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Analysis of NMR J couplings in partially protected galactopyranosides*
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry.
2002 (English)In: Organic Letters, ISSN 1523-7052, Vol. 4, no 11, 1831-1834 p.Article in journal (Refereed) Published
Abstract [en]

Hydrogen bond mediated NMR J couplings offer additional structural information. The interpretation of these usually small hJ couplings are,however, not necessarily straightforward. In the present case of a carbohydrate system, a four-bond classical W coupling, 4JHO4,H5, is morereasonable on the basis of, in particular, density functional theory calculations of spin-spin coupling constants at the UB3LYP/6-311G** levelof theory.

Place, publisher, year, edition, pages
American Chemical Society , 2002. Vol. 4, no 11, 1831-1834 p.
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:su:diva-23168DOI: 10.1021/ol0200347OAI: oai:DiVA.org:su-23168DiVA: diva2:190475
Note
Part of urn:nbn:se:su:diva-172Available from: 2004-05-13 Created: 2004-05-13 Last updated: 2009-12-28Bibliographically approved
In thesis
1. Synthesis, structure and conformation of oligo- and polysaccharides
Open this publication in new window or tab >>Synthesis, structure and conformation of oligo- and polysaccharides
2004 (English)Doctoral thesis, comprehensive summary (Other academic)
Abstract [en]

Carbohydrates are a complex group of biomolecules with a high structural diversity. Their almost omnipresent occurrence has generated a broad field of research in both biology and chemistry. This thesis focuses on three different aspects of carbohydrate chemistry, synthesis, structure elucidation and the conformational analysis of carbohydrates.

The first paper describes the synthesis of a penta- and a tetrasaccharide related to the highly branched capsular polysaccharide from Streptococcus pneumoniae type 37. In the second paper, the structure of the O-antigenic repeating unit from the lipopolysaccharide of E. coli 396/C1 was determined along with indications of the structure of the biological repeating unit. In addition, its structural and immunological relationship with E. coli O126 is discussed. In the third paper, partially protected galactopyranosides were examined to clarify the origin of an intriguing 4JHO,H coupling, where a W-mediated coupling pathway was found to operate. In the fourth paper, the conformation of methyl a-cellobioside is studied with a combination of molecular dynamics simulations and NMR spectroscopy. In addition to the expected syn-conformation, detection and quantification of anti-ø and anti-ψ conformers was also possible.

Place, publisher, year, edition, pages
Stockholm: Institutionen för organisk kemi, 2004. 40 p.
National Category
Organic Chemistry
Identifiers
urn:nbn:se:su:diva-172 (URN)91-7265-872-X (ISBN)
Public defence
2004-06-03, Magnélisalen, Kemiska övningslaboratoriet, Svante Arrhenius väg 12 A, Stockholm, 14:00
Opponent
Supervisors
Available from: 2004-05-13 Created: 2004-05-13Bibliographically approved

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