CHRISTOPHE DUPLAIS EcoFoG Lab (Ecology of Guianan Forests) At the Pasteur Institute of French Guiana 23, avenue Pasteur 97306 Cayenne French Guiana, France

Office: +594-594-293-134 Cell: +594-694-236-921 Email: [email protected] https://twitter.com/Chemistophe http://www.ecofog.gf/spip.php?article454

Born in 1980, Caen (Normandy), France POSITIONS (2016) Scientific affiliate at the Field Museum of Chicago. Corrie Moreau Lab http://moreaulab.org/ CNRS Chargé de Recherche first class (CR1) (Oct. 2011 - Present) CNRS Chargé de Recherche (CR2) - research scientist (group leader) EcoFoG Lab, Cayenne, French Guiana, France. 2011 CNRS job application N°16/05, rank: 1 in natural products, chemical ecology 2011 CNRS job application N°12/03, rank: 1 in organic chemistry, catalysis

(2011) Postdoctoral Fellow, University of Paris XIII, France Department of Chemistry, Dr. Gérard Cahiez (CNRS). (2008 - 2011) Postdoctoral Fellow, University of California, Santa Barbara, US Department of Chemistry and Biochemistry, Dr. Bruce Lipshutz. EDUCATION (2016) HDR (Habilitation à Diriger des Recherches) – University of French Guiana (France) Medicinal chemistry against malaria and chemical ecology in French Guiana. (2004 - 2008) Ph.D. – University of Cergy-Pontoise (France) Manganese- and iron-catalyzed cross-coupling reactions and preparation of functionalized organomanganese compounds. Advisor: Dr. Gérard Cahiez (CNRS). (2003 - 2004) M.Sc. – University of Cergy-Pontoise (France) Fine organic chemistry and total synthesis. Master’s thesis project on iron catalysis. Advisor: Dr. Gérard Cahiez (CNRS). (2001 - 2004) Chemical Engineer Engineer school in organic and inorganic chemistry (ESCOM, Cergy-Pontoise, France)

RESEARCH INTERESTS: Organic chemistry - Green catalysis - Natural Products Chemistry - Chemical Ecology Analytical Chemistry - Biochemistry Member of the American Chemical Society (ACS), the American Society of Pharmacognosy (ASP), the International Society of Chemical Ecology (ISCE), Société Chimique de France (SCF), Société de Chimie Thérapeutique (SCT). Christophe Duplais

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PUBLICATIONS (22 publications since 2007; 1073 citations; average citations per item: 48.7; h-index: 15) Peer-Reviewed 22. J. Bossu, J. Beauchêne, Y. Estevez, C. Duplais, B. Clair, "New insights on wood dimensional stability influenced by secondary metabolites: the case of a fast-growing tropical species Bagassa guianensis Aubl." PLoS ONE, 2016, 11, 3, e0150777. 21. L-J. Leba, L. Musset, S. Pelleau, Y. Estevez, C. Birer, S. Briolant, B. Witkowski, D. Menard, M. Delves, E. Legrand, C. Duplais, J. Popovici, "Use of Plasmodium falciparum cultureadapted field isolates for in vitro exflagellation-blocking assay" Malaria Journal, 2015, 14, 214. 20. K. Cottet, Y. Fromentin, M. Kritsanida, R. Grougnet, G. Odonne, C. Duplais, S. Michel, M.-C. Lallemand"Isolation of Guttiferones from renewable parts of Symphonia globulifera by centrifugal partition chromatography Comparative" Planta Med. 2015, 81, 1606. 19. K. Cottet, G. Genta-Jouve, Y. Fromentin, G. Odonne, C. Duplais, O. Laprevote, S. Michel, M.C. Lallemand"Comparative LC-MS-based metabolite profiling of the ancient tropical rainforest tree Symphonia globulifera" Phytochemistry. 2014, 108, 102. 18. T. M. Casella, V. Eparvier, H. Mandavad, A. Bendelac, G. Odonne, C. Duplais, L. S. Espindola, D. Stien"Antimicrobial and cytotoxic secondary metabolites from tropical leaf endophytes: Isolation of antibacterial agent pyrrocidine C from Lewia infectoria SNBGTC2402" Phytochemistry. 2013, 96, 370. 17. B. H. Lipshutz, B. R. Taft, A. R. Abela, S. Ghorai, A. Krasovskiy, C. Duplais, "Catalysis in the Service of Green Chemistry : Nobel Prize-Winning Palladium-Catalyzed Cross-Couplings, Run in Water at Room Temperature" Platinium Metals Rev. 2012, 56, 64. 16. C. Duplais, A. Krasovskiy, B. H. Lipshutz, "Organozinc Chemistry Enabled by Micellar Catalysis. Pd-Catalyzed Cross-Couplings Between Alkyl and Aryl Bromides in Water at Room Temperature" Organometallics, 2011, 30, 6090. 15. B. H. Lipshutz, S. Ghorai, A. R. Abela, R. Moser, T. Nishikata, C. Duplais, A. Krasovskiy, R. D. Gaston, R. C. Gadwood "TPGS-750-M : A Second-Generation Amphiphile for MetalCatalyzed Cross-Couplings in Water at Room Temperature" J. Org. Chem. 2011, 76, 4379. 14. A. Krasovskiy, I. Thomé, J. Graff, V. Krasovskaya, P. Konopelski, C. Duplais, B. H. Lipshutz, "Cross-Couplings of Alkyl Halides with Heteroaromatic Halides, in Water at Room Temperature" Tetrahedron Lett. 2011, 52, 2203. 13. A. Krasovskiy, C. Duplais, B. H. Lipshutz, "Stereoselective Negishi-like Couplings Between Alkenyl and Alkyl Halides in Water at Room Temperature" Org. Lett. 2010, 12, 4742.

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12. B. H. Lipshutz, A. R. Abela, Z. V. Boskovic, T. Nishikata, C. Duplais, A. Krasovskiy, "Greening Up : Cross-Coupling Chemistry" Top. Catal. 2010, 53, 985. 11. C. Duplais, A. J. Forman, B. A Baker, B. H. Lipshutz, "UC Pd. A New Form of Pd/C for Sonogashira Couplings" Chem. Eur. J. 2010, 16, 3366. 10. C. Duplais, A. Krasovskiy, Alina Wattenberg, B. H. Lipshutz, "Cross-Couplings Between Benzylic and Aryl Halides ‘‘on Water.’’ Synthesis of Diarylmethanes" Chem. Commun. 2010, 562. Chem. Commun Top 10 most read articles in January 2010. 9.

A. Krasovskiy, C. Duplais, B. H. Lipshutz, "Zn-Mediated, Pd-Catalyzed Cross-Couplings in Water at Room Temperature Without Prior Formation of Organozinc reagents" J. Am. Chem. Soc. 2009, 131, 15592. J. Am. Chem. Soc.Top 10 most read articles in October 2009. C&EN News, 2009, 87, 43, 6.

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G. Cahiez, C. Duplais, J. Buendia, "The Chemistry of Organomanganese Compounds" Chem. Rev. 2009, 109, 1434.

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G. Cahiez, C. Duplais, J. Buendia, "Manganese-Catalyzed Oxydative Cross-Couplings of Grignard Reagents Using Oxygen as Oxidant" Angew. Chem. Int. Ed. 2009, 48, 6731.

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G. Cahiez, C. Chaboche, C. Duplais, A. Moyeux, "A New Efficient Catalytic System for the Chemoselective Cobalt-Catalyzed Cross-Coupling of Aryl Grignard Reagents with Primary and Secondary Alkyl Bromides" Org. Lett. 2009, 11, 277. Synfacts, 2009, 4, 425.

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G. Cahiez, C. Chaboche, C. Duplais, A. Gulianni, A. Moyeux, "Cobalt-Catalyzed CrossCoupling Reaction Between Functionnalized Primary and Secondary Alkyl Halides and Aliphatic Grignard Reagents" Adv. Synth. Catal. 2008, 350, 1484.

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G. Cahiez, A. Moyeux, J. Buendia, C. Duplais, "Manganese- or Iron-Catalyzed Homocoupling of Grignard Reagents Using Atmospheric Oxygen as an Oxidant" J. Am. Chem. Soc. 2007, 129, 13788. J. Am. Chem. Soc. Top 10 most read articles in December 2007.

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G. Cahiez, C. Duplais, A. Moyeux, "Iron-Catalyzed Alkylation of Alkenyl Grignard Reagents" Org. Lett. 2007, 9, 3253. Synfacts 2007, 11, 1197.

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G. Cahiez, V. Habiak, C. Duplais, A. Moyeux, "Iron-Catalyzed Alkylations of Aromatic Grignard Reagents" Angew. Chem. Int. Ed. 2007, 46, 4364. Synfacts 2007, 8, 851.

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C. Duplais, F. Bures, I. Sapountzis, T. J. Korn, G. Cahiez, P. Knochel, "An Efficient Synthesis of Diaryl Ketones by Iron-Catalyzed Arylation of Aroyl Cyanides" Angew. Chem. Int. Ed. 2004, 43, 2968. Book Chapters

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A-M Cortesero, M. Profitt, C. Duplais, F. Viard, "Chemical ecology: an integrative and experimental science". In : A. G. Bagnères, M. Hossaert-McKey, editors, New Advances in Chemical Ecology. Coll. ISTE-WILEY. 2016. DOI: 10.1002/9781119329695.ch2 1. G. Cahiez, C. Duplais, "Iron-Catalyzed Reactions of Grignard Reagents", The chemistry of organomagnesium compounds (Ed.: Z. Rappoport, I. Marek), Wiley, Chichester, 2008. Manuscripts Submitted and In Preparation R. Duval, C. Duplais, (Submitted). "Fluorescent natural products as probes and tracers in biology". In review at Natural Products Reports. L-J. Leba, J. Popovici, Y. Estevez, S. Pelleau, E. Legrand, L. Musset, C. Duplais, (Submitted). "Contrasted antiplasmodial activities of triarylmethane analogues Brilliant Green, Green S and Patent Blue V against Plasmodium falciparum asexual and sexual stages". In preparation for International Journal for Parasitology: drugs and drug resistance. C. Birer, N. Tysklind, L. Zinger, C. Duplais. "Comparative analysis of DNA extraction protocols to assess cuticular bacterial diversity of ants". In preparation for Molecular Ecology Resources. C. Flora, Y. Estevez, N. Amusant, C. Duplais. "qNMR spectroscopy, IR- and NIRS spectrometry comparative methods to predict wood natural durability: the case of Dicorynia guianensis in French Guiana". In preparation for Phytochemistry. A. Touchard, I. Boulogne, M. de Waard, R. Béroud, J. Orivel, A. Dejean, C. Duplais. "Heterodimeric disulfite peptide with insecticide activity from the venom of the Amazonian ants Pseudomyrmex penetrator". In preparation for Toxicon. INVITED TALK AND CONFERENCE 8.

Corrie Moreau lab, Field Museum of Chicago, USA, 2016.

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Naomi Pierce lab, Harvard University, USA, 2016.

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32rd Annual Meeting of the International Society of Chemical Ecology (ISCE), Brazil, 4-8 July 2016.

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School of Pharmacy, University of Brazilia, Brazil, 2014.

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3ème Symposium francophone de Synthèse totale, School of Pharmacy, Montpellier, France, 2014.

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Novartis, Emeryville, USA, 2014.

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Journées de Chimie Organique (JCO), Ecole Polytechnique, Paris, France, 2010.

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C. Duplais, C. Kofink, P. Knochel, G. Cahiez, DFG-CNRS Evaluation Worshop, Böhn, Allemagne, 2006.

AWARDS AND HONORS - 2011 Presidential Green Chemistry Award: Bruce Lipshutz. C. Duplais awarded as coworker, Washington, 2011. - Oral Communication Award: Journées de Chimie Organique, (JCO), Ecole Polytechnique, France, 2010. - Poster Award: 15th IUPAC Symposium on Organometallic Chemistry Directed Towards Organic Synthesis (OMCOS), Glasgow, 2009. ADVISORY BOARDS: 01/2015: Member of the Scientific Council of Laboratoire d’Excellence CEBA (Center for the study of Amazonian Biodiversity). (12 M Grant from the French National Research Agency (ANR) for 8 years (2011-2019), 6 labs in French Guiana, 6 labs in France) 01/2015: Elected member of the Board of Directors at the University of French Guiana GRANTS AND FUNDING Labex CEBA 2015, Project: DILATE (Coord. C. Baraloto, EcoFoG/Florida International University): 20 k€ Diversity of latex in French Guianan trees Partners: UMR8172 EcoFoG, University of Florida, UMR5629 LCPO (Bordeaux) CNRS - PEPS Interdisciplinaire ExoMod 2013-2014, Project: DefANTS (Coord. C. Duplais): 18 k€/year Biodiversity and distribution of cuticular microbiota of Guianan ants and bio-evaluation of associated metabolites Partners: UMR8172 EcoFoG, UMR8076 BioCIS (Châtenay-Malabry), UMR5174 EDB (Toulouse), IPG (Guyane). Labex CEBA 2013-2014, Project: FUN CHEM (Coord. C. Duplais & D. Stien (LOMIC): 100 k€/year Functional Chemodiversity Partners: UMR8172 EcoFoG, UPR2301 ICSN (Gif-sur-Yvette), UMR8076 BioCIS (ChâtenayMalabry), UMR5174 EDB (Toulouse), IPG (Guyane), UMR AMAP (Montpellier), UMR LOMIC (Banuyls), USR3456 CNRS-Guyane. Labex CEBA 2014, Project: AntPep (Coord. A. Dejean (EcoFoG) & C. Duplais): 20 k€ Ant nesting habits impact on venom peptide activities Partners: UMR8172 EcoFoG, Start-up Smartox.

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CNRS - DEFI Interdisciplinaire Enviromics 2013-2016, Project: AERA (Coord. G. GentaJouve, University of Paris V): 27 k€/year Analysis of the evolutive response of tropical trees: combining genomics and metabolomics Partners: UMR8638 Paris Descartes, UMR8172 EcoFoG, UMR518 INRA (AgroParisTech) Pasteur Institute, Project ACIP 2013-2014, (Coord. E. Legrand, IPG): 30 k€/year. Setting an experimental platform to identify new therapeutic and transmission-blocking molecules from Amazonian natural substances to control Plasmodium falciparum malaria Partners: UMR8172 EcoFoG, IPG, Institut Pasteur du Cambodge, Fiocruz (Brésil) Labex CEBA 2013, Projet VisualFACT (Coord. C. Duplais): 8 k€ Is the visual fluorescence a relevant signal in the communication between Mimosa pudica and Ministrymon azia: an interspecific experimental study Partners: UMR8172 EcoFoG, UMR8531 PPSM (Cachan), UMR8218 ACTE (Paris I). Ph.D Fundings: Ph.D. CNRS fellowship (2013-2017) for Caroline Birer Ph.D. University of French Guiana fellowship (2014-2018) for Claudiane Flora Postdoctoral Fundings: CNRS fellowship (poste rouge) for C. Duplais, University of Paris XIII. Zymes llc. Fellowship for C. Duplais, University of California, Santa Barbara. TEACHING EXPERIENCE Course in organic chemistry (42h per year, 2012-2014) entitled "Organic chemistry: from the synthesis of molecules to drug development" for B.Sc. students at the University of French Guiana, France. Course in analytical chemistry (35h per year, 2012-2014) entitled "NMR spectrometry structural determination " for B.Sc. students University of French Guiana, France. Course in pharmacological chemistry (20h, 2013) entitled "Molecules and Medicines" for B.Sc. and Ph.D. students Federal University of Amapa, Brazil. MENTORING ACTIVITIES Postdoctoral researchers: - Jean Popovici (now researcher at the Pasteur Institute of Cambodia): 2012–2013 - Louis-Jérôme Leba 2012-2013 (now Assistant Professor in biology at the University of French Guiana): - Isabelle Boulogne 2014 (now Assistant Professor in biology at the University of Rouen, France) Ph.D. graduate students: - Caroline Birer (University of French Guiana, CNRS Fellowship) thesis advisor: 2013–present - Claudiane Flora (University of French Guiana, CNRS Fellowship) thesis advisor: 2014–present Undergraduate students: - Joan Balmot (March-June 2016), M.Sc in tropical ecology, University of Montpellier Christophe Duplais

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- Giovany Marie-Rose (April-May 2016), B.Sc. in biology and chemistry, University of French Guiana - Sacha Cataldo (April-May 2015), B.Sc. in biology and chemistry, University of French Guiana - Marie-Claire Izeros (April-May 2014), B.Sc. in biology and chemistry, University of French Guiana - Pierre Freyre (Janvier-Juin 2013), M.Sc in tropical ecology, University of French Guiana BIOGRAPHIC SKETCH: Christophe Duplais is a chemical engineer (Ph.D., ESCOM, 2004) who studied for 7 years organometallic chemistry, green catalysis and crosscouplings under the supervision of outstanding mentors: undergraduate project with Paul Knochel (LMU, Munich), PhD with Gérard Cahiez (Chimie ParisTech), postdoctoral studies with Bruce Lipshutz (UC Santa Barbara). In 2011 he obtained a CNRS position in natural products chemistry and joined the EcoFoG lab, a research unit in ecology and evolution in French Guiana. Since then he attempts to combine methods in analytical chemistry and molecular ecology to decipher the biosynthetic pathways of natural products in an evolutionary context. Currently his research interests focus on (i) the impact of bacteria in ant evolution, (ii) the impact of latex in plant evolution, (iii) the mechanism of heartwood formation in tropical woods.

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