荧光二苯并呋喃α-氨基酸的合成：酪氨酸构象刚性类似物

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-03-02 DOI:10.1021/acs.orglett.5c0043310.1021/acs.orglett.5c00433

Liyao Zeng, Olivia Marshall, Rochelle McGrory, Rebecca Clarke, Ryan J. Brown, Malcolm Kadodwala, Andrew R. Thomson and Andrew Sutherland*,

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引用次数: 0

摘要

我们报道了制备二苯并呋喃α-氨基酸的两种合成策略，扩大了荧光探针的结构工具箱。这些策略包括通过Pd（II）催化的C-O环化合成二苯并呋喃，以及有效的根岸偶联方法，以更快地获得类似物。与蛋白质生成氨基酸相比，这些刚性酪氨酸模拟物具有增强的荧光特性，这是通过将先导化合物用作FRET供体来监测丝氨酸蛋白酶对肽的水解而证明的。

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Synthesis of Fluorescent Dibenzofuran α-Amino Acids: Conformationally Rigid Analogues of Tyrosine

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.

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来源期刊

Organic Letters 化学-有机化学

CiteScore

9.30

自引率

11.50%

发文量

1607

审稿时长

1.5 months

期刊介绍： Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.