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Séminaire Chimie ED459

Design of novel site-specific ligation chemistries for the synthesis of complex scaffolds or for the vectorization of drugs

Prof. Oleg Melnyk (UMR CNRS 8161, Institut de Biologie de Lille, Institut Pasteur de Lille)

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Le Jeudi 13 Novembre 2008 à 13h45
Salle de cours SC-16.01 (UM2)

Co-Authors : Oleg Melnyk, Nathalie Ollivier, Soizic Besret, Reda Mhidia

The peptide chemist tool box contains a variety of chemoselective ligation methods that allow the convergent assembly of natural proteins or synthetic peptide scaffolds. Novel ligation methods are needed to create native peptide bond or non native bonds within polypeptides molecules. In the past, the lab has been deeply involved in Schiff-base ligation chemistry, and in particular hydrazone or semicarbazone ligation. The presentation will be focussed on recent developments using different strategies. The first part is based on the chemistry of phenylthiocarbonyl group, which can be easily introduced into peptides on α or ε amino groups using phenylthiochloroformate and standard solid-phase methods. Two ligation methods will be described : the chemoselective reaction of the phenylthiocarbonyl (PTC) group with cysteinyl peptides to give an alkylthiocarbamate bond, or the reaction of PTC group with a peptide hydrazide to give an azapeptide bond. The second part of the presentation will be focussed on a novel ligation method based on the chemistry of C-terminal peptide thioacids, and its application for the targeted delivery of drugs.

References
Nathalie Ollivier, Jean-Bernard Behr, Ouafâa El-Mahdi, Annick Blanpain and Oleg Melnyk, Org. Lett. 2005, 7, 2647-2650.
V. Souplet, O. Carion, C. Maillet, C. Olivier, N. Médard, O. El-Mahdi, J.-O. Durand and O. Melnyk, ChemBioChem 2007, 8, 315-322.
C. Roux, F. Chai, N. Ollivier, S. Winter, O. Melnyk, H. F. Hildebrandt, Biomolecular Engineering, 2007, 24, 549-554.
Lionel Marcon, Didier Stiévenard, Oleg Melnyk, Bioconjugate Chem. 2008, 802-805.
Vianney Souplet, Clément Roux, Oleg Melnyk, In : Peptide Microarrays, Humana Press, 2008, Marina Cretich and Marcella Chiari Eds. (chapter book, in press).
Ouafâa El-Mahdi, Vianney Souplet, Olivier Carion, Clément Roux, Jean-Michel Garcia, Céline Maillet, Christophe Olivier, Jean-Olivier Durand and Oleg Melnyk, In : Colloidal Nanoparticles in Biotechnologies, Elaissari, A. Ed., John Wiley & Sons, US, 2008, 299-327.
Soizic Besret, Nathalie Ollivier, Annick Blanpain, Oleg Melnyk, J. Pep. Sci. 2008, in press.

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