Polyfluorinated carbohydrates

Stereoselective synthesis, conformation, lipophilicity, and biological evaluations
Wednesday, 20 November 2019 - 11:30 am
Location
Room number: 
214
Registration
Registration required: 
No
Cost to attend: 
Free of charge
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Abstract

Carbohydrates bearing a fluorine atom in place of a hydroxyl group have found applications as mechanistic probes or to study lectin-carbohydrate interactions. Polyfluorinated carbohydrates could represent a good strategy to improve protein-carbohydrate affinities via desolvation together with attractive dipolar interactions mediated by polar C-F bonds.

As part of our ongoing program related to the synthesis of fluorinated carbohydrates, our attention was turned towards the preparation of polyfluorinated hexopyranosides. A Chiron approach was used to access these crucial molecules to render them readily available for further biological investigations. Structural analysis of single-crystal X-ray diffractions and NMR studies confirm the conservation of favored 4C1 conformation for fluorinated carbohydrate analogs. The relative stereochemistry of multi-vicinal fluorine atoms has a strong effect on the lipophilicities (logP), this was exemplified with all trifluorinated analogues of glucose. Finally, this synthetic endeavours allowed us to unveil new reactivity of 1,6-anhydro sugars.

Speaker

Denis Giguère obtained his undergraduate degree in Biopharmaceutical sciences from the University of Ottawa in 2003. He earned his MSc in organic chemistry with René Roy at Université du Québec à Montréal and his PhD with Stephen Hanessian at Montreal University working on the synthesis of 4-deoxy hexopyranoses, C-disaccharides and biologically active C-glycosides (co-director René Roy). He trained as a postdoctoral fellow with K. C. Nicolaou at the Scripps Research Institute working on the total synthesis of dithiodiketopiperazine natural products (2010-2012). After 2 years working in industry at OmegaChem, he started his independent career at Laval University as an Assistant Professor of Chemistry in 2014 and he is now Associate Professor since the summer of 2019. He is a 2015 recipient of the Thieme Chemistry Journals Award and was awarded 2017 Professeur Étoile, Faculté des sciences et de genie, Université Laval. His research group focuses on the synthesis, biological activities, and physical properties of carbohydrate analogues.