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)
- Regular member of the INRS-UQAC Joint Research Unit | Sustainable Health
- Co-chair of the Joint Management Committee of the INRS-UQAC Joint Research Unit | Sustainable Health
- Research group website
Armand-Frappier Santé Biotechnologie Research Centre
531 des Prairies Blvd.
Laval, Quebec H7V 1B7
Canada
Research interests
Carbohydrates, long viewed primarily as energy sources or structural components, are now recognized as essential mediators in a wide range of fundamental biological processes. They actively participate in cell-cell recognition, immune regulation, microbial adhesion, and the progression of diseases, including infectious and oncological conditions. This functional role stems directly from their remarkable structural diversity, enabled by multiple hydroxylation sites, stereochemical configurations, and glycosidic linkage patterns, a complexity that far exceeds that of nucleic acids or proteins. While this molecular richness gives glycoconjugates exceptional potential in biology and therapeutics, it also poses a major challenge for their isolation from natural sources, where they typically occur as heterogeneous mixtures at low abundance.
Synthetic chemistry therefore emerges as an indispensable approach to access homogeneous, well-defined glycomolecules free from biological contaminants. It is at this strategic intersection of organic chemistry, chemical biology, and translational pharmacology that my research program at INRS is situated.
Our work is guided by two key objectives:
- Advancing carbohydrate chemistry by developing efficient and stereoselective synthetic routes to natural glycoconjugates and their functional mimetics;
- Translating these chemical advances into biomedical solutions, including glycoconjugate vaccines, safe adjuvants, novel antimicrobials, and sustainable surfactants derived from natural molecules.
Our approach integrates molecular design, synthetic innovation, and functional evaluation through close collaborations with experts in microbiology, immunology, and pharmacology. In recent years, we have developed efficient syntheses of oligosaccharides from multidrug-resistant bacteria, paving the way for targeted vaccines against high-priority pathogens. We design and evaluate mimetics of immunostimulatory saponins, including QS-21 analogs bearing Lewis-X motifs, capable of interfering with dendritic cell lectins such as DC-SIGN involved in HIV transmission (Gamboa Marin et al., Chem. Eur. J. 2025ab). Our work on aminated Kdo derivatives has enabled access to novel heterocyclic scaffolds with important mechanistic implications (Manmode et al., Chem. Eur. J. 2024), while our study of C7 epimerization in idopyranosides provided new insights into the conformational flexibility of rare sugars (Cloutier et al., J. Org. Chem. 2022). The total synthesis of the ananatosides, naturally occurring macrodilactone-containing rhamnolipids, revealed promising surfactant properties and biological activities, highlighting the potential of these glycolipids as multifunctional agents (Cloutier et al., Chem. Sci. 2021).
Supported by a strong network of national and international collaborations, my team is committed to transforming carbohydrate chemistry into a strategic driver of health innovation. By bridging fundamental excellence with biomedical relevance, we aim to lay the foundation for a new generation of glycan-based therapeutics designed to address pressing global challenges in antimicrobial resistance, inflammatory diseases, and immunotherapy.
For more information, please visit our research group website.
Most Significant Recent Publications (5):
- Gamboa Marin, O. J.; Ng, K.; Verma, N.; Yapi, A. G. F.; Pantophlet, R.; Gauthier, C.* Lewis-X-containing triterpenoid saponins inhibit DC-SIGN- and L-SIGN-mediated transfer of HIV-1 infection. Chem. Eur. J. 2025, e202500993 (link)
- Gamboa Marin, O. J.; Adda-Bouchard, Y.; Sylla, B.; Verma, N.; Charpentier, T.; Huber, M.; Lopez, G.; Pichette, A.; Lamarre, A.; Gauthier, C.* Immunological and toxicological assessment of triterpenoid saponins bearing Lewis-X and QS-21-based trisaccharides. Chem. Eur. J. 2025, e202500994 (link)
- 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)
Team
Kameshwar Prasad
(Postdoc, 2025-présent)
Matteo Cattin
(Postdoc, 2024-present)
Surabhi Gupta
(Postdoc, 2023-present)
Joseph Nganga
(PhD student, 2023-present)
Eddy Goyer
(postdoc, 2025-present)
Hoang Danh Nguyen
(PhD student, 2025-present)
Sylia Sassane
(MSc student, 2024-present)
Sarah van den Bussche
(MSc student, 2025-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 65 peer-reviewed papers and book chapters since the start of his career, and has supervised/co-supervised the work of over 60 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
70. Piochon, M.; Mshvildadze, V.; Legault, J.; Gauthier, C.*, Pichette, A. Phytochemical and ethnopharmacological insights into medicinal plants of Nitassinan. 2025, under review
69. Duchateau, S.; Borrego, C.; Verdelet, S.; Dorey, S.; Aziz, A.; Dhont-Cordelier, S.; Gauthier, C.; Déziel, E.; Cordelier, S.; Crouzet, J. Growth-promoting and biocontrol features of Pantoea ananatis BRT175 in tomato. 2025, under review
68. Gupta, S.; Gauthier, C.* Cross-coupling reactions: a powerful tool in carbohydrate chemistry. In: Cross-Coupling Reactions, 1st edition, Ed.: Varma, R. S.; De Gruyter Brill, 2025, under review (invited contribution)
67. Delar, E.; Cloutier, M.; Gauthier, C.* Exploring anthocyanins and their derivatives: therapeutic relevance, synthesis, and physicochemical properties. In: Studies in Natural Products Chemistry (Bioactive Natural Products), 1st edition, Ed.: Atta-ur-Rahman; Elsevier, 2025, accepted (invited contribution)
66. 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.; 2025, CRC Press, accepted (invited contribution)
65. Cloutier, M.; Verma, N.; Douchez, I.; Gauthier, C.* Intra- and intermolecular glycosylation of D-idopyranosyl and 6-deoxy-D–ido-heptopyranosyl donors: toward the repeating unit of Campylobacter jejuni HS:4c capsular polysaccharide. Eur. J. Org. Chem. 2025, accepted
64. Gamboa Marin, O. J.; Verma, N.; Cloutier, M.; Gauthier, C.* Synthesis of rhamnose-modified Lewis-X-containing saponins. Eur. J. Org. Chem. 2025, 28, e202500285 (link) (invited contribution)
63. Gamboa Marin, O. J.; Ng, K.; Verma, N.; Yapi, A. G. F.; Pantophlet, R.; Gauthier, C.* Lewis-X-containing triterpenoid saponins inhibit DC-SIGN- and L-SIGN-mediated transfer of HIV-1 infection. Chem. Eur. J. 2025, 31, e202500993 (link)
62. Gamboa Marin, O. J.; Adda-Bouchard, Y.; Sylla, B.; Verma, N.; Charpentier, T.; Huber, M.; Lopez, G.; Pichette, A.; Lamarre, A.; Gauthier, C.* Immunological and toxicological assessment of triterpenoid saponins bearing Lewis-X and QS-21-based trisaccharides. Chem. Eur. J. 2025, 31, e202500994 (link)
61. Gupta, S.; Gauthier, C.* 1-Thiosugars: from synthesis to applications. Curr. Org. Chem. 2025, 29, 359 (link) (invited contribution to the special issue “Chemistry and biology of carbohydrates”)
60. Delar, E.; Tigherghar, Y.; Girard, L.; Haddad, M.; Ramassamy, C.; Legault, J.; Gauthier, C.* Synthesis and pharmacological evaluation of nature-inspired phenacyl glycosides. Carbohydr. Res. 2024, 545, 109281 (link) (invited contribution to the special issue in honor of Prof. Richard R. Schmidt’s 90th anniversary)
59. 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. Bioorg. Chem. 2024, 153, 107767 (link)
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 (link) (invited contribution)
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 to the special issue “Microbial glycans: the chemistry behind and the biology beyond”)
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 to the special issue “Recent advances in carbohydrate chemistry”)
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 to the special issue “Gut pathogens”)
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 to the special issue “Glycosylation: new methodologies and applications”)
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 to the special issue in memory of Prof. André Lubineau)
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 to the special issue “New trends in saponins”)
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)