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Synthesis of Tetrapeptides Containing Dehydroalanine, Dehydrophenylalanine and Oxazole as Building Blocks for Construction of Foldamers and Bioinspired Catalysts

The incorporation of dehydroamino acid or fragments of oxazole into peptide chain is accompanied by a distorted three-dimensional structure and additionally enables the introduction of non-typical side-chain substituents. Thus, such compounds could be building blocks for obtaining novel foldamers an...

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Autores principales: Lenartowicz, Paweł, Beelen, Maarten, Makowski, Maciej, Wanat, Weronika, Dziuk, Błażej, Kafarski, Paweł
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9102237/
https://www.ncbi.nlm.nih.gov/pubmed/35565962
http://dx.doi.org/10.3390/molecules27092611
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author Lenartowicz, Paweł
Beelen, Maarten
Makowski, Maciej
Wanat, Weronika
Dziuk, Błażej
Kafarski, Paweł
author_facet Lenartowicz, Paweł
Beelen, Maarten
Makowski, Maciej
Wanat, Weronika
Dziuk, Błażej
Kafarski, Paweł
author_sort Lenartowicz, Paweł
collection PubMed
description The incorporation of dehydroamino acid or fragments of oxazole into peptide chain is accompanied by a distorted three-dimensional structure and additionally enables the introduction of non-typical side-chain substituents. Thus, such compounds could be building blocks for obtaining novel foldamers and/or artificial enzymes (artzymes). In this paper, effective synthetic procedures leading to such building blocks—tetrapeptides containing glycyldehydroalanine, glycyldehydrophenylalanine, and glycyloxazole subunits—are described. Peptides containing serine were used as substrates for their conversion into peptides containing dehydroalanine and aminomethyloxazole-4-carboxylic acid while considering possible requirements for the introduction of these fragments into long-chain peptides at the last steps of synthesis.
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spelling pubmed-91022372022-05-14 Synthesis of Tetrapeptides Containing Dehydroalanine, Dehydrophenylalanine and Oxazole as Building Blocks for Construction of Foldamers and Bioinspired Catalysts Lenartowicz, Paweł Beelen, Maarten Makowski, Maciej Wanat, Weronika Dziuk, Błażej Kafarski, Paweł Molecules Article The incorporation of dehydroamino acid or fragments of oxazole into peptide chain is accompanied by a distorted three-dimensional structure and additionally enables the introduction of non-typical side-chain substituents. Thus, such compounds could be building blocks for obtaining novel foldamers and/or artificial enzymes (artzymes). In this paper, effective synthetic procedures leading to such building blocks—tetrapeptides containing glycyldehydroalanine, glycyldehydrophenylalanine, and glycyloxazole subunits—are described. Peptides containing serine were used as substrates for their conversion into peptides containing dehydroalanine and aminomethyloxazole-4-carboxylic acid while considering possible requirements for the introduction of these fragments into long-chain peptides at the last steps of synthesis. MDPI 2022-04-19 /pmc/articles/PMC9102237/ /pubmed/35565962 http://dx.doi.org/10.3390/molecules27092611 Text en © 2022 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Lenartowicz, Paweł
Beelen, Maarten
Makowski, Maciej
Wanat, Weronika
Dziuk, Błażej
Kafarski, Paweł
Synthesis of Tetrapeptides Containing Dehydroalanine, Dehydrophenylalanine and Oxazole as Building Blocks for Construction of Foldamers and Bioinspired Catalysts
title Synthesis of Tetrapeptides Containing Dehydroalanine, Dehydrophenylalanine and Oxazole as Building Blocks for Construction of Foldamers and Bioinspired Catalysts
title_full Synthesis of Tetrapeptides Containing Dehydroalanine, Dehydrophenylalanine and Oxazole as Building Blocks for Construction of Foldamers and Bioinspired Catalysts
title_fullStr Synthesis of Tetrapeptides Containing Dehydroalanine, Dehydrophenylalanine and Oxazole as Building Blocks for Construction of Foldamers and Bioinspired Catalysts
title_full_unstemmed Synthesis of Tetrapeptides Containing Dehydroalanine, Dehydrophenylalanine and Oxazole as Building Blocks for Construction of Foldamers and Bioinspired Catalysts
title_short Synthesis of Tetrapeptides Containing Dehydroalanine, Dehydrophenylalanine and Oxazole as Building Blocks for Construction of Foldamers and Bioinspired Catalysts
title_sort synthesis of tetrapeptides containing dehydroalanine, dehydrophenylalanine and oxazole as building blocks for construction of foldamers and bioinspired catalysts
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9102237/
https://www.ncbi.nlm.nih.gov/pubmed/35565962
http://dx.doi.org/10.3390/molecules27092611
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