Abstract
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.
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