Charles Gauthier

Training openings for students or interns

Areas of expertise

Chemistry of carbohydrates and natural products

  • INRS Professor

Phone
450-687-5010 poste 8886

Fax
450-686-5566

E-mail
charles.gauthier@iaf.inrs.ca

Armand-Frappier Santé Biotechnologie Research Centre

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

See research centre

Interested research topics

Carbohydrates are a class of natu rally occurring compounds involved in important biological processes such as immune response, tumour development and bacterial infections. Pure and structurally well-defined glycans are urgently 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. Two major challenges are still facing carbohydrate chemistry today, i.e. the cumbersome multiple protection/glycosylation steps needed for the synthesis of high molecular weight glycans, and the lack of general procedures for glycosidic bonds formation.

Along these lines, the long-term goals of our research program are three-fold:

  1. the development of novel one-pot protection/glycosylation methodologies aiming at streamlining the synthesis of oligosaccharides and their derivatives;
  2. the development of efficient and stereoselective glycosylation reactions for the synthesis of biologically important glycosidic linkages found in the polysaccharides of pathogenic bacteria; and
  3. the application of these procedures to the total synthesis of complex oligosaccharides and glycolipids in the context of developing vaccines, diagnostics and therapeutic agents.

Dr Charles Gauthier was born in Péribonka (Canada), which is a little town of no more than 500 people in the North of Quebec Province. In 2000, he attended Université du Québec à Chicoutimi (UQAC) to study chemistry at BSc level. After a summer work placement in polymer chemistry (Alcan), he discovered the field of natural products chemistry in LASEVE laboratory. He then pursued his graduate education (MSc and PhD) at UQAC under the guidance of Prof. André Pichette, chemist, and Prof. Jean Legault, clinical pharmacologist. His PhD studies (2005-2008), funded by the Fonds Québécois de Recherche sur la Nature et les Technologies (FQRNT), were focused on the synthesis of lupane-type triterpenoid saponins as a novel class of non-haemolytic anticancer agents. His MSc and PhD results have been published in twelve peer-reviewed papers and two patent applications. In 2009, Charles left the Canada and moved to France to undertake a postdoctoral fellowship (Vasant & Kusum Joshi and Bourses Emile-Roux) at the Institut Pasteur in Paris under the supervision of Dr Laurence Mulard. He worked there on the synthesis of acetylated decasaccharides as mimetic fragments of the Shigella flexneri serotype 2a antigen-O.

The aim of his studies was to prepare a glycoconjugate vaccine in order to prevent shigellosis infections caused by S. flexneri 2a in developing countries. Funded by the FQRNT (2010-2011), he then came to the University of Oxford, UK, to undertake a second postdoctoral position within the Ben Davis group. His research focused on the preparation of chemically modified adenovirus vectors in collaboration with the Dept of Clinical Pharmacology. In September 2011, Charles came back to France and accepted a tenured position of “Maître de Conférences” in organic chemistry at the Université de Poitiers. His research project aiming at developing a semi-synthetic vaccine against melioidosis has been funded by the Agence Nationale de la Recherche Jeunes Chercheuses Jeunes Chercheurs (ANR JCJC) and by the Direction Générale de l’Armement (DGA). He has been an Adjunct Professor at UQAC since May 2012. Charles has published  more than 30 papers in peer-reviewed journals and presented his results in numerous national and international scientific meetings. Since July 2016, Charles is back to the “Belle Province” to start a new academic position as an Assistant Professor at INRS-Institut Armand-Frappier in Laval (Québec), Canada. This research University is the only member in North America of the Institut Pasteur International Network.

2016-present: Assistant Professor, INRS-Institut Armand-Frappier, Laval (Québec), Canada
2012-present: Adjunct Professor, Université du Québec à Chicoutimi, Canada
2011-2016: Maître de Conférences, Université de Poitiers, Institut de Chimie IC2MP, Poitiers, France
2010-2011: Postdoctoral Fellow, University of Oxford, UK, Prof Ben G. Davis
2009-2010: Postdoctoral Fellow, Institut Pasteur, Paris, France, Dr Laurence Mulard
2005-2008: PhD in Natural Products Chemistry, Réseau de l’Université du Québec, Canada (thesis)
2003-2005: MSc in Natural Products Chemistry, Université du Québec à Chicoutimi, Canada (thesis)
2000-2003: BSc in Chemistry, Université du Québec à Chicoutimi, Canada

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 Jeunes Chercheurs 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 (La Société des Fourmis)
1998: Nominated for the Governor General’s Academic Medal

Publications

41. Modulation of bacterial multicellularity via spatiotemporal polysaccharide secretion.
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.
BioRxiv 2020, https://doi.org/10.1101/2020.02.20.957654(preprint)

40. Synthesis and antimicrobial activity of Burkholderia-related 4-hydroxy-3-methyl-2-alkenylquinolones (HMAQs) and their N-oxide counterparts.
Piochon, M.; Coulon, P. M. L.; Caulet, A.; Groleau, M.-C.; Déziel, E.; Gauthier, C.*
ChemRxiv 2020, https://doi.org/10.26434/chemrxiv.11859144.v1 (preprint)

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

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

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

Graphical abstract: Synthesis, cytotoxicity and anti-inflammatory activity of rhamnose-containing ursolic and betulinic acid saponins

 

36. Melioidosis patient serum-reactive synthetic tetrasaccharides bearing the predominant epitopes of Burkholderia pseudomallei and Burkholderia mallei O-antigens.
Cloutier, M.; Delar, E.; Muru, K.; Ndong, S.; Hoyeck, R. R.; Kaewarpai, T.; Chantratita, N.; Burtnick, M. N.; Brett, P. J.; Gauthier, C.*
Organic & Biomolecular Chemistry 2019, 17, 8878-8901

Contribution invitée pour l’édition web thématique “Glycosylation: New methodologies for oligosaccharide and glycoconjugate synthesis and their applications”
(link) (supporting information)

OBC_2019

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

ananatoside

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

Org_Lett_2018

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

Burkholderia

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

31. Deciphering minimal antigenic epitopes associated with Burkholderia pseudomallei and Burkholderia mallei lipopolysaccharide O-antigens.
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.*
Nature Communications 2017, 8, 115
(open access) (supporting information) (peer review file)

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

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

JOC_2016

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

image

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

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

JNP_2015

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

JOC_2015

24. Burkholderia pseudomallei capsular polysaccharide recognition by a monoclonal antibody reveals key details toward a biodefense vaccine and diagnostics against melioidosis.
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. ACS Chemical Biology 2015, 10, 2295-2302
(link) (supporting information)

ACSCB_2015

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

JNP_2015b

22. Synthesis of 1,2-trans-2-acetamido-2-deoxy-homoiminosugars.
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.
Organic Letters 2014, 16, 5516-5519
(link) (supporting information)

OL_2015A

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

OL_2015b

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

image

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

OBC_2014

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

JOC_2014

17. Conformationally restricted glycoside derivatives as mechanistic probes and/or inhibitors of sugar processing enzymes.
Maaliki, C.; Gauthier, C.; Massinon, O.; Sagar, R.; Vincent, S.; Blériot, Y.
In: RSC Specialist Periodical Reports in Carbohydrate Chemistry 2014, 40, 418-444
Invited contribution for special issue in the memory of Pr André Lubineau
(link)

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

1860-5397-9-150

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

EuroJOC

14. Synthesis and cytotoxicity of lupane-type triterpenoid glyceryl esters.
Thibeault, D.; Gauthier, C.; Legault, J.; Bouchard, J.; Gagné, L.; Pichette, A.
Bioorganic & Medicinal Chemistry Letters 2012, 22, 4735-4739 (Contribution égale) (link)

Full-size image (24 K)

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

OL_2012

12. Advances in the synthesis and pharmacological activity of lupane-type triterpenoid saponins.
Gauthier, C.*; Legault, J.; Piochon-Gauthier, M.; Pichette, A.
Phytochemistry Reviews 2011, 10, 521-544
Article invitée pour l’édition spéciale: “New Trends in Saponins”  (link)

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

Graphical Abstract

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

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

image

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

image

7. Synthesis and cytotoxicity of bidesmosidic betulin and betulinic acid saponins.
Gauthier, C.; Legault, J.; Lavoie, S.; Rondeau, S.; Tremblay, S.; Pichette, A.
Journal of Natural Products 2009, 72, 72-81 (link)

JNP_2009

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

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

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

image

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

image

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

image

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

Full-size image (8 K)