Department of Earth and Environmental Sciences, Graduate School of Environmental Studies, Nagoya University, Nagoya 464-8601, Japan.
Department of Earth and Environmental Sciences, Graduate School of Environmental Studies, Nagoya University, Nagoya 464-8601, Japan.
J Chromatogr A. 2018 Sep 7;1566:118-123. doi: 10.1016/j.chroma.2018.06.051. Epub 2018 Jun 21.
2,5-Diketopiperazines (DKPs) are widely recognized as chiral molecules with great potential in medicinal chemistry. Complete separation of DKP stereoisomers is very important for efficiently investigating the chemical characteristics of DKPs. The combination of esterification and acylation caused the enantiomers of cyclo(d-Ala-d-Ala) and cyclo(l-Ala-l-Ala) to ring-open and generate their dipeptide derivatives. These derivatives were completely separated by chiral gas chromatography (GC), and the determined isomer ratios were the same as the original isomer ratios. The derivatization also caused the ring-opening of cyclo(l-Asp-l-Phe) and cyclo(l-Met-l-Pro), and their derivatives were determined by the chiral GC method. The present study is the first report of the complete separation of cis-DKPs using chiral GC. This separation procedure can substantially contribute to the development of the chemistry of chiral DKPs.
2,5-二酮哌嗪（DKP）被广泛认为是具有很大药用化学潜力的手性分子。完全分离 DKP 的对映异构体对于高效研究 DKP 的化学特性非常重要。酯化和酰化的结合导致环（D-丙氨酰-D-丙氨酸）和环（L-丙氨酰-L-丙氨酸）的对映异构体开环并生成它们的二肽衍生物。这些衍生物通过手性气相色谱（GC）完全分离，测定的异构体比例与原始异构体比例相同。衍生化还导致环（L-天冬氨酰-L-苯丙氨酸）和环（L-蛋氨酰-L-脯氨酸）开环，其衍生物通过手性 GC 法确定。本研究首次报道了使用手性 GC 完全分离顺式 DKP。这种分离程序可以为手性 DKP 的化学发展做出重大贡献。
