Charles Gauthier

Areas of expertise

Chemistry of carbohydrates and natural products

Associate Professor, INRS, Laval (Québec), Canada

(2020-present)

 

Assistant Professor, INRS, Laval (Québec), Canada

(2016-2020)

 

Adjunct Professor, UQAC, Chicoutimi (Québec), Canada

(2012-present)

 

Senior Lecturer (Organic Chemistry), University of Poitiers, Poitiers, France

(2011-2016)

 

Postdoctoral Research Fellow (Chemical Biology), University of Oxford, Oxford, UK

(2010-2011)

 

Postdoctoral Research Fellow (Carbohydrate Chemistry), Institut Pasteur, Paris, France

(2009-2010)

 

PhD Student (Natural Product Chemistry), UQAC, Chicoutimi (Québec), Canada

(2005-2008)

Phone
+1 450-687-5010 ext. 8886

Fax
+1 450-686-5566

E-mail
charles.gauthier@inrs.ca

Armand-Frappier Santé Biotechnologie Research Centre

531, boulevard des Prairies
Laval (Québec), Canada
H7V 1B7

See research centre

Interested research topics

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:

  1. To develop novel methodologies and synthetic routes allowing access to carbohydrate-based compounds from natural origin;
  2. 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 developed an expertise for 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. For more information, please visit our research group website.

 

Most Significant Publications (5):

  • 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)
  • Cloutier, M.; Delar, E.; Muru, K.; Ndong, S.; Hoyeck, R. R.; Kaewarpai, T.; Chantratita, N.; Burtnick, M. N.; Brett, P. J.; Gauthier, C.* Melioidosis patient serum-reactive synthetic tetrasaccharides bearing the predominant epitopes of Burkholderia pseudomallei and Burkholderia mallei O-antigens. Org. Biomol. Chem. 2019, 17, 8878-8901 (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)
  • Mazur, M.; Barycza, B.; Andriamboavonjy, H.; Lavoie, S.; Tamigney Kenfack, M.; Laroussarie, A.; Blériot, Y.; Gauthier, C.* 4′-Methoxyphenacyl-assisted synthesis of β-Kdo glycosides. J. Org. Chem. 2016, 81, 10585-10599 (Featured article and cover page) (link)
  • Laroussarie, A.; Barycza, B.; Andriamboavonjy, H.; Tamigney Kenfack, M.; Blériot, Y.; Gauthier, C.* Synthesis of the tetrasaccharide repeating unit of the β-Kdo-containing exopolysaccharide from Burkholderia pseudomallei and B. cepacia complex. J. Org. Chem. 2015, 80, 10386-10396 (link)

Team

 

Arasakumar Thangaraj

(Postdoc, 2020-present)

 

Maude Cloutier

(PhD, 2019-present)

 

Emmanilo Delar

(PhD), 2019-present)

 

Kevin Muru

(PhD, 2017-present)

 

Oscar Javier Gamboa Marin

(MSc, 2019-present)

 

Samar Hadj Amor

(MSc, 2019-present)

 

Mathilde Grosset-Magagne

(MSc, 2020-present)

Professor Charles Gauthier obtained his PhD in natural product chemistry at UQAC in 2008. Following postdoctoral internships at the Institut Pasteur (2009-2010) and the University of Oxford (2010-2011), he obtained in 2011 an academic position of Senior Lecturer at the University of Poitiers in France. In 2016, he accepted a position of Assistant Professor at the INRS and was promoted to the rank of Associate Professor in 2020. Professor Gauthier has published more than 40 research papers in peer-reviewed journals and presented his results at numerous scientific meetings. Professor Gauthier’s research program is funded by several granting agencies including the FRQNT, FRQS, NSERC, IPIN, and FNRS.

  1. Total synthesis of natural glycolipids
  2. Development of synthetic glycoconjugate vaccines against melioidosis, glanders, and campylobacteriosis
  3. Development of inhibitors of sugar-processing enzymes
  4. Synthesis and isolation of polyphenols and microbial surfactants

2018-2020: FRQS Research Scholars Junior 2

2015-2016: PhD Supervising and Research Bonus, Conseil National des Universités (CNU)

2012-2016: Agence Nationale de la Recherche Starting Grant (ANR JCJC)

2012-2013: Direction Générale de l’Armement (DGA) Funding

2010-2011: Fonds de Recherche Nature et Technologies (FQRNT) Postdoctoral Fellowship

2009-2010: Bourse Emile-Roux Postdoctoral Fellowship

2009: Vasant & Kusum Joshi Postdoctoral Fellowship

2009: Fondation Canadienne Louis-Pasteur Postdoctoral Fellowship (declined)

2008: Fondation de l’UQAC PhD Fellowship

2007-2008: Fonds de Recherche Nature et Technologies (FQRNT) PhD Fellowship

2007: Fondation de l’UQAC PhD Fellowship (declined)

2007: First Prize Science for Laymen, Université du Québec Network

2007: Association Francophone pour le Savoir (ACFAS) Bernard-Belleau Award (link)

2006-2007: Institutional Funding Program (PAIR-UQAC) PhD Fellowship

2005-2006: Abitibi-Consolidated MSc Fellowship

2004-2005: Gaston-L. Tremblay MSc Fellowship

2004: Work Abroad MSc Fellowship

2000-2001: Professors of Chemistry BSc Fellowship

2000-2001: Fondation du Royaume BSc Fellowship

1999-2000: Provigo-Loblaws Leadership Fellowship

1999: First Prize Science for Laymen, CEGEP de St-Félicien (Québec), Canada

1998: Nominated for the Governor General’s Academic Medal

Publications

44. Klaus, J. R.; Majerczyk, C.; Moon, S.; Eppler, N. A.; Smith, S.; Tuma, E.; Groleau, M.-C.; Asfahl, K. L.; Smalley, N. E.; Hayden, H.; Piochon, M.; Ball, P. N.; Dandekar, A. A.; Gauthier, C.; Déziel, E.; Chandler, J. R. Burkholderia thailandensis methylated hydroxy-alkylquinolines: biosynthesis and antimicrobial activity in co-cultures. Appl. Environ. Microbiol. 2020, sous presse (link)

43. Cloutier, M.; Gauthier, C.* Progress towards the development of glycan-based vaccines against campylobacteriosis. ACS Infect. Dis. 2020, sous presse (link)

42. 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) (supporting information)

41. Piochon, M.; Coulon, P. M. L.; Caulet, A.; Groleau, M.-C.; Déziel, E.; Gauthier, C.* Synthesis and antimicrobial activity of Burkholderia-related 4-hydroxy-3-methyl-2-alkenylquinolines (HMAQs) and their N-oxide counterparts. J. Nat. Prod. 2020, 83, 2145-2154 (link) (supporting information)

40. Islam, S. T.; Alvarez, I. V.; Saïdi, F.; Giuseppi, A.; Vinogradov, E.; Morrone, C.; Brasseur, G.; Sharma, G.; Benarouche, A.; Bridot, J.-L.; Ravicoularamin, G.; Cagna, A.; Gauthier, C.; Singer, M.; Fierobe, H.-P.; Mignot, T.; Mauriello, E. M. F. Modulation of bacterial multicellularity via spatiotemporal polysaccharide secretion. PLoS Biol. 2020, 18, e3000728 (link)

39. Cloutier, M.; Gauthier, C.* 3-Deoxy-D-manno-oct-2-ulosonic acid (Kdo) derivatives in antibacterial drug discovery. In: Carbohydrates in Drug Discovery and Development, 1st edition, Ed.: Tiwari, V. K.; Elsevier, 700 pp, 2020 (link)

38. Cloutier, M.; Muru, K.; Gauthier, C.* Synthesis of oligosaccharides related to potential bioterrorist pathogens. In: Recent Trends in Carbohydrate Chemistry, 1st edition, Ed.: Rauter, A. P.; Christensen, B.; Somsak, L.; Kosma, P.; Adamo, R.; Elsevier, 532 pp, 2020 (link)

37. Sylla, B.; Lavoie, S.; Legault, J.; Gauthier, C.*; Pichette, A. Synthesis, cytotoxicity and anti-inflammatory activity of rhamnose-containing ursolic and betulinic acid saponins. RSC Adv. 2019, 9, 39743-39757 (open access) (supporting information)

36. Cloutier, M.; Delar, E.; Muru, K.; Ndong, S.; Hoyeck, R. R.; Kaewarpai, T.; Chantratita, N.; Burtnick, M. N.; Brett, P. J.; Gauthier, C.* Melioidosis patient serum-reactive synthetic tetrasaccharides bearing the predominant epitopes of Burkholderia pseudomallei and Burkholderia mallei O-antigens. Org. Biomol. Chem. 2019, 17, 8878-8901 Contribution invitée (link) (supporting information)

35. Gauthier, C.*; Lavoie, S.; Piochon, M.; Martinez, S.; Milot, S.; Déziel, E. Structural determination of ananatoside A: an unprecedented 15-membered macrodilactone-containing glycolipid from Pantoea ananatis. Carbohydr. Res. 2019, 471, 13-18 (link) (supporting information)

34. St-Gelais, A.; Alsarraf, J.; Legault, J.; Gauthier, C.; Pichette, A. Soft-enolization Baker-Venkataraman rearrangement enabled total synthesis of dirchromones and related 2-substituted chromones. Org. Lett. 2018, 20, 7424-7428 (link) (supporting information)

33. Cloutier, M.; Muru, K.; Ravicoularamin, G.; Gauthier, C.* Polysaccharides from Burkholderia species as targets for vaccine development, immunomodulation and chemical synthesis. Nat. Prod. Rep. 2018, 35, 1251-1293 (link) (cover art)

32. Mihoub, M.; Pichette, A.; Sylla, B.; Gauthier, C.; Legault, J. Bidesmosidic betulin saponin bearing L-rhamnopyranoside moieties induces apoptosis and inhibition of lung cancer cells growth in vitro and in vivo. PLoS ONE 2018, 13, e0193386 (open access)

31. 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 (open access) (supporting information) (peer review file)

30. Lavoie, S.; Côté, I.; Pichette, A.; Gauthier, C.; Ouellet, M.; Nagau-Lavoie, F.; Mshvildadze, V.; Pichette, A.; Legault, J. Chemical composition and anti-herpes simplex virus type 1 (HSV-1) activity of extracts from Cornus canadensis. BMC Complem. Altern. Med. 2017, 17, 123 (open access) (peer review file)

29. Mazur, M.; Barycza, B.; Andriamboavonjy, H.; Lavoie, S.; Tamigney Kenfack, M.; Laroussarie, A.; Blériot, Y.; Gauthier, C.* 4′-Methoxyphenacyl-assisted synthesis of β-Kdo glycosides. J. Org. Chem. 2016, 81, 10585-10599 Featured Article” et page couverture (link) (supporting information) (cover art)

28. Simard, F.; Gauthier, C.; Legault, J.; Lavoie, S.; Mshvildadze, V.; Pichette, A. Structure elucidation of anti-methicillin resistant Staphylococcus aureus (MRSA) flavonoids from balsam poplar buds. Bioorg. Med. Chem. 2016, 24, 4188-4198 (link) (supporting information)

27. Lavoie, S.; Ouellet, M.; Fleury, P.-Y.; Gauthier, C.; Legault, J.; Pichette, A. Complete 1H and 13C NMR assignments of a series of pergalloylated tannins. Magn. Reson. Chem. 2016, 54, 168-174 (link) (supporting information)

26. Lavoie, S.; Gauthier, C.; Mshvildadze, V.; Legault, J.; Roger, B.; Pichette, A. DFT calculations and ROESY NMR data for the diastereochemical characterization of cytotoxic tetraterpenoids from the oleoresin of Abies balsamea. J. Nat. Prod. 2015, 78, 2896-2907 (Contribution égale) (link) (supporting information)

25. Laroussarie, A.; Barycza, B.; Andriamboavonjy, H.; Tamigney Kenfack, M.; Blériot, Y.; Gauthier, C.* Synthesis of the tetrasaccharide repeating unit of the β-Kdo-containing exopolysaccharide from Burkholderia pseudomallei and B. cepacia complex. J. Org. Chem. 2015, 80, 10386-10396 (link) (supporting information)

24. Marchetti, R.; Dillon, M. J.; Burtnick, M. N.; Hubbard, M. A.; Tamigney Kenfack, M.; Blériot, Y.; Gauthier, C.; Brett, P. J.; AuCoin, D. P.; Lanzetta, R.; Silipo, A.; Molinaro, A. Burkholderia pseudomallei capsular polysaccharide recognition by a monoclonal antibody reveals key details toward a biodefense vaccine and diagnostics against melioidosis. ACS Chem. Biol. 2015, 10, 2295-2302 (link) (supporting information)

23. Simard, F.; Gauthier, C.; Chiasson, E.; Lavoie, S.; Mshvildadze, V.; Legault, J.; Pichette, A. Antibacterial balsacones J-M, hydroxycinnamoylated dihydrochalcones from Populus balsamifera buds. J. Nat. Prod. 2015, 78, 1147-1153 (link) (supporting information)

22.Blériot, Y.; Tran, A. T.; Prencipe, G.; Jagadeesh, Y.; Auberger, N.; Zhu, S.; Gauthier, C.; Zhang, Y.; Désiré, J.; Adachi, I.; Kato, A.; Sollogoub, M. Synthesis of 1,2-trans-2-acetamido-2-deoxy-homoiminosugars. Org. Lett. 2014, 16, 5516-5519 (link) (supporting information)

21. Blériot, Y.; Auberger, N.; Jagadeesh, Y.; Gauthier, C.; Prencipe, G.; Tran, A. T.; Marrot, J.; Désiré, J.; Yamamoto, A.; Kato, A.; Sollogoub, M. Synthesis of 1,2-cis homoiminosugars derived from GlcNAc and GalNAc exploiting a β-aminoalcohol skeletal rearrangement. Org. Lett. 2014, 16, 5512-5515 (link) (supporting information)

20. Sylla, B.; Gauthier, C.; Legault, J.; Fleury, P.-Y.; Lavoie, S.; Mshvildadze, V.; Muzashvili, T.; Kemertelidze, E. Pichette, A. Isolation of a new disaccharide nucleoside from Helleborus caucasicus: structure elucidation and total synthesis of hellecaucaside A and its β-anomer. Carbohydr. Res. 2014, 398, 80-89 (Contribution égale) (link) (supporting information)

19. Gauthier, C.; Chassagne, P.; Theillet, F.-X.; Guerreiro, C.; Thouron, F.; Nato, F.; Delepierre, M.; Sansonetti, P. J.; Phalipon, A.; Mulard, L. A. Non-stoichiometric O-acetylation of Shigella flexneri 2a O-specific polysaccharide: synthesis and antigenicity. Org. Biomol. Chem. 2014, 12, 4218-4232 (link) (supporting information)

18. Tamigney Kenfack, M.; Blériot, Y.; Gauthier, C.* Intramolecular aglycon delivery enables the synthesis of 6-deoxy-β-D-manno-heptosides as fragments of Burkholderia pseudomallei and Burkholderia mallei capsular polysaccharide. J. Org. Chem. 2014, 79, 4615-4634 (link) (supporting information)

17. Maaliki, C.; Gauthier, C.; Massinon, O.; Sagar, R.; Vincent, S.; Blériot, Y. Conformationally restricted glycoside derivatives as mechanistic probes and/or inhibitors of sugar processing enzymes. Carbohydr. Chem. 2014, 40, 418-444 Invited contribution (link)

16. Lavoie, S.; Gauthier, C.; Legault, J.; Mshvildadze, V.; Pichette, A. Lanostane- and cycloartane-type triterpenoids from Abies balsamea oleoresin. Beilstein J. Org. Chem. 2013, 9, 1333-1339 (Contribution égale) (link) (supporting information)

15. Chassagne, P.; Fontana, C.; Guerreiro, C.; Gauthier, C.; Phalipon, A.; Widmalm, G.; Mulard, L. A. Structural studies of the O-acetyl containing O-antigen from a Shigella flexneri serotype 6 and synthesis of oligosaccharide fragments thereof. Eur. J. Org. Chem. 2013, 4085-4106 (link) (supporting information)

14. Thibeault, D.; Gauthier, C.; Legault, J.; Bouchard, J.; Gagné, L.; Pichette, A. Synthesis and cytotoxicity of lupane-type triterpenoid glyceryl esters. Bioorg. Med. Chem. Lett. 2012, 22, 4735-4739 (Contribution égale) (link)

13. Lavoie, S.; Legault, J.; Gauthier, C.; Mshvildadze, V.; Mercier, S.; Pichette, A. Abibalsamins A and B, two new tetraterpenoids from Abies balsamea oleoresin. Org. Lett. 2012, 14, 1504-1507 (link) (supporting information)

12. Gauthier, C.*; Legault, J.; Piochon-Gauthier, M.; Pichette, A. Advances in the synthesis and pharmacological activity of lupane-type triterpenoid saponins. Phytochem. Rev. 2011, 10, 521-544 Contribution invitée (link)

11. Thibeault, D.; Legault, J.; Gauthier, C.; Lavoie, S.; Bouchard, J.; Pichette, A. Acid-catalyzed E-ring expansion and isomerization of 3-acetylbetulin: synthesis of cytotoxic anhydrobetulin saponins. Synth. Commun. 2010, 40, 213-221(link)

10. Gauthier, C.; Legault, J.; Pichette, A. Recent progress in the synthesis of naturally occurring triterpenoid saponins. Mini-Rev. Org. Chem. 2009, 6, 321-344 (link)

9. Gauthier, C.; Legault, J.; Piochon, M.; Lavoie, S.; Tremblay, S.; Pichette, A. Synthesis, cytotoxicity, and haemolytic activity of chacotrioside lupane-type neosaponins and their germanicane-type rearrangement products. Bioorg. Med. Chem. Lett. 2009, 19, 2310-2314 (link)

8. Gauthier, C.; Legault, J.; Girard-Lalancette, K.; Mshvildadze, V.; Pichette, A. Haemolytic activity, cytotoxicity and membrane cell permeabilization of semi-synthetic and natural lupane- and oleanane-type saponins. Bioorg. Med. Chem. 2009, 17, 2002-2008 (link)

7. Gauthier, C.; Legault, J.; Lavoie, S.; Rondeau, S.; Tremblay, S.; Pichette, A. Synthesis and cytotoxicity of bidesmosidic betulin and betulinic acid saponins. J. Nat. Prod. 2009, 72, 72-8 (link)

6. Gauthier, C.; Legault, J.; Rondeau, S.; Pichette, A. Synthesis of betulinic acid acyl glucuronide for application in anticancer prodrug monotherapy. Tetrahedron Lett. 2009, 50, 988-991 (link)

5. Piochon, M.; Legault, J.; Gauthier, C.; Pichette, A. Synthesis and cytotoxicity evaluation of natural α-bisabolol β-D-fucopyranoside and analogues. Phytochemistry 2009, 70, 228-236 (link)

4. Gauthier, C.; Legault, J.; Lavoie, S.; Rondeau, S.; Tremblay, S.; Pichette, A. Synthesis of two natural betulinic acid saponins containing α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranose and their analogues. Tetrahedron 2008, 64, 7386-7399 (link)

3. Thibeault, D.; Gauthier, C.; Legault, J.; Bouchard, J.; Dufour, P.; Pichette, A. Synthesis and structure-activity relationships study of cytotoxic germanicane- and lupane-type 3β-O-monodesmosidic saponins starting from betulin. Bioorg. Med. Chem. 2007, 15, 6144-6157 (Contribution égale) (link)

2. Mshvildadze, V.; Legault, J.; Lavoie, S.; Gauthier, C.; Pichette A. Anticancer diarylheptanoid glycosides from the inner bark of Betula papyrifera. Phytochemistry 2007, 68, 2531-2536 (link)

1. Gauthier, C.; Legault, J.; Lebrun, M.; Dufour, P.; Pichette, A. Glycosidation of lupane-type triterpenoids as potent in vitro cytotoxic agents. Bioorg. Med. Chem. 2006, 14, 6713-6725 (link)