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Homochiral MOF as Chiroptical Sensor for Determination of Absolute Configuration and Enantiomeric Ratio of Chiral Tryptophan
Author(s) -
Zhu Yanyu,
Zhou Yanan,
Zhang Xu,
Sun Zhengang,
Jiao Chengqi
Publication year - 2021
Publication title -
advanced optical materials
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 2.89
H-Index - 91
ISSN - 2195-1071
DOI - 10.1002/adom.202001889
Subject(s) - enantioselective synthesis , enantiomer , absolute configuration , circular dichroism , tryptophan , amino acid , enantiomeric excess , materials science , stereochemistry , combinatorial chemistry , chemistry , organic chemistry , catalysis , biochemistry
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 = HOOCC 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.