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Reconnaissance biomoléculaire, Comparaison de l'impact du soufre et de l'oxygène dans la liaison glycosidique
KTH, School of Chemical Science and Engineering (CHE).
2011 (French)Independent thesis Advanced level (degree of Master (Two Years)), 20 credits / 30 HE creditsStudent thesisAlternative title
Biomolecular Recognition, the Importance of Sulfur/Oxygen in Oligosaccharide Linkages (English)
Abstract [en]

Interactions between carbohydrates and proteins play a key role in many biological processes. Cell-cell interactions, cell communication and cell proliferation are examples of processes based on highly specific interactions between proteins and complex oligosaccharides. The synthesis of carbohydrate mimics is essential for the study and understanding of such recognition processes, and has therefore become increasingly popular over the latest decades. In synthesis, thiol derivatives have several advantages. Thus, the combined nucleophilicity and chemical stability of sulfhydryl groups render thiol carbohydrate analogs as excellent building blocks for glycosylation processes. The objectives of the present project were to investigate the differences between naturally occurring oligosaccharides and their sulfur-analogs in biomolecular interactions with specific proteins. Convenient methodologies to the synthesis of a range of D-mannopyranose thioanalogs were developed. These strategies allows for the access to 1,2- and 1,6-linked dimannosides by glycosylation. A carbohydrate-protein interaction methodology to test the developed compounds against a mannose-specific lectin (Concanavalin A) using quartz crystal microbalance (QCM) methodology was furthermore developed.

Place, publisher, year, edition, pages
2011. , 98 p.
Keyword [en]
synthesis, carbohydrates, molecular recognition, lectins, analysis
National Category
Organic Chemistry
URN: urn:nbn:se:kth:diva-49888OAI: diva2:460576
Subject / course
Organic Chemistry
Physics, Chemistry, Mathematics
Available from: 2011-11-30 Created: 2011-11-30 Last updated: 2011-11-30Bibliographically approved

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