Biphasic Enantioselective Fluorescent Recognition of Amino Acids by a Fluorophilic Probe

A fluorophilic fluorescent probe based on a perfluoroalkyl‐substituted bis(binaphthyl) compound was designed and synthesized. It displayed a highly enantioselective fluorescence response toward structurally diverse amino acids in a biphasic fluorous/aqueous system with enantiomeric fluorescent enhan...

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Bibliographic Details
Published in:Chemistry : a European journal 2019-06, Vol.25 (33), p.7866-7873
Main Authors: Zhu, Yuan‐Yuan, Wu, Xue‐Dan, Abed, Mehdi, Gu, Shuang‐Xi, Pu, Lin
Format: Article
Language:English
Subjects:
Amino acids
Chemistry
Composition
Enantiomers
enantioselectivity
enzyme catalysis
Fluorescence
Fluorescent indicators
fluorescent probes
Histidine
NMR
Nuclear magnetic resonance
Perfluoroalkyl & polyfluoroalkyl substances
Phenylalanine
Recognition
zinc
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Summary:A fluorophilic fluorescent probe based on a perfluoroalkyl‐substituted bis(binaphthyl) compound was designed and synthesized. It displayed a highly enantioselective fluorescence response toward structurally diverse amino acids in a biphasic fluorous/aqueous system with enantiomeric fluorescent enhancement ratio (ef; ΔID/ΔIL) values up to 45.2 (histidine). It can be used to determine the enantiomeric compositions of amino acids and also allows the amino acid enantiomers to be visually discriminated. NMR and mass‐spectroscopic investigations provided insights into the observed high enantioselectivity. This biphasic fluorescent recognition was used to determine the enantiomeric composition of the crude phenylalanine products generated by an enzyme‐catalyzed asymmetric hydrolysis under various reaction conditions. The fluorous‐phase‐based fluorescence measurement under the biphasic conditions was able to minimize the interference of other reaction components and thus has potential in asymmetric reaction screening. Enantioselective: A fluorophilic fluorescent probe based on a perfluoroalkyl‐substituted bis(binaphthyl) compound was designed and synthesized. It shows a highly enantioselective fluorescence response toward structurally diverse amino acids in a biphasic fluorous/aqueous system (see figure) and can be used to determine the amino acid enantiomeric compositions as well as their enantiomers.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201900880