Position-dependent impact of hexafluoroleucine and trifluoroisoleucine on protease digestion

Scholarly Works

• Lunkov, S. S.; Kostromitin, V. S.; Zemtsov, A. A.; Levin, V. V.; Dilman, A. D. A photocatalytic method for the generation of the 1,1,1,3,3,3-hexafluoroisopropyl radical. Organic Chemistry Frontiers 2024, 11, 4762–4768. doi:10.1039/d4qo01023j
• Brumă Călin, M.; Vasilean, I.; Grigore-Gurgu, L.; Banu, I.; Aprodu, I. Advances in Understanding the Antioxidant and Antigenic Properties of Egg-Derived Peptides. Molecules (Basel, Switzerland) 2024, 29, 1327. doi:10.3390/molecules29061327
• Terzani, F.; Belhattab, S.; Le Guern, A.; Guitot, K.; Monasson, O.; Zanato, C.; Chelain, E.; Leroy-Dudal, J.; Pytkowicz, J. Synthesis and biological evaluation of selective Pepstatin based trifluoromethylated inhibitors of Cathepsin D. European journal of medicinal chemistry 2024, 267, 116178. doi:10.1016/j.ejmech.2024.116178
• Boutahri, Y.; Ben Haj Salah, K.; Tisserand, N.; Lensen, N.; Crousse, B.; Brigaud, T. Difluoroalanine: Synthesis, Incorporation in Peptides, and Hydrophobic Contribution Assessment. Organic letters 2023, 25, 6937–6941. doi:10.1021/acs.orglett.3c02853
• Miles, S. A.; Nillama, J. A.; Hunter, L. Tinker, Tailor, Soldier, Spy: The Diverse Roles That Fluorine Can Play within Amino Acid Side Chains. Molecules (Basel, Switzerland) 2023, 28, 6192. doi:10.3390/molecules28176192
• Khan, M. F.; Chowdhary, S.; Koksch, B.; Murphy, C. D. Biodegradation of Amphipathic Fluorinated Peptides Reveals a New Bacterial Defluorinating Activity and a New Source of Natural Organofluorine Compounds. Environmental science & technology 2023, 57, 9762–9772. doi:10.1021/acs.est.3c01240
• Chowdhary, S.; Pelzer, T.; Saathoff, M.; Quaas, E.; Pendl, J.; Fulde, M.; Koksch, B. Fine‐tuning the antimicrobial activity of β‐hairpin peptides with fluorinated amino acids. Peptide Science 2023, 115. doi:10.1002/pep2.24306
• Pytkowicz, j. Synthesis and Biological Evaluation of Selective Pepstatin Based Trifluoromethylated Inhibitors of Cathepsin D. Elsevier BV 2023. doi:10.2139/ssrn.4636657
• Naulet, G.; Delamare, A.; Guichard, G.; Compain, G. In Situ Generated DBU⋅HF Acts as a Fluorinating Agent in a Hexafluoroisobutylation Tandem Reaction: An Effective Route to 5,5,5,5',5',5'‐Hexafluoroleucine. European Journal of Organic Chemistry 2022, 26. doi:10.1002/ejoc.202201148
• Delamare, A.; Naulet, G.; Kauffmann, B.; Guichard, G.; Compain, G. Hexafluoroisobutylation of enolates through a tandem elimination/allylic shift/hydrofluorination reaction. Chemical science 2022, 13, 9507–9514. doi:10.1039/d2sc02871a
• Leppkes, J.; Dimos, N.; Loll, B.; Hohmann, T.; Dyrks, M.; Wieseke, A.; Keller, B. G.; Koksch, B. Fluorine-induced polarity increases inhibitory activity of BPTI towards chymotrypsin. RSC chemical biology 2022, 3, 773–782. doi:10.1039/d2cb00018k
• Devillers, E.; Chelain, E.; Dalvit, C.; Brigaud, T.; Pytkowicz, J. (R)-α-Trifluoromethylalanine as a 19F NMR Probe for the Monitoring of Protease Digestion of Peptides. Chembiochem : a European journal of chemical biology 2021, 23, e202100470. doi:10.1002/cbic.202100470
• Sanchez, C.; Gadais, C.; Diarra, S.; Bordessa, A.; Lensen, N.; Chelain, E.; Brigaud, T. Synthesis of enantiopure α-Tfm-proline and α-Tfm-pipecolic acid from oxazolo-pyrrolidines and -piperidines. Organic & biomolecular chemistry 2021, 19, 6771–6775. doi:10.1039/d1ob01173a
• Lai, X.; Tang, J. X.; ElSayed, M. E. H. Recent advances in proteolytic stability for peptide, protein, and antibody drug discovery. Expert opinion on drug discovery 2021, 16, 1467–1482. doi:10.1080/17460441.2021.1942837
• Sanchez, C.; Gadais, C.; Chaume, G.; Girard, S.; Chelain, E.; Brigaud, T. Enantiopure 5-CF3-Proline: Synthesis, Incorporation in Peptides, and Tuning of the Peptide Bond Geometry. Organic letters 2020, 23, 382–387. doi:10.1021/acs.orglett.0c03880
• Sloand, J. N.; Miller, M. A.; Medina, S. H. Fluorinated peptide biomaterials. Peptide science (Hoboken, N.J.) 2020, 113. doi:10.1002/pep2.24184
• Leppkes, J.; Hohmann, T.; Koksch, B. Improved enantioselective gram scale synthesis route to N-Fmoc-protected monofluoroethylglycine. Journal of Fluorine Chemistry 2020, 232, 109453. doi:10.1016/j.jfluchem.2020.109453
• Ouerfelli, O.; Simon, J.; Chelain, E.; Pytkowicz, J.; Besbes, R.; Brigaud, T. Enantiopure α-Trifluoromethylated Aziridine-2-carboxylic Acid (α-TfmAzy): Synthesis and Peptide Coupling. Organic letters 2020, 22, 2946–2949. doi:10.1021/acs.orglett.0c00645
• Mei, H.; Han, J.; Klika, K. D.; Izawa, K.; Sato, T.; Meanwell, N. A.; Soloshonok, V. A. Applications of fluorine-containing amino acids for drug design. European journal of medicinal chemistry 2019, 186, 111826. doi:10.1016/j.ejmech.2019.111826
• Christensen, M. V.; Kongstad, K. T.; Sondergaard, T. E.; Staerk, D.; Nielsen, H. M.; Franzyk, H.; Wimmer, R. 19 F-substituted amino acids as an alternative to fluorophore labels: monitoring of degradation and cellular uptake of analogues of penetratin by 19 F NMR. Journal of biomolecular NMR 2019, 73, 167–182. doi:10.1007/s10858-019-00239-3

Explore citations to this article at