Synthesis of dehydrodipeptide esters and their evaluation as inhibitors of cathepsin C

The procedures for the synthesis of esters of dehydropeptides containing C-terminal (Z)-dehydrophenylalanine and dehydroalanine have been elaborated. These esters appeared to be moderate or weak inhibitors of cathepsin C, with some of them exhibiting slow-binding behavior. As shown by molecular mode...

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Autores principales: Makowski, Maciej, Lenartowicz, Paweł, Oszywa, Bartosz, Jewgiński, Michał, Pawełczak, Małgorzata, Kafarski, Paweł
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Springer US 2015
Materias:
Original Research
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4500854/
https://www.ncbi.nlm.nih.gov/pubmed/26190908
http://dx.doi.org/10.1007/s00044-015-1366-0
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author Makowski, Maciej
Lenartowicz, Paweł
Oszywa, Bartosz
Jewgiński, Michał
Pawełczak, Małgorzata
Kafarski, Paweł
author_facet Makowski, Maciej
Lenartowicz, Paweł
Oszywa, Bartosz
Jewgiński, Michał
Pawełczak, Małgorzata
Kafarski, Paweł
author_sort Makowski, Maciej
collection PubMed
description The procedures for the synthesis of esters of dehydropeptides containing C-terminal (Z)-dehydrophenylalanine and dehydroalanine have been elaborated. These esters appeared to be moderate or weak inhibitors of cathepsin C, with some of them exhibiting slow-binding behavior. As shown by molecular modeling, they are rather bound at the surface of the enzyme and are not submersed in its binding cavities. ELECTRONIC SUPPLEMENTARY MATERIAL: The online version of this article (doi:10.1007/s00044-015-1366-0) contains supplementary material, which is available to authorized users.
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spelling pubmed-45008542015-07-17 Synthesis of dehydrodipeptide esters and their evaluation as inhibitors of cathepsin C Makowski, Maciej Lenartowicz, Paweł Oszywa, Bartosz Jewgiński, Michał Pawełczak, Małgorzata Kafarski, Paweł Med Chem Res Original Research The procedures for the synthesis of esters of dehydropeptides containing C-terminal (Z)-dehydrophenylalanine and dehydroalanine have been elaborated. These esters appeared to be moderate or weak inhibitors of cathepsin C, with some of them exhibiting slow-binding behavior. As shown by molecular modeling, they are rather bound at the surface of the enzyme and are not submersed in its binding cavities. ELECTRONIC SUPPLEMENTARY MATERIAL: The online version of this article (doi:10.1007/s00044-015-1366-0) contains supplementary material, which is available to authorized users. Springer US 2015-04-16 2015 /pmc/articles/PMC4500854/ /pubmed/26190908 http://dx.doi.org/10.1007/s00044-015-1366-0 Text en © The Author(s) 2015 Open AccessThis article is distributed under the terms of the Creative Commons Attribution 4.0 International License (http://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution, and reproduction in any medium, provided you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made.
spellingShingle Original Research
Makowski, Maciej
Lenartowicz, Paweł
Oszywa, Bartosz
Jewgiński, Michał
Pawełczak, Małgorzata
Kafarski, Paweł
Synthesis of dehydrodipeptide esters and their evaluation as inhibitors of cathepsin C
title Synthesis of dehydrodipeptide esters and their evaluation as inhibitors of cathepsin C
title_full Synthesis of dehydrodipeptide esters and their evaluation as inhibitors of cathepsin C
title_fullStr Synthesis of dehydrodipeptide esters and their evaluation as inhibitors of cathepsin C
title_full_unstemmed Synthesis of dehydrodipeptide esters and their evaluation as inhibitors of cathepsin C
title_short Synthesis of dehydrodipeptide esters and their evaluation as inhibitors of cathepsin C
title_sort synthesis of dehydrodipeptide esters and their evaluation as inhibitors of cathepsin c
topic Original Research
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4500854/
https://www.ncbi.nlm.nih.gov/pubmed/26190908
http://dx.doi.org/10.1007/s00044-015-1366-0
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