|论文题目||Detection and Chiral Recognition of alpha-Hydroxyl Acid through H-1 and CEST NMR Spectroscopy Using a Ytterbium Macrocyclic Complex|
|作 者||; Haonan He, Kelu Zhao,Long Xiao, Yi Zhang, Yi Cheng, Sikang Wan, Shizhen Chen, Lei Zhang,Xin Zhou, Kai Liu, Hongjie Zhang|
|刊物名称||ANGEWANDTE CHEMIE-INTERNATIONAL EDITION|
Chiral alpha-hydroxyl acids are of great importance in chemical synthesis. Current methods for recognizing their chirality by H-1 NMR are limited by their small chemical shift differences and intrinsic solubility problem in organic solvents. Herein, we developed three YbDO3A(ala)(3) derivatives to recognize four different commercially available chiral alpha-hydroxyl acids in aqueous solution through H-1 NMR and chemical exchange saturation transfer (CEST) spectroscopy. The shift difference between chiral alpha-hydroxyl acid observed by proton and CEST NMR ranged from 15-40 and 20-40 ppm, respectively. Our work demonstrates for first time, that even one chiral center on the side-arm chain of cyclen could set the stage for rotation of the other two non-chiral side chains into a preferred position. This is ascribed to the lower energy state of the structure. The results show that chiral YbDO3A-like complexes can be used to discriminate chiral alpha-hydroxyl acids with a distinct signal difference.