Municio Sofía, Mato Sergio, Alonso José L, Alonso Elena R, León Iker
Grupo de Espectrocopía Molecular (GEM), Edificio Quifima, Laboratorios de Espectroscopia y Bioespectroscopia, Unidad Asociada CSIC, Parque Científico UVa, Universidad de Valladolid, Valladolid 47011, Spain.
ACS Phys Chem Au. 2025 Jun 3;5(4):338-345. doi: 10.1021/acsphyschemau.4c00108. eCollection 2025 Jul 23.
Neutral gabapentin has been vaporized by laser ablation and supersonically expanded to record its rotational spectrum using Fourier transform microwave spectroscopy. We report the detection of five stable conformers, which differ in the intramolecular interactions between the different functional groups (OH, C=O, and NH). Two configurations, and , are possible depending on the chair form of the cyclohexane ring, and both forms are detected, with the latter being predominant. The conformational landscape of gabapentin is compared with that of GABA, and significant differences are observed. One of the most meaningful results of such a comparison is that the relationship between the intramolecular interactions and the relative abundance within each type is reversed from GABA to gabapentin. It could explain the distinction in the mechanism of action of GABA and gabapentin, despite being structurally similar.
中性加巴喷丁已通过激光烧蚀蒸发，并通过傅里叶变换微波光谱法进行超声膨胀以记录其转动光谱。我们报告检测到五种稳定构象异构体，它们在不同官能团（OH、C=O和NH）之间的分子内相互作用上有所不同。根据环己烷环的椅式构象，有两种构型，即 和 ，两种构型均被检测到，后者占主导。将加巴喷丁的构象态势与GABA的进行比较，观察到显著差异。这种比较最有意义的结果之一是，分子内相互作用与每种类型内相对丰度之间的关系从GABA到加巴喷丁发生了逆转。这可以解释GABA和加巴喷丁尽管结构相似但作用机制的差异。
