Separation of a New Antidiabetic Agent,N-(Trans-4-Isopropylcyclohexylcarbonyl)-D-Phenylalanine,and its Isomers by Chiral High-Performance Liquid Chromatography

Abstract

N-(trans-4-Isopropylcyclohexylcarbonyl)-D-phenylalanine (A4166) is a new oral antidiabetic agent. In order to determine the purity of chemical samples of A4166, a high-performance liquid chromatographic method for the separation of A4166 and synthetic by-products (an L-enantiomer and a cis-iosmer of A4166) has been developed. A chiral stationary phase column packed with 5 μm N-(tert-butylaminocarbonyl)-L-valylaminopropyl silica gel was used for the direct separation of A4166 and its isomers after derivatization with a non-chiral reagent.