Institut de Chimie Moléculaire et des Matériaux d'Orsay

Sylvie Robin

Enseignant-Chercheur
Bât. 670, bureau 3204 – CP3A – ICMMO - UMR 8182
Université Paris-Saclay
Bâtiment 670
17-19 Avenue des Sciences
91400 Orsay
FRANCE

+33 1 69 15 76 30
sylvie.robin@universite-paris-saclay.fr

Sylvie Robin obtained her Ph.D in 1992, from the University of Paris-Sud, in Orsay with Professor F. Huet, working on optically active lactone synthesis. She spent a postdoctoral year at Oxford University with Professor L. M. Harwood, studying cycloadditions with chiral azomethines. Coming back in France, she obtained a teaching position at the Faculty of Pharmacology (Univ. Paris V). In 1995, she joined Dr. G. Rousseau's theme at the University of Paris-Sud, where she studied the reactivity of electrophilic reagents. Since 2009, in Pr. D. J. Aitken’s group, she first worked on the synthesis of conformationally restricted GABA and to the folding behavior of their homo-oligomers and hetero-β,γ-oligomers. Recently she turned her interest to the role of the non-covalent interaction S-H...N in the peptidomimetic oligomers folding. Keywords: amino acids, peptide synthesis, photochemistry, cyclisation, chiral resolution.

Synthesis of enantiopure conformationally restricted GABA via photochemical reaction conditions

Synthesis of sulfured non canonic amino acids

Preparation of homo-oligomers of cis-2,3-cyclobutyl-GABA

Preparation of hetero-oligomers of β,γ-peptides

Publications :

Effects of sulfoxide and sulfone sidechain–backbone hydrogen bonding on local conformations in peptide models. D. Liu, S. Robin, E. Gloaguen, V. Brenner, M. Mons, D. J. Aitken, Chemical Communications, 2024, 60, 2074-2077

trans-3-Benzyloxycarbonylamino-1-methyl-3-(methylcarbamoyl)azetidine-1-oxide. D. Liu, R. Guillot, S. Robin, D. J. Aitken, Molbank, 2023, 2023, M1726

Length-Dependent Transition from Extended to Folded Shapes in Short Oligomers of an Azetidine-Based α-Amino Acid: The Critical Role of NH···N H-Bonds. D. Liu, J.-X. Bardaud, Z. Imani, S. Robin, E. Gloaguen, V. Brenner, D. J. Aitken, M. Mons, Molecules, 2023, 28, 5048

A Post-Synthetic Modification Strategy for the Preparation of Homooligomers of 3-Amino-1-methylazetidine-3-carboxylic acid. D. Liu, Z. Imani, C. Gourson, R. Guillot, S. Robin, D. J. Aitken, Synlett, 2023, 34, 1787-1790

β-N-Heterocyclic Cyclobutane Carboximides: Synthesis Via a Tandem Base-Catalyzed Amidation/aza-Michael Addition Protocol and Facile Transformations. S. Barranco, F. Cuccu, D. Liu, S. Robin, R. Guillot, F. Secci, V. Brenner, M. Mons, P. Caboni, D. J. Aitken, A. Frongia, European Journal of Organic Chemistry, 2023, 26, e202300183

Non-covalent interactions reveal the protein chain δ conformation in a flexible single-residue model. Z. Imani, V. R. Mundlapati, V. Brenner, E. Gloaguen, K. Le Barbu-Debus, A. Zehnacker-Rentien, S. Robin, D. J. Aitken, M. Mons, Chemical Communications, 2023, 59, 1161-1164

N–H···X interactions stabilize C5 intra-residue hydrogen bonding in heterocyclic α-amino acid derivatives. V. R. Mundlapati, Z. Imani, V. C. D'Mello, V. Brenner, E. Gloaguen, J.-P. Baltaze, S. Robin, M. Mons, D. J. Aitken, Chemical Science, 2021, 12, 14826-14832

A theoretical and experimental case study of the hydrogen bonding predilection of S-methylcysteine. V. R. Mundlapati, Z. Imani, G. Goldsztejn, E. Gloaguen, V. Brenner, K. Le Barbu-Debus, A. Zehnacker-Rentien, J.-P. Baltaze, S. Robin, M. Mons, D. J. Aitken, Amino Acids, 2021, 53, 621-633

Conformation control through concurrent N–H⋯S and N–H⋯O=C hydrogen bonding and hyperconjugation effects. Z. Imani, V. R. Mundlapati, G. Goldsztejn, V. Brenner, E. Gloaguen, R. Guillot, J.-P. Baltaze, K. Le Barbu-Debus, S. Robin, A. Zehnacker, M. Mons, D. J. Aitken, Chem. Sci., 2020, 11, 9191-9197

Preparation of cyclobutene acetals and tricyclic oxetanes through photochemical tandem and cascade reactions. J. Buendia, Z. Chang, H. Eijsberg, R. Guillot, A. Frongia, F. Secci, J. Xie, S. Robin, T. Boddaert, D. J. Aitken, Angewandte Chemie International Edition, 2018, 57, 6592-6596

β-Cyclodextrin-Mediated Enantioselective Photochemical Electrocyclization of 1,3-Dihydro-2H-azepin-2-one. A. T. Mansour, J. Buendia, J. Xie, F. Brisset, S. Robin, D. Naoufal, O. Yazbeck, D. J. Aitken, J. Org. Chem., 2017, 82, 9832-9836

Conformational effects through hydrogen bonding in a constrained γ-peptide template: from intra-residue 7-membered rings to a gel-forming sheet structure. H. Awada, C. M. Grison, F. Charnay-Pouget, J.-P. Baltaze, F. Brisset, R. Guillot, S. Robin, A. Hachem, N. Jaber, D. Naoufal, O. Yazbeck, D. J. Aitken, J. Org. Chem., 2017, 82, 4819–4828

An α-Helix-Mimicking 12,13-Helix: Designed α/β/γ-Foldamers as Selective Inhibitors of Protein–Protein Interactions. C. M. Grison, J. A. Miles, S. Robin, A. J. Wilson, D. J. Aitken, Angewandte Chemie International Edition, 2016, 55, 11096-11100

13-Helix folding of a β/γ-peptide manifold designed from a "minimal-constraint" blueprint. C. M. Grison, S. Robin, D. J. Aitken, Chem. Commun., 2016, 52, 7802-7805

The discovery of 9/8-ribbons, β/γ-peptides with curved shapes governed by a combined configuration-conformation code. C. M. Grison, S. Robin, D. J. Aitken, Chem. Commun., 2015, 51, 16233-16236

Pushing the limits of signal resolution to make coupling measurement easier. J. E. H. Pucheta, D. Pitoux, C. M. Grison, S. Robin, D. Merlet, D. J. Aitken, N. Giraud, J. Farjon, Chem Commun, 2015, 51, 7939-7942

Practical Syntheses of Both Enantiomers of the Conformationally Restricted GABA Analogue cis-(2-Aminocyclobutyl)acetic Acid. H. Awada, S. Robin, R. Guillot, O. Yazbeck, D. Naoufal, N. Jaber, A. Hachem, D. J. Aitken, European Journal of Organic Chemistry, 2014, 2014, 7148-7155