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  • About
  • The Global ETD Search service is a free service for researchers to find electronic theses and dissertations. This service is provided by the Networked Digital Library of Theses and Dissertations.
    Our metadata is collected from universities around the world. If you manage a university/consortium/country archive and want to be added, details can be found on the NDLTD website.
1

Total Synthesis of the Tumor-Associated Carbohydrate Antigen Lewis A Lewis X Hexasaccharide and Selected Fragments

Mickael, Guillemineau 13 August 2012 (has links)
Carbohydrates constitute the most abundant class of natural products in the living world and they play various roles. They are notably involved in cell-cell interactions and immune reactions. It has been observed that tumor cells express, on their surface, unusual oligosaccharides named Tumor-Associated Carbohydrate Antigen (TACA). One TACA of interest to our research group is the Lewis A Lewis X hexasaccharide that is displayed on the surface of squamous lung carcinoma cells. Since carbohydrates are involved in immune reactions and can be recognized by antibodies, it becomes possible to design a carbohydrate-based vaccine against these tumor cells. This thesis describes the total synthesis of the TACA Lewis A Lewis X hexasaccharide and the preparation of two fragments: one tetra- and one pentasaccharide. These molecules were prepared as hexyl and aminohexylglycosides. In addition, the hexasaccharide was synthesized as a disulfide. This diversity of these synthons will allow conjugation to a protein, analysis by nuclear magnetic resonance techniques, and immobilization on gold of the antigen. Without doubt, this work is a significant contribution to the development of an anti cancer vaccine as it constitutes the first stage of the process.

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