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.

Zeitschriftenaufsatz | Veröffentlicht | Englisch
 
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Autor*in
Latajka, R.; Jewginski, M.; Makowski, M.; Paweiczak, M.; Huber, T.; Sewald, NorbertUniBi ; Kafarski, P.
Abstract / Bemerkung
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.
Stichworte
conformation; inhibitors of cathepsin C; dehydropeptide
Erscheinungsjahr
2008
Zeitschriftentitel
Journal of Peptide Science
Band
14
Ausgabe
10
Seite(n)
1084-1095
ISSN
1075-2617
eISSN
1099-1387
Page URI
https://pub.uni-bielefeld.de/record/1585817

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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. https://doi.org/10.1002/psc.1045
Latajka, R., Jewginski, M., Makowski, M., Paweiczak, M., Huber, T., Sewald, Norbert, 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 (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.

7 Zitationen in Europe PMC

Daten bereitgestellt von Europe PubMed Central.

Synthesis of dehydrodipeptide esters and their evaluation as inhibitors of cathepsin C.
Makowski M, Lenartowicz P, Oszywa B, Jewgiński M, Pawełczak M, Kafarski P., Med Chem Res 24(8), 2015
PMID: 26190908
Conformation of dehydropentapeptides containing four achiral amino acid residues - controlling the role of L-valine.
Jewgiński M, Krzciuk-Gula J, Makowski M, Latajka R, Kafarski P., Beilstein J Org Chem 10(), 2014
PMID: 24778717
Discovery of novel cyanamide-based inhibitors of cathepsin C.
Lainé D, Palovich M, McCleland B, Petitjean E, Delhom I, Xie H, Deng J, Lin G, Davis R, Jolit A, Nevins N, Zhao B, Villa J, Schneck J, McDevitt P, Midgett R, Kmett C, Umbrecht S, Peck B, Davis AB, Bettoun D., ACS Med Chem Lett 2(2), 2011
PMID: 24900293
Effect of the ΔPhe residue configuration on a didehydropeptides conformation: A combined CD and NMR study.
Lisowski M, Jaremko L, Jaremko M, Mazur A, Latajka R, Makowski M., Biopolymers 93(12), 2010
PMID: 20632395

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