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Homochiral MOF as Chiroptical Sensor for Determination of Absolute Configuration and Enantiomeric Ratio of Chiral Tryptophan

Yan‐Yu Zhu, Yanan Zhou, Xu Zhang, Zhen‐Gang Sun, Cheng‐Qi Jiao

2021Advanced Optical Materials52 citationsDOI

Abstract

Abstract The development of a highly selective and sensitive optical method for quantitative enantioselective sensing of chiral amino acids in the presence of other amino acid interferences has remained a major challenge to date. Herein, a homochiral metal–organic framework (MOF), [Zn(L)(2,2′‐bipy)]·H 2 O ( LNNU‐1 ) (H 2 L = HOOCC 6 H 4 CH 2 PO(OH)(OC 2 H 5 ), 2,2′‐bipy = 2,2′‐bipyridine), is designed to interact with tryptophan via multiple noncovalent interactions. The interactions result in the emergence of a strong induced circular dichroism signal. This enables accurate determination of the absolute configuration and enantiomeric ratio of chiral tryptophan in water, mixed natural amino acids, and blood plasma components without any interference from other coexistent species. A simple device with advantageous characteristics of reusability and simple manipulation is designed for enantioselective sensing assay. The obtained results suggest that the rationally designed homochiral MOF is a promising candidate for enantioselective sensing of chiral species.

Topics & Concepts

Enantioselective synthesisEnantiomerAbsolute configurationCircular dichroismTryptophanAmino acidEnantiomeric excessMaterials scienceMetal-organic frameworkStereochemistryCombinatorial chemistryChemistryOrganic chemistryCatalysisAdsorptionBiochemistryMetal-Organic Frameworks: Synthesis and ApplicationsMolecular Sensors and Ion DetectionMolecular spectroscopy and chirality