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49. Bacterial rhamnolipids and their 3-hydroxyalkanoate precursors activate Arabidopsis innate immunity through two independent mechanisms. Schellenberger, R.; Crouzet, J.; Nickzad, A.; 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. 2021, revision submitted (preprint)

48. Total synthesis of the proposed structures of gladiosides I and II. Hussain, N.; Delar, E.; Piochon, M.; Groleau, M.-C.; Tebbji, F.; Sellam, A.; Déziel, E.; Gauthier, C.* Carbohydr. Res. 2021, in press (invited contribution for the special issue on "Microbial glycans: the chemistry behind and the biology beyond") (link) (issue)

gladiosides

47. Total synthesis, isolation, surfactant properties, and biological evaluation of ananatosides and related macrodilactone-containing rhamnolipids. 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.* Chem. Sci. 2021, 12, 7533-7546 (link) (supporting information) (preprint)

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

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

Chem_Rec_2021

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

ACS_2020

44. Click approach to lipoic acid glycoconjugates. Tremblay, T.; Carpentier, A.; Giguère, D.; Gauthier, C. In: Carbohydrate Chemistry: Proven Synthetic Methods, Volume 5, Ed.: Kosma, P.; Wrodnigg, T. M.; Stütz, A.; 2020, CRC Press, 344 pp (invited contribution) (link)

Carbohydrate Chemistry : Proven Synthetic Methods, Volume 5 book cover

43.  Burkholderia thailandensis methylated hydroxy-alkylquinolines: biosynthesis and antimicrobial activity in co-cultures. 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. Appl. Environ. Microbiol. 2020, 86, e01452-20 (preprint) (link)

Home | Applied and Environmental Microbiology

42. Total synthesis of 6-amino-2,6-dideoxy-α-Kdo from D-mannose. Gamboa Marin, O. J.; Hussain, N.; Ravicoularamin, G.; Ameur, N.; Gormand, P.; Sauvageau, J.; Gauthier, C.* Org. Lett. 2020, 22, 5783-5788 (link) (supporting information)

OL_2020

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

JNP_2020

40. Modulation of bacterial multicellularity via spatio-specific 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. PLoS Biol. 2020, 18, e3000728 (link)

Institut Sophia Agrobiotech - PLOS Biology

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.; 2020, Elsevier, 700 pp (invited contribution) (link)

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

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

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

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 Adv. 2019, 9, 39743-39757 (link) (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.* Org. Biomol. Chem. 2019, 17, 8878-8901 (invited contribution for the web themed issue on "Glycosylation: New methodologies and applications") (link) (supporting information) (issue)

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. Carbohydr. Res. 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. Org. Lett. 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.* Nat. Prod. Rep. 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)

Résultats de recherche d'images pour « PLOS ONE »

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.* Nat. Commun. 2017, 8, 115 (open access) (supporting information) (peer review file) (merged file)

Nature Communications

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.; Legault, J. BMC Complem. Altern. Med. 2017, 17, 123 (open access) (peer review file)

BMC

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.* J. Org. Chem. 2016, 81, 10585-10599 ("Featured Article" & Cover Page of Issue #22) (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. Bioorg. Med. Chem. 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. Magn. Reson. Chem. 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. J. Nat. Prod. 2015, 78, 2896-2907 (†These authors contributed equally) (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.* J. Org. Chem. 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 Chem. Biol. 2015, 10, 2295-2302 (link) (supporting information) (Highlighted in www.glycopedia.eu)

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. J. Nat. Prod. 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. Org. Lett. 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. Org. Lett. 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. Carbohydr. Res. 2014, 398, 80-89 (*These authors contributed equally) (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. Org. Biomol. Chem. 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.* J. Org. Chem. 2014, 79, 4615-4634 (link) (supporting information) (video)

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. P.; Blériot, Y. Carbohydr. Chem. 2014, 40, 418-444 (Invited contribution in the memory of Pr André Lubineau) (link)

CC_2014

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

1860-5397-9-150

15. Structural studies of the O-acetyl containing O-antigen from a Shigella flexneri serotype 6 strain and synthesis of oligosaccharide fragments thereof. Chassagne, P.; Fontana, C.; Guerreiro, C.; Gauthier, C.; Phalipon, A.; Widmalm, G.; Mulard, L. A. Eur. J. Org. Chem. 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. Bioorg. Med. Chem. Lett. 2012, 22, 4735-4739 (†These authors contributed equally) (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. Org. Lett. 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. Phytochem. Rev. 2011, 10, 521-544 (Invited contribution for Special Issue: New Trends in Saponins) (link)

PR_2011

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. Synth. Commun. 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-Rev. Org. Chem. 2009, 6, 321-344 (link)

Journal Image

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. Bioorg. Med. Chem. Lett. 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. Bioorg. Med. Chem. 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. J. Nat. Prod. 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 Lett. 2009, 50, 988-991 (link)

image 


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)

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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. Bioorg. Med. Chem. 2007, 15, 6144-6157 (†These authors contributed equally) (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. Bioorg. Med. Chem. 2006, 14, 6713-6725 (link)

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PATENTS

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

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

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

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