Areas of expertise
Chemistry of carbohydrates and natural products
- Full Professor, Institut national de la recherche scientifique (INRS)
- Adjunct Professor, Université du Québec à Chicoutimi (UQAC)
- Member of the INRS-UQAC Joint Research Unit in Sustainable Health
- Research group website
Armand-Frappier Santé Biotechnologie Research Centre
531 des Prairies Blvd.
Laval, Quebec H7V 1B7
Canada
Research interests
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 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):
- Manmode, S.; Hussain, N.; Gamboa Marin, O. J.; Kato, A.; Veytia-Bucheli, J. I.; Vincent, S. P.; Gauthier, C.* Thioarylation of 6-amino-2,3,6-trideoxy-D-manno-oct-2-ulosonic acid (iminoKdo): access to 3,6-disubstituted picolinates and mechanistic insights. Chem. Eur. J. 2024, 30, e202303940 (link) (invited contribution)
- 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)
- 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)
Team
Dr. Matteo Cattin
(Postdoc, 2024-present)
Dr. Surabhi Gupta
(Postdoc, 2023-present)
Seyedehsheida Moghadasiboroujerdi
(MSc student, 2022-present)
Joseph Nganga
(PhD student, 2023-present)
Dr. Maude Cloutier
(MSc then PhD student then postdoc, 2018-present)
Emmanilo Delar
(M2 then PhD student, 2019-present)
Oscar Javier Gamboa Marin
(MSc then PhD student, 2019-present)
Yasmine Adda-Bouchard
(MSc student, 2021-present)
Sylia Sassane
(MSc student, 2024-present)
Dr. Charles Gauthier completed his PhD in natural products chemistry at the Université du Québec à Chicoutimi (2008), followed by postdoctoral fellowships in carbohydrate chemistry at the Institut Pasteur in Paris (2010) and in chemobiology at University of Oxford in United Kingdom (2011). After a stint as Maître de Conférences at the Université de Poitiers in France (2011-2016), Dr. Gauthier joined the Centre Armand-Frappier Santé Biotechnologie of the Institut national de la recherche scientifique (INRS) as Assistant Professor in 2016. He was promoted to the rank of Associate Professor in 2020 and Full Professor in 2023. Since 2022, he has been co-director of the Unité mixte de recherche (UMR) INRS-UQAC en santé durable. His research program focuses on the synthesis of microbial glycans for the development of prophylactic and therapeutic approaches. Dr. Gauthier has published over 55 peer-reviewed papers and book chapters since the start of his career, and has supervised/co-supervised the work of over 55 students, trainees, and postdocs. Dr. Gauthier’s research program is funded by several national and international granting agencies, including NSERC, CIHR, NIH, and the Pasteur Network. He has received FRQS salary support as a Junior 2 and Senior Scholar. Dr. Gauthier is an active member of several national and international learned societies, including Oxford University’s VALIDATE network, GlycoNet, CRIPA, RISUQ, CISD, and CERMO-FC.
- Total synthesis of natural products
- Development of synthetic antimicrobial glycoconjugate vaccines
- Development of compounds interacting with sugar-processing enzymes
- Synthesis of saponins as antiviral and immunostimulatory agents
- Isolation of bioactive natural products
2023: FRQS Research Scholars Senior
2022: RSC Advances Outstanding Reviewer for 2021
2021: RSC Advances Outstanding Reviewer for 2020
2018-2020: FRQS Research Scholars Junior 2
2015-2016: PhD Supervising and Research Bonus, Conseil National des Universités (CNU)
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
62. Delar, E.; Tigherghar, Y.; Girard, L.; Haddad, M.; Ramassamy, C.; Legault, J.; Gauthier, C.* Synthesis and pharmacological evaluation of nature-inspired phenacyl glycosides. 2024, in preparation
61. Cao, J.; Veytia-Bucheli, J. I.; Liang, L.; Wouters, J.; Silva-Rosero, I.; Bussmann, J.; Gauthier, C.; De Bolle, X.; Groleau, M.-C.; Déziel, E.; Vincent, S. P. Exploring fluorinated heptose phosphate analogues as inhibitors of HldA and HldE, key enzymes in the biosynthesis of lipopolysaccharides. 2024, submitted.
60. Verma, N.; Cloutier, M.; Clément, D.; Gauthier, C.* Synthesis of α-D-idose pentaacetate from β-D-glucose pentaacetate via Paulsen acetoxonium rearrangement. In: Carbohydrate Chemistry: Proven Synthetic Methods, Volume 6, Ed.: Giguère, D.; Vincent, S. P.; 2024, CRC Press, accepted (invited contribution)
59. Gupta, S.; Gauthier, C.* 1-Thiosugars: from synthesis to applications. Curr. Org. Chem. 2024, accepted (invited contribution)
58. Sylla, B.; Jost, G.; Lavoie, S.; Legault, J.; Gauthier, C.*; Pichette, A. Synthesis and cytotoxicity evaluation of D– and L-sugar-containing mono- and bidesmosidic ursane-type saponins. Bioorg. Med. Chem. 2024, 106, 117737 (link)
57. Manmode, S.; Hussain, N.; Gamboa Marin, O. J.; Kato, A.; Veytia-Bucheli, J. I.; Vincent, S. P.; Gauthier, C.* Thioarylation of 6-amino-2,3,6-trideoxy-D-manno-oct-2-ulosonic acid (iminoKdo): access to 3,6-disubstituted picolinates and mechanistic insights. Chem. Eur. J. 2024, 30, e202303904 (link) (invited contribution)
56. Gauthier, C.*; Lavoie, S.; Kubicki, S.; Piochon, M.; Cloutier, M.; Dagenais, M.; Groleau, M.-C.; Pichette, A.; Thies, S.; Déziel, E. Structural characterization of a nonionic rhamnolipid from Burkholderia lata. Carbohydr. Res. 2024, 535, 108991 (link)
55. Deimel, L. P.; Xue, X.; Khan, A.; Moynie, L.; Buchanan, C. J.; Sun, G.; McBride, R.; Schuster, H.; Gauthier, C.; Saliba, R.; Leonavicus, K.; Minall, L.; Bort, G.; Russell, R. A.; Sezgin, E.; Paulson, J. C.; Anthony, D. C.; Baldwin, A. J.; Naismith, J.; Schiffner, T.; Davis, B. G.; Sattentau, Q. J. Engineered display of ganglioside-sugars on protein elicits a clonally and structurally constrained B cell response. bioRxiv 2023 (link)
54. Verma, N.; Cloutier, M.; Gauthier, C.* Thioglycoside-based glycosylations in oligosaccharide synthesis. In: Synthetic Strategies in Carbohydrate Chemistry, 1st edition, Ed.: Tiwari, V. K.; Elsevier, 746 pp, 2023 (link) (invited contribution)
53. Gamboa Marin, O. J.; Heis, F.; Gauthier, C.* Synthesis of immunostimulatory saponins: a sweet challenge for carbohydrate chemists. Carbohydr. Res. 2023, 530, 108851 (invited contribution) (link)
52. Saïdi, F.; Gamboa Marin, O. J.; Veytia-Bucheli, J. I.; Vinogradov, E.; Ravicoularamin, G.; Jolivet, N. Y.; Kezzo, A. A.; Ramirez Esquivel, E.; Panda, A.; Sharma, G.; Vincent, S. P.; Gauthier, C.*; Islam, S. T. Evaluation of azido 3-deoxy-D-manno-oct-2-ulosonic acid (Kdo) analogues for click chemistry-mediated metabolic labelling of Myxococcus xanthus DZ2 lipopolysaccharide. ACS Omega 2022, 7, 34997-35013 (link)
51. 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)
50. 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, 86, 15357-15375 (link) (supporting information)
49. Schellenberger, R.; Crouzet, J.; Nickzad, A.; Shu, L.-J.; Kutschera, A.; Gerster, T.; Borie, N.; Dawid, C.; Cloutier, M.; Villaume, S.; Dhondt-Cordelier, S.; Hubert, J.; Cordelier, S.; Mazeyrat-Gourbeyre, F.; Schmid, C.; Ongena, M.; Renault, J. H.; Haudrechy, A.; Hofmann, T.; Baillieul, F.; Clément, C.; Zipfel, C.; Gauthier, C.; Déziel, E.; Ranf, S.; Dorey, S. Bacterial rhamnolipids and their 3-hydroxyalkanoate precursors activate Arabidopsis innate immunity through two independent mechanisms. Proc. Natl. Acad. Sci. USA 2021, 118, e2101366118 (link)
48. Hussain, N.; Delar, E.; Piochon, M.; Groleau, M.-C.; Tebbji, F.; Sellam, A.; Déziel, E.; Gauthier, C.* Total synthesis of the proposed structures of gladiosides I and II. Carbohydr. Res. 2021, 507, 108373 (link) (issue) (invited contribution)
47. 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) (supporting information)
46. Muru, K.; Gauthier, C.* Glycosylation and protecting group strategies towards the synthesis of saponins and bacterial oligosaccharides: a personal account. Chem. Rec. 2021, 21, 2990-3004 (link) (invited contribution)
45. Cloutier, M.; Gauthier, C.* Progress towards the development of glycan-based vaccines against campylobacteriosis. ACS Infect. Dis. 2021, 7, 969-986 (link) (issue) (invited contribution)
44. Tremblay, T.; Carpentier, A.; Giguère, D.; Gauthier, C. Click approach to lipoic acid glycoconjugates. In: Carbohydrate Chemistry: Proven Synthetic Methods, Volume 5, Ed.: Kosma, P.; Wrodnigg, T. M.; Stütz, A.; CRC Press, 280 pp, 2020 (link) (invited contribution)
43. 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, 86, e01452-20 (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) (invited contribution)
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) (invited contribution)
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 (link) (supporting information) (invited contribution)
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 (link) (invited contribution)
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 (link) (invited contribution)
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)
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