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仿生手性感应与吡哆醛-5'-磷酸。

Biomimetic Chirality Sensing with Pyridoxal-5'-phosphate.

机构信息

Department of Chemistry, Georgetown University , Washington, D.C. 20057, United States.

出版信息

J Am Chem Soc. 2017 Feb 8;139(5):1758-1761. doi: 10.1021/jacs.6b12056. Epub 2017 Jan 30.

DOI:10.1021/jacs.6b12056
PMID:28128945
Abstract

Pyridoxal-5'-phosphate (PLP) is introduced to a biomimetic indicator displacement assay for simultaneous determination of the absolute configuration, enantiomeric composition and concentration of unprotected amino acids, amino alcohols and amines. The chiroptical assay is based on fast imine metathesis with a PLP aryl imine probe to capture the target compound for circular dichroism and fluorescence sensing analysis. The substrate binding yields characteristic Cotton effects that provide information about the target compound ee and the synchronous release of the indicator results in a nonenantioselective off-on fluorescence response that is independent of the enantiomeric sample composition and readily correlated to the total analyte concentration.

摘要

吡哆醛-5'-磷酸(PLP)被引入仿生指示剂置换分析中,用于同时测定未保护的氨基酸、氨基醇和胺的绝对构型、对映体组成和浓度。手性分析基于与 PLP 芳基亚胺探针的快速亚胺复分解反应,以捕获目标化合物进行圆二色性和荧光传感分析。底物结合产生特征的Cotton 效应,提供有关目标化合物 ee 的信息,并且指示剂的同步释放导致非对映选择性的开-关荧光响应,该响应与对映体样品组成无关,并且易于与总分析物浓度相关。

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