Novel exo-glycal synthetic methodologies applied to the preparation of biochemical probes

Exo-glycals constitute a large family of polyhydroxylated chiral synthons,
exploited both as synthetic and biosynthetic intermediates, but also as final
molecules for biochemical applications.
Based on a novel photoredox trifluoromethylation reaction that we just
developed, we wish to extend this synthetic methodology to the formation
of challenging carbohydrate mimetics.
This project pursues two general goals: 1) To develop new synthetic
methods allowing the access of unprecedented and highly functionalized
exo-glycals 2) To synthesize, from exo-glycal scaffolds, inhibitors and/or
mechanistic probes of biologically relevant enzymes.
The final molecules, analogues of nucleotide-sugars and glycolipids, have
been designed to allow binding or mechanistic studies of essential bacterial
enzymes participating in the cell wall biosynthesis. Our main target is the
most important cell wall component of Mycobacterium tuberculosis: the
mycolyl-arabinogalactan complex.