Squaramide Fluorescence Probe for Chiral Recognition of α-Amino Acids†

doi:10.7503/cjcu20180641

Abstract

Abstract:

Four novel squaramide fluorescence probes were synthesised using natural amino acids as chiral sources, which featuers concise synthetic route, simple work-up and purification without column chromatography. The chiral recognition effects of these squaramide probes for phenylalanine, valine and proline were tested using fluorescence spectrum, which indicated that probe 5 could effectively discriminate two enantiomers of phenylalanine. The fluorescence intensity of probe 5 was remarkably enhanced after adding L-phenylalanine; on the contrary, it was observably reduced when D-phenylalanine was added, and the fluorescence intensity ratio of two enantiomers(I_L/I_D) was up to 2.4.

Key words: Chiral recognition, Fluorescence spectrum, Squaramide, α-Amino acid;

CLC Number:

O653

TrendMD:

BAI Lei,HUO Shuhui,CHEN Jing,LU Xiaoquan. Squaramide Fluorescence Probe for Chiral Recognition of α-Amino Acids^†[J]. Chem. J. Chinese Universities, 2019, 40(1): 41.

Figures/Tables 7

Scheme 1 Synthetic procedure of compounds 5 and 6

Scheme 2 Synthetic procedure of compounds 7 and 8

Fig.1 Fluorescence spectra of probes 5 and 6 with and without α-amino acid(A) a. L-Phe+probe 5; b. probe 5; c. D-Phe+probe 5; λex=230 nm, slit=5 nm/5 nm; (B) a. probe 5; b. L-Val+probe 5; c. D-Val+probe 5; λex=230 nm, slit=5 nm/5 nm; (C) a. D-Pro+probe 5; b. L-Pro+probe 5; c. probe 5; λex=230 nm, slit=5 nm/5 nm; (D) a. D-Phe+probe 6; b. probe 6; c. L-Phe+probe 6; λex=225 nm, slit=5 nm/5 nm; (E) a. D-Val+probe 6; b. L-Val+probe 6; c. probe 6; λex=225 nm, slit=5 nm/5 nm; (F) a. L-Pro+probe 6; b. D-Pro+Probe 6; c. probe 6; λex=225 nm, slit=5 nm/5 nm.

Fig.2 Fluorescence spectra of probes 7 and 8 with and without α-amino acid(A) a. Probe 7; b. D-Phe+probe 7; c. L-Phe+probe 7; λex=230 nm, slit=20 nm/20 nm; (B) a. Probe 7; b. L-Val+probe 7; c. D-Val+probe 7; λex=230 nm, slit=20 nm/20 nm; (C) a. L-Pro+probe 7; b. probe 7; c. D-Pro+probe 7. λex=230 nm, slit=20 nm/20 nm; (D) a. L-Phe+probe 8; b. probe 8; c. D-Phe+probe 8; λex=230 nm, slit=20 nm/20 nm; (E) a. Probe 8; b. D-Val+probe 8; c. L-Val+probe 8; λex=230 nm, slit=20 nm/20 nm; (F) a. D-Pro+probe 8; b. probe 8; c. L-Pro+probe 8; λex=230 nm, slit=20 nm/20 nm.

Table 1 Fluorescence intensity ratios of probes 5—8 with amino acids

Probe	I_L/I_D or I_D/I_L
Probe	Phe	Val	Pro
5	2.4	1.2	1.0
6	1.1	1.1	1.0
7	1.1	1.1	1.1
8	1.1	1.0	1.3

Fig.3 IL/ID plots of probe 5 at various concentrations of L-Phe or D-Phe at λem=358 nm(A) and IL/ID plots of probe 5 at various molar ratios of probe 5 to L-Phe or D-Phe at λem=358 nm(B)λex=230 nm, slit=5 nm/5 nm.

Fig.4 Proposed interaction mode between probe 5 and L-Phe(A) or D-Phe(B)

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