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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Bibliographic Details
Published in:Molecules (Basel, Switzerland) Switzerland), 2022-04, Vol.27 (9), p.2611
Main Authors: Lenartowicz, Paweł, Beelen, Maarten, Makowski, Maciej, Wanat, Weronika, Dziuk, Błażej, Kafarski, Paweł
Format: Article
Language:English
Subjects:
Alanine - analogs & derivatives
Alanine - chemistry
aminomethyloxazole-4-carboxylic acid
artzymes
Carboxylic acids
Catalysts
Chromatography
Construction
dehydroalanine
dehydrophenylalanine
Enzymes
Fluorides
foldamers
Fragments
Oxazole
Oxazoles - chemistry
Peptides
Peptides - chemistry
Phenylalanine - analogs & derivatives
tetrapeptides
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Summary: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.
ISSN:1420-3049
1420-3049
DOI:10.3390/molecules27092611