetamido derivatives (RhoANAc) and carried 1-carboxyethylidene groups that bridged the O-7 and O-9 positions. Treatment of the capsular polysaccharide with dilute acetic acid and/or anhydrous hydrogen fluoride under hydrolytic/solvolytic conditions, resulted in the formation of four different oligosaccharide species. The 1H and 13C NMR resonances of these oligosaccharide fragments and of the native serotype 4 capsular polysaccharides were fully assigned by homo- and heteronuclear chemical shift correlation methods.
structure, capsular polysaccharide, NMR spectroscopy, Rhodococcus equi, Rhodococcus, 5-Amino-3, 5-dideoxynonulosonic acid, Rhodaminic acid
NCBI PubMed ID: 10573859Publication DOI: 10.1016/s0008-6215(99)00138-xJournal NLM ID: 0043535Publisher: Elsevier
Correspondence: severnw@agresearch.cri.nz
Institutions: AgResearch,Wallaceville Animal Research, Centre Hutt, New Zealand
Methods: NMR
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8. Compound ID: 5459
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a-D-GlcpA-(1-3)-+
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S-Pyr-(2-4:2-3)-b-D-Galp-(1-6)-b-D-Manp-(1-4)-D-Man-ol
|
b-D-Glcp-(1-4)-+ |
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Structure type: oligomer
Compound class: CPS
Contained glycoepitopes: IEDB_114705,IEDB_115136,IEDB_136044,IEDB_137472,IEDB_137485,IEDB_140630,IEDB_141794,IEDB_142488,IEDB_144983,IEDB_146664,IEDB_152206,IEDB_190606,IEDB_983930,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_44,SB_7,SB_72,SB_88
The structure is contained in the following publication(s):
- Article ID: 2296
Ravenscroft N, Parolis LAS, Parolis H "Bacteriophage degradation of Klebsiella K30 capsular polysaccharide. An NMR investigation of the 3,4-pyruvated galactose-containing repeating oligosaccharide" -
Carbohydrate Research 254 (1994) 333-340
Journal NLM ID: 0043535Publisher: Elsevier
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9. Compound ID: 7777
Structure type: oligomer
Trivial name: tetrasaccharide-alditol
Contained glycoepitopes: IEDB_114705,IEDB_115136,IEDB_130701,IEDB_140630,IEDB_142488,IEDB_144983,IEDB_144998,IEDB_146664,IEDB_152206,IEDB_423153,IEDB_983930,IEDB_983931,SB_192,SB_44,SB_67,SB_72
The structure is contained in the following publication(s):
- Article ID: 3462
Dobruchowska JM, Gerwig GJ, Babuchowski A, Kamerling JP "Structural studies on exopolysaccharides produced by three different propionibacteria strains" -
Carbohydrate Research 343(4) (2008) 726-745
The exopolysaccharides produced by three propionibacteria strains, Propionibacterium freudenreichii 109, Propionibacterium freudenreichii 111, and Propionibacterium thoenii 126, grown on whey-based media, were found to be charged heteropolymers, composed of d-glucose, d-mannose, and d-glucuronic acid in molar ratios of 2:2:1. By means of methylation analysis, mass spectrometry, partial acid hydrolysis, and 1D/2D NMR ((1)H and (13)C) studies, it was determined that all three exopolysaccharides contain the same branched, pentasaccharide repeating unit:
NMR, exopolysaccharide, structural analysis, EPS, MS, Propionibacterium
NCBI PubMed ID: 18184608Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: j.p.kamerling@uu.nl
Institutions: Bijvoet Center, Department of Bio-Organic Chemistry, Utrecht University, Utrecht, The Netherlands, Chair of Food Biotechnology, University of Warmia and Mazury, Heweliusza 1, 10-957 Olsztyn, Poland
Methods: 13C NMR, 1H NMR, methylation, NMR-2D, GLC-EI-MS, partial acid hydrolysis, sugar analysis, GLC, MALDI-TOF MS
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10. Compound ID: 9828
Structure type: oligomer
Contained glycoepitopes: IEDB_114705,IEDB_130701,IEDB_136104,IEDB_140116,IEDB_141111,IEDB_143632,IEDB_144983,IEDB_152206,IEDB_164174,IEDB_164176,IEDB_983930,SB_136,SB_196,SB_197,SB_44,SB_67,SB_72
The structure is contained in the following publication(s):
- Article ID: 4106
Sandal I, Inzana TJ, Molinaro A, De Castro C, Shao JQ, Apicella MA, Cox AD, St Michael F, Berg G "Identification, structure, and characterization of an exopolysaccharide produced by Histophilus somni during biofilm formation" -
BMC Microbiology 11(1) (2011) 186
ABSTRACT: BACKGROUND: Histophilus somni, a gram-negative coccobacillus, is an obligate inhabitant of bovine and ovine mucosal surfaces, and an opportunistic pathogen responsible for respiratory disease and other systemic infections in cattle and sheep. Capsules are important virulence factors for many pathogenic bacteria, but a capsule has not been identified on H. somni. However, H. somni does form a biofilm in vitro and in vivo, and the biofilm matrix of most bacteria consists of a polysaccharide. RESULTS: Following incubation of H. somni under growth-restricting stress conditions, such as during anaerobiosis, stationary phase, or in hypertonic salt, a polysaccharide could be isolated from washed cells or culture supernatant. The polysaccharide was present in large amounts in broth culture sediment after H. somni was grown under low oxygen tension for 4-5 days (conditions favorable to biofilm formation), but not from planktonic cells during log phase growth. Immuno-transmission electron microscopy showed that the polysaccharide was not closely associated with the cell surface, and was of heterogeneous high molecular size by gel electrophoresis, indicating it was an exopolysaccharide (EPS). The EPS was a branched mannose polymer containing some galactose, as determined by structural analysis. The mannose-specific Moringa M lectin and antibodies to the EPS bound to the biofilm matrix, demonstrating that the EPS was a component of the biofilm. The addition of N-acetylneuraminic acid to the growth medium resulted in sialylation of the EPS, and increased biofilm formation. Real-time quantitative reverse transcription-polymerase chain reaction analyses indicated that genes previously identified in a putative polysaccharide locus were upregulated when the bacteria were grown under conditions favorable to a biofilm, compared to planktonic cells. CONCLUSIONS: H. somni is capable of producing a branching, mannose-galactose EPS polymer under growth conditions favorable to the biofilm phase of growth, and the EPS is a component of the biofilm matrix. The EPS can be sialylated in strains with sialyltransferase activity, resulting in enhanced density of the biofilm, and suggesting that EPS and biofilm formation may be important to persistence in the bovine host. The EPS may be critical to virulence if the biofilm state is required for H. somni to persist in systemic sites.
exopolysaccharide, virulence factor, Biofilm, coccobacillus, Histophilus somni
NCBI PubMed ID: 21854629Publication DOI: 10.1186/1471-2180-11-186Journal NLM ID: 100966981Publisher: Biomed Central
Correspondence: tinzana@vt.edu
Institutions: Center for Molecular Medicine and Infectious Diseases, Virginia-Maryland Regional College of Veterinary Medicine, Virginia Tech, Blacksburg, Virginia, USA.
Methods: 13C NMR, 1H NMR, GLC-MS, NMR-2D, PCR, de-O-acylation, sugar analysis, enzymatic hydrolysis, ESI-MS, GLC, NMR-1D, serological methods, PAGE, acetolysis, immuno-transmission electron microscopy
- Article ID: 6610
Kobayashi H, Shibata N, Watanabe M, Komido M, Hashimoto N, Hisamichi K, Suzuki S "Mild acetolysis and NMR studies of the D-mannan of Saccharomyces cerevisiae X2180-1A wild-type strain" -
Carbohydrate Research 231 (1992) 317-323
NCBI PubMed ID: 1394323Journal NLM ID: 0043535Publisher: Elsevier
Institutions: Second Department of Hygienic Chemistry, Tohoku College of Pharmacy, Miyagi, Japan
Methods: 13C NMR, 1H NMR, gel filtration, methylation analysis, mild acetolysis
- Article ID: 7844
Takahashi S, Kudoh A, Okawa Y, Shibata N "Significant differences in the cell-wall mannans from three Candida glabrata strains correlate with antifungal drug sensitivity" -
FEBS Journal 279(10) (2012) 1844-1856
Candida glabrata is often the second or third most common cause of candidiasis after Candida albicans. C. glabrata infections are difficult to treat, often resistant to many azole antifungal agents and are associated with a high mortality rate in compromised patients. We determined the antigenic structure of the cell-wall mannoproteins from three C. glabrata strains, NBRC 0005, NBRC 0622 and NBRC 103857. 1H NMR and methylation analyses of the acetolysis products of these mannoproteins showed a significant difference in the amount of the β-1,2-linked mannose residue and side-chain structure. The C. glabrata NBRC 103857 strain contained up to the triose side chains and the nonreducing terminal of the triose was predominantly the β-1,2-linked mannose residue. By contrast, the mannans of the two former strains possessed up to the tetraose side chains and the amount of the β-1,2-linked mannose residue was very low. Larger oligosaccharides than tetraose in the acetolysis products of these mannans were identified as incomplete cleavage fragments by analyzing methylation, 1H NMR spectra and the α1-2,3 mannosidase degradation reaction. Resistance to the antifungal drugs itraconazole and micafungin was significantly different in these strains. Interestingly, the NBRC 103857 strain, which involved a large amount of the β-1,2-linked mannose residues, exhibited significant sensitivity to these antifungal drugs.
oligosaccharide, polysaccharide, NMR spectroscopy, azole resistance, cell-wall mannan
NCBI PubMed ID: 22404982Publication DOI: 10.1111/j.1742-4658.2012.08564.xJournal NLM ID: 101229646Publisher: Blackwell Publishing
Correspondence: nshibata@tohoku-pharm.ac.jp
Institutions: Department of Infection and Host Defense, Tohoku Pharmaceutical University, Sendai, Japan
Methods: 1H NMR, methylation, GC-MS, acid hydrolysis, biological assays, enzymatic digestion, extraction, acetylation, acetolysis, reduction, cell growth, DQF-COSY
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11. Compound ID: 9829
Structure type: oligomer
Contained glycoepitopes: IEDB_114705,IEDB_130701,IEDB_136044,IEDB_136104,IEDB_137472,IEDB_141794,IEDB_143632,IEDB_144983,IEDB_152206,IEDB_190606,IEDB_983930,SB_136,SB_165,SB_166,SB_187,SB_195,SB_196,SB_44,SB_67,SB_7,SB_72,SB_88
The structure is contained in the following publication(s):
- Article ID: 4106
Sandal I, Inzana TJ, Molinaro A, De Castro C, Shao JQ, Apicella MA, Cox AD, St Michael F, Berg G "Identification, structure, and characterization of an exopolysaccharide produced by Histophilus somni during biofilm formation" -
BMC Microbiology 11(1) (2011) 186
ABSTRACT: BACKGROUND: Histophilus somni, a gram-negative coccobacillus, is an obligate inhabitant of bovine and ovine mucosal surfaces, and an opportunistic pathogen responsible for respiratory disease and other systemic infections in cattle and sheep. Capsules are important virulence factors for many pathogenic bacteria, but a capsule has not been identified on H. somni. However, H. somni does form a biofilm in vitro and in vivo, and the biofilm matrix of most bacteria consists of a polysaccharide. RESULTS: Following incubation of H. somni under growth-restricting stress conditions, such as during anaerobiosis, stationary phase, or in hypertonic salt, a polysaccharide could be isolated from washed cells or culture supernatant. The polysaccharide was present in large amounts in broth culture sediment after H. somni was grown under low oxygen tension for 4-5 days (conditions favorable to biofilm formation), but not from planktonic cells during log phase growth. Immuno-transmission electron microscopy showed that the polysaccharide was not closely associated with the cell surface, and was of heterogeneous high molecular size by gel electrophoresis, indicating it was an exopolysaccharide (EPS). The EPS was a branched mannose polymer containing some galactose, as determined by structural analysis. The mannose-specific Moringa M lectin and antibodies to the EPS bound to the biofilm matrix, demonstrating that the EPS was a component of the biofilm. The addition of N-acetylneuraminic acid to the growth medium resulted in sialylation of the EPS, and increased biofilm formation. Real-time quantitative reverse transcription-polymerase chain reaction analyses indicated that genes previously identified in a putative polysaccharide locus were upregulated when the bacteria were grown under conditions favorable to a biofilm, compared to planktonic cells. CONCLUSIONS: H. somni is capable of producing a branching, mannose-galactose EPS polymer under growth conditions favorable to the biofilm phase of growth, and the EPS is a component of the biofilm matrix. The EPS can be sialylated in strains with sialyltransferase activity, resulting in enhanced density of the biofilm, and suggesting that EPS and biofilm formation may be important to persistence in the bovine host. The EPS may be critical to virulence if the biofilm state is required for H. somni to persist in systemic sites.
exopolysaccharide, virulence factor, Biofilm, coccobacillus, Histophilus somni
NCBI PubMed ID: 21854629Publication DOI: 10.1186/1471-2180-11-186Journal NLM ID: 100966981Publisher: Biomed Central
Correspondence: tinzana@vt.edu
Institutions: Center for Molecular Medicine and Infectious Diseases, Virginia-Maryland Regional College of Veterinary Medicine, Virginia Tech, Blacksburg, Virginia, USA.
Methods: 13C NMR, 1H NMR, GLC-MS, NMR-2D, PCR, de-O-acylation, sugar analysis, enzymatic hydrolysis, ESI-MS, GLC, NMR-1D, serological methods, PAGE, acetolysis, immuno-transmission electron microscopy
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12. Compound ID: 9830
Structure type: oligomer
Contained glycoepitopes: IEDB_114705,IEDB_130701,IEDB_136104,IEDB_143632,IEDB_144983,IEDB_152206,IEDB_983930,SB_136,SB_196,SB_44,SB_67,SB_72
The structure is contained in the following publication(s):
- Article ID: 4106
Sandal I, Inzana TJ, Molinaro A, De Castro C, Shao JQ, Apicella MA, Cox AD, St Michael F, Berg G "Identification, structure, and characterization of an exopolysaccharide produced by Histophilus somni during biofilm formation" -
BMC Microbiology 11(1) (2011) 186
ABSTRACT: BACKGROUND: Histophilus somni, a gram-negative coccobacillus, is an obligate inhabitant of bovine and ovine mucosal surfaces, and an opportunistic pathogen responsible for respiratory disease and other systemic infections in cattle and sheep. Capsules are important virulence factors for many pathogenic bacteria, but a capsule has not been identified on H. somni. However, H. somni does form a biofilm in vitro and in vivo, and the biofilm matrix of most bacteria consists of a polysaccharide. RESULTS: Following incubation of H. somni under growth-restricting stress conditions, such as during anaerobiosis, stationary phase, or in hypertonic salt, a polysaccharide could be isolated from washed cells or culture supernatant. The polysaccharide was present in large amounts in broth culture sediment after H. somni was grown under low oxygen tension for 4-5 days (conditions favorable to biofilm formation), but not from planktonic cells during log phase growth. Immuno-transmission electron microscopy showed that the polysaccharide was not closely associated with the cell surface, and was of heterogeneous high molecular size by gel electrophoresis, indicating it was an exopolysaccharide (EPS). The EPS was a branched mannose polymer containing some galactose, as determined by structural analysis. The mannose-specific Moringa M lectin and antibodies to the EPS bound to the biofilm matrix, demonstrating that the EPS was a component of the biofilm. The addition of N-acetylneuraminic acid to the growth medium resulted in sialylation of the EPS, and increased biofilm formation. Real-time quantitative reverse transcription-polymerase chain reaction analyses indicated that genes previously identified in a putative polysaccharide locus were upregulated when the bacteria were grown under conditions favorable to a biofilm, compared to planktonic cells. CONCLUSIONS: H. somni is capable of producing a branching, mannose-galactose EPS polymer under growth conditions favorable to the biofilm phase of growth, and the EPS is a component of the biofilm matrix. The EPS can be sialylated in strains with sialyltransferase activity, resulting in enhanced density of the biofilm, and suggesting that EPS and biofilm formation may be important to persistence in the bovine host. The EPS may be critical to virulence if the biofilm state is required for H. somni to persist in systemic sites.
exopolysaccharide, virulence factor, Biofilm, coccobacillus, Histophilus somni
NCBI PubMed ID: 21854629Publication DOI: 10.1186/1471-2180-11-186Journal NLM ID: 100966981Publisher: Biomed Central
Correspondence: tinzana@vt.edu
Institutions: Center for Molecular Medicine and Infectious Diseases, Virginia-Maryland Regional College of Veterinary Medicine, Virginia Tech, Blacksburg, Virginia, USA.
Methods: 13C NMR, 1H NMR, GLC-MS, NMR-2D, PCR, de-O-acylation, sugar analysis, enzymatic hydrolysis, ESI-MS, GLC, NMR-1D, serological methods, PAGE, acetolysis, immuno-transmission electron microscopy
- Article ID: 7571
Munro CA, Bates S, Buurman ET, Hughes HB, MacCallum DM, Bertram G, Atrih A, Ferguson MA, Bain JM, Brand A, Hamilton S, Westwater C, Thomson LM, Brown AJ, Odds FC, Gow NA "Mnt1p and Mnt2p of Candida albicans are partially redundant α-1,2-mannosyltransferases that participate in O-linked mannosylation and are required for adhesion and virulence" -
Journal of Biological Chemistry 280(2) (2005) 1051-1060
The MNT1 gene of the human fungal pathogen Candida albicans is involved in O-glycosylation of cell wall and secreted proteins and is important for adherence of C. albicans to host surfaces and for virulence. Here we describe the molecular analysis of CaMNT2, a second member of the MNT1-like gene family in C. albicans. Mnt2p also functions in O-glycosylation. Mnt1p and Mnt2p encode partially redundant α-1,2-mannosyltransferases that catalyze the addition of the second and third mannose residues in an O-linked man no se pentamer. Deletion of both copies of MNT1 and MNT2 resulted in reduction in the level of in vitro mannosyltransferase activity and truncation of O-mannan. Both the mnt2Δ and mnt1Δ single mutants were significantly reduced in adherence to human buccal epithelial cells and Matrigel-coated surfaces, indicating a role for O-glycosylated cell wall proteins or O-mannan itself in adhesion to host surfaces. The double mnt1Δmnt2Δ mutant formed aggregates of cells that appeared to be the result of abnormal cell separation. The double mutant was attenuated in virulence, underlining the importance of O-glycosylation in pathogenesis of C. albicans infections.
Candida albicans, α-1, fungal pathogen, gene deletion, 2-mannosyltransferase
NCBI PubMed ID: 15519997Publication DOI: 10.1074/jbc.M411413200Journal NLM ID: 2985121RPublisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
Correspondence: n.gow@abdn.ac.uk
Institutions: School of Medical Sciences, Institute of Medical Sciences, University of Aberdeen, Aberdeen, UK, School of Life Sciences, Wellcome Trust Building, University of Dundee, Dundee, UK, AstraZeneca R and D Boston, Waltham, MA, USA, Molecular and Cellular Biology Building, University of Minnesota, Minneapolis, USA, Division of Medical Mycology, Department of Microbiology and Immunology, Medical University of South Carolina, Charleston, USA, Department of Medical Microbiology, Polwarth Building, University of Aberdeen, Aberdeen, UK
Methods: methylation, DNA sequencing, GC-MS, TLC, HPAEC, biological assays, radiolabeling, enzymatic digestion, HPAEC-PAD, extraction, cloning, ESI-QTOF-MS, cell growth, enzymatic assay, reductive beta-elimination, TEM, beta-elimination
- Article ID: 7844
Takahashi S, Kudoh A, Okawa Y, Shibata N "Significant differences in the cell-wall mannans from three Candida glabrata strains correlate with antifungal drug sensitivity" -
FEBS Journal 279(10) (2012) 1844-1856
Candida glabrata is often the second or third most common cause of candidiasis after Candida albicans. C. glabrata infections are difficult to treat, often resistant to many azole antifungal agents and are associated with a high mortality rate in compromised patients. We determined the antigenic structure of the cell-wall mannoproteins from three C. glabrata strains, NBRC 0005, NBRC 0622 and NBRC 103857. 1H NMR and methylation analyses of the acetolysis products of these mannoproteins showed a significant difference in the amount of the β-1,2-linked mannose residue and side-chain structure. The C. glabrata NBRC 103857 strain contained up to the triose side chains and the nonreducing terminal of the triose was predominantly the β-1,2-linked mannose residue. By contrast, the mannans of the two former strains possessed up to the tetraose side chains and the amount of the β-1,2-linked mannose residue was very low. Larger oligosaccharides than tetraose in the acetolysis products of these mannans were identified as incomplete cleavage fragments by analyzing methylation, 1H NMR spectra and the α1-2,3 mannosidase degradation reaction. Resistance to the antifungal drugs itraconazole and micafungin was significantly different in these strains. Interestingly, the NBRC 103857 strain, which involved a large amount of the β-1,2-linked mannose residues, exhibited significant sensitivity to these antifungal drugs.
oligosaccharide, polysaccharide, NMR spectroscopy, azole resistance, cell-wall mannan
NCBI PubMed ID: 22404982Publication DOI: 10.1111/j.1742-4658.2012.08564.xJournal NLM ID: 101229646Publisher: Blackwell Publishing
Correspondence: nshibata@tohoku-pharm.ac.jp
Institutions: Department of Infection and Host Defense, Tohoku Pharmaceutical University, Sendai, Japan
Methods: 1H NMR, methylation, GC-MS, acid hydrolysis, biological assays, enzymatic digestion, extraction, acetylation, acetolysis, reduction, cell growth, DQF-COSY
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13. Compound ID: 9974
|
a-D-Manp3Me-(1-3)-b-D-Manp-(1-2)-a-D-Manp-(1-2)-a-D-Manp-(1-3)-b-D-Manp-(1-2)-a-D-Manp-(1-2)-D-Man-ol |
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Structure type: oligomer
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_114705,IEDB_130701,IEDB_136104,IEDB_137485,IEDB_140116,IEDB_142357,IEDB_143632,IEDB_144983,IEDB_144995,IEDB_152206,IEDB_164479,IEDB_2278480,IEDB_983930,SB_136,SB_196,SB_197,SB_44,SB_67,SB_72
The structure is contained in the following publication(s):
- Article ID: 2952
Jansson PE, Lönngren J, Widmalm G, Leontein K, Slettengren K, Svenson SB, Wrangsell G, Dell A, Tiller PR "Structural studies of the O-antigen polysaccharides of Klebsiella O5 and Escherichia coli O8" -
Carbohydrate Research 145 (1985) 59-66
The O-antigen polysaccharides of Klebsiella serotype O5 and Escherichia coli serotype O8 are serologically very similar or identical. The structures of these two polysaccharides have now been re-investigated. N.m.r. spectroscopy, chromium trioxide oxidation, hydrolysis with a specific phage enzyme, and f.a.b. mass spectrometry were the principal methods used. It is concluded that the O-antigen has the following structure, in which D-Man3Me is 3-O-methyl-D-mannose and n is approximately 10. (Formula: see text) Biosynthetic studies indicate that these antigens are synthesised by addition of D-mannopyranosyl groups to the "non-reducing" end of the mannan chain, and it seems possible that addition of a 3-O-methyl-D-mannopyranosyl group involves termination.
NCBI PubMed ID: 3912042Publication DOI: 10.1016/S0008-6215(00)90412-9Journal NLM ID: 0043535Publisher: Elsevier
Institutions: Department of Organic Chemistry, Arrhenius Laboratory, University of Stockholm, Stockholm, Sweden, Department of Biochemistry, Imperial College of Science and Technology, London, Great Britain)
Methods: 13C NMR, 1H NMR, methylation, FAB-MS
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14. Compound ID: 10858
Structure type: monomer
Trivial name: CDP-D-mannitol
Contained glycoepitopes: IEDB_114705,IEDB_141494
The structure is contained in the following publication(s):
- Article ID: 4415
Wang Q, Xu Y, Perepelov AV, Knirel YA, Reeves PR, Shashkov AS, Ding P, Guo X, Feng L "Characterization of the CDP-D-mannitol biosynthetic pathway in Streptococcus pneumoniae 35A" -
Glycobiology 22(12) (2012) 1760-1767
Streptococcus pneumoniae is a major human pathogen associated with diseases worldwide. The capsular polysaccharides (CPSs) are considered a major virulence factor and are targets for a vaccine. d-Mannitol was found to be present in the CPS of several S. pneumoniae serotypes. Two genes, mnp1 and mnp2, which are located in the CPS gene cluster, were proposed to be responsible for the synthesis of NDP-d-mannitol (the nucleotide activated form of d-mannitol). However, the pathway has never been identified by experimental methods and we aimed to characterize it in the present study. To achieve this, the two genes, mnp1 and mnp2, were cloned and the gene products were overexpressed, purified, and analyzed in vitro for their respective enzymatic activities. Products of reactions catalyzed by Mnp1 and Mnp2 were detected by capillary electrophoresis and validated using electrospray ionization mass spectrometry and nuclear magnetic resonance spectroscopy. We show that Mnp1 is responsible for the transfer of CMP from CTP to d-fructose-6-phosphate (Fru-6-P) to form CDP-d-fructose, whereas Mnp2 catalyzed the conversion of CDP-d-fructose to CDP-d-mannitol. Therefore, Mnp1 (renamed as mnpA) was identified as Fru-6-P cytidylyltransferase-encoding gene, and mnp2 (renamed as mnpB) as a CDP-d-fructose reductase-encoding gene. The kinetics of Mnp1 for the substrate (Fru-6-P and CTP) and of Mnp2 for the substrate (CDP-d-fructose) and the cofactor NADH or NADPH fitted the Michaelis-Menten model. The effects of temperature, pH and cations on the two enzymes were analyzed. This is the first time that the biosynthetic pathway of CDP-d-mannitol has been identified biochemically.
CDP-D-mannitol, cytidyltransferase, eductase
NCBI PubMed ID: 22833313Publication DOI: 10.1093/glycob/cws113Journal NLM ID: 9104124Publisher: IRL Press at Oxford University Press
Correspondence: fenglu63@nankai.edu.cn
Institutions: N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, TEDA School of Biological Sciences and Biotechnology, Nankai University, Tianjin, China, School of Molecular and Microbial Biosciences (G08), University of Sydney, Sydney, NSW 2006, Australia
Methods: 13C NMR, 1H NMR, NMR-2D, HF solvolysis, sugar analysis, 31P NMR, ESI-MS, GLC, genetic methods, enzymatic analysis, RP-HPLC, CE
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15. Compound ID: 11030
Structure type: polymer chemical repeating unit
Compound class: teichoic acid
Contained glycoepitopes: IEDB_114705
The structure is contained in the following publication(s):
- Article ID: 4456
Potekhina NV, Evtushenko LI, Senchenkova SN, Shashkov AS, Naumova IB "Structures of cell wall teichoic acids of Brevibacterium iodinum VKM Ac-2106T" -
Biochemistry (Moscow) 69(12) (2004) 1353-1359
The structures of two cell wall teichoic acids of Brevibacterium iodinum VKM Ac-2106(T) were studied. The structure of mannitol teichoic acid described earlier was mainly confirmed. This polymer is 1,6-poly(mannitol phosphate) bearing β-D-glucopyranosyl residues at the C-2 of mannitol and pyruvic acid residues at the C-4 and C-5. The absolute configurations of D-mannitol and S-pyruvic acid were found. The following distinctions from the earlier described structure were found: unsubstituted 1,6-poly(mannitol phosphate) residues and residues substituted only by β-D-glucopyranosyl at the C-2 of mannitol but unsubstituted by pyruvic acid are present in the chain. The structure of glycerol teichoic acid present in the cell wall as a minor component (~7%) is also described. This acid is identified as 1,3-poly(glycerol phosphate) substituted at the C-2 of glycerol by 2-acetamido-2-deoxy-α-D-galactopyranosyl residues bearing R-pyruvic acid residues at the C-4 and C-6 of galactose. This polymer is for the first time described in the cell wall of Gram-positive bacteria.
teichoic acids, Brevibacterium, poly(glycerol phosphate), Pyruvic acid acetal, NMR-spectroscopy, poly(mannitol phosphate)
NCBI PubMed ID: 15627390Journal NLM ID: 0376536Publisher: Nauka/Interperiodica
Correspondence: potekchina@hotbox.ru
Institutions: Faculty of Biology, Lomonosov Moscow State University, Moscow, Russia
Methods: 13C NMR, 1H NMR, HF solvolysis, sugar analysis, acid hydrolysis, paper chromatography, paper electrophoresis, 32P NMR
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