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Biomimetic Recognition and Optical Sensing of Carboxylic Acids in Water by Using a Buried Salt Bridge and the Hydrophobic Effect
Angewandte Chemie International Edition ( IF 16.6 ) Pub Date : 2020-10-21 , DOI: 10.1002/anie.202012467 Xuan Huang 1 , Xiaoping Wang 1 , Mao Quan 1 , Huan Yao 1 , Hua Ke 1 , Wei Jiang 1
Angewandte Chemie International Edition ( IF 16.6 ) Pub Date : 2020-10-21 , DOI: 10.1002/anie.202012467 Xuan Huang 1 , Xiaoping Wang 1 , Mao Quan 1 , Huan Yao 1 , Hua Ke 1 , Wei Jiang 1
Affiliation
Buried salt bridges widely exist in protein structures but are rarely used in synthetic systems for molecular recognition in water. By mimicking the binding pocket of bioreceptors, we designed and synthesized a pair of endo‐functionalized macrocyclic hosts with secondary ammonium groups in a hydrophobic cavity. We found that these macrocycles are able to selectively recognize carboxylic acids in water through salt bridges and the hydrophobic effect. Moreover, it was demonstrated that these macrocyclic receptors can be used in circular‐dichroism‐based optical chirality sensing of chiral carboxylic acids and fluorescent sensing of phenylpyruvic acid—a biomarker for phenylketonuria. This research showcases that buried salt bridges can be effectively used by endo‐functionalized macrocyclic hosts for molecular recognition in water, where solvent screening on polar noncovalent interactions is high.
中文翻译:
埋盐桥的仿生识别与光敏性及疏水效应
埋入式盐桥广泛存在于蛋白质结构中,但很少用于水分子识别的合成系统中。通过模仿生物受体的结合口袋,我们设计并合成了一对在疏水腔中具有仲铵基团的内官能化大环宿主。我们发现这些大环化合物能够通过盐桥和疏水作用选择性识别水中的羧酸。此外,已证明这些大环受体可用于手性羧酸的基于圆二色性的光学手性传感和苯基丙酮酸(一种苯丙酮尿症的生物标志物)的荧光传感。这项研究表明,埋入式盐桥可以被内窥镜有效地利用官能化的大环宿主,可在水中进行分子识别,因为对极性非共价相互作用的溶剂筛选很高。
更新日期:2020-10-21
中文翻译:
埋盐桥的仿生识别与光敏性及疏水效应
埋入式盐桥广泛存在于蛋白质结构中,但很少用于水分子识别的合成系统中。通过模仿生物受体的结合口袋,我们设计并合成了一对在疏水腔中具有仲铵基团的内官能化大环宿主。我们发现这些大环化合物能够通过盐桥和疏水作用选择性识别水中的羧酸。此外,已证明这些大环受体可用于手性羧酸的基于圆二色性的光学手性传感和苯基丙酮酸(一种苯丙酮尿症的生物标志物)的荧光传感。这项研究表明,埋入式盐桥可以被内窥镜有效地利用官能化的大环宿主,可在水中进行分子识别,因为对极性非共价相互作用的溶剂筛选很高。