Carbohydrate engineering with Sulfur

Different topics linking sulfur chemistry and glycochemistry are developed in our team.

1- Small thio/aza-heterocycles anchored on carbohydrate backbones (fused or spiro):

We have developed various methods to anchor heterocycles such as 1,3-oxazolidine-2-thione (OZT) and 1,3-oxazoline-2-thione (OXT) on carbohydrate templates. Here are some examples of various molecules we prepared:

The aims of the preparation of these molecules was to target new antibacterial and antifungal properties through the elaboration of new sp²-iminosugars templates able to inhibit glycosidase as well as new structures targeting monosaccharide transporters (GluTs).

The anchored heterocycles have been explored to develop sulfur based functions. These can be used to create C-C bonds by applying the Liebeskind-Srogl reaction. Our group has developed this reaction on chiral templates using carbohydrate backbones, and has applied it to small heterocycles. This work has also been extended to Sonogashira coupling and work is currently in progress to apply it to unusual thiofunctions such as thioimidates.

2- Original thiofunctions : thioimidate N-oxides

We have developed original scaffolds incorporating a thioimidate N-oxide function on carbohydrate backbone giving access to new sp²-iminosugars.

New chemical routes were developed to prepare these molecules from a wide range of monosaccharides, with a key step of cyclisation. This key step has been successfully achieved using either a Mitsunobu reaction or a fluoride induced desilylative cyclisation.

This uncommon TINO thiofunction is studied to give access through chemical processes to new imino-C-nucleosides and new C-iminosugars.