Towards the total synthesis of the trisaccharide associated with Pseudomonas putida BIM B-1100

Jose, Joe P. (2018) Towards the total synthesis of the trisaccharide associated with Pseudomonas putida BIM B-1100. Masters thesis, Indian Institute of Science Education and Research Kolkata.

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Abstract

Carbohydrates are one of the important bioorganic compounds existing on earth. They have tremendous role in energy storage, transport, providing structural architecture etc. They are also found in the cell surface and plays important role in cellular activities like cell- cell recognition, cell transport and adhesion; they appear in all cells in some form or the other, for example, as peptide and proteoglycans, glycoproteins, nucleic acids, lipopolysaccharides or glycolipids. Study of carbohydrates which was once known as “glycobiology” is now separately called as “glycomics” as in “proteomics” and in “genomics” because of its importance in sustaining life. The carbohydrates play in the mode of actions of many drugs since they contribute to variety of processes like active membrane transport, stabilization of protein folding and enzyme inhibition. Even the human blood groups are differentiated based on the different oligosaccharide moieties found in them. The chemical synthesis of oligosaccharides found on the surface of various infectious bacteria paved way for the development of new vaccines because of the fact that these synthetic glyco moieties are recognized by the receptors found on the surface of cell which in turn releases the antibodies against this in blood, which will destroy the bacteria that enters which enters into our body. These synthetic carbohydrates can also block the receptors on cell surface from the attack of bacteria and even displace the bacteria attached to the receptors since the synthetic carbohydrates have more degree of freedom than the bacteria itself. The present thsis describes the synthesis of two monosaccharides and partial synthesis of one monosaccharide related to Pseudomonas putida BIM B – 1100 through rational protecting group manipulations and stereoselective glycosidations.

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