Change search
ReferencesLink to record
Permanent link

Direct link
Conformational flexibility and dynamics of a (1-6)-linked disaccharide related to an oligosaccharide epitope expressed on malignant tumor cells
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Manuscript (Other academic)
URN: urn:nbn:se:su:diva-24632OAI: diva2:197974
Part of urn:nbn:se:su:diva-7283Available from: 2008-01-10 Created: 2008-01-09 Last updated: 2010-01-13Bibliographically approved
In thesis
1. Structural Studies of O-antigen polysaccharides, Synthesis of 13C-labelled Oligosaccharides and Conformational Analysis thereof, using NMR Spectroscopy
Open this publication in new window or tab >>Structural Studies of O-antigen polysaccharides, Synthesis of 13C-labelled Oligosaccharides and Conformational Analysis thereof, using NMR Spectroscopy
2008 (English)Doctoral thesis, comprehensive summary (Other academic)
Abstract [en]

In order to understand biological processes, to treat and diagnose diseases, find appropriate vaccines and to prevent the outbreak of epidemics, it is essential to obtain more knowledge about carbohydrate structures. This thesis deals with structure and conformation of carbohydrates, analysed by NMR spectroscopy and MD simulations.In the first two papers, the structures of O-antigen polysaccharides (PS) from two different E. coli bacteria were determined using NMR spectroscopy. The O-antigenic PS from E. coli O152 (paper I) consists of branched pentasaccharide repeating units, built up of three different carbohydrate residues and a phosphodiester, whilst the repeating unit of the O-antigen from E. coli O176 (paper II) is built up of a linear tetrasaccharide consisting of two different monosaccharides.

In papers III and IV, the conformational analysis of different disaccharides is described. Conformational analysis was performed using NMR spectroscopy and MD simulations (paper IV). In paper III four different glucobiosides were studied using coupling constants and Karplus-type relationships. By use of specific 13C isotopically labelled derivatives, additional coupling constants were obtained and the number of possible torsion angles was reduced by half. In paper IV, we examine the conformations of two disaccharides that are part of an epitope of malignant cells. From NOE and T-ROE experiments, short proton-proton distances around the glycosidic linkage were estimated. Furthermore, interpretation of the extracted coupling constants using Kaplus relationships gave the values of the torsion angles. As in paper III, isotopically labelled compounds were synthesised in order to enhance the sensitivity of the analysis. Finally, MD simulations were performed and the results were compared with results from NMR data.

Place, publisher, year, edition, pages
Stockholm: Institutionen för organisk kemi, 2008. 67 p.
NMR spectroscopy, conformation, Escherichia coli, lipopolysaccharide, O-antigen, carbohydrates, structure, isotopic labelling
National Category
Organic Chemistry
Research subject
Organic Chemistry
urn:nbn:se:su:diva-7283 (URN)978-91-7155-560-1 (ISBN)
Public defence
2008-02-08, Magnélisalen, Kemiska övningslaboratoriet, Svante Arrhenius väg 12 A, Stockholm, 10:00
Available from: 2008-01-10 Created: 2008-01-09Bibliographically approved

Open Access in DiVA

No full text

By organisation
Department of Organic Chemistry

Search outside of DiVA

GoogleGoogle Scholar
The number of downloads is the sum of all downloads of full texts. It may include eg previous versions that are now no longer available

Total: 5 hits
ReferencesLink to record
Permanent link

Direct link