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Article

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

1
Faculty of Chemistry, University of Opole, ul. Oleska 48, 45-052 Opole, Poland
2
Department of Chemistry, Odisee University of Applied Sciences, Gebroeders De Smetstraat 1, 9000 Ghent, Belgium
3
Faculty of Chemistry, Wrocław University of Science and Technology, Wybrzeże Wyspiańskiego 27, 50-370 Wrocław, Poland
4
Faculty of Agriculture and Forestry, Warmia and Mazury University of Olsztyn, pl. Łódzki 4, 10-957 Olsztyn, Poland
*
Authors to whom correspondence should be addressed.
Maciej Makowski passed away.
Academic Editor: Ivo Piantanida
Molecules 2022, 27(9), 2611; https://doi.org/10.3390/molecules27092611
Received: 9 March 2022 / Revised: 14 April 2022 / Accepted: 15 April 2022 / Published: 19 April 2022
(This article belongs to the Section Bioorganic Chemistry)
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. View Full-Text
Keywords: tetrapeptides; dehydroalanine; dehydrophenylalanine; aminomethyloxazole-4-carboxylic acid; foldamers; artzymes tetrapeptides; dehydroalanine; dehydrophenylalanine; aminomethyloxazole-4-carboxylic acid; foldamers; artzymes
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MDPI and ACS Style

Lenartowicz, P.; Beelen, M.; Makowski, M.; Wanat, W.; Dziuk, B.; Kafarski, P. Synthesis of Tetrapeptides Containing Dehydroalanine, Dehydrophenylalanine and Oxazole as Building Blocks for Construction of Foldamers and Bioinspired Catalysts. Molecules 2022, 27, 2611. https://doi.org/10.3390/molecules27092611

AMA Style

Lenartowicz P, Beelen M, Makowski M, Wanat W, Dziuk B, Kafarski P. Synthesis of Tetrapeptides Containing Dehydroalanine, Dehydrophenylalanine and Oxazole as Building Blocks for Construction of Foldamers and Bioinspired Catalysts. Molecules. 2022; 27(9):2611. https://doi.org/10.3390/molecules27092611

Chicago/Turabian Style

Lenartowicz, Paweł, Maarten Beelen, Maciej Makowski, Weronika Wanat, Błażej Dziuk, and Paweł Kafarski. 2022. "Synthesis of Tetrapeptides Containing Dehydroalanine, Dehydrophenylalanine and Oxazole as Building Blocks for Construction of Foldamers and Bioinspired Catalysts" Molecules 27, no. 9: 2611. https://doi.org/10.3390/molecules27092611

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