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- Jonsson, Hanna,1979-Stockholms universitet,Institutionen för organisk kemi,Göran Widmalm (author)
Exploring the structure of oligo- and polysaccharides : Synthesis and NMR spectroscopy studies
- BookEnglish2010
Publisher, publication year, extent ...
- Stockholm :Department of Organic Chemistry, Stockholm University,2010
- 61 s.
- electronicrdacarrier
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- LIBRIS-ID:oai:DiVA.org:su-37680
- ISBN:9789174470413
- https://urn.kb.se/resolve?urn=urn:nbn:se:su:diva-37680URI
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- Language:English
- Summary in:English
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- At the time of the doctoral defense, the following papers were unpublished and had a status as follows: Paper 4: Manuscript. Paper 5: Manuscript.
- A deeper understanding of the diversity of carbohydrates and the many applications of oligo- and polysaccharides found in nature are of high interest. Many of the processes involving carbohydrates affect our everyday life. This thesis is based on six papers all contributing to an extended perspective of carbohydrate property and functionality. An introduction to carbohydrate chemistry together with a presentation of selected carbohydrate synthesis and analysis methods introduces the reader to the research field. The first paper is an NMR spectroscopy reinvestigation of the structures of the O-antigens from the lipopolysaccharides (LPS) of Shigella dysenteriae type 3 and Escherichia coli O124. The repeating units were concluded to be built of identical branched pentasaccharides now with the correct anomeric configurations. Paper II is a structural investigation of the O-antigen from the LPS of E. coli O74 which is built of branched tetrasaccharide repeating units including the uncommon monosaccharide d-Fuc3NAc. Paper III is a conformational study of a rhamnose derivative, using NMR spectroscopy and X-ray crystallography. The benzoyl ester group positioned at C4 prefers an “eclipsed” conformation in the crystal as well as in solution. The use of site-specifically 13C-labeled compounds in conformational studies is discussed in Papers IV and V. The disaccharide α-L-Rhap-(1→2)-α-L-Rhap-OMe was synthesized together with two 13C-isotopologues and studied with NMR spectroscopy to give seven J-couplings related to torsion angles φ and ψ. The trisaccharide α-L-Rhap-(1→2)[α-L-Rhap-(1→3)]-α-L-Rhap-OMe was synthesized with 13C-labeling at two positions which presented a solution to a problem of overlapping signals in the 1H NMR spectrum. The site-specific labeling also facilitated the measurement of two 3JCC and two 2JCH coupling constants. Finally, chapter 6 gives a short introduction to glycosynthase chemistry and discusses the synthesis of α-glycosyl fluorides. A novel cyclic heptasaccharide was synthesized from α-laminariheptaosyl fluoride using a mutant of the enzyme laminarase 16A and subsequently analyzed by NMR spectroscopy.
Subject headings and genre
- NATURVETENSKAP Kemi Organisk kemi hsv//swe
- NATURAL SCIENCES Chemical Sciences Organic Chemistry hsv//eng
- Carbohydrates
- NMR spectroscopy
- synthesis
- lipopolysaccharides
- conformational studies
- Organic chemistry
- Organisk kemi
- organisk kemi
- Organic Chemistry
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- Widmalm, Göran,ProfessorStockholms universitet,Institutionen för organisk kemi(Swepub:su)gm (thesis advisor)
- Molinaro, Antonio,ProfessorUniversità degli Studi di Napoli “Federico II”, Dipartimento di Chimica Organica e Biochimica (opponent)
- Stockholms universitetInstitutionen för organisk kemi (creator_code:org_t)
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