用于手性识别α-氨基酸的方酰胺荧光探针分子

doi:10.7503/cjcu20180641

高等学校化学学报 ›› 2019, Vol. 40 ›› Issue (1): 41.doi: 10.7503/cjcu20180641

用于手性识别α-氨基酸的方酰胺荧光探针分子

白蕾, 霍淑慧, 陈晶, 卢小泉()

西北师范大学化学化工学院, 甘肃省生物电化学与环境分析重点实验室, 兰州 730070

收稿日期:2018-09-14 出版日期:2019-01-10 发布日期:2018-11-28
作者简介:
联系人简介: 卢小泉, 男, 博士, 教授, 主要从事界面电化学及生物电化学方面的研究. E-mail: luxq@nwnu.edu.cn
基金资助:
国家自然科学基金(批准号: 21575115, 21462036)、教育部长江学者与创新研究团队计划项目(批准号: IRT1283)和甘肃省自然科学基金(批准号: 18JR3RA085)资助.

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

BAI Lei, HUO Shuhui, CHEN Jing, LU Xiaoquan^*()

College of Chemistry and Chemical Engineering, Northwest Normal University, Key Laboratory of Bioelectrochemistry & Environmental Analysis of Gansu Province, Lanzhou 730070, China

Received:2018-09-14 Online:2019-01-10 Published:2018-11-28
Contact: LU Xiaoquan E-mail:luxq@nwnu.edu.cn
Supported by:
† Supported by the National Natural Science Foundation of China(Nos.21575115, 21462036), the Changjiang Scholar and Innovation Team Research Program of Ministry of Education, China(No.IRT1283) and the Natural Science Foundation of Gansu Province, China(No.18JR3RA085).

摘要/Abstract

摘要：

以天然氨基酸为手性原料合成了4种新型的手性方酰胺荧光探针分子(5~8), 该合成路线简短, 后处理简单, 无需柱层析纯化. 以荧光光谱为检测手段, 测试了此类探针分子对苯丙氨酸、缬氨酸和脯氨酸的手性识别效果, 结果表明, 探针分子5可以有效识别苯丙氨酸的2个对映异构体. 当加入L-苯丙氨酸后, 探针分子5的荧光强度显著增强, 而加入D-苯丙氨酸后探针分子5的荧光强度显著减弱, 2种异构体的荧光强度比(I_L/I_D)可达2.4.

关键词: 手性识别, 荧光光谱, 方酰胺, α-氨基酸;

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;

中图分类号:

O653

TrendMD:

白蕾, 霍淑慧, 陈晶, 卢小泉. 用于手性识别α-氨基酸的方酰胺荧光探针分子. 高等学校化学学报, 2019, 40(1): 41.

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

图/表 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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用于手性识别α-氨基酸的方酰胺荧光探针分子

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

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用于手性识别α-氨基酸的方酰胺荧光探针分子

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

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