Synthesis of S-linked cello-oligosaccharides

Research output: Book/ReportPh.D. thesis

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Abstract

Plant cell walls represent almost 50% of the biomass found in plants and therefore constitute one of the main targets for biotechnological research. For this reason, the transition to a sustainable bio-resource for future energy can primarily be founded on plant cell walls. Thus, in order to achieve a sustainable development, it is necessary to optimize plant production and its utilization. The polysaccharides present in the plant cell wall vary depending on the plant species and change during the developmental stage of the plant. As a result, this makes it very challenging to address the function of each individual component. The conversion of lignocellulosic biomass still remains a big challenge nowadays with the enzymatic hydrolysis being the limiting step. Indeed, characterization of the enzymes involved in this process can help the optimization development. For this reason, structurally well-defined oligosaccharides made via chemical synthesis can be used as models for the more complex polysaccharides in the investigation of properties such as polysaccharide biosynthesis, degradation and protein-carbohydrate interactions. For this purpose, non-natural substrate analogues forming irreversible binding to the enzyme can be employed. Thio-oligosaccharides represent the largest class of specific non-natural inhibitors for glycanases. In this thesis the chemical synthesis of some thio-glucans is presented. The formation of thio-linkages using a classical and non-classical method is investigated. Two strategies, relying on either a linear or a convergent strategy, have been employed in the synthesis towards two target molecules. Furthermore, the activity of a glycosyltransferase responsible for the elongation of a pectic polysaccharide has been investigated and partially characterized.
Original languageEnglish
PublisherDTU Chemistry
Number of pages140
Publication statusPublished - 2016

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