Thématiques Poste BioCIS

Fluorinated amino acids as tools for peptide engineering and medicinal chemistry


 

Enantiopure fluorinated aminoacids syntheses

thematique 1
thematique 1

- Huguenot, F.; Brigaud, T. J. Org. Chem. 2006, 71, 2159.
- Huguenot, F.; Billac, A.; Brigaud, T.; Portella, C. J. Org. Chem. 2008, 73, 2564.
- Chaume, G.; Lensen, N.; Caupène, N.; Brigaud, T. Eur. J. Org. Chem. 2009, 5717.
- Simon, J.; Nguyen, T. T.; Chelain, E.; Lensen, N.; Pytkowicz, J.; Chaume, G.; Brigaud, T. Tetrahedron: Asymmetry 2011, 22, 309.
- Gadais, C.; Saraiva-Rosa, N.; Chelain, E.; Pytkowicz, J.; Brigaud, T. Eur. J. Org. Chem. 2017, 246. Huguenot, F.; Brigaud, T. J. Org. Chem. 2006, 71, 7075.
thematique 2
thematique 2

- Chaume, G., Van Severen, M.-C., Marinkovic, S.; Brigaud, T. Org. Lett. 2006, 8, 6123.

- Chaume, G.; Van Severen, M.-C.; Ricard, L.; Brigaud, T. J. Fluorine Chem. 2008, 129, 1104–1109.
- Caupène, C.; Chaume, G., Ricard, L.; Brigaud, T. Org. Lett. 2009, 11, 209.
- Chaume, G.; Barbeau, O.; Lesot, P., Brigaud, T. J. Org. Chem. 2010, 75, 4135.
- Chaume, G.; Simon, J.; Caupène, C.; Lensen, N.; Miclet, E.; Brigaud, T. J. Org. Chem. 2013, 78, 10144−10153.
- Lensen, N.; Marais, J.; Brigaud, T. Org. Lett. 2015, 17, 342.
- Lubin, H.; Pytkowicz, J.; Chaume, G.; Sizun-Thomé, G.; Brigaud, T. J. Org. Chem. 2015, 80, 2700.
- Simon, J.; Pytkowicz, J.; Lensen, N.; Chaume, G.; Brigaud, T. J. Org. Chem. 2016, 81, 5381.
- Malquin, N.; Rahgoshay, K.; Lensen, N.; Chaume, G.; Miclet, E.; Brigaud, T. Chem. Commun. 2019, 55, 12487-12490.
- Ouerfelli, O.; Simon, J.; Chelain, E.; Pytkowicz, J.; Besbes, R.; Brigaud, T. Org. Lett. 2020, 22, 2946–2949.
- Sanchez, C. A.; Gadais, C.; Chaume, G.; Girard, S.; Chelain, E.; Brigaud, T. Org. Lett. 2021, 23, 382–387.

Hydrophobicity and medicinal chemistry

thematique 3
thematique 3

- Gadais, C.; Devillers, E.; Gasparik, V.; Chelain, E.; Pytkowicz, J.; Brigaud, T. ChemBioChem 2018, 19, 1026.
- Devillers, E.; Pytkowicz, J.; Chelain, E.; Brigaud, T. Amino Acids 2016, 48, 1457.
Fluorinated analogs of PLG
thematique 4
thematique 4

- Jlalia, I.; Lensen, N.; Chaume, G.; Dzhambazova, E.; Astasidi, L.; Hadjiolova, R.; Bocheva, A.; Brigaud, T. Eur. J. Med. Chem. 2013, 62, 122.
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Bocheva, A.; Nocheva, H., Jlalia, I., Lensen, N., Chaume, G.; Brigaud, T. Med. Chem. 2013, 3, 206.
- Martin, O.; Gadais, C.; García-Pindado, J.; Teixido, M.; Lensen, N.; Chaume, G.; Brigaud, T. RSC Advances 2018, 8, 14597.
Hydrophobic short Peptide for the Inhibition of Amyloid Peptide Fibrillation
thematique 5
thematique 5

- Botz, A.; Gasparik, V.; Devillers, E.; Hoffmann, A. R. F.; Caillon, L.; Chelain, E.; Lequin, O.; Brigaud, T.; Khemtemourian, L. Biopolymers: Peptide Science 2015, 104, 601.
 

19F NMR probe

Harzianin antimicrobial peptide

thematique 6
thematique 6

- Grage, S. L.; Kara, S.; Bordessa, A.; Doan, V.; Rizzolo, F.; Putzu, M.; Kubař, T.; Papini, A. M.; Chaume, G.; Brigaud, T.; Afonin, S.; Ulrich, A.S. Chem. Eur. J. 2018, 24, ,4328.
- Putzu, M.; Kara, S.; Afonin, S.; Grage, S. L.; Bordessa, A.; Chaume, G.; Brigaud, T.; Ulrich, A. S; Kubar, T. Biophys. J. 2017, 112, 2602.

Conformational constraints

Trans/Cis amide conformation control and ring puckering

thematique 7
thematique 7

- 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.
- Chaume, G.; Feytens, D.; Chassaing, G.; Lavielle, S.; Brigaud, T.; Miclet, E. New J. Chem. 2013, 37, 1336.
- Malquin, N.; Rahgoshay, K.; Lensen, N.; Chaume, G.; Miclet, E.; Brigaud, T. Chem. Commun. 2019, 55, 12487-12490
thematique 8
thematique 8

- Sanchez, C. A.; Gadais, C.; Chaume, G.; Girard, S.; Chelain, E.; Brigaud, T. Org. Lett. 2021, 23, 382.
thematique 9
thematique 9

Chaume, G.; Simon, J.; Lensen, N.; Pytkowicz, J.; Brigaud, T.; Miclet, E. J. Org.
Chem. 2017, 82, 13602