Preparation of a new doubly tethered chiral stationary phase based on (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid and its application.
A new doubly tethered chiral stationary phase (CSP) based on (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid was prepared by attaching the second tethering group to silica gel through a carbon atom of the first tethering group of the corresponding singly tethered CSP, which was previously developed in our laboratory. The new doubly tethered CSP was applied successfully to the resolution of various racemic alpha-amino acids, amines and amino alcohols containing a primary amino group. In most cases, the chiral recognition efficiency of the new doubly tethered CSP was superior to that of the corresponding singly tethered one in the resolution of alpha-amino acids, amines and amino alcohols. In the resolution of some racemic primary amino compounds, the new doubly tethered and the corresponding singly tethered CSPs were complementary with each other. The chiral resolution behaviors on the new doubly tethered CSP were examined with the variation of the type and content of organic and acidic modifiers in aqueous mobile phase and the column temperature. The chiral resolution behaviors on the new doubly tethered CSP were generally quite similar to those on the corresponding singly tethered CSP. The stability of the new doubly tethered CSP was greater than that of the corresponding singly tethered CSP.
Hyun
Myung Ho
MH
Department of Chemistry and Chemistry Institute for Functional Materials, Pusan National University, Kuemjeong-Ku, Busan 609-735, South Korea. mhhyun@pusan.ac.kr
Song
Yanci
Y
Cho
Yoon Jae
YJ
Kim
Do Hun
DH
D002851:Chromatography, High Pressure Liquid / Q000295:instrumentation*; D043844:Crown Ethers / Q000737:chemistry*; D013056:Spectrophotometry, Ultraviolet
D043844:Crown Ethers; C090732:18-crown-6 2,3,11,12-tetracarboxylic acid