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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Zeitschriftenaufsatz | Veröffentlicht | Englisch
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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.
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JOURNAL OF PEPTIDE SCIENCE
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14
Zeitschriftennummer
10
Seite
1084-1095
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eISSN
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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. doi:10.1002/psc.1045
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

26 References

Daten bereitgestellt von Europe PubMed Central.

Effects of dehydroalanine on peptide conformations
Palmer, J. Am. Chem. Soc. 114(), 1992
Lantibiotics - ribosomally synthesized biologically active polypeptides containing sulfide bridges and α,β-didehydroaminoacids
Jung, Angew. Chem. Int. Ed. Engl. 30(), 1991
Solution structure of dehydropeptides: a CD investigation.
Pieroni O, Fissi A, Jain RM, Chauhan VS., Biopolymers 38(1), 1996
PMID: 8679945
The synthesis of N-acyl- -mercaptoalanine derivatives.
Patel SM, Currie JO Jr, Olsen RK., J. Org. Chem. 38(1), 1973
PMID: 4682657
Design of helical motif using a,b-dehydrophenylalanine residues: Crystal structure of Boc-Val-dPhe-Phe-Ala-Phe-dPhe-Val-dPhe-Gly-OCH3, a 310-helical nonapeptide
Rajashankar, J. Am. Chem. Soc. 114(), 1992
Crystal and molecular structure of Boc-D-Ala-delta Phe-Gly-delta Phe- D-Ala-OMe: a 3 10-helical dehydropeptide.
Ciajolo MR, Tuzi A, Pratesi CR, Fissi A, Pieroni O., Biopolymers 30(9-10), 1990
PMID: 2092820
Synthesis of delta(E)Phe-containing tripeptide via photoisomerization and its conformation in solution.
Inai Y, Kurashima S, Hirabayashi T, Yokota K., Biopolymers 53(6), 2000
PMID: 10775064

Turk, 1998
Sequence of Schistosoma mansoni cathepsin C and its structural comparison with papain and cathepsins B and L of the parasite
Butler, Protein Pept. Lett. 2(), 1995
Loss-of-function mutations in the cathepsin C gene result in periodontal disease and palmoplantar keratosis.
Toomes C, James J, Wood AJ, Wu CL, McCormick D, Lench N, Hewitt C, Moynihan L, Roberts E, Woods CG, Markham A, Wong M, Widmer R, Ghaffar KA, Pemberton M, Hussein IR, Temtamy SA, Davies R, Read AP, Sloan P, Dixon MJ, Thakker NS., Nat. Genet. 23(4), 1999
PMID: 10581027
The synthesis and reactions of dehydro phenylalanine anilide
Breitholle, Tetrahedron Lett. 28(), 1975
Combined effect of the DeltaPhe or DeltaAla residue and the p-nitroanilide group on a didehydropeptides conformation.
Lisowski M, Latajka R, Picur B, Lis T, Bryndal I, Rospenk M, Makowski M, Kafarski P., Biopolymers 89(3), 2008
PMID: 18041062
Peptide p-nitrophenylanilides containing (E)-dehydrophenylalanine - synthesis, structural studies and evaluation of their activity towards cathepsin C
Latajka, N. J. Chem. 30(7), 2006
3(10)-Helices, helix screw sense and screw sense reversal in the dehydro-peptide Boc-Val-delta Phe-Gly-delta Phe-Val-OMe.
Tuzi A, Ciajolo MR, Picone D, Crescenzi O, Temussi PA, Fissi A, Pieroni O., J. Pept. Sci. 2(1), 1996
PMID: 9225245
Synthesis and activity of phosphinic tripeptide inhibitors of cathepsin C.
Mucha A, Pawel M, Hurek J, Kafarski P., Bioorg. Med. Chem. Lett. 14(12), 2004
PMID: 15149655

Frisch, 2004
Structure of human dipeptidyl peptidase I (cathepsin C): exclusion domain added to an endopeptidase framework creates the machine for activation of granular serine proteases.
Turk D, Janjic V, Stern I, Podobnik M, Lamba D, Dahl SW, Lauritzen C, Pedersen J, Turk V, Turk B., EMBO J. 20(23), 2001
PMID: 11726493

AUTHOR UNKNOWN, 0
Automated docking using a Lamarckian genetic algorithm and an empirical binding free energy function
Morris, J. Comput. Chem. 19(), 1998
Atomic charges derived from semiempirical methods
Besler, J. Comput. Chem. 11(), 1990

Goddard, 0
The Xplor-NIH NMR molecular structure determination package
Schwieters, J. Magn. Res. 160(), 2003
Preparation and specificity of dipeptidyl peptidase I
McDonald, Methods Ezymol. 25B(), 1971

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