Preparation And Evaluation Of Peptide-Peptoid Hybrid Chiral Stationary Phase

Chiral separation and preparation are important in various chemical fields that deal with bioactive compounds, in particular drug discovery, food additive research, fragrance development, etc. It is still the trend to use compounds with wide range of sources as raw materials to develop general chiral stationary phase in high performance liquid chromatography. These years, a new class of polypeptide based stationary phases have been synthesized and the results showed that it’s a class of chiral stationary phase with broad enantioselectivity. Based on these studies, several peptoid based CSP with similar structures as polypeptide CSP were prepared and investigated in our group, the results showed that it is a class of potential chiral stationary phase. Peptide-peptoid hybrids compound also has similar structures both with peptide and peptoid, it may have better performance than polypeptide and peptoid CSP.In this study,6kinds of peptide-peptoid hybrids chiral stationary phase were prepared with L-proline or L-leucine as main chain’s monomers,(S)-(-)-phenylethylamine or (R)-(+)-phenylethylamine or benzylamine as side chain’s monomers respectively. These CSPs were designed to study the effect of its structures on chiral separation. After evaluated in HPLC, the results showed that these CSPs performed better than peptoid CSPs and the chiral side chain’s conformation was important factors to affect its enantio-selectivity. We also studied the influence of of enantiomers’ structures such as H-bond, aromatic nucleus, mobile phase system and column temperature on chiral seperation. These research helps us to have a better understanding in peptide-peptoid hybrid CSP and further study.