Institute of Organic Chemistry, Justus-Liebig University, Heinrich-Buff-Ring 17, 35392, Giessen, Germany.
Chemistry. 2018 Aug 14;24(46):11904-11907. doi: 10.1002/chem.201802119. Epub 2018 Jun 27.
We demonstrate that the simple achiral amino acid glycine as its methyl ester inherits the chiral imprint of methyl lactate upon complexation, resulting in induced vibrational optical activity of the methylene C-H bonds. To mimic conditions of ice on comets that are considered long-term reaction as well as storage entities for (organic) molecules, we employ the matrix isolation technique in conjunction with vibrational circular dichroism spectroscopy and DFT computations. The observed chirality transfer is likely a key element for the realization of concepts rationalizing chirogenesis, that is, the generation of a chiral imbalance.
我们证明了手性氨基酸甘氨酸甲酯在复合物中继承了甲基乳酸酯的手性印迹,导致亚甲基 C-H 键产生诱导振动旋光活性。为了模拟被认为是长期反应以及(有机)分子的储存实体的彗星上冰的条件,我们采用了基质隔离技术,结合振动圆二色光谱和 DFT 计算。所观察到的手性转移可能是实现合理手性发生(即产生手性不平衡)概念的关键要素。