Pentapeptides containing two dehydrophenylalanine residues - synthesis, structural studies and evaluation of their activity towards cathepsin C

Latajka R, Jewginski M, Makowski M, Paweiczak M, Huber T, Sewald N, Kafarski P (2008)
JOURNAL OF PEPTIDE SCIENCE 14(10): 1084-1095.

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Abstract
Synthesis, structural and biological studies of pentapeptides containing two Delta Phe residues (Z and E isomers) in position 2 and 4 in peptide chain were performed. All the investigated peptides adopted bent conformation and majority of them could exist as two different. conformers in solution. Only pentapeptides. containing free N-termini appeared to act as weak inhibitors of cathepsin C with the slow-binding, competitive mechanism of inhibition. free acids being bound slightly better than their methyl esters. Results of Molecular modeling suggested significant difference between peptides, depending of the type of amino acid residue in position 5 in peptide chain. Dehydropeptides containing GIN, residue in this position may act as competitive slow-reacting substrates and therefore exhibit inhibitory-like properties. Copyright (C) 2008 European Peptide Society and John Wiley & Sons, Ltd.
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Latajka R, Jewginski M, Makowski M, et al. Pentapeptides containing two dehydrophenylalanine residues - synthesis, structural studies and evaluation of their activity towards cathepsin C. JOURNAL OF PEPTIDE SCIENCE. 2008;14(10):1084-1095.
Latajka, R., Jewginski, M., Makowski, M., Paweiczak, M., Huber, T., Sewald, N., & Kafarski, P. (2008). Pentapeptides containing two dehydrophenylalanine residues - synthesis, structural studies and evaluation of their activity towards cathepsin C. JOURNAL OF PEPTIDE SCIENCE, 14(10), 1084-1095.
Latajka, R., Jewginski, M., Makowski, M., Paweiczak, M., Huber, T., Sewald, N., and Kafarski, P. (2008). Pentapeptides containing two dehydrophenylalanine residues - synthesis, structural studies and evaluation of their activity towards cathepsin C. JOURNAL OF PEPTIDE SCIENCE 14, 1084-1095.
Latajka, R., et al., 2008. Pentapeptides containing two dehydrophenylalanine residues - synthesis, structural studies and evaluation of their activity towards cathepsin C. JOURNAL OF PEPTIDE SCIENCE, 14(10), p 1084-1095.
R. Latajka, et al., “Pentapeptides containing two dehydrophenylalanine residues - synthesis, structural studies and evaluation of their activity towards cathepsin C”, JOURNAL OF PEPTIDE SCIENCE, vol. 14, 2008, pp. 1084-1095.
Latajka, R., Jewginski, M., Makowski, M., Paweiczak, M., Huber, T., Sewald, N., Kafarski, P.: Pentapeptides containing two dehydrophenylalanine residues - synthesis, structural studies and evaluation of their activity towards cathepsin C. JOURNAL OF PEPTIDE SCIENCE. 14, 1084-1095 (2008).
Latajka, R., Jewginski, M., Makowski, M., Paweiczak, M., Huber, T., Sewald, Norbert, and Kafarski, P. “Pentapeptides containing two dehydrophenylalanine residues - synthesis, structural studies and evaluation of their activity towards cathepsin C”. JOURNAL OF PEPTIDE SCIENCE 14.10 (2008): 1084-1095.
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