Facile Enantiomer Analysis by Combination of N‐Dansyl Amino Acid as Diastereomerizer and Molecular‐Shape Recognitive RP‐HPLC Using Comb‐Shaped Polymer‐Immobilized Silica

Abstract

Poly(octadecyl acrylate)‐grafted silica has been developed as a special stationary phase showing molecular‐shape recognition in high‐performance liquid chromatography. The bonded polymer phase is characterized by the fact that the polymer forms highly‐ordered structures similar to a solvated crystalline state on silica and multiple π–π interaction between carbonyl groups in the polymer and aromatic solutes is promoted. This paper shows that the selectivity for DL‐amino acids diastereomerized with N‐dansyl L‐proline can be enhanced by using the polymer stationary phase instead of octadecylated silica (ODS).

Keywords:

• Liquid chromatography
• Diastereomer
• Chiral discrimination
• Dansyl amino acid
• Proline
• π–π interaction
• Polymeric stationary phase
• Molecular shape selectivity

Acknowledgments

We thank Dr. K. Nobuhara of Fuji Silysia Industry, Co., Ltd. for providing Super Micro Bead silica gel. This work was partially supported by a Grant‐in‐Aid for Scientific Research of the Ministry for Education, Culture, Sports, Science, and Technology of Japan.