Quaranta Calogero, d'Anciães Almeida Silva Igor, Moos Sven, Bartalucci Ettore, Hendrickx Leeroy, Fahl Benjamin M D, Pasqualini Claudia, Puccetti Francesco, Zobel Mirijam, Bolm Carsten, Wiegand Thomas
Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074, Aachen, Germany.
Max Planck Institute for Chemical Energy Conversion, Stiftstr. 34-36, 45470, Mülheim/Ruhr, Germany.
Angew Chem Int Ed Engl. 2024 Oct 21;63(43):e202410801. doi: 10.1002/anie.202410801. Epub 2024 Sep 5.
Molecular-recognition events are highly relevant in biology and chemistry. In the present study, we investigated such processes in the solid state under mechanochemical conditions using the formation of racemic phases upon reacting enantiopure entities as example. As test systems, α-(trifluoromethyl)lactic acid (TFLA) and the amino acids serine and alanine were used. The effects of ball-milling and resonant acoustic mixing (RAM) on the formation of racemic phases were probed by using solid-state Nuclear Magnetic Resonance (NMR) spectroscopy. In a mixer mill, a highly efficient and fast racemic phase formation occurred for both TFLA and the two amino acids. RAM led to the racemic phase for TFLA also, and this process was facilitated upon employing pre-milled enantiopure entities. In contrast, under comparable conditions RAM did not result in the formation of racemic phases for serine and alanine.
分子识别事件在生物学和化学中高度相关。在本研究中，我们以对映纯实体反应时外消旋相的形成为例，研究了机械化学条件下固态中的此类过程。作为测试系统，使用了α-（三氟甲基）乳酸（TFLA）以及氨基酸丝氨酸和丙氨酸。通过使用固态核磁共振（NMR）光谱来探究球磨和谐振声学混合（RAM）对外消旋相形成的影响。在混合球磨机中，TFLA和两种氨基酸均发生了高效且快速的外消旋相形成。RAM也导致了TFLA的外消旋相形成，并且在使用预研磨的对映纯实体时这一过程得到了促进。相比之下，在可比条件下，RAM并未导致丝氨酸和丙氨酸形成外消旋相。
