A near-IR Fluorescent Probe for Enantioselective Recognition of Amino Acids in Aqueous Solution

Feng Zhao; Jun Tian; Xuedan Wu; Shuo Li; Yu Chen; Shanshan Yu; Xiaoqi Yu; Lin Pu

doi:10.1021/acs.joc.0c00725

A near-IR Fluorescent Probe for Enantioselective Recognition of Amino Acids in Aqueous Solution

J Org Chem. 2020 Jun 5;85(11):7342-7348. doi: 10.1021/acs.joc.0c00725. Epub 2020 May 27.

Authors

Feng Zhao^{1

2}, Jun Tian¹, Xuedan Wu², Shuo Li^{2

3}, Yu Chen¹, Shanshan Yu¹, Xiaoqi Yu¹, Lin Pu²

Affiliations

¹ Key Laboratory of Green Chemistry and Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, China.
² Department of Chemistry, University of Virginia, McCormick Rd, Charlottesville, Virginia 22904, United States.
³ School of Chemical Engineering, Chongqing University of Technology, Chongqing 400054, China.

PMID: 32397707
DOI: 10.1021/acs.joc.0c00725

Abstract

A novel BINOL-based near-IR fluorescent probe was designed and synthesized by incorporating a rhodamine-like dye. In the presence of Zn(II), this compound was found to exhibit highly enantioselective fluorescence enhancement at λ_emi > 730 nm and λ_exc = 690 nm when treated with 14 common amino acids in aqueous solution. An enantioselective fluorescence enhancement ratio up to 163 was observed. The mechanism of the fluorescence response of this probe was investigated by various spectroscopic methods.

Publication types

Research Support, U.S. Gov't, Non-P.H.S.
Research Support, Non-U.S. Gov't