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Visible Enantiomer Discrimination via Diphenylalanine-Based Chiral Supramolecular Self-Assembly on Multiple Platforms.
Langmuir ( IF 3.9 ) Pub Date : 2020-02-23 , DOI: 10.1021/acs.langmuir.9b03449
Minggao Qin 1 , Yaqian Zhang 1 , Jinying Liu 1 , Chao Xing 1 , Changli Zhao 1 , Xiaoqiu Dou 1 , Chuanliang Feng 1
Affiliation  

The development of enantioselective recognition is of great significance in medical science and pharmaceutical industry, which associates with molecular recognition phenomenon widely observed in biological systems. In particular, the facile and straight achievement of visual enantioselective recognition has been drawing increasing consideration but still challengeable. Herein, a heterochiral diphenylalanine-based gelator (LFDF) is synthesized, presenting left-handed nanofibers during self-assembled in ethanol, which accomplish the phenylalaninol enantiomer recognition on multiple platforms. When adding L- or D-phenylalaninol into LFDF supramolecular solution followed by ultrasonic treatment, precipitate and gel are formed, respectively. Meanwhile, LFDF supramolecular gel completely collapses in a minutes after dropping L-phenylalaninol, while the gel almost remains when D-type is employed. Moreover, a fluorescent supramolecular xerogel (ThT-LFDF) is fabricated by introducing Thioflavine T (ThT), which could detect L-phenylalaninol accompanying with fluorescence quenching and D-type with barely decreasing. And the ThT-LFDF xerogel system shows a good sensitivity for the detection of L-phenylalaninol reaches to ppm. It is found that the chirality of the assembled nanofibers, as well as amino and carboxyl of phenylalaninol play critical role on the discrimination process. The multiple and visible enantioselective recognition of phenylalaninol through chiral supramolecular self-assemblies show potential applications in the fields of medical science and pharmaceutical industry.

中文翻译:

通过基于二苯丙氨酸的手性超分子自组装在多个平台上的可见对映体区分。

对映选择性识别的发展在医学和制药工业中具有重要意义,它与在生物系统中广泛观察到的分子识别现象有关。特别地,视觉对映选择性识别的简便而直接的实现已经引起越来越多的考虑,但是仍然具有挑战性。本文中,合成了一种基于异手性二苯丙氨酸的凝胶剂(LFDF),在乙醇中自组装过程中出现了左手纳米纤维,从而在多个平台上实现了苯丙氨醇对映体的识别。当将L-或D-苯丙氨醇添加到LFDF超分子溶液中,然后进行超声处理时,分别形成沉淀和凝胶。同时,LFDF超分子凝胶在滴入L-苯丙氨醇后的一分钟内完全崩解,当使用D型时,凝胶几乎保留。此外,通过引入硫黄素T(ThT)制备了荧光超分子干凝胶(ThT-LFDF),该硫黄素T(ThT)可以检测伴随荧光猝灭的L-苯丙氨醇和几乎没有减少的D型。ThT-LFDF干凝胶系统对检测L-苯丙氨醇达到ppm时显示出良好的灵敏度。发现组装的纳米纤维的手性以及苯丙氨醇的氨基和羧基在鉴别过程中起关键作用。通过手性超分子自组装对苯丙氨醇的多种可见的对映选择性识别显示了在医学和制药工业领域的潜在应用。通过引入硫黄素T(ThT)制备了荧光超分子干凝胶(ThT-LFDF),该硫黄素T(ThT)可以检测伴随荧光猝灭的L-苯丙氨醇和几乎不减少的D型。ThT-LFDF干凝胶系统对L-苯丙氨醇的检测灵敏度达到ppm。发现组装的纳米纤维的手性以及苯丙氨醇的氨基和羧基在鉴别过程中起关键作用。通过手性超分子自组装对苯丙氨醇的多种可见的对映选择性识别显示了在医学和制药工业领域的潜在应用。通过引入硫黄素T(ThT)制备了荧光超分子干凝胶(ThT-LFDF),该硫黄素T(ThT)可以检测伴随荧光猝灭的L-苯丙氨醇和几乎没有减少的D型。ThT-LFDF干凝胶系统对检测L-苯丙氨醇达到ppm时显示出良好的灵敏度。发现组装的纳米纤维的手性以及苯丙氨醇的氨基和羧基在鉴别过程中起关键作用。通过手性超分子自组装对苯丙氨醇的多种可见的对映选择性识别显示了在医学和制药工业领域的潜在应用。ThT-LFDF干凝胶系统对检测L-苯丙氨醇达到ppm时显示出良好的灵敏度。发现组装的纳米纤维的手性以及苯丙氨醇的氨基和羧基在鉴别过程中起关键作用。通过手性超分子自组装对苯丙氨醇的多种可见的对映选择性识别显示了在医学和制药工业领域的潜在应用。ThT-LFDF干凝胶系统对检测L-苯丙氨醇达到ppm时显示出良好的灵敏度。发现组装的纳米纤维的手性以及苯丙氨醇的氨基和羧基在鉴别过程中起关键作用。通过手性超分子自组装对苯丙氨醇的多种可见的对映选择性识别显示了在医学和制药工业领域的潜在应用。
更新日期:2020-03-06
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