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Chromatographic Resolution of α ‐Amino Acids by ( R )‐(3,3'‐Halogen Substituted‐1,1'‐binaphthyl)‐20‐crown‐6 Stationary Phase in HPLC
Author(s) -
Wu Peng,
Wu Yuping,
Zhang Junhui,
Lu Zhenyu,
Zhang Mei,
Chen Xuexian,
Yuan Liming
Publication year - 2017
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.201600664
Subject(s) - chemistry , halogen , crown ether , amino acid , high performance liquid chromatography , proline , valine , chromatography , resolution (logic) , chiral stationary phase , organic chemistry , biochemistry , alkyl , artificial intelligence , computer science , ion
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 = Cl, Br and I). The experimental results showed that R ‐(3,3'‐dibromo‐1,1'‐binaphthyl)‐20‐crown‐6 ( CSP ‐1 ) possesses more prominent enantioselectivity than the two other halogen‐substituted crown ether derivatives. All twenty‐one α ‐amino acids have different degrees of separation on R ‐(3,3'‐dibromo‐1,1'‐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 separation factors ( α ) and the resolution ( R s ) 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 valine, 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.