Unusual enantiomeric separation due to residual amines in chiral crown ether stationary phase linked by long alkyl chain

TALANTA

卷:235

Article

Sung, Ji Yeong¹  Jin, Sun-Mi¹  Lee, Sumin^1,2  An, Sung-Young³  Jin, Jong Sung¹ 

[1] Korea Basic Sci Inst, Busan Ctr, 30 Gwahaksandan 1 Ro 60 Gil, Busan 46742, South Korea

[2] Natl Inst Environm Res NIER, Chem Res Div, Incheon 22689, South Korea

[3] Chiral Technol Korea, Daejeon 34013, South Korea

关键词: Chiral stationary phase;    Enantiomeric separation;    Residual aminoundecyl groups;    TOF-SIMS;    (+)-(18-crown-6)-2;    3;    11;    12-tetracarboxylic acid;   

DOI  :  10.1016/j.talanta.2021.122739

来源: Elsevier

【 摘 要 】

A new chiral stationary phase (CSP) in which (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid was linked to a silica gel surface through a long alkyl chain and which did not contain additional aminoundecyl groups was prepared. Generally, when enantiomers containing a primary amine group are optically resolved using a crownether-type CSP, a higher resolution is achieved if the surface of the CSP does not contain any residual amine. In this study, the chiral separation factor and resolution factor of a CSP with a long alkyl chain such as the aminoundecyl group were unusually low in the absence of the residual aminoundecyl groups. In this study, a chiral column was prepared by introducing a chiral selector having a long alkyl chain on the surface of silica gel to separate enantiomers of alpha-amino acids. Furthermore, it was confirmed that the residualamine-containing CSP, which was easier to synthesize, facilitated more effective enantiomeric separation than the CSP without residual amines.

【 授权许可】

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