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63. 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

62. Delar, E.; Cloutier, M.; Gauthier, C.* Exploring anthocyanins and their derivatives: synthesis, physicochemical properties, and therapeutic potential. In: Studies in Natural Products Chemistry (Bioactive Natural Products), 1st edition, Ed.: Atta-ur-Rahman, Elsevier, 2024, submitted (invited contribution)

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 lipopolysaccharide. 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 for the special issue on "Chemistry and biology of carbohydrates")

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) (SI)


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 (invited contribution) (link) (SI)


56. Gauthier, C.*; Lavoie, S.; Kubicki, S.; Piochon, M.; Cloutier, M.; Dagenais Roy, 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.; 2023, Elsevier, 747 pp (invited contribution) (link)


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) (SI)


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) (SI)


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, 21, 15357-15375 (link) (SI)

JOC 2021

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, e210136118 (link)
Home page - PNAS
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 (invited contribution for the special issue on "Microbial glycans: the chemistry behind and the biology beyond") (link) (issue)


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) (SI) (preprint)

Graphical abstract: Total synthesis, isolation, surfactant properties, and biological evaluation of ananatosides and related macrodilactone-containing rhamnolipids

46. Muru, K.; Gauthier, C.* Glycosylation and protecting group strategies towards the synthesis of saponins and bacterial oligosaccharides: a personal account. Chem. Rec. 2021, 11, 2990-3004 (invited contribution for the special issue on "Recent advances in carbohydrate chemistry") (link)


45. Cloutier, M.; Gauthier, C.*  Progress towards the development of glycan-based vaccines against campylobacteriosis. ACS Infect. Dis. 2021, 7, 969-986 (invited contribution for the special issue on "Gut pathogens") (link) (issue)


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.; 2020, CRC Press, 344 pp (invited contribution) (link)


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 (preprint) (link)

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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) (SI)


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) (SI) (preprint)


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 spatio-specific polysaccharide secretion. PLoS Biol. 2020, 18, e3000728 (link)
Institut Sophia Agrobiotech - PLOS Biology
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.; 2020, Elsevier, 700 pp (invited contribution) (link)

Carbohydrates in Drug Discovery and Development - 1st Edition - ISBN: 9780128166758

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.;  2020, Elsevier, 532 pp (invited contribution) (link)

Recent Trends in Carbohydrate Chemistry - 1st Edition - ISBN: 9780128174678

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 (link) (SI)

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

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 (invited contribution for the web themed issue on "Glycosylation: New methodologies and applications") (link) (SI) (issue)


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) (SI)


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) (SI)


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)

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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) (SI) (peer review file) (merged file)

Nature Communications

30. Lavoie, S.; Côté, I.; Pichette, A.; Gauthier, C.; Ouellet, M.; Nagau-Lavoie, F.; Mshvildadze, V.; 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" & Cover Page of Issue #22) (link) (SI) (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) (SI)


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) (SI)


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 (Equal contribution) (link) (SI)


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) (SI)


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) (SI)


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) (SI)


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) (SI)


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) (SI)


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 (*Equal contribution) (link) (SI)


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) (SI)


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) (SI)


17. Maaliki, C.; Gauthier, C.; Massinon, O.; Sagar, R.; Vincent, S. P.; Blériot, Y. Conformationally restricted glycoside derivatives as mechanistic probes and/or inhibitors of sugar processing enzymes. Carbohydr. Chem. 201440, 418-444 (Invited contribution in the memory of Pr André Lubineau) (link)


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


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 strain and synthesis of oligosaccharide fragments thereof. Eur. J. Org. Chem. 2013, 4085-4106 (link) (SI)


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 (Equal contribution) (link)

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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) (SI)


 Gauthier, C.*; Legault, J.; Piochon-Gauthier, M.; Pichette, A. Advances in the synthesis and pharmacological activity of lupane-type triterpenoid saponins. Phytochem. Rev. 201110, 521-544 (Invited contribution for Special Issue: New Trends in Saponins) (link)


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)

Graphical Abstract

 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)


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, 72-81 (link)


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)

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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 (Equal contribution) (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)

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4. Gauthier, C.; Cloutier, M. Tetrasaccharides for diagnosis, prevention, and treatment of melioidosis and glanders. PCT application 2019, 62/857,346, 71 pp.

3. Mulard, L. A.; Gauthier, C. Novel O-acetylated decasaccharides. European Patent Application 2011, EP-2386563A1, 70 pp (link)

2. Pichette, A.; Legault, J.; Gauthier, C. Bidesmosidic betulin and betulinic acid saponins and uses thereof as antitumor agents. PCT International Patent Application 2010, WO-2010028487, 93 pp (link)

1. Pichette, A.; Legault, J.; Gauthier, C. Triterpene derivatives and uses thereof as antitumor agents or anti-inflammatory agents. Canadian & United States Patent Application 2008, CA-2,586,614 & US-11/924,789, 73 pp (link)