Faculty of Chemistry, University of Opole, ul. Oleska 48, 45-052 Opole, Poland.
Department of Chemistry, Odisee University of Applied Sciences, Gebroeders De Smetstraat 1, 9000 Ghent, Belgium.
Molecules. 2022 Apr 19;27(9):2611. doi: 10.3390/molecules27092611.
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.
将去氢氨基酸或噁唑片段掺入肽链中会伴随扭曲的三维结构，并能额外引入非典型的侧链取代基。因此，这些化合物可能成为获得新型的折叠体和/或人工酶（artzymes）的构建块。在本文中，描述了导致这些构建块——含有甘氨酰脱氢丙氨酸、甘氨酰脱氢苯丙氨酸和甘氨酰噁唑亚单位的四肽——的有效合成方法。使用含有丝氨酸的肽作为底物，将其转化为含有脱氢丙氨酸和氨甲基噁唑-4-羧酸的肽，同时考虑了在合成的最后步骤中将这些片段引入长链肽中的可能要求。
