This project focuses on the preparation of potentially biologically active fluorinated glycoconjugates (mainly lipids, amino acids, peptides and eventually proteins) and also to explore the biological and biophysical properties of these molecules in vitro and in living cells that are decorated with these unnatural fluorinated elements on their surfaces. For this purpose, the project will first focus on the preparation of a range of fluorinated carbohydrates and lipids with configurations related to those recognized by lectins. The synthesis of fluorinated carbohydrates and lipids will be carried out using already established procedures and by developing new procedures based on carbohydrate chemistry or asymmetric synthesis. The next step will consist of attaching the prepared fluorinated materials to the corresponding aglycons, amino acids, peptides or proteins (in the case of F-carbohydrates) or to the corresponding sugars in the case of F-lipids. In the second part of the project, the conformation of these F-glycoconjugates will be studied using leading spectroscopic techniques (mainly 19F STD-NMR, X-ray, etc.). This will provide valuable information on how these molecules might interact with target proteins and receptors. Next, those constructs with most interesting properties will be employed for proteomic analysis as multifunctional affinity-based probes, to screen, detect and isolate carbohydrate-binding proteins with/without enzymatic activity. Finally, the sensitivity and the absence of a F background signal in 19F NMR will be used to study the metabolic profile of those F-glycoconjugates (by 19F NMR) and establish correlations between alteration of biosynthetic pathways, biodistribution, metabolite concentrations, immune response and disease.
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