CBL Chemical Biology Lab

Grégory Chaume

Associate Professor

Education & Career :

2003 : PhD in organic synthesis

University of Cergy-Pontoise. Toward the total synthesis of Griseoviridin (Advisor: Prof. J. Ardisson & DR A. Pancrazi)

2004 : Post-doc position in Prof. G. Pattenden Laboratory.

Nottingham University - England. Contribution to the total synthesis of Ulapualide A.

2005 : Temporary Associate professor.

University of Cergy-Pontoise. Prof. T. Brigaud’s group. Organofluorine Chemistry

2006-  : Associate professor.

University of Cergy-Pontoise.

 

Research Interests :

Chiral fluorinated compounds (amino acids, pseudopeptides, amino alcohols, diamines…)

Fluorinated peptides, fluorinated bioactive molecules.

Asymmetric synthesis .

 

Recent Publications

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.

Effects of enantiopure (S)-a-trifluoromethyl proline containing MIF-1’s analogue on stress-induced analgesia,Bocheva, A.; Nocheva, H.; Jlalia, I.; Lensen, N.; Chaume, G.; Brigaud, T. Med. Chem. 2013, 3, 206-209.

Synthesis of a MIF-1 analogue containing Enantiopure (S)-α-Trifluoromethyl Proline and Biological Evaluation on Nociception, Jlalia, I.; Lensen, N.; Chaume, G.; Dzhambazova, E.; Astasidi, L.; Hadjiolova, R.; Bocheva, A.; Brigaud, T. Eur. J. Med. Chem. 2013, 62, 122-129.

Conformational properties of peptides incorporating a fluorinated pseudoproline residue, Chaume, G.; Feytens, D.; Chassaing, G.; Lavielle, S.; Brigaud, T.; Miclet, E. New J. Chem. 2013, 37, 1336-1342

Local control of the cis-trans isomerization and backbone dihedral angles in peptides using trifluoromethylated pseudoprolines, Feytens, D.; Chaume, G.; Chassaing, G.; Lavielle, S.; Brigaud, T.; Byun, B. J.; Kang, Y. K.; Miclet, E. J. Phys. Chem. B 2012, 116, 4069-4079.

Concise Synthesis of Enantiopure (S)- and (R)-alpha-Trifluoromethyl Aspartic Acid and alpha-Trifluoromethyl Serine from Chiral Trifluoromethyl Oxazolidines (Fox) via the Strecker-type Reaction, Simon, J.; Nguyen, T. T.; Chelain, E.; Lensen, N.; Pytkowicz, J.; Chaume, G.; Brigaud, T. Tetrahedron : Asymmetry 2011, 22, 309-314.

Highly Diastereoselective alfa-Hydroxylation of Fox Chiral Auxiliary-Based Amide Enolates with Molecular Oxygen, Lubin, H. ; Tessier, A. ; Chaume, G. ; Pytkowicz, J. ; Brigaud, T. Org. Lett. 2010, 12, 1496-1499.

Synthesis of 2-Trifluoromethyl-1,3-oxazolidines as Hydrolytically Stable Pseudoprolines, Chaume, G. ; Barbeau, O. ; Lesot, P. ; Brigaud, T. J. Org. Chem. 2010, 75, 4135-4145.

Iodocyclization of Chiral CF3-Allylmorpholinones : A Versatile Strategy for the Synthesis of Enantiopure alfa-Tfm-Prolines and alfa-Tfm-Dihydroxyprolines, Caupène, C. ; Chaume, G. ; Ricard, L. ; Brigaud, T. Org. Lett. 2009, 11, 209-212

Convenient Synthesis of N-Terminal Tfm-Dipeptides from Unprotected Enantiopure alfa-Tfm-Proline and alfa-Tfm-Alanine, Chaume, G. ; Lensen, N. ; Caupène, C. ; Brigaud, T. Eur. J. Org. Chem. 2009, 33, 5717-5724

Concise access to enantiopure (S)- and (R)-α-trifluoromethyl pyroglutamic acids from ethyl trifluoropyruvate-based chiral CF3-oxazolidines (Fox), Chaume, G. ; Van Severen, M. -C. ; Ricard, L. ; Brigaud, T. J. Fluorine Chem. 2008, 129, 1104-1109

The stereoselective synthesis of alfa-Tfm-amino acids from chiral CF3 building blocks, Brigaud, T. ; Chaume, G., Pytkowicz, J. ; Huguenot, F. Chim. Oggi 2007, 25(Supl), 8-10

Straightforward synthesis of (S)- and (R)-alfa-trifluoromethyl proline from chiral oxazolidines derived from ethyl trifluoropyruvate, Chaume, G., Van Severen, M.-C., Marinkovic, S. ; Brigaud, T. Org. Lett. 2006, 8, 6123-6126