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

Authors :
Paweł Lenartowicz
Maarten Beelen
Maciej Makowski
Weronika Wanat
Błażej Dziuk
Paweł Kafarski
Source :
Molecules, Vol 27, Iss 9, p 2611 (2022)
Publication Year :
2022
Publisher :
MDPI AG, 2022.

Abstract

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.

Details

Language :
English
ISSN :
14203049
Volume :
27
Issue :
9
Database :
Directory of Open Access Journals
Journal :
Molecules
Publication Type :
Academic Journal
Accession number :
edsdoj.2f72f3fb445b39ee824169cb5523f
Document Type :
article
Full Text :
https://doi.org/10.3390/molecules27092611