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Carbohydrates are a class of naturally occurring compounds involved in important biological processes such as immune response, tumour development, and bacterial infections. Pure and structurally well-defined glycans are needed for the in-depth understanding of these mechanisms as well as for the elaboration of sugar-based medicines. Glycans are often found as highly complex heterogeneous structures complicating their isolation from biological sources. Therefore, chemical synthesis stands as a method of choice for the preparation of pure glycans. The long-term goals of our research program are:

• To develop novel methodologies and synthetic routes allowing access to carbohydrate-based compounds from natural origin;

• To assess the pharmacological potential of these synthetic carbohydrate-based compounds as therapeutics and prophylactics.

The general objective is therefore twofold. It consists, on the one hand, in advancing fundamental knowledge in carbohydrate chemistry and, on the other hand, in generating biomolecules derived from sugars with potential applications in the biomedical field. In order to meet these general objectives, several research projects have emerged in my team in recent years. We have built an expertise in the synthesis of complex oligosaccharides from resistant pathogenic bacteria to create glycoconjugate vaccines. We are working with our microbiologist colleagues to find alternatives to antibiotics from natural compounds and their mimetics. We are developing innovative synthetic routes for the preparation of marine and bacterial glycolipids, and natural products with intriguing molecular structures, which could find application as surfactants or therapeutics. We are also interested in the discovery of non-toxic vaccine adjuvants based on carbohydrate-based natural products readily available from plant residues. The implementation of these research projects requires a vast network of collaborators that we have put in place in recent years.

Examples of active research projects:

• Total synthesis of glycolipids and natural products;
  

• Development of semi-synthetic glycoconjugate antibacterial vaccines;
  

• Synthesis of sugar-based inhibitors of bacterial glycosyltransferases.

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Five most important papers:

Cloutier, M.; Lavoie, S.; Gauthier, C.* C7 epimerization of benzylidene-protected β-D-idopyranosides brings structural insights into idose conformational flexibility. J. Org. Chem. 2022, 87, 12932-12953 (link)

Muru, K.; Cloutier, M.; Provost-Savard, A.; Di Cintio, S.; Burton, O.; Cordeil, J.; Groleau, M.-C.; Legault, J.; Déziel, E.; Gauthier, C.* Total synthesis of a chimeric glycolipid bearing the partially acetylated backbone of sponge-derived agminoside E. J. Org. Chem. 2021, 21, 15357-15375 (link)

Cloutier, M.; Prévost, M.-J.; Lavoie, S.; Feroldi, T.; Piochon, M.; Groleau, M.-C.; Legault, J.; Villaume, S.; Crouzet, J.; Dorey, S.; De Rienzo, M. A. D.; Déziel, E.; Gauthier, C.* Total synthesis, isolation, surfactant properties, and biological evaluation of ananatosides and related macrodilactone-containing rhamnolipids. Chem. Sci. 2021, 12, 7533-7546 (link)

Gamboa Marin, O. J.; Hussain, N.; Ravicoularamin, G.; Ameur, N.; Gormand, P.; Sauvageau, J.; Gauthier, C.* Total synthesis of 6-amino-2,6-dideoxy-α-Kdo from D-mannose. Org. Lett. 2020, 22, 5783-5788. (link)

Tamigney Kenfack, M.; Mazur, M.; Nualnoi, T.; Shaffer, T. L.; Ngassimou, A.; Blériot, Y.; Marrot, J.; Marchetti, R.; Sintiprungrat, K.; Chantratita, N.; Silipo, A.; Molinaro, A.; AuCoin, D. P.; Burtnick, M. N.; Brett, P. J.; Gauthier, C.* Deciphering minimal antigenic epitopes associated with Burkholderia pseudomallei and Burkholderia mallei lipopolysaccharide O-antigens. Nat. Commun. 2017, 8, 115 (link)