Synthetic chemistry and molecular modelling groups at CBMN in 01/2007
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1 Biomimetic Supramolecular Chemistry Synthetic chemistry and molecular modelling groups at CBMN in 01/2007 Permanent staff Ivan Huc (GL, DR CNRS) Frédéric Godde (MdC UB) Organic & Medicinal Chemistry Permanent staff Léon Ghosez (GL, Guest Prof.) Modelling of Biomolecules Permanent staff Juan Elezgaray (GL, CR CNRS) Jean Dessolin (CR CNRS) Michel Laguerre (DR CNRS)
2 Biomimetic Supramolecular Chemistry Permanent staff Ivan Huc (GL, DR CNRS) Yann Ferrand (CR CNRS) Victor Maurizot (CR CNRS) Lucile Fischer-Durola (CR CNRS) Eric Merlet (AI CNRS) Biomimetic and therapeutic chemistry Peptidomimetic Chemistry Permanent staff Gilles Guichard (GL, DR CNRS) Céline Douat (CR CNRS) Christel Dolain (MdC UB) Morgane Pasco (CR CNRS) Molecular Modelling for Bioengineering Organic & Medicinal Chemistry Permanent staff Léon Ghosez (Guest Prof.) Permanent staff Isabelle Bestel (GL, Prof. UB) Jean Dessolin (CR CNRS) Eduard Badarau (MdC UB) Nada Taib (CR CNRS)
3 FOLDING SYNTHESIS MOLECULAR DESIGN MOLECULAR INTERACTIONS THERAPEUTIC TARGETTING STRUCTURAL ANALYSIS
4 Build up of the crystallography platform at IECB 2004 Installation of 1 st generator, SAXS and XRD setups 2004 Recruitment of B. Kauffmann (IR CNRS) 2013 Complete renewal of equipments
5 2010 The Structure of the Oligourea Helix at Atomic Resolution ACIE 2010
6 2015 Interfacing Peptides and Oligourea Foldamers α-helix oligourea?? Oligourea 2.5-helix peptide α-helix Oligourea 2.5-helix ACIE 2015; CR Chimie 2016
![Bacillus anthracis [coll P. Goossens, Institut Pasteur] [Coll. with A. Kichler & B.](/docs-images/93/114178212/images/7-5.jpg "Bechinger, Strasbourg] CIE 2010; J. Phys. Chem. B 2011; J. Med.")
7 Biological Applications of Amphipathic Helical Foldamers Host-defense peptide mimics : Dichotomy between isomorphic oligourea and oligoamide backbones Foldamer/pDNA assemblies for DNA delivery into cells Oligourea analogues of LAH4 : KKALLALALHHLAHLALHLALALKKA X = NH X = CH 2 oligourea gamma-peptide capsulated Bacillus anthracis [coll P. Goossens, Institut Pasteur] [Coll. with A. Kichler & B. Bechinger, Strasbourg] CIE 2010; J. Phys. Chem. B 2011; J. Med. Chem 2016 Tetrahedron 2011; ACIE 2015
![E u E u L u L u [θ] x 10-4](/docs-images/93/114178212/images/8-4.jpg "(deg.cm 2.dmol -1.")
8 2015 : Self-assemblies of Amphiphilic Oligourea Foldamers : Helix Bundles K u K u A u Y u L u 1 Lu L u E u E u L u L u [θ] x 10-4 (deg.cm 2.dmol -1.residue -1 ) λ / nm 38 Å 32 Å 60 o N-termini N-termini X-ray crystal structure Nat. Chem 2015; Chem. Commun. 2016, JACS 2016
9 Molecular Modelling & Bioengineering Team Expertise All-atom and United atom Molecular dynamics High throughput screening - docking Coarse grained Molecular dynamics Molecular engineering
10 Research Area 1: LIPIDS AND SURFACTANTS ASSEMBLIES, AGGREGATION PROCESSES ( ) Amphiphilic Nucleic acids Amphiphilic Riboflavin J Am Chem Soc 2008 Langmuir, J Colloid Interface Sci Biomaterials 2016, Bioconjugate Chem 2016, Int J Nanomedicine 2017
11 Research Area 2: SOLUBLE PROTEINS ( ) Kinases Pontin/reptin J Chem Biol 2009, Science Signal 2010, Adv Biol Regul 2010, Biochem J 2012, Biochem Soc Trans Biochem J 2012, Bioorg Med Chem 2014.
12 Research Area 3: PSEUDOPEPTIDE, PEPTIDE or PROTEIN/MEMBRANE INTERACTIONS ( ) Pseudopeptide Guest encapsulation Protein/membrane interactions Tannin-lipid interactions J Am Chem Soc 2017 Protein reconstruction Riboflavin transporter
13 Organic and medicinal Chemistry 1. Design and synthesis of natural products inspired privileged scaffolds an invaluable source of molecules of therapeutic import ( see Dr. E. Pair contribution tomorrow) 2. Silylated triflimides : a new class of silicon-derived superacid catalysts for the activation of highly functionalized substrates under mild and sustainable conditions. Easy to prepare in situ : R 3 SiH + HNTf 2 100% R 3 SiNTf 2 Unusual acidities : TMS-NTf 2 > TMS-OTf while HNTF 2 << HOTf TriisopropylSiNTf 2 > TrimethylSiNTf 2 bulkiness increases acidity : against the dogma in silicon chemistry! Catalyze efficiently many reactions through activation of a carbonyl group : eg : alkylation can be effected without the use of genotoxic reagents O C O Me TMSNTf 2 TMS O = Me C O - NTf 2 OTMS rt O 93% OMe O + SPh rt PhS O TMSOTf 0% TMSNTf 2 93% OMe OMe
14 AROMATIC AMIDE FOLDAMER STRUCTURES 7 nm ibuo X-ray NH N O units 11.7 kda 19 helical turns Org. Lett JACS 2009 X-ray
15 molecular recognition ACIE 2008; JACS 2010; JACS 2017 Nat. Chem molecular motion & nano-assemblies Science 2011, Nat. Nanotech. 2017
16 Biomimetic and therapeutic chemistry BORDEAUX, FRANCE, Jan , 2010 Foldamers: from design to protein recognition BORDEAUX, FRANCE, Jan. 30- Feb. 2, 2012 Bordeaux 2012 symposium on Foldamers PARIS, FRANCE, April 10-12, 2013 Paris 2013 symposium on Foldamers BORDEAUX, FRANCE, Jan , 2015 Bordeaux 2015 symposium on foldamers BORDEAUX, FRANCE, Sept , 2016 Bordeaux 2016 symposium on foldamers
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