Enantioselective Fluorescent Recognition of Amino Acids by Amide Formation: An Unusual Concentration Effect

Chao Wang; Chaoyuan Zeng; Xiaoling Zhang; Lin Pu

doi:10.1021/acs.joc.7b02456

Enantioselective Fluorescent Recognition of Amino Acids by Amide Formation: An Unusual Concentration Effect

Chao Wang, Chaoyuan Zeng, Xiaoling Zhang^*, Lin Pu

^*Corresponding author for this work

School of Chemistry and Chemical Engineering

Research output: Contribution to journal › Article › peer-review

19 Citations (Scopus)

Abstract

A BINOL-based perfluoroalkyl ketone shows a highly enantioselective fluorescence enhancement in the presence of various amino acid-TBA salts and can be used to determine the enantiomeric composition of these compounds. It was found that the amino acid-TBA salts can act as nucleophiles to cleave the perfluoroalkyl group off of the ketones to form the corresponding amides at room temperature in DMSO. This is the first example of an enantioselective fluorescent sensor for the recognition of amino acids by forming amide bonds under very mild conditions. This study has also revealed an unusual concentration effect leading to an "off-on-off" fluorescence response of the sensor toward one enantiomer of the amino acids.

Original language	English
Pages (from-to)	12669-12673
Number of pages	5
Journal	Journal of Organic Chemistry
Volume	82
Issue number	23
DOIs	https://doi.org/10.1021/acs.joc.7b02456
Publication status	Published - 1 Dec 2017

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abstract = "A BINOL-based perfluoroalkyl ketone shows a highly enantioselective fluorescence enhancement in the presence of various amino acid-TBA salts and can be used to determine the enantiomeric composition of these compounds. It was found that the amino acid-TBA salts can act as nucleophiles to cleave the perfluoroalkyl group off of the ketones to form the corresponding amides at room temperature in DMSO. This is the first example of an enantioselective fluorescent sensor for the recognition of amino acids by forming amide bonds under very mild conditions. This study has also revealed an unusual concentration effect leading to an {"}off-on-off{"} fluorescence response of the sensor toward one enantiomer of the amino acids.",

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T1 - Enantioselective Fluorescent Recognition of Amino Acids by Amide Formation

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AU - Zeng, Chaoyuan

AU - Zhang, Xiaoling

AU - Pu, Lin

PY - 2017/12/1

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N2 - A BINOL-based perfluoroalkyl ketone shows a highly enantioselective fluorescence enhancement in the presence of various amino acid-TBA salts and can be used to determine the enantiomeric composition of these compounds. It was found that the amino acid-TBA salts can act as nucleophiles to cleave the perfluoroalkyl group off of the ketones to form the corresponding amides at room temperature in DMSO. This is the first example of an enantioselective fluorescent sensor for the recognition of amino acids by forming amide bonds under very mild conditions. This study has also revealed an unusual concentration effect leading to an "off-on-off" fluorescence response of the sensor toward one enantiomer of the amino acids.

AB - A BINOL-based perfluoroalkyl ketone shows a highly enantioselective fluorescence enhancement in the presence of various amino acid-TBA salts and can be used to determine the enantiomeric composition of these compounds. It was found that the amino acid-TBA salts can act as nucleophiles to cleave the perfluoroalkyl group off of the ketones to form the corresponding amides at room temperature in DMSO. This is the first example of an enantioselective fluorescent sensor for the recognition of amino acids by forming amide bonds under very mild conditions. This study has also revealed an unusual concentration effect leading to an "off-on-off" fluorescence response of the sensor toward one enantiomer of the amino acids.

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ER -

Enantioselective Fluorescent Recognition of Amino Acids by Amide Formation: An Unusual Concentration Effect

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