Thierry BRIGAUD 

Professor 



Biological Chemistry, Permanent


bureau
thierry.brigaud@cyu.fr




Site de Cergy


ORCID
https://orcid.org/0000-0003-0932-5971


Research interests


Chiral fluorinated compounds (amino acids, pseudopeptides, amino alcohols, amines, diamines….), synthesis of fluorinated peptides and biological applications (inhibition of amyloid peptides aggregation, nociception, antimicrobial peptides, proteases inhibition…)


https://www.cyu.fr/m-thierry-brigaud
























38 documents







Journal articles29 document




    

  • Thierry Brigaud, Greta Varchi. Editorial: Recent advances in synthetic organic chemistry at the biomedical interface: honoring Professor Iwao Ojima on the occasion of his 80th birthday. Frontiers in Chemistry, 2025, 13, ⟨10.3389/fchem.2025.1721249⟩. ⟨hal-05325129⟩
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  • Julien Pytkowicz, Grégory Chaume, Nathalie Lensen, Evelyne Chelain, Thierry Brigaud. Two decades of fluorine chemistry in Cergy. Comptes Rendus. Chimie, 2024, 27 (G1), pp.353-383. ⟨10.5802/crchim.360⟩. ⟨hal-04823676⟩
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  • Aurélie Honfroy, Jolien Bertouille, Ana-Maria Turea, Thibault Cauwenbergh, Jessica Bridoux, et al.. Fluorinated Peptide Hydrogels Result in Longer In Vivo Residence Time after Subcutaneous Administration. Biomacromolecules, 2024, 25 (10), pp.6666-6680. ⟨10.1021/acs.biomac.4c00872⟩. ⟨hal-04782661⟩
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  • Nathan Picois, Lizeth Bodero, Pierre T Milbeo, Thierry Brigaud, Grégory Chaume. Bimodal use of chiral α‐Trifluoromethylalanine in Aib Foldamers: study of the position impact towards the helical screw‐sense preference. Chemistry - A European Journal, In press, ⟨10.1002/chem.202400540⟩. ⟨hal-04516499⟩
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  • Chloé Cayrou, Astrid Walrant, Delphine Ravault, Karine Guitot, Sylvie Noinville, et al.. Incorporation of CF 3 -pseudoprolines into polyproline type II foldamers confers promising biophysical features. Chemical Communications, In press, ⟨10.1039/D4CC02895C⟩. ⟨hal-04660873⟩
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  • Nathan Picois, Yazid Boutahri, Pierre Milbeo, Chiara Zanato, Nathalie Lensen, et al.. Asymmetric α-Fluoroalkyl-α-Amino Acids: Recent Advances in Their Synthesis and Applications. Molecules, 2024, 29 (6), pp.1408. ⟨10.3390/molecules29061408⟩. ⟨hal-04516441⟩
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  • Jure Gregorc, Nathalie Lensen, Grégory Chaume, Jernej Iskra, Thierry Brigaud. Trifluoromethylthiolation of Tryptophan and Tyrosine Derivatives: A Tool for Enhancing the Local Hydrophobicity of Peptides. Journal of Organic Chemistry, 2023, 88 (18), pp.13169-13177. ⟨10.1021/acs.joc.3c01373⟩. ⟨hal-04273944⟩
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  • Anaïs Terrien, Keyvan Rahgoshay, Emelyne Renaglia, Nathalie Lensen, Yves Jacquot, et al.. Inviting C5-Trifluoromethylated Pseudoprolines into Collagen Mimetic Peptides. Biomacromolecules, 2023, 24 (4), pp.1555-1562. ⟨10.1021/acs.biomac.2c01242⟩. ⟨hal-04265852⟩
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  • Emmanuelle Devillers, Evelyne Chelain, Claudio Dalvit, Thierry Brigaud, Julien Pytkowicz. ( R )‐α‐Trifluoromethylalanine as a 19 F NMR Probe for the Monitoring of Protease Digestion of Peptides. ChemBioChem, 2022, 23 (1), pp.e202100470. ⟨10.1002/cbic.202100470⟩. ⟨hal-03549211⟩
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  • Lizeth Bodero, Karine Guitot, Nathalie Lensen, Olivier Lequin, Thierry Brigaud, et al.. Introducing the Chiral Constrained α‐Trifluoromethylalanine in Aib Foldamers to Control, Quantify and Assign the Helical Screw‐Sense**. Chemistry - A European Journal, 2022, 28 (8), pp.e202103887. ⟨10.1002/chem.202103887⟩. ⟨hal-03626224⟩
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  • Clément A Sanchez, Charlène Gadais, Sitan Diarra, Andrea Bordessa, Nathalie Lensen, et al.. Synthesis of enantiopure α-Tfm-proline and α-Tfm-pipecolic acid from oxazolo-pyrrolidines and -piperidines. Organic & Biomolecular Chemistry, 2021, 19 (31), pp.6771-6775. ⟨10.1039/d1ob01173a⟩. ⟨hal-03549199⟩
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  • Thierry Brigaud, Clément A Sanchez, Charlène Gadais, Grégory Chaume, Sylvaine Girard, et al.. Enantiopure 5-CF 3 –Proline: Synthesis, Incorporation in Peptides, and Tuning of the Peptide Bond Geometry. Organic Letters, 2021, 23 (2), pp.382-387. ⟨10.1021/acs.orglett.0c03880⟩. ⟨hal-03549152⟩
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  • Oussema Ouerfelli, Julien Simon, Evelyne Chelain, Julien Pytkowicz, Rafâa Besbes, et al.. Enantiopure α-Trifluoromethylated Aziridine-2-carboxylic Acid (α-TfmAzy) : Synthesis and Peptide Coupling. Organic Letters, 2020, 22 (8), pp.2946-2949. ⟨10.1021/acs.orglett.0c00645⟩. ⟨hal-03549179⟩
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  • N Malquin, K Rahgoshay, Nathalie Lensen, G Chaume, E Miclet, et al.. CF2H as hydrogen bond donor group for the fine tuning of peptide bond geometry with difluoromethylated pseudoprolines. Chemical Communications, 2019, 55 (83), pp.12487-12490. ⟨10.1039/C9CC05771D⟩. ⟨hal-03549249⟩
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  • Martin Oliver, Charlene Gadais, Júlia García-Pindado, Meritxell Teixidó, Nathalie Lensen, et al.. Trifluoromethylated proline analogues as efficient tools to enhance the hydrophobicity and to promote passive diffusion transport of the l -prolyl- l -leucyl glycinamide (PLG) tripeptide. RSC Advances, 2018, 8 (26), pp.14597-14602. ⟨10.1039/c8ra02511h⟩. ⟨hal-04823753⟩
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  • Thierry Brigaud, Charlène Gadais, Julien Pytkowicz, Evelyne Chelain, Nathalie Saraiva Rosa. Tailored Approaches towards the Synthesis of l-S-(Trifluoromethyl)cysteine- and l-Trifluoromethionine-Containing Peptides. European Journal of Organic Chemistry, 2017, 2, pp.246-251. ⟨10.1002/ejoc.201601318⟩. ⟨hal-02980393⟩
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  • Gregory Chaume, Julien Simon, Nathalie Lensen, Julien Pytkowicz, Thierry Brigaud, et al.. Homochiral versus Heterochiral Trifluoromethylated Pseudoproline Containing Dipeptides: A Powerful Tool to Switch the Prolyl-Amide Bond Conformation. Journal of Organic Chemistry, 2017, 82 (24), pp.13602-13608. ⟨10.1021/acs.joc.7b01944⟩. ⟨hal-01675297⟩
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  • Julien Pytkowicz, Gregory Chaume, Nathalie Lensen, Julien Simon, Thierry Brigaud. Incorporation of Trifluoromethylated Proline and Surrogates into Peptides: Application to the Synthesis of Fluorinated Analogues of the Neuroprotective Glycine-Proline-Glutamate (GPE) Tripeptide. Journal of Organic Chemistry, 2016, 13, pp.5381-5392. ⟨10.1021/acs.joc.6b00704⟩. ⟨hal-02980190⟩
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  • Thierry Brigaud, Emmanuelle Devillers, Evelyne Chelain, Julien Pytkowicz. Synthesis of Protected Enantiopure (R) and (S)-a-Trifluoromethylalanine Containing Dipeptide Building Blocks Ready to Use for Solid Phase Peptide Synthesis.. Amino Acids, 2016, 6, pp.1457-1468. ⟨10.1007/s00726-016-2200-9⟩. ⟨hal-02980191⟩
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  • Alexandra Botz, Vincent Gasparik, Emmanuelle Devillers, Anais R. F. Hoffmann, Lucie Caillon, et al.. (R)-alpha-Trifluoromethylalanine Containing Short Peptide in the Inhibition of Amyloid Peptide Fibrillation. Biopolymers, 2015, 104 (5, SI), pp.601-610. ⟨10.1002/bip.22670⟩. ⟨hal-01366197⟩
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  • Cécile Barthes, Arnaud Rives, Valérie Maraval, Evelyne Chelain, Thierry Brigaud, et al.. First example of ring carbo-mer of 1,4-cyclohexadiene. French-Ukrainian Journal of Chemistry, 2015, 3 (1), pp.60-65. ⟨10.17721/fujcV3I1P60-65⟩. ⟨hal-01916646⟩
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  • J.-M. Vincent, T. Brigaud, Dominique Cahard. Preface. Journal of Fluorine Chemistry, 2015, 171, pp.1. ⟨10.1016/j.jfluchem.2014.10.011⟩. ⟨hal-02024989⟩
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  • Grégory Chaume, Julien Simon, Caroline Caupène, Nathalie Lensen, Emeric Miclet, et al.. Incorporation of CF3-Pseudoprolines into Peptides: a Methodological Study.. Journal of Organic Chemistry, 2013, 78 (20), pp.10144-10153. ⟨10.1021/jo401494q⟩. ⟨hal-00862576⟩
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  • Gregory Chaume, Debby Feytens, Gérard Chassaing, Solange Lavielle, Thierry Brigaud, et al.. Conformational properties of peptides incorporating a fluorinated pseudoproline residue. New Journal of Chemistry, 2013, 37 (5), pp.1336-1342. ⟨10.1039/c3nj41084f⟩. ⟨hal-01366405⟩
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  • Debby Feytens, Grégory Chaume, Gérard Chassaing, Solange Lavielle, Thierry Brigaud, et al.. Local control of the cis-trans isomerization and backbone dihedral angles in peptides using trifluoromethylated pseudoprolines.. Journal of Physical Chemistry B, 2012, 116 ((13)), pp.4069-79. ⟨10.1021/jp300284u⟩. ⟨hal-00692355⟩
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  • Fabien Massicot, Alex Mor Iriarte, Thierry Brigaud, Aurélien Lebrun, Charles Portella. Synthesis of trifluoromethyl cyclohexyl, cyclohexenyl and aryl compounds via stepwise Robinson annulation. Organic & Biomolecular Chemistry, 2011, 9 (2), pp.600-603. ⟨10.1039/c0ob00518e⟩. ⟨hal-03561540⟩
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  • C.G. Chaume,, D, Feytens,, C, Caupene,, O. Barbeau,, E. Miclet,, et al.. CF3-pseudoprolines : Synthesis and conformational study of hydrolytically stable proline surrogate containing dipeptides.. Journal of Peptide Science, 2010, 16, pp.53-54. ⟨hal-00604817⟩
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  • Grégory Chaume, Olivier Barbeau, Philippe Lesot, Thierry Brigaud. Synthesis of 2-Trifluoromethyl-1,3-oxazolidines as Hydrolytically Stable Pseudoprolines. Journal of Organic Chemistry, 2010, 75 (12), pp.4135-4145. ⟨10.1021/jo100518t⟩. ⟨hal-02310997⟩
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  • Gregory Chaume, Marie-Céline van Severen, Louis Ricard, Thierry Brigaud. Concise access to enantiopure (S)- and (R)-alpha-trifluoromethyl pyroglutamic acids from ethyl trifluoropyruvate-based chiral CF3-oxazolides (Fox). Journal of Fluorine Chemistry, 2008, 129 (11), pp.1104-1109. ⟨10.1016/j.jfluchem.2008.07.019⟩. ⟨hal-00362507⟩
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Conference papers4 document




    

  • Emeric Miclet, Anas Terrien, Claire Loison, Luminita Duma, Thierry Brigaud, et al.. New insights into the structural and dynamics properties of collagen model peptides using CD spectroscopy, MD simulations and innovative NMR approaches. 35th European Peptide Symposium, Aug 2018, Dublin, Ireland. pp.192-194, ⟨10.17952/35EPS.2018.192⟩. ⟨hal-02057961⟩
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  • Grégory Chaume, Olivier Barbeau, Philippe Lesot, Emeric Miclet, Thierry Brigaud. Methodological Study of the Peptide Coupling of the N-desactivated Stable Proline Surrogate CF3-pseudoproline. 32nd European Peptide Symposium, 2012, Sitges, France. pp.S58-S200, ⟨10.1002/psc.2449⟩. ⟨hal-02316083⟩
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  • Emeric Miclet, D, Feytens,, Gilles Guichard, Francelin Bouillère, Valérie Alezra, et al.. Accurate measurement of scalar couplings in peptidomimetic molecules bearing diastereotopic methylene protons.. Accurate measurement of scalar couplings in peptidomimetic molecules bearing diastereotopic methylene protons., Jun 2010, France. ⟨hal-00665771⟩
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  • Debby Feytens, E. Miclet,, Gérard Chassaing, Gregory Chaume, Thierry Brigaud, et al.. Cis-trans isomerization in trifluoromethylated pseudoprolines: study by NMR.. Cis-trans isomerization in trifluoromethylated pseudoprolines: study by NMR., Jan 2010, France. ⟨hal-00665787⟩
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Poster communications2 document




    

  • F. Coste, G. Chaume, J.-B. Madinier, I. Rahioui, B. Castaing, et al.. Incorporation of trifluoromethylated pseudoproline in an entomotoxic knottin: effects on oxidative folding, 3D structure and biological activity. 21e congrès du Groupe Français des Peptides et des Protéines (GFPP), May 2019, Amboise, France. ⟨hal-02893471⟩
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  • F. Coste, G. Chaume, J.-B. Madinier, I. Rahioui, B. Castaing, et al.. Incorporation of trifluoromethylated pseudoproline in an entomotoxic knottin: effects on oxidative folding, 3D structure and biological activity. 35th European Peptide Symposium (EPS35), Aug 2018, Dublin, Ireland. ⟨hal-02894161⟩
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Book sections1 document




    

  • Thierry Brigaud, B. Crousse, T. Lequeux. Perfluoroalkylated Biomolecules for Medicinal Chemistry and Biological Studies. Perfluoroalkyl Substances, The Royal Society of Chemistry; The Royal Society of Chemistry, pp.459-476, 2022, ⟨10.1039/9781839167591-00459⟩. ⟨hal-04098116⟩
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Preprints, Working Papers2 document




    

  • Yazid Boutahri, Khoubaib Ben Haj Salah, Nicolas Tisserand, Nathalie Lensen, Benoit Crousse, et al.. Difluoroalanine: Synthesis, Incorporation in Peptides, and Hydrophobic Contribution Assessment. 2023. ⟨hal-04249424⟩
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  • Anaïs Terrien, Keyvan Rahgoshay, Emelyne Renaglia, Nathalie Lensen, Yves Jacquot, et al.. Inviting Trifluoromethylated Pseudoprolines into Collagen Model Peptides. 2022. ⟨hal-03845893⟩
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Education & Career :


    

  • PhD (1990): University Claude Bernard, Lyon I, direction Prof. E. Laurent
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  • Post-doc (1990-1991): State University of New York at Stony Brook, USA, (Prof. I. Ojima)
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  • Associate Professor (1991-2002): Université de Reims-Champagne-Ardenne, UMR 6519 (Prof. C. Portella’s group). Habilitation in 1999.
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  • Full Professor (2002-present):Cergy Paris Université University of Cergy-Pontoise
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  • Director of the Laboratory of Chemical Biology (LCB, EA 4505) from 1/10/2012 to 31/12/2019 and director of the Chemical Biology Team of BioCIS
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  • Deputy director of BioCIS (UMR-CNRS-8076)  from 1/01/2020
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  • Direction of the organofluorine group of the Chemical Biology Team of BioCIS
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Other activities


    

  • Professor of organic chemistry
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  • Director of the second year in physics – chemistry – earth sciences of the University of Cergy-Pontoise 2005-2017
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  • Member of the organizing committees of 14 national and international symposiums.
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  • Member of the international advisory board of the 18th European Symposium on Fluorine Chemistry. Kiev, August 7-12 2016.
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  • Coordinator of the fluorine and life science section of the French Fluorine Network (GIS CNRS)
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  • Associate editor of Frontiers in Chemistry – Organic Chemistry section
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  • Guest editor of The Journal of Fluorine Chemistry (Special issue of the 2014 Bordeaux Fluorine Days)
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  • Member of the selection committee of the ANR SIMI 7 (2012, 2013)
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  • Expert for the ANR (Blanc, JCJC, PCV, émergence, grand défis sociétaux, MRSI)
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  • Advisor for Central Glass Company (Japan)
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  • Expert for ERC, fonds québécois de recherche sur la nature et les technologies, Royal Chemical Society, Israel Science Foundation, Humboldt Foundation, Fulbright Foundation, Research Council Romania …
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  • Member of the scientific council (2008-2012) and the studies council (2006-2008) of the University of Cergy-Pontoise
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  • Member of more than 20 University selection committees, 71 PhD and habilitation committees
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Funded projects


    

  • Coordinator of a French – Bulgarian program RILA : Analgesic effects of MIF-analogues containing CF3-prolines or CF3-pseudoprolines
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  • Coordinator of the ANR-DFG 2012-2015 “CF3-Peptaibols” in collaboration with the group of Prof Anne S. Ulrich (Karlsruhe Institute of Technology)
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  • Isite Paris-Seine Post-doc program 2017
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  • Projet SESAME Région IDF ROMANCE (RMN)
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  • Coordinator of the ANR 2019-2022 “F-LAIR”
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  • 2 EUTOPIA PhD cotutelle (University of Ljubljana andVrije University of Brussel)
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  • Coordinator of the INEX Ambition project Biomol
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