Zeng Liyao, Marshall Olivia, McGrory Rochelle, Clarke Rebecca, Brown Ryan J, Kadodwala Malcolm, Thomson Andrew R, Sutherland Andrew
School of Chemistry, The Joseph Black Building, University of Glasgow, Glasgow G12 8QQ, United Kingdom.
Org Lett. 2025 Mar 14;27(10):2475-2479. doi: 10.1021/acs.orglett.5c00433. Epub 2025 Mar 2.
We report two synthetic strategies for the preparation of dibenzofuran α-amino acids, expanding the structural toolbox of fluorescent probes. The strategies involved dibenzofuran synthesis via a Pd(II)-catalyzed C-O cyclization, alongside an efficient Negishi coupling approach for faster access to analogues. These rigid tyrosine mimics possess enhanced fluorescent properties compared to proteinogenic amino acids as demonstrated by application of the lead compound as a FRET donor for monitoring peptide hydrolysis by a serine protease.
我们报道了两种合成二苯并呋喃α-氨基酸的策略，扩展了荧光探针的结构工具箱。这些策略包括通过钯（II）催化的C-O环化反应合成二苯并呋喃，以及一种高效的根岸偶联方法，以便更快地获得类似物。这些刚性的酪氨酸模拟物与蛋白质原氨基酸相比具有增强的荧光特性，这一点通过将先导化合物用作荧光共振能量转移（FRET）供体来监测丝氨酸蛋白酶催化的肽水解得以证明。
