Biomimetic Chirality Sensing with Pyridoxal-5′-phosphate

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 metathe...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2017-02, Vol.139 (5), p.1758-1761
Main Authors: Pilicer, Samantha L, Bakhshi, Pegah R, Bentley, Keith W, Wolf, Christian
Format: Article
Language:English
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Summary: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.
ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.6b12056