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Structural elucidation of the O-antigenic polysaccharide from Escherichia coli O175
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry.
2011 (English)In: Carbohydrate Research, ISSN 0008-6215, E-ISSN 1873-426X, Vol. 346, no 3, 449-453 p.Article in journal (Refereed) Published
Abstract [en]

The structure of the O-antigen polysaccharide (PS) from Escherichia coli O175 has been elucidated. Component analysis together with 1H and 13C NMR spectroscopy experiments were used to determine the structure. Inter-residue correlations were determined by 1H,1H-NOESY, and 1H,13C-heteronuclear multiple-bond correlation experiments. The PS is composed of pentasaccharide repeating units with the following structure:

→2)-α-d-Glcp-(1→4)-α-d-GlcpA-(1→3)-α-d-Manp-(1→2)-α-d-Manp-(1→3)-β-d-GalpNAc-(1→

Cross-peaks of low intensity from an α-linked glucopyranosyl residue were present in the 1H,1H-TOCSY NMR spectra. The α-d-Glcp residue is suggested to originate from the terminal part of the polysaccharide and consequently the biological repeating unit has a 3-substituted N-acetyl-d-galactosamine residue at its reducing end. The repeating unit of the E. coli O175 O-antigen is similar to those from E. coli O22 and O83, both of which carry an α-d-Glcp-(1→4)-d-GlcpA structural element, thereby explaining the reported cross-reactivities between the strains.

Place, publisher, year, edition, pages
2011. Vol. 346, no 3, 449-453 p.
Keyword [en]
Escherichia coli, lipopolysaccharide, NMR, biological repeating unit
National Category
Organic Chemistry
Research subject
Organic Chemistry
Identifiers
URN: urn:nbn:se:su:diva-59722DOI: 10.1016/j.carres.2010.12.005ISI: 000293037400010OAI: oai:DiVA.org:su-59722DiVA: diva2:430021
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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