Department of Chemistry, Biology, and Pharmacy, Institute of Pharmacy/Medicinal Chemistry, Freie Universität Berlin, Königin-Luise-Strasse 2 + 4, 14195 Berlin, Germany.
Department of Chemistry, Quaid-i-Azam University, Islamabad 45320, Pakistan.
Org Lett. 2020 Apr 17;22(8):2976-2980. doi: 10.1021/acs.orglett.0c00713. Epub 2020 Mar 30.
The flexible variation of peptidomimetics is of great interest for the identification of optimized protein ligands. Here we present a general concept for introducing side-chain modifications into peptides using triarylphosphonium amino acids. Building blocks and are activated for amidation and incorporated into stable peptides. The obtained phosphoranylidene peptides undergo Wittig olefinations and 1,3-dipolar cycloaddition reactions, yielding peptidomimetics with vinyl ketones and 5-substituted 1,2,3-triazoles as non-native peptide side chains.
肽模拟物的灵活变化对于鉴定优化的蛋白质配体非常重要。在这里，我们提出了一种使用三芳基鏻氨基酸在肽中引入侧链修饰的通用概念。砌块 和 被激活进行酰胺化并并入稳定的肽中。得到的磷杂烯肽经历Wittig 烯丙基化和 1,3-偶极环加成反应，生成具有乙烯基酮和 5-取代 1,2,3-三唑作为非天然肽侧链的肽模拟物。
