Liu Qin, Zhang Shuzhen, Wu Bidong, Guo Jifen, Xie Jianwei, Gu Mingsong, Zhao Yimin, Yun Liuhong, Liu Keliang
Beijing Institute of Pharmacology and Toxicology, 27 Taiping Road, Beijing 100850, P. R. China.
Anal Chem. 2005 Aug 15;77(16):5302-10. doi: 10.1021/ac050318f.
A novel class of chiral melamine derivatives has been designed and synthesized. The ability of these compounds to perform chiral recognition toward 19 natural chiral alpha-amino acids has been investigated by electrospray ionization tandem mass spectrometry for the first time. The enantioselectivities of these new chiral selectors are encouraging. To elucidate some mechanism and regularity in the chiral recognition process using chiral melamine derivatives as chiral selectors, the effect of different noncovalent interactions caused by various chiral or achiral moieties in melamine derivatives on the chiral recognition in the gas phase has been studied at the same time. The result shows that electrostatic, hydrogen bond, pi-pi stacking, and steric interaction between selector and analyte play important roles in the association and enantioselective recognition of amino acids with the chiral melamine derivatives as chiral selectors. Enantiodiscrimination for analytes with different structures and properties could be improved by modifying substituents in melamine derivatives on purpose.
设计并合成了一类新型手性三聚氰胺衍生物。首次通过电喷雾电离串联质谱研究了这些化合物对19种天然手性α-氨基酸进行手性识别的能力。这些新型手性选择剂的对映选择性令人鼓舞。为了阐明以手性三聚氰胺衍生物作为手性选择剂在手性识别过程中的一些机理和规律，同时研究了三聚氰胺衍生物中各种手性或非手性部分引起的不同非共价相互作用对气相中手性识别的影响。结果表明，选择剂与分析物之间的静电、氢键、π-π堆积和空间相互作用在手性三聚氰胺衍生物作为手性选择剂对氨基酸的缔合和对映选择性识别中起重要作用。通过有意修饰三聚氰胺衍生物中的取代基，可以提高对具有不同结构和性质的分析物的对映体区分能力。
