TY - JOUR
T1 - Preparation and evaluation of a chiral stationary phase covalently bound with chiral pseudo-18-crown-6 ether having 1-phenyl-1,2-cyclohexanediol as a chiral unit
AU - Hirose, Keiji
AU - Yongzhu, Jin
AU - Nakamura, Takashi
AU - Nishioka, Ryota
AU - Ueshige, Tetsuro
AU - Tobe, Yoshito
PY - 2005/6/17
Y1 - 2005/6/17
N2 - A chiral stationary phase (CSP) has been prepared by chemically bonding a chiral pseudo-18-crown-6 type host having a 1-phenyl-1,2-cyclohexanediol unit to 3-aminopropyl silica gel. The chiral column was prepared by the slurry-packing method in a stainless steel HPLC column. Normal mobile phases can be used with this CSP in contrast to conventional dynamic coating type CSPs. Enantiomers of 20 out of 30 amino compounds, including 20 amino acids, 2 amino acid methyl esters, 6 amino alcohols, and 2 lipophilic amines, were efficiently separated on columns with this CSP. It is noteworthy that 15 amino compounds out of 30 were separated with better separation factors and shorter retention times compared to the corresponding CSP having pseudo-18-crown-6 with 1-phenyl-1,2-ethanediol as a chiral unit. In view of the correlation between the enantiomer selectivities observed in chromatography and those obtained in gas phase FABMS-EL methods and solution phase titrations, chiral recognition in the host-guest interaction likely contributes to enantiomer separation.
AB - A chiral stationary phase (CSP) has been prepared by chemically bonding a chiral pseudo-18-crown-6 type host having a 1-phenyl-1,2-cyclohexanediol unit to 3-aminopropyl silica gel. The chiral column was prepared by the slurry-packing method in a stainless steel HPLC column. Normal mobile phases can be used with this CSP in contrast to conventional dynamic coating type CSPs. Enantiomers of 20 out of 30 amino compounds, including 20 amino acids, 2 amino acid methyl esters, 6 amino alcohols, and 2 lipophilic amines, were efficiently separated on columns with this CSP. It is noteworthy that 15 amino compounds out of 30 were separated with better separation factors and shorter retention times compared to the corresponding CSP having pseudo-18-crown-6 with 1-phenyl-1,2-ethanediol as a chiral unit. In view of the correlation between the enantiomer selectivities observed in chromatography and those obtained in gas phase FABMS-EL methods and solution phase titrations, chiral recognition in the host-guest interaction likely contributes to enantiomer separation.
KW - Amines
KW - Amino acids
KW - Amino alcohols
KW - Chemically bounded type
KW - Chiral stationary phases
KW - Crown ethers
KW - ESI
KW - Enantiomer separation
KW - LCMS
UR - http://www.scopus.com/inward/record.url?scp=20444498257&partnerID=8YFLogxK
U2 - 10.1016/j.chroma.2005.04.071
DO - 10.1016/j.chroma.2005.04.071
M3 - Article
C2 - 16007979
AN - SCOPUS:20444498257
VL - 1078
SP - 35
EP - 41
JO - Journal of Chromatography A
JF - Journal of Chromatography A
SN - 0021-9673
IS - 1-2
ER -