Pyridoxal-5’-phosphate (PLP) is a ubiquitous cofactor of a large variety of enzymes also playing important roles in the biosynthesis and metabolism of amino acids, lipids, carbohydrates, and neurotransmitters. We have now found another application showing that PLP derived aryl imines can be used for the quantitative chiroptical chemosensing of amino acids, primary amines, and amino alcohols at submillimolar concentrations. A practical indicator displacement assay with a PLP aryl imine probe for comprehensive analysis of the ee, absolute configuration, and total amount of chiral compounds was developed. Altogether, this approach successfully exploits fast and irreversible imine metathesis, producing distinct circular dichroism and fluorescence signals that are used for quantitative chiroptical analysis.

Biomimetic comprehensive chirality sensing with pyridoxal-5’-phosphate

254th National Meeting (2017)

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