Fluorous-Phase- and Chiral-Axis-Enhanced Fluorescent Sensitivity and Chemoselectivity for Cysteine Recognition

IF 5 1区 化学 Q1 CHEMISTRY, ORGANIC Organic Letters Pub Date : 2025-01-06 DOI:10.1021/acs.orglett.4c04175
Jiaqiao Yang, Cheng Qian, Hanyu Su, Ji Zhang, Shanshan Yu, Xiaoqi Yu, Lin Pu
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Abstract

Highly fluorinated naphthyl aldehyde 1 and binaphthyl aldehyde (R)-2 were designed and synthesized for fluorous-phase-based sensing. Greatly enhanced sensitivity and chemoselectivity in going from 1 to (R)-2 in the fluorescent detection of cysteine has been discovered. This is attributed to the increased structural rigidity of the axially chiral binaphthyl unit in (R)-2 upon reaction with cysteine to form the corresponding thiazolidine product. The fluorous-phase-based detection of cysteine not only can allow the analysis to be conducted in a phase away from the interference of other organic and inorganic species but also results in significantly increased fluorescence response.

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荧光相和手性轴增强半胱氨酸识别的荧光敏感性和化学选择性
设计并合成了高氟化萘醛1和联萘醛(R)-2用于荧光相传感。在半胱氨酸荧光检测中,从1到(R)-2的灵敏度和化学选择性大大提高。这是由于(R)-2中轴向手性联萘基单元与半胱氨酸反应形成相应的噻唑烷产物后结构刚性增加所致。基于荧光相的半胱氨酸检测不仅可以使分析在远离其他有机和无机物种干扰的相中进行,而且还可以显着增加荧光响应。
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来源期刊
Organic Letters
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.
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