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Structural studies of the capsular polysaccharide produced by Leuconostoc mesenteroides ssp. cremoris PIA2
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry.
2011 (English)In: Biomacromolecules, ISSN 1525-7797, E-ISSN 1526-4602, Vol. 12, no 7, 2496-2501 p.Article in journal (Refereed) Published
Abstract [en]

The structure of the capsular polysaccharide (CPS) produced by Leuconostoc mesenteroides ssp. cremoris PIA2 has been determined using component analysis and NMR spectroscopy. 1H and 13C resonances were assigned using 2D NMR experiments, and sequential information was obtained by 1H,1H-NOESY and 1H,13C-HMBC experiments. The CPS consists of linear pentasaccharide repeating units with the following structure: →3)-β-d-Galf-(1→6)-β-d-Galf-(1→2)-β-d-Galf-(1→6)-β-d-Galf-(1→3)-β-d-Galp-(1→, in which four out of the five sugar residues have the furanoid ring form, a structural entity found in bacteria but not in mammals. The analysis of the magnitude of the homonuclear three-bond coupling constants of the anomeric protons for the five-membered sugar rings indicates that the sugar residues substituted at a primary carbon atom show one kind of conformational preferences, whereas those substituted at a secondary carbon atom show another kind of conformational preferences.

Place, publisher, year, edition, pages
2011. Vol. 12, no 7, 2496-2501 p.
National Category
Organic Chemistry
Research subject
Organic Chemistry
Identifiers
URN: urn:nbn:se:su:diva-59717DOI: 10.1021/bm200177zISI: 000292617700009OAI: oai:DiVA.org:su-59717DiVA: diva2:429994
Funder
Swedish Research CouncilKnut and Alice Wallenberg Foundation
Available from: 2011-07-06 Created: 2011-07-06 Last updated: 2017-12-11Bibliographically approved
In thesis
1. Structural and Conformational Studies of Oligo- and Polysaccharides
Open this publication in new window or tab >>Structural and Conformational Studies of Oligo- and Polysaccharides
2012 (English)Doctoral thesis, comprehensive summary (Other academic)
Abstract [en]

The focus of this thesis is to examine the structural properties of polysaccharides produced by bacteria, as well as the dynamic and conformational behavior of a synthetically derived oligosaccharide.

The primary structures of the O-polysaccharide repeating units of four different Escherichia coli (E. coli) strains, namely O175, O177, O103 and TD2158, as well as the first report of a capsular polysaccharide produced by lactic acid bacteria Leuconostoc mesenteroides ssp. cremoris PIA2 are reported in paper I–V. Structural analyses have been performed using a combination of nuclear magnetic resonance spectroscopy and chemical component analysis.

The elucidated structures in paper I–III, as well as paper V, are composed of linear repeating units of varying composition and length. In paper IV, the structure of the O-polysaccharide repeating unit of E. coli TD2158 is determined to be a branched hexasaccharide structure with a heterogeneous substitution pattern, with either a β-GlcpNAc or β-Glcp residue branching to the backbone chain. Incubation with bacteriophage HK620 tailspike protein shows that the polysaccharide is selectively cleaved at the α-GlcpNAc-(1→2)-α-Rhap-linkage of the backbone chain, yielding a 9:1 ratio of β-GlcpNAc/β-Glcp containing hexasaccharides after digestion.

In paper VI the conformational properties of a trisaccharide, which constitutes an internal epitope of the LeaLex hexasaccharide over-expressed on the surface of squamous lung cancer cells, have been analyzed using NMR spectroscopy and molecular dynamics simulations. The β-(1→3)-linkage of the trisaccharide was shown to be highly flexible.

Place, publisher, year, edition, pages
Stockholm: Department of Organic Chemistry, Stockholm University, 2012. 54 p.
Keyword
NMR spectroscopy, structural analysis, conformational analysis, carbohydrates, polysaccharides
National Category
Organic Chemistry
Research subject
Organic Chemistry
Identifiers
urn:nbn:se:su:diva-75050 (URN)978-91-7447-457-2 (ISBN)
Public defence
2012-05-04, Magnélisalen, Kemiska övningslaboratoriet, Svante Arrhenius väg 16 B, Stockholm, 10:00 (English)
Opponent
Supervisors
Note

At the time of the doctoral defense, the following papers were unpublished and had a status as follows: Paper 4: Submitted. Paper 6: Submitted.

Available from: 2013-04-09 Created: 2012-04-03 Last updated: 2013-11-18Bibliographically approved

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