Chromatographic Resolution of a-Amino Acids by （R）-（3,3＇-Halogen Substituted-l,l＇-binaphthyl）-20-crown-6 Stationary Phase in HPLC

Three new chiral stationary phases （CSPs） for high-performance liquid chromatography were prepared from R-（3,3＇-halogen substituted-1,1＇-binaphthyl）-20-crown-6 （halogen=C1, Br and I ）. The experimental results showed that R-（3,3＇-dibromo-l,l＇-binaphthyl）-20-crown-6 （CSP-1） possesses more prominent e...

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Published in中国化学：英文版 Vol. 35; no. 7; pp. 1037 - 1042
Main Author Peng Wu Yuping Wu JunhuiZhang Zhenyu Lu Mei Zhang Xuexian Chen Liming Yuan
Format Journal Article
LanguageEnglish
Published 2017
Subjects
HPLC
α-氨基酸
冠醚衍生物
卤素
商业价值
手性固定相
联萘
谱分辨率
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Summary:Three new chiral stationary phases （CSPs） for high-performance liquid chromatography were prepared from R-（3,3＇-halogen substituted-1,1＇-binaphthyl）-20-crown-6 （halogen=C1, Br and I ）. The experimental results showed that R-（3,3＇-dibromo-l,l＇-binaphthyl）-20-crown-6 （CSP-1） possesses more prominent enantioselectivity than the two other halogen-substituted crown ether derivatives. All twenty-one a-amino acids have different degrees of sep- aration on R-（3,3＇-dibromo-l,l＇-binaphthyl）-20-crown-6-based CSP-1 at room temperature. The enantioselectivity of CSP-1 is also better than those of some commercial R-（1, 1＇-binaphthyl）-20-crown-6 derivatives. Both the separa- tion factors （a） and the resolution （Rs） are better than those of commercial crown ether-based CSPs [CROWNPAK CR（＋） from Daicel] under the same conditions for asparagine, threonine, proline, arginine, serine, histidine and va- line, which cannot be separated by commercial CR（＋）. This study proves the commercial usefulness of the R-（3,3＇-dibromo- 1, 1＇-binaphthyl）-20-crown-6 chiral stationary phase.
Bibliography:α-amino acid, chiral crown ethers, stationary phase, high-performance liquid chromatography
31-1547/O6
Three new chiral stationary phases （CSPs） for high-performance liquid chromatography were prepared from R-（3,3＇-halogen substituted-1,1＇-binaphthyl）-20-crown-6 （halogen=C1, Br and I ）. The experimental results showed that R-（3,3＇-dibromo-l,l＇-binaphthyl）-20-crown-6 （CSP-1） possesses more prominent enantioselectivity than the two other halogen-substituted crown ether derivatives. All twenty-one a-amino acids have different degrees of sep- aration on R-（3,3＇-dibromo-l,l＇-binaphthyl）-20-crown-6-based CSP-1 at room temperature. The enantioselectivity of CSP-1 is also better than those of some commercial R-（1, 1＇-binaphthyl）-20-crown-6 derivatives. Both the separa- tion factors （a） and the resolution （Rs） are better than those of commercial crown ether-based CSPs [CROWNPAK CR（＋） from Daicel] under the same conditions for asparagine, threonine, proline, arginine, serine, histidine and va- line, which cannot be separated by commercial CR（＋）. This study proves the commercial usefulness of the R-（3,3＇-dibromo- 1, 1＇-binaphthyl）-20-crown-6 chiral stationary phase.
ISSN:1001-604X
1614-7065