Grégory CHAUME 

Professor 



Biological Chemistry, Permanent


bureau
gregory.chaume@cyu.fr




Site de Cergy


ORCID
https://orcid.org/0000-0001-7460-4876


Chiral fluorinated compounds


Stereoselective synthesis of fluorinated amino acids, amino alcohols, pseudoprolines, …


Fluorinated peptides and peptidomimetics


Development of coupling conditions for the incorporation of fluorinated aminoacids into peptide chains;

Design and synthesis of fluorinated peptides and peptidomimetics of biological interests (nociception, antimicrobial peptides, PPIase inhibition, …);

Design of fluorinated biomaterials and peptidomimrtics (collagen model peptides, foldamers, peptide hydrogels, …)


Physicochemical properties, conformational and structural analysis, biological activities


Evaluation of kinetic and thermodynamic parameters, hydrophobicity index measurement, measurement of the pKa values of the neighboring chemical functions, assignement of peptide amide bond geometry and ring pucker conformation, secondary structure elucidation, thermal stability of tertiary structure, protein-protein interactions, capacity to interact with membranes or to cross them, use of the fluorinated groups as 19F NMR probe, antimicrobial activity, inhibition of amyloid protein aggregation, analgesia, …
























25 documents







Journal articles18 document




    

  • 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⟩
    • 

  • 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⟩
    • 

  • 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⟩
    • 

  • 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⟩
    • 

  • 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⟩
    • 

  • 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⟩
    • 

  • 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⟩
    • 

  • 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⟩
    • 

  • 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⟩
    • 

  • 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⟩
    • 

  • 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⟩
    • 

  • 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⟩
    • 

  • 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⟩
    • 

  • 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⟩
    • 

  • 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⟩
    • 

  • 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⟩
    • 

  • 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⟩
    • 

  • 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⟩
    • 












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⟩
    • 

  • 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⟩
    • 

  • 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⟩
    • 

  • 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⟩
    • 












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⟩
    • 

  • 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⟩
    • 












Preprints, Working Papers1 document




    

  • Anaïs Terrien, Keyvan Rahgoshay, Emelyne Renaglia, Nathalie Lensen, Yves Jacquot, et al.. Inviting Trifluoromethylated Pseudoprolines into Collagen Model Peptides. 2022. ⟨hal-03845893⟩
    • 
















Powered by HAL logo




Education

DEUG Sciences de la Matières option “Physique-Chimie” (1997), University of Cergy-Pontoise

Licence de Chimie – B.Sc. (1998), University of Cergy-Pontoise

Maitrise de Chimie Organique (1999), University of Cergy-Pontoise

DEA de Chimie Organique – M.Sc. (2000),University of Cergy-Pontoise

Doctorat de Chimie Organique – PhD (2003), University of Cergy-Pontoise, direction : J. Ardisson & A. Pancrazi


Career

Post-doc (2003-2004) : Nottingham University, England (Prof G. Pattenden)

ATER (2004-2005) : Cergy-Pontoise University, (Prof T. Brigaud)

CNRS Temporary Researcher (2016-2018) : Laboratory of Biomolecules, Sorbonne University

Associate Professor (2005-2023) : CY Cergy Paris University

Full Professor (since 2023) : CY Cergy Paris University


Funded project

Coordinator of ANR “Young Researchers” Program 2009-2012 “CF3-GPE”

Initiative d’Excellence Paris//Seine Post-doc Program 2017 “F-LAIR”

Initiative d’Excellence Paris//Seine Post-doc Program 2019 “FluoSPep”

EUTOPIA PhD cotutelle 2020-2024 “EXPLORE”


Awards

Prime d’Excellence Scientifique (PES) 2010-2014

Prime d’Encadrement Doctoral et de Recherche (PEDR) 2014-2018

Prime d’Encadrement Doctoral et de Recherche (PEDR) 2020-2024




Scientific production


32 publications and 22 proceedings (h-index = 16), 9 seminars (2 to foreign Universities), 10 oral communications (1 as invited speaker) and 111 posters.