Liquid chromatographic direct resolution of beta-amino acids on a doubly tethered chiral stationary phase containing N--H amide linkage based on (+)-(18-crown-6)- 2,3,11,12-tetracarboxylic acid.
A doubly tethered chiral stationary phase (CSP) prepared by bonding (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid to doubly tethered primary aminoalkyl silica gel was used for the resolution of various beta-amino acids. All the beta-amino acids tested were resolved quite well, the separation (alpha) and the resolution factors (RS) being in the ranges 1.34-2.09 and 2.52-7.45, respectively, with a mobile phase of methanol-water (50:50, v/v) containing 10 mM acetic acid. The chiral recognition efficiency of the doubly-tethered CSP was found to be generally superior to that of the corresponding singly-tethered CSP in the resolution of beta-amino acids. The chiral recognition behaviors for the resolution of beta-amino acids on the doubly tethered CSP were examined by varying the type and content of organic and acidic modifiers in the aqueous mobile phase and the column temperature.
Hyun
Myung Ho
MH
Department of Chemistry, Pusan National University, Busan, Republic of Korea. mhhyun@pusan.ac.kr
Song
Yanci
Y
Cho
Yoon Jae
YJ
Choi
Hee Jung
HJ
D000577:Amides / Q000737:chemistry; D000596:Amino Acids / Q000737:chemistry* / Q000302:isolation & purification*; D002851:Chromatography, High Pressure Liquid / Q000379:methods; D043844:Crown Ethers; D007202:Indicators and Reagents; D013237:Stereoisomerism
D000577:Amides; D000596:Amino Acids; D043844:Crown Ethers; D007202:Indicators and Reagents; C090732:18-crown-6 2,3,11,12-tetracarboxylic acid