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

Molecules

Paweł Kafarski¹  Maciej Makowski²  Maarten Beelen²  Paweł Lenartowicz²  Weronika Wanat³  Błażej Dziuk³ 

[1] Faculty of Agriculture and Forestry, Warmia and Mazury University of Olsztyn, pl. Łódzki 4, 10-957 Olsztyn, Poland;Faculty of Chemistry, University of Opole, ul. Oleska 48, 45-052 Opole, Poland;Faculty of Chemistry, Wrocław University of Science and Technology, Wybrzeże Wyspiańskiego 27, 50-370 Wrocław, Poland;

关键词: tetrapeptides;    dehydroalanine;    dehydrophenylalanine;    aminomethyloxazole-4-carboxylic acid;    foldamers;    artzymes;   

DOI  :  10.3390/molecules27092611

来源: DOAJ

【 摘 要 】

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.

【 授权许可】

Unknown