Multivalency in Carbohydrate Chemistry : From Oligosaccharides to Oligovalency and Beyond
Rahkila, Jani (2018-02-16)
Åbo Akademis förlag - Åbo Akademi University Press
16.02.2018
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https://urn.fi/URN:ISBN:978-951-765-886-7
https://urn.fi/URN:ISBN:978-951-765-886-7
Tiivistelmä
Carbohydrates are among the most abundant biomolecules on earth and can be found in all living things. Their role in nature ranges from structural components such as cellulose in plants and chitin in the exoskeletons of arthropods, to fundamental building blocks of DNA and RNA, to the most important energy storage molecules in organisms in the form of starch and glycogen.
The practically unlimited ways in which individual monosaccharides can be connected make the information storage potential of this class of compounds exponentially greater than that of DNA or proteins. This property does, however, also result in some complications as, while the potential for storing information in carbohydrate structures is great, the process of doing so and reading the information back is complicated by this exact same phenomenon. A majority of the early carbohydrate investigations focused on the elucidation of the structures of carbohydrates and the pioneering work in this field was done by Emil Fischer at the end of the 19th century. Later the focus shifted towards creating glycosidic linkages, and over the years, countless methods have been developed allowing for the preparation of complex structures. The advances in the field have enabled the investigation of the biological roles of this class of compounds.
This thesis explores the world of carbohydrates starting from small oligosaccharides, expanding towards multivalent structures and finally into modification of polysaccharides for preparing well-defined mimics of natural polysaccharides. Potential biological applicability is always a consideration when designing the compound and a recurring theme throughout the thesis are β-(1→2) linked mannosides which are an interesting class of compounds due to their biological impact, their unique structure and problems associated with their synthesis. Particular attention has been paid to the analysis of products by NMR spectroscopy and complete assignment of the spectra. Where feasible, the spectra were simulated by NMR simulation software PERCH to allow a more complete interpretation.
The practically unlimited ways in which individual monosaccharides can be connected make the information storage potential of this class of compounds exponentially greater than that of DNA or proteins. This property does, however, also result in some complications as, while the potential for storing information in carbohydrate structures is great, the process of doing so and reading the information back is complicated by this exact same phenomenon. A majority of the early carbohydrate investigations focused on the elucidation of the structures of carbohydrates and the pioneering work in this field was done by Emil Fischer at the end of the 19th century. Later the focus shifted towards creating glycosidic linkages, and over the years, countless methods have been developed allowing for the preparation of complex structures. The advances in the field have enabled the investigation of the biological roles of this class of compounds.
This thesis explores the world of carbohydrates starting from small oligosaccharides, expanding towards multivalent structures and finally into modification of polysaccharides for preparing well-defined mimics of natural polysaccharides. Potential biological applicability is always a consideration when designing the compound and a recurring theme throughout the thesis are β-(1→2) linked mannosides which are an interesting class of compounds due to their biological impact, their unique structure and problems associated with their synthesis. Particular attention has been paid to the analysis of products by NMR spectroscopy and complete assignment of the spectra. Where feasible, the spectra were simulated by NMR simulation software PERCH to allow a more complete interpretation.
Kokoelmat
- 116 Kemia [51]