Chiroptical sensing of amino acids by stereodynamic imprinting into the ZnII-Complex generating a dihedral chirality

Add time:08/20/2019    Source:sciencedirect.com

A stereodynamic chiroptical sensor based on three-component assembly of 3-(di-2-picolylaminoacetamido)-2-formyl-naphthalene (1), ZnII and amino acids was developed. The imine formed between 1 and an amino acid has six coordination sites to bind tightly ZnII ion. The crystal structure of the ZnII complex, 1-Zn-D-Phe, revealed that the naphthyl ring is tilted to one pyridine ring to generate axial chirality. The dihedral conformations observed in 1-Zn-D-Phe were herein arbitrarily designated as α1 and α2. DFT calculation suggests that the D-Phe binding prefer the α1-conformer: the energy of D-Phe-α1 is more stable than L-Phe-α1 by 5.5 kcal/mol. This preference to one diastereomer generates amplification of CD signal with Cotton effect, which can be applied to the determination of ee values of the amino acid.

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