Final Report Summary - FGLYP (FLUORINATED SUGARS: CHEMICAL TOOLS FOR THE STUDY OF CARBOHYDRATE-BINDING PROTEINS)
1. We have efficiently developed a methodology for accessing a series of neo-glycolipids with galacto configuration and different groups at C-2 position (F, OH, H and NHAc).
2. The interaction of those glycolipids (forming micelles with a detergent due to their poor solubility in water) with a model galactose-binding lectin viscum album agglutinin (Viscumin – VAA) was evaluated using leading spectroscopic techniques (1H and 19F-DOSY/STD/trNOE-NMR experiments, etc.).
3. We have synthesized 2-deoxy-2-fluorohexopyranoses with different configurations (gluco, galacto, manno) and anomeric linkages (N3, S, Se) for chemical protein modification.
4. We have synthesized 1-chalcogenopyranoses with different configurations (gluco, galacto) and anomeric linkages (S, S2, Se and Se2) as potential antioxidant agents for vascular disease treatment.
5. We have developed a general strategy for the synthesis of 2-CF3-glycals. The use of reliable, efficient cross-coupling of 2-iodoglycals with fluoroform-derived CuCF3 proceeds with complete regioselectivity at C-2 and enables access to 2-CF3-glycals with different configurations in excellent yields.
6. The stereoselective synthesis of important fluorinated precursors (2-Fpyranose, 2,2’-diFpyranose and 2-Fglycal) with different protecting groups (Ac, Bn) from D-glycals was achieved.
7. The preparation of key intermediates that will give access to fluorosugars with rare configurations/substitution patterns through olefination-cyclization-glycosylation reactions was explored.
8. We have explored different routes towards the preparation of perfluorinated analogues of KRN7000.
9. We have synthesized a series of multivalent glycolipids that mimic the clustering of ligands usually found in biological receptors.