Les membres de l’équipe
Thématiques
Depuis 2002, notre équipe s’est attachée à la mise au point de méthodes stéréosélectives d’accès aux composés fluorés chiraux. L’introduction d’un groupement fluoré au sein d’une molécule permet de modifier de façon importante ses propriétés stéréoélectroniques, ce qui a pour effet de modifier ses propriétés physiques et biologiques. Ainsi la demande de synthons fluorés est grandissante, aussi bien dans le domaine de la chimie pharmaceutique que celui des matériaux. Dans ce contexte, nous avons développé des voies d’accès rapides et stéréosélectives à divers composés fluorés.
Le développement de nouveaux accès aux glycoconjugués est devenu d’un grand intérêt en chimie de synthèse. En particulier, les glycoconjugués possédant une liaison non naturelle sont largement étudiés en raison de leurs stabilités enzymatiques et chimiques par rapport aux liaisons naturelles C-O et C-N.
Notre expertise porte sur la fonctionnalisation catalysée par un métal de substrats glycaux en utilisant deux réactivités différentes :
– Réactions de couplage croisé sur des composés 2-iodoglycals de départ pour la formation de liaisons C-C, C-N ou C-P : aminocarbonylation catalysée au palladium (A), réaction de Suzuki-Miyaura carbonylative (C), cyanation en milieu aqueux (D) dual nickel/cuivre -amidation catalysée (E) et phosphonylation catalysée par le palladium (F).
– Réactions de fonctionnalisation C-H dirigées de la position pseudo-anomérique des C2-amidoglycals : arylation C-H catalysée par le palladium et alcénylation C-H catalysée par le nickel (B).
1. “CO” as a Carbon Bridge to Build Complex C2-Branched Glycosides Using a Palladium-Catalyzed Carbonylative Suzuki–Miyaura Reaction from 2-Iodoglycals. de Robichon, M.; Bordessa, A.; Lubin-Germain, N.; Ferry, A. J. Org. Chem. 2019, 84, 3328-3339.
2. Access to C-aryl/alkenylglycosides by directed Pd-catalyzed C–H functionalisation of the anomeric position in glycal-type substrates. de Robichon, M.; Bordessa, A.; Malinowski, M.; Uziel, J.; Lubin-Germain, N.; Ferry, A. Chem. Commun. 2019, 55, 11806-11808.
3. Mild Palladium‐Catalyzed Cyanation of Unprotected 2‐Iodoglycals in Aqueous Media as Versatile Tool to Access Diverse C2‐Glycoanalogues. Malinowski, M.; Tran, T. V.; de Robichon, M.; Lubin-Germain, N.; Ferry, A. Adv. Synth. Catal. 2020, 362, 1184-1189.
4. Glycosamine Derivatives through Metal-Catalyzed C−N Bond Formation on Protected and Unprotected 2-Iodoglycals. Malinowski, M.; Banoun, C.; de Robichon, M.; Lubin-Germain, N.; Ferry, A. Eur. J. Org. Chem. 2021, 1521–1524
5. Directed Nickel-Catalyzed Pseudo-Anomeric C−H Alkynylation of Glycals as an Approach towards C-Glycoconjugate Synthesis. de Robichon, M.; Branquet, D.; Uziel, J.; Lubin-Germain, N.; Ferry, A. Adv. Synth. Catal. 2021,363 (22), pp. 5138-5148
Une des limitations à l’utilisation des peptides comme agents thérapeutiques est leur dégradation rapide par les peptidases ainsi que leur faible lipophilie. Notre laboratoire s’intéresse à la mise au point de réactions de couplage peptidique efficace qui permettent l’incorporation d’aminoacides α-trifluorométhylés énantiopurs dans des chaînes peptidiques. Leur utilisation est d’un grand intérêt du fait des propriétés uniques de l’atome de fluor. Leur incorporation dans des chaînes peptidiques est prometteuse du fait des contraintes conformationnelles, des effets électroniques et de l’augmentation de l’hydrophobie induits par les groupements fluorés. Ainsi une stabilité métabolique accrue vis-à-vis des protéases et des structures tridimensionnelles originales sont attendues. L’augmentation local du charactère hydrophobe peut permettre de faciliter le passage de la barrière hémato-encéphalique. Par ailleurs ces peptides fluorés présentent un fort potentiel analytique en tant que sonde RMN (19F) pour l’élucidation des structures, la compréhension des mécanismes biologiques et les études pharmacocinétiques de ces peptides non protéogéniques.
Nous avons récemment développé une méthode efficace pour la synthèse de dipeptides N-terminaux à partir d’α-Tfm-Alanine et d’α-Tfm-Proline non protégé utilisant les conditions de couplage peptidique classique HOBt, EDCI. La synthèse de dipeptides C-terminaux est beaucoup plus délicate du fait de la forte désactivation de l’azote par le groupement CF3. Une étude méthodologique réalisée à partir de pseudoprolines trifluorométhylées chirales a permis d’effectuer la réaction de couplage avec des acides aminés activés sous forme de chlorures d’acyle. L’optimisation des conditions réactionnelles est en cours au laboratoire et elles sont appliquées à la synthèse de divers peptides d’intérêts.
1. Introducing the chiral constrained α-trifluoromethylalanine in aib foldamers to control, quantify and assign the helical screw-sense, Bodero, L., Guitot, K., Lensen, N., Lequin, O., Brigaud, T., Ongeri, S., Chaume, G. Chemistry – A European Journal, 2022, ASAP article
2. (R)-α-Trifluoromethylalanine as a 19F NMR Probe for the Monitoring of Protease Digestion of Peptides. Devillers, E.; Chelain, E.; Dalvit, C.; Brigaud, T.; Pytkowicz, J., ChemBioChem 2022,23, e202100470
3. Enantiopure 5-CF3–Proline: Synthesis, Incorporation in Peptides, and Tuning of the Peptide Bond Geometry. C. A. Sanchez, C. Gadais, C.;Chaume, G.; Girard, S.; Chelain, E.; Brigaud, T. Org. Lett. 2021, 382-387
4. Trifluoromethylated Proline Surrogates as Part of « Pro-Pro » Turn-Inducing Templates. Gadais, C.; Van holsbeeck, K.; Moors, S. L. C.; Buyst, D.; Feher, K.; Van Hecke, K.; Tourwe, D.; Brigaud, T.; Martin, C.; De Proft, F.; Pytkowicz, J.; Martins, J. C.; Chaume, G.; Ballet, S. ChemBioChem 2019, 20, 2513-2518.
5. CF2H as hydrogen bond donor group for the fine tuning of peptide bond geometry with difluoromethylated pseudoprolines. Malquin, N.; Rahgoshay, K.; Lensen, N.; Chaume, G.; Miclet, E.; Brigaud, T. Chem. Commun. 2019, 55, 12487-12490.
6. 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. Oliver, M.; Gadais, C.; Garcia-Pindado, J.; Teixido, M.; Lensen, N.; Chaume, G.; Brigaud, T. RSC Adv. 2018, 8, 14597-14602.
7. Probing the outstanding local hydrophobicity increase of peptide sequences induced by trifluoromethylated amino acids incorporation. Gadais, C.; Devillers, E.; Gasparik, V.; Chelain, E.; Pytkowicz, J.; Brigaud, T. ChemBioChem 2018, 19, 1026–1030.
8. Tailored Approaches towards the Synthesis of L-S-(Trifluoromethyl)cysteine- and L-Trifluoromethionine-Containing Peptides. Gadais, C.; Saraiva-Rosa, N.; Chelain, E.; Pytkowicz, J.; Brigaud, T. Eur. J. Org. Chem. 2017, 246-251.
9. Homochiral versus Heterochiral Trifluoromethylated Pseudoproline Containing Dipeptides: A Powerful Tool to Switch the Prolyl-Amide Bond Conformation. Chaume, G.; Simon, J.; Lensen, N.; Pytkowicz, J.; Brigaud, T.; Miclet, E. J. Org. Chem. 2017, 82, 13602-13608.
10. Synthesis of protected enantiopure (R) and (S)-α-trifluoromethylalanine containing dipeptide building blocks ready to use for solid phase peptide synthesis. Devillers, E.; Pytkowicz, J.; Chelain, E.; Brigaud, T. Amino Acids 2016, 48, 1457-1468.
11. Incorporation of CF3−Pseudoprolines into Peptides: A Methodological Study, Chaume, G.; Simon, J.; Caupène, C.; Lensen, N.; Miclet, E.; Brigaud, T. J. Org. Chem. 2013, 78, 10144-10153.
Catalyseurs bifonctionnels iminophosphorane/(thio)urée
Récemment, les organocatalyseurs bifonctionnels ont permis le développement de transformations hautement stéréosélectives en raison de leur capacité à organiser et à activer simultanément des substrats électrophiles par le biais de liaison H et des réactifs pro-nucléophiles par le biais de la déprotonation. Cependant, les faibles vitesses de réaction et les charges élevées de catalyseur restent les principales limitations dans ce domaine. De plus, certaines limitations subsistent quant aux partenaires compatibles avec ces catalyseurs.
Nous étudions au laboratoire la conception et la synthèse de nouveaux catalyseurs bifonctionnels iminophosphorane/(thio)urée contenant un groupe trifluorométhyle chiral (F-BIMP) offrant une réactivité améliorée tout en maintenant des niveaux élevés de contrôle énantiomérique.
L’équipe capitalise sur les outils méthodologiques développés en synthèse asymétrique, synthèse d’acides aminées non-canoniques, synthèse peptidique et chimie du fluor pour mettre au point des molécules possédant une activité anticancéreuse. Cela se manifeste par le dévelopement de nouveaux dégradeurs, ou de nouveaux inhibiteurs de protéases aspartiques, mais encore par l’accès à de nouveau outils diagnostics de type radiotraceurs.
Actualités
Félicitations Dr Boutahri
Toute l'équipe félicite Yazid Boutahri après sa soutenance de thèse et l'obtention du grade de Docteur de CY Cergy-Paris Université. [...]
Félicitations Dr Honfroy
Toute l'équipe félicite Aurélie Honfroy après sa soutenance de thèse et l'obtention du grade de Docteure en Chimie de CY [...]
Les ANR
Articles dans une revue
- Alessia Distefano, Paolo Corsaro, Nunzio Tuccitto, Francesca Laneri, Olivier Monasson, et al.. Intrinsically photoluminescent hydrogels to measure peptides‑copper binding affinities. Journal of Inorganic Biochemistry, 2025, 268, pp.112914. ⟨10.1016/j.jinorgbio.2025.112914⟩. ⟨hal-05052019⟩
- Shashank Pandey, Elisa Peroni, Dagmar Jarkovska, Magdalena Chottova Dvorakova, Olivier Monasson, et al.. Role of Neuropeptide B/W Signaling in Modulating Intracellular Calcium in Human Skin Fibroblasts. Frontiers in Bioscience-Landmark, 2025, 30 (2), ⟨10.31083/FBL26760⟩. ⟨hal-04971764⟩
- Alicia Maroto, Olivier Briand, Alessia Distefano, Filiz Arioz, Olivier Monasson, et al.. Differentiation of Isomeric TAT1-CARNOSINE Peptides by Energy-Resolved Mass Spectrometry and Principal Component Analysis. Molecules, 2025, Special Issue Design, Synthesis, and Analysis of Potential Drugs, 3rd Edition, 30 (4), pp.853. ⟨10.3390/molecules30040853⟩. ⟨hal-04943837⟩
- Lorenzo Meneghelli, Stephanie Davidson, Anthony Gineste, Lamia El Guermah, Sabrina Kellouche-Gaillard, et al.. Design and synthesis of a clickable cell-permeable pseudopeptide Pin1 inhibitor with antiproliferative effects on human multiple myeloma cell line. Chemical Communications, 2025, ⟨10.1039/D4CC05968A⟩. ⟨hal-05003977⟩
- Yuqing Zhang, Myriam Eveno, Nadège Lubin-Germain, Agnès Lattuati-Derieux, Nadège Lubin-Germain, et al.. Partially fluorinated derivatives as a powerful tool for the restoration of blanched easel paintings. Progress in Organic Coatings, 2025, 207, pp.109375. ⟨10.1016/j.porgcoat.2025.109375⟩. ⟨hal-05104320⟩
- Farzin Arjmand, Alima Chali, Youssef Snoussi, David Troadec, Gilles Patriarche, et al.. In-situ chemical grafting of aminophenyl and RGD peptide on an equimolar high-entropy HfNbTaTiZr alloy: electrochemical behavior and surface characterization. Emergent Materials, 2024, ⟨10.1007/s42247-024-00963-z⟩. ⟨hal-04854358⟩
- 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⟩
- Pieter Langerhorst, Melissa Baerenfaenger, Purva Kulkarni, Simon Nadal, Charissa Wijnands, et al.. N-linked glycosylation of the M-protein variable region: glycoproteogenomics reveals a new layer of personalized complexity in multiple myeloma. Clinical Chemistry and Laboratory Medicine, 2024, 62 (8), pp.1626-1635. ⟨10.1515/cclm-2023-1189⟩. ⟨hal-05085563⟩
- Farzin Arjmand, Adrien Mourgout, Alima Chali, Madjid Djemai, Credson-Yannick Langueh, et al.. L-PBF processing and characterization of a Ti 35 Nb 30 Zr 29 Mo 3 Ta 3 multiprincipal element alloy for medical implants. Applied Physics Letters, 2024, 125 (4), pp.041904. ⟨10.1063/5.0208341⟩. ⟨hal-04739764⟩
- Luca Paoletti, Francesco Baschieri, Claudia Migliorini, Chiara Di Meo, Olivier Monasson, et al.. 3D printing of gellan‐dextran methacrylate IPNs in glycerol and their bioadhesion by RGD derivatives. Journal of Biomedical Materials Research Part A, 2024, ⟨10.1002/jbm.a.37698⟩. ⟨hal-04488395⟩
- Francesco Terzani, Sherazade Belhattab, Aurore Le Guern, Karine Guitot, Olivier Monasson, et al.. Synthesis and biological evaluation of selective Pepstatin based trifluoromethylated inhibitors of Cathepsin D. European Journal of Medicinal Chemistry, 2024, 267, pp.116178. ⟨10.1016/j.ejmech.2024.116178⟩. ⟨hal-04455850⟩
- 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⟩
- Dongxu Zhai, Shuxin Yan, James Samsom, Le Wang, Ping Su, et al.. Small-molecule targeting AMPA-mediated excitotoxicity has therapeutic effects in mouse models for multiple sclerosis. Science Advances , 2023, 9 (49), ⟨10.1126/sciadv.adj6187⟩. ⟨hal-04604036⟩
- Linhua Shen, Olivier Monasson, Elisa Peroni, Franck Le Bideau, Samir Messaoudi. Electrochemical Nickel-Catalyzed Selective Inter-and Intramolecular Arylations of Cysteine-Containing Peptides. Angewandte Chemie International Edition, 2023, 62 (50), ⟨10.1002/anie.202315748⟩. ⟨hal-04905239v2⟩
- William Godefroy, Lionel Faivre, Caroline Sansac, Briac Thierry, Jean-Marc Allain, et al.. Development and qualification of clinical grade decellularized and cryopreserved human esophagi. Scientific Reports, 2023, 13, pp.18283. ⟨10.1038/s41598-023-45610-5⟩. ⟨hal-04269788⟩
- Camille Lozada, Simon Gonzalez, Rémy Agniel, Mathilde Hindie, Luca Manciocchi, et al.. Introduction of constrained Trp analogs in RW9 modulates structure and partition in membrane models. Bioorganic Chemistry, 2023, 139, pp.106731. ⟨10.1016/j.bioorg.2023.106731⟩. ⟨hal-04272386⟩
- Karen Thompson, Sonia Watson, Chiara Zanato, Sergio Dall'Angelo, Joriene de Nooij, et al.. The atypical ‘hippocampal’ glutamate receptor coupled to phospholipase D that controls stretch‐sensitivity in primary mechanosensory nerve endings is homomeric purely metabotropic GluK2. Experimental Physiology, 2023, ⟨10.1113/EP090761⟩. ⟨hal-04273805⟩
- Yuqing Zhang, Myriam Eveno, Florian Gallier, Mara Camaiti, Agnès Lattuati-Derieux, et al.. Synthesis of novel partially perfluorinated C-glycosides and their application in blanching easel painting restoration. Journal of Cultural Heritage, 2023, 62, pp.493-500. ⟨10.1016/j.culher.2023.06.019⟩. ⟨hal-04172828⟩
- Alessandro Auditore, Nunzio Tuccitto, Giuseppe Grasso, Olivier Monasson, Elisa Peroni, et al.. Time-of-flight SIMS investigation of peptides containing cell penetrating sequences. Biointerphases, 2023, 18 (3), ⟨10.1116/6.0002671⟩. ⟨hal-04274581⟩
- Pierre Milbeo, Arthur Lebrêne, Mariia Savchuk, Giang Vo-Thanh, Sylvain Oudeyer, et al.. An Organocatalytic and Stereoselective Vinylogous Domino Process Towards Thiochromans. Chemistry - A European Journal, 2023, pp.e202301311. ⟨10.1002/chem.202301311⟩. ⟨hal-04102949⟩
- 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⟩
- 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⟩
- Alessia Distefano, Federico Calì, Massimiliano Gaeta, Nunzio Tuccitto, Alessandro Auditore, et al.. Carbon dots surface chemistry drives fluorescent properties: New tools to distinguish isobaric peptides. Journal of Colloid and Interface Science, 2022, 625, pp.405-414. ⟨10.1016/j.jcis.2022.06.050⟩. ⟨hal-03794232⟩
- Simon Gonzalez, Gabriela Brzuska, Abdelhakim Ouarti, Florian Gallier, Carmen Solarte, et al.. Anti-HCV and Zika activities of ribavirin C-nucleosides analogues. Bioorganic and Medicinal Chemistry Letters, 2022, 68, pp.116858. ⟨10.1016/j.bmc.2022.116858⟩. ⟨hal-03805895⟩
- Nazarii Sabat, Abdelhakim Ouarti, Evelyne Migianu-Griffoni, Marc Lecouvey, Olivier Ferraris, et al.. Synthesis, antiviral and antitumor activities investigations of a series of Ribavirin C-nucleoside analogue prodrugs. Bioorganic Chemistry, 2022, 122, pp.105723. ⟨10.1016/j.bioorg.2022.105723⟩. ⟨hal-03627511⟩
- Severin Lechner, Martin Ian P. Malgapo, Christian Grätz, Raphael Steimbach, Agnes Baron, et al.. Target deconvolution of HDAC pharmacopoeia reveals MBLAC2 as common off-target. Nature Chemical Biology, 2022, 18 (8), pp.812-820. ⟨10.1038/s41589-022-01015-5⟩. ⟨hal-05085539⟩
- Khoubaib Ben Haj Salah, Francesco Terzani, Marine Pietri, Chiara Zanato, Evelyne Chelain, et al.. Highly stereoselective multigram scale synthesis of (3S,4S)-Statine and (3S,4S)-N-Benzylstatine. Results in Chemistry, 2022, 4, pp.100333. ⟨10.1016/j.rechem.2022.100333⟩. ⟨hal-04098168⟩
- Olivier Monasson, Maciej Malinowski, Nadège Lubin-Germain, Angélique Ferry. Hirao Cross-Coupling Reaction as an Efficient Tool to Build Non-natural C2-Phosphonylated Sugars. Synthesis: Journal of Synthetic Organic Chemistry, 2022, ⟨10.1055/a-1709-3305⟩. ⟨hal-03630601⟩
- 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⟩
- Yuqing Zhang, Laura Vespignani, Maria Grazia Balzano, Leonardo Bellandi, Mara Camaiti, et al.. Low Fluorinated Oligoamides for Use as Wood Protective Coating. Coatings, 2022, 12 (7), pp.927. ⟨10.3390/coatings12070927⟩. ⟨hal-03714187⟩
- Camille Lozada, Thomas M A Barlow, Simon Gonzalez, Nadège Lubin-Germain, Steven Ballet. Identification and Characteristics of Fusion Peptides Derived From Enveloped Viruses. Frontiers in Chemistry, 2022, 12, pp.689006. ⟨10.3389/fchem.2021.689006⟩. ⟨hal-03714204⟩
- Hendrik Rusche, Edoardo Marrani, Feliciana Real-Fernandez, Roberta Ponti, Francesco Terzani, et al.. A peptide-based anti-Adalimumab antibody assay to monitor immune response to biologics treatment in juvenile idiopathic arthritis and childhood chronic non-infectious uveitis. Scientific Reports, 2021, 11 (1), pp.16393. ⟨10.1038/s41598-021-95920-9⟩. ⟨hal-03792564⟩
- Ganyuan Xiao, Magnus Alphey, Fanny Tran, Lisa Pirrie, Pierre Milbeo, et al.. Next generation Glucose-1-phosphate thymidylyltransferase (RmlA) inhibitors: An extended SAR study to direct future design. Bioorganic and Medicinal Chemistry, 2021, 50, pp.116477. ⟨10.1016/j.bmc.2021.116477⟩. ⟨hal-05087058⟩
- 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⟩
- Joshua Mclean, Pierre Milbeo, Dylan Lynch, Lauren Mcsweeney, Eoin Scanlan. Radical‐Mediated Acyl Thiol‐Ene Reaction for Rapid Synthesis of Biomolecular Thioester Derivatives. European Journal of Organic Chemistry, 2021, 2021 (29), pp.4148-4160. ⟨10.1002/ejoc.202100615⟩. ⟨hal-05087069⟩
- Monica Piras, Ilaria Patruno, Christina Nikolakopoulou, Janet Willment, Nikki Sloan, et al.. Synthesis of the Fungal Metabolite YWA1 and Related Constructs as Tools to Study MelLec-Mediated Immune Response to Aspergillus Infections. Journal of Organic Chemistry, 2021, 86 (9), pp.6044-6055. ⟨10.1021/acs.joc.0c02324⟩. ⟨hal-03630255⟩
- Pierre Milbeo, Jean Martinez, Muriel Amblard, Monique Calmès, Baptiste Legrand. 1-Aminobicyclo[2.2.2]octane-2-carboxylic acid and derivatives as chiral constrained bridged scaffolds for foldamers and chiral catalysts. Accounts of Chemical Research, 2021, 54 (3), pp.685-696. ⟨10.1021/acs.accounts.0c00680⟩. ⟨hal-03371473⟩
- Pierre Milbeo, François Quintin, Laure Moulat, Claude Didierjean, Jean Martinez, et al.. Synthesis, characterisation and cytotoxic activity evaluation of new metal-salen complexes based on the 1,2-bicyclo[2.2.2]octane bridge. Tetrahedron Letters, 2021, 63, pp.152706. ⟨10.1016/j.tetlet.2020.152706⟩. ⟨hal-03103305⟩
- 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⟩
- Brian Josephson, Charlie Fehl, Patrick Isenegger, Simon Nadal, Tom Wright, et al.. Light-driven post-translational installation of reactive protein side chains. Nature, 2020, 585 (7826), pp.530-537. ⟨10.1038/s41586-020-2733-7⟩. ⟨hal-05085267⟩
- Oriana Osta, Marianne Bombled, David Partouche, Florian Gallier, Nadège Lubin-Germain, et al.. Direct Synthesis of Mesoporous Organosilica and Proof-of-Concept Applications in Lysozyme Adsorption and Supported Catalysis. ACS Omega, 2020, 5 (30), pp.18842-18848. ⟨10.1021/acsomega.0c01996⟩. ⟨hal-03036887⟩
- Oriana Osta, Marianne Bombled, David Partouche, Florian Gallier, Nadège Lubin-Germain, et al.. Direct Synthesis of Mesoporous Organosilica and Proof-of-Concept Applications in Lysozyme Adsorption and Supported Catalysis. ACS Omega, 2020, 5, pp.18842 - 18848. ⟨10.1021/acsomega.0c01996⟩. ⟨hal-03553249⟩
- Pierre Milbeo, Matthieu Simon, Claude Didierjean, Emmanuel Wenger, Emmanuel Aubert, et al.. A bicyclic unit reversal to stabilize the 12/14-helix in mixed homochiral oligoureas. Chemical Communications, 2020, 56 (57), pp.7921-7924. ⟨10.1039/d0cc02902e⟩. ⟨hal-03080580⟩
- 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⟩
- Nazarii Sabat, Evelyne Migianu-Griffoni, Tiffany Tudela, Marc Lecouvey, Sabrina Kellouche, et al.. Synthesis and antitumor activities investigation of a C-nucleoside analogue of ribavirin. European Journal of Medicinal Chemistry, 2020, 188, pp.112009. ⟨10.1016/j.ejmech.2019.112009⟩. ⟨hal-03364298⟩
- Simon Gonzalez, Maria Dumitrascuta, Emilie Eiselt, Stevany Louis, Linda Kunze, et al.. Optimized Opioid-Neurotensin Multitarget Peptides: From Design to Structure−Activity Relationship Studies. Journal of Medicinal Chemistry, 2020, 63 (21), pp.12929-12941. ⟨10.1021/acs.jmedchem.0c01376⟩. ⟨hal-03150260⟩
- Anaïs Wambecke, Carine Laurent-Issartel, Johanne Leroy-Dudal, Florence Giffard, Fanny Cosson, et al.. Evaluation of the potential of a new ribavirin analog impairing the dissemination of ovarian cancer cells. PLoS ONE, 2019, 14 (12), pp.e0225860. ⟨10.1371/journal.pone.0225860⟩. ⟨inserm-02429497⟩
- Emilie Eiselt, Simon Gonzalez, Charlotte Martin, Magali Chartier, Cecilia Betti, et al.. Neurotensin Analogues Containing Cyclic Surrogates of Tyrosine at Position 11 Improve NTS2 Selectivity Leading to Analgesia without Hypotension and Hypothermia. ACS Chemical Neuroscience, 2019, 10 (11), pp.4535-4544. ⟨10.1021/acschemneuro.9b00390⟩. ⟨hal-02400886⟩
- Marion Alter, Laurent Binet, Nadia Touati, Nadège Lubin-Germain, Anne-Solenn Le Hô, et al.. Photochemical Origin of the Darkening of Copper Acetate and Resinate Pigments in Historical Paintings. Inorganic Chemistry, 2019, 58 (19), pp.13115-13128. ⟨10.1021/acs.inorgchem.9b02007⟩. ⟨hal-03773633⟩
- Morgane de Robichon, Andrea Bordessa, Nadège Lubin-Germain, Angélique Ferry. “CO” as a Carbon Bridge to Build Complex C2-Branched Glycosides Using a Palladium-Catalyzed Carbonylative Suzuki–Miyaura Reaction from 2-Iodoglycals. Journal of Organic Chemistry, 2019, 84 (6), pp.3328-3339. ⟨10.1021/acs.joc.8b03248⟩. ⟨hal-03821214⟩
- Simon Gonzalez, Florian Gallier, Sabrina Kellouche, Franck Carreiras, Ettore Novellino, et al.. Studies of membranotropic and fusogenic activity of two putative HCV fusion peptides. Biochimica et Biophysica Acta:Biomembranes, 2019, 1861 (1), pp.50-61. ⟨10.1016/j.bbamem.2018.10.011⟩. ⟨hal-01920493⟩
- N Malquin, K Rahgoshay, N 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⟩
- Matthieu Simon, Pierre Milbeo, Hongtao Liu, Christophe Andre, Emmanuel Wenger, et al.. 12/10‐Helix in Mixed β‐Peptides Alternating Bicyclic and Acyclic β‐Amino Acids: Probing the Relationship between Bicyclic Side Chain and Helix Stability. Chemistry - A European Journal, 2018, 24 (70), pp.18795-18800. ⟨10.1002/chem.201804404⟩. ⟨hal-02403147⟩
- Simon Nadal, Ritu Raj, Shabaz Mohammed, Benjamin Davis. Synthetic post-translational modification of histones. Current Opinion in Chemical Biology, 2018, 45, pp.35-47. ⟨10.1016/j.cbpa.2018.02.004⟩. ⟨hal-05085237⟩
- Mark Stappers, Alexandra Clark, Vishukumar Aimanianda, Stefan Bidula, Delyth Reid, et al.. Recognition of DHN-melanin by a C-type lectin receptor is required for immunity to Aspergillus. Nature, 2018, 555 (7696), pp.382-386. ⟨10.1038/nature25974⟩. ⟨pasteur-02501369⟩
- Pierre Milbeo, Laure Moulat, Claude Didierjean, Emmanuel Aubert, Jean Martinez, et al.. C 1 -Symmetric 1,2-Diaminobicyclo[2.2.2]octane Ligands in Copper-Catalyzed Asymmetric Henry Reaction: Catalyst Development and DFT Studies. European Journal of Organic Chemistry, 2018, 2018 (2), pp.178-187. ⟨10.1002/ejoc.201701452⟩. ⟨hal-02419329⟩
- 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⟩
- Florian Gallier, Arnaud Martel, Gilles Dujardin. Enantioselective Access to Robinson Annulation Products and Michael Adducts as Precursors. Angewandte Chemie International Edition, 2017, 56 (41), pp.12424 - 12458. ⟨10.1002/anie.201701401⟩. ⟨hal-01912415⟩
- Jacques Uziel, Fanny Cosson, Aline Faroux, Jean-Pierre Baltaze, Jonathan Farjon, et al.. Synthesis of ribavirin 2’-Me-C-nucleoside analogues. Beilstein Journal of Organic Chemistry, 2017, 13, pp.755 - 761. ⟨10.3762/bjoc.13.74⟩. ⟨hal-03553300⟩
- Pierre Milbeo, Laure Moulat, Claude Didierjean, Emmanuel Aubert, Jean Martinez, et al.. Synthesis of Enantiopure 1,2-Diaminobicyclo[2.2.2]octane Derivatives, C 1 -Symmetric Chiral 1,2-Diamines with a Rigid Bicyclic Backbone. Journal of Organic Chemistry, 2017, 82 (6), pp.3144 - 3151. ⟨10.1021/acs.joc.7b00122⟩. ⟨hal-01552321⟩
- 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⟩
- Nadege Lubin-Germain, Andrea Bordessa, Angélique Ferry. Access to complex C2-branched glycoconjugates via palladium-catalyzed aminocarbonylation reaction of 2-iodoglycals.. Journal of Organic Chemistry, 2016, 24, pp.12459-12465. ⟨10.1021/acs.joc.6b02278⟩. ⟨hal-02980121⟩
- 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⟩
- Nadege Lubin-Germain, Jacques Uziel, Patrick Wagner, Alexandra Basilio-Lopes, Martine Schmitt, et al.. Functionalization of 2H 1,2,3-Triazole C-Nucleoside Template via N2 Selective Arylation. Journal of Organic Chemistry, 2016, 11, pp.4540-4549. ⟨10.1021/acs.joc.6b00323⟩. ⟨hal-02980120⟩
- Pierre Milbeo, Kelly Maurent, Laure Moulat, Aurelien Lebrun, Claude Didierjean, et al.. N-Pyrrolidine-based alpha/beta-peptides incorporating ABOC, a constrained bicyclic beta-amino acid, for asymmetric aldol reaction catalysis. Tetrahedron, 2016, 72 (13), pp.1706-1715. ⟨10.1016/j.tet.2016.02.027⟩. ⟨hal-01532027⟩
- Chiara Testa, Mario Scrima, Manuela Grimaldi, Anna M D’ursi, Marvin L Dirain, et al.. 1,4-Disubstituted-[1,2,3]triazolyl-Containing Analogues of MT-II: Design, Synthesis, Conformational Analysis, and Biological Activity. Journal of Medicinal Chemistry, 2014, 57, pp.9424 - 9434. ⟨10.1021/jm501027w⟩. ⟨hal-05104322⟩
- Ibtissem Jlalia, Florian Gallier, Nancy Brodie-Linder, Jacques Uziel, Jacques Augé, et al.. Copper(II) SBA-15: A reusable catalyst for azide–alkyne cycloaddition. Journal of Molecular Catalysis A: Chemical, 2014, 393, pp.56-61. ⟨10.1016/j.molcata.2014.06.003⟩. ⟨hal-03553460⟩
- 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⟩
- Dancho Lyubenov Danalev, Nadege Lubin-Germain, Stephane Serfaty, Jean-Yves Le Huerou, Jacques Augé, et al.. Titan Based Hybrid Organic-Inorganic Gels Comprising Carbohydrate Moiety. Phosphorus, Sulfur, and Silicon and the Related Elements, 2011, 186 (11), pp.2216-2225. ⟨10.1080/10426507.2011.586384⟩. ⟨hal-00750858⟩
- Christophe Decroos, Yun Li, Gildas Bertho, Yves Frapart, Daniel Mansuy, et al.. Synthetic studies towards diazepanone scaffolds. Tetrahedron: Asymmetry, 2009, 20 (20), pp.2320-2330. ⟨10.1016/j.tetasy.2009.09.022⟩. ⟨hal-03685013⟩
- Florian Gallier, Hidayat Hussain, Arnaud Martel, Andreas Kirschning, Gilles Dujardin. Hetero-Diels-Alder Reactions of Cyclic Ketone Derived Enamide. A New and Efficient Concept for the Asymmetric Robinson Annulation. Organic Letters, 2009, 11 (14), pp.3060-3063. ⟨10.1021/ol901065e⟩. ⟨hal-00414358⟩
- Eike Kunst, Florian Gallier, Gilles Dujardin, Andréas Kirchning. Glycosidations of 2-deoxy glycosyl dithiophosphates using a tagged iodine(III)-promoter for simple purification. Organic & Biomolecular Chemistry, 2008, 6, pp.893-898. ⟨10.1039/B718642H⟩. ⟨hal-00326908⟩
- Olivier Monasson, Maryon Ginisty, Gildas Bertho, Christine Gravier-Pelletier, Yves Le Merrer. Efficient synthesis of polyfunctionalised enantiopure diazepanone scaffolds. Tetrahedron Letters, 2007, 48 (46), pp.8149-8152. ⟨10.1016/j.tetlet.2007.09.098⟩. ⟨hal-03685046⟩
- Eike Kunst, Florian Gallier, Gilles Dujardin, Mekhman S. Yusubov, Andreas Kirschning. Tagged Hypervalent Iodine Reagents: A New Purification Concept Based on Ion Exchange through Sn2 Substitution. Organic Letters, 2007, 9 (25), pp.5199-5202. ⟨hal-00199817⟩
- Sopa Chewchanwuttiwong, Arnaud Martel, Duang Buddhasukh, Eric Brown, Florian Gallier, et al.. Towards a [4+2] Route to (+/-)-decarestrictines J and H: Synthesis of a Bicyclic Key-intermediate. Chiang Mai J. Sci, 2004, 31 (2), pp.181-184. ⟨hal-02313828⟩
Communications dans un congrès
- 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⟩
- Virginie Doceul, Vincent Mallet, Nadege Lubin-Germain, Benjamin Onfroy, Jacques Uziel, et al.. Effect of a ribavirin analogue on the replication of hepatitis E virus in vitro. 17. Réunion du Réseau National Hépatites, Agence Nationale de la Recherche sur le SIDA et les hépatites (ANRS). FRA.; Université de Cergy Pontoise. FRA., Mar 2017, Paris, France. ⟨hal-02784814⟩
Poster de conférence
- Linhua Shen, Olivier Monasson, Linhua Shen, Elisa Peroni, Franck Le Bideau, et al.. New electrochemical method for Arylation of Cysteine containing peptides. European Peptide symposium 2024, Aug 2024, Florence, Italy. ⟨hal-04724342⟩
- Adrien Mourgout, F. Arjmand, E. Groult, Olivier Monasson, S. Ammar, et al.. Enhancing biomedical metal implants with synthetic peptides: improved bioactivity and in vitro safety. European Peptide symposium 2024, Aug 2024, Florence, Italy. ⟨hal-04727725⟩
- Olivier Monasson, Alima Chali, Sonia Touharia, Adrien Mourgout, Farzin Arjmand, et al.. Novel biocompatible alloys via peptides surface engineering. A decade of Peptide Materials, Oct 2023, Sorrento, Italy. . ⟨hal-04725375⟩
- Virginie Doceul, Vincent Mallet, Nadege Lubin-Germain, Benjamin Onfroy, Jacques Uziel, et al.. Impact d’un analogue de la ribavirine sur la réplication du virus de l’hépatite E in vitro. 19. Journées Francophones de Virologie, Mar 2017, Paris, France. John Libbey Eurotext, Virologie, 21, pp.93-100, 2017, ⟨10.1684/vir.2017.0691⟩. ⟨hal-02733548⟩
Proceedings/Recueil des communications
- Lorenzo Meneghelli, Lamia El Guermah, Maud Larregola, Sabrina Kellouche-Gaillard, Franck Carreiras, et al.. Design and Synthesis of Pin1-PROTACs as Potential Therapeutic Tools for Cancer Treatment. 36th European Peptide Symposium, Aug 2022, Sitges (Barcelona), Spain. The European Peptide Society, pp.285-287, 2022, ⟨10.17952/36EPS/36EPS.2022.285⟩. ⟨hal-05003974⟩
Chapitres d'ouvrage
- 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⟩
- Angélique Ferry, Florian Gallier, Simon Gonzalez, Nadège Lubin-Germain, Leandro Soter de Mariz E Miranda, et al.. Recent advances in the functionalization of unprotected carbohydrates. Amélia Pilar Rauter; Thisbe K Lindhorst; Yves Queneau. Carbohydrate Chemistry: Chemical and Biological Approaches, 45, Royal Society of Chemistry, pp.239-304, 2021, SPR - Carbohydrate Chemistry, 978-1-83916-390-6. ⟨10.1039/9781839164538-00239⟩. ⟨hal-03667486⟩
Pré-publications, Documents de travail
- 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⟩
Thèses
- Pierre Milbéo. Synthèse de bicycles contraints originaux pour l’élaboration de nouveaux catalyseurs chiraux et de nouveaux foldamères. Chimie organique. Université Montpellier, 2017. Français. ⟨NNT : 2017MONTT209⟩. ⟨tel-03824580⟩
- Simon Gonzalez. Galactosides et peptides de fusion pour l'amélioration de l'activité anti-VHC d'un C-nucléoside. Chimie organique. Université de Cergy Pontoise, 2017. Français. ⟨NNT : 2017CERG0900⟩. ⟨tel-01778113⟩
- Florian Gallier. Décanolides hydroxylés : nouvelles approches synthétiques et glycosylation par de nouveaux réactifs à base d'iode hypervalent. Autre. Université du Maine, 2007. Français. ⟨NNT : ⟩. ⟨tel-00203092⟩
Habilitations à diriger des recherches
- Chiara Zanato. From total synthesis to chemical biology: an overview of my scientific career. Chemical Sciences. CYU Cergy Paris Université, 2024. ⟨tel-05012925⟩
Documents récupérés de l'archive ouverte HAL 