Synthesis of alanine methyl ester-calix[4]arene-appended silica particles as a chiral stationary phase for HPLC

Subject Areas :

صادق یعقوب نژاد ¹ , کورش تبار حیدر ² , سید حمید احمدی ³ , رضا زادمرد ⁴

1 - دکترای شیمی تجزیه، پژوهشکده فناوری‌های پاک، پژوهشگاه شیمی و مهندسی شیمی ایران، تهران، ایران
2 - دانشیار، پژوهشکده فناوری‌های پاک، پژوهشگاه شیمی و مهندسی شیمی ایران، تهران، ایران
3 - دانشیار، پژوهشکده فناوری‌های پاک، پژوهشگاه شیمی و مهندسی شیمی ایران، تهران، ایران
4 - دانشیار، گروه شیمی آلی، پژوهشگاه شیمی و مهندسی شیمی ایران، تهران، ایران

Received: 2017-12-11 Accepted : 2018-02-09 Published : 2019-02-20

Keywords: HPLC, High-performance liquid chromatography, Calix[4]arne, chiral stationary phase,

Abstract :

Here we report the synthesis of a novel covalently immobilized calix[4]arne derivative as a chiral stationary phase )CSP( for HPLC. In the structure of CSP, the upper rim of calix[4]arne is substituted with two L-alanine units and the lower rim of calix[4]arene is linked to the silica gel by thiol-ene click chemistry. Elemental analysis of the CSP showed 120 μmol of chiral selector bonded per gram of silica gel. 1-Hexene was used for end-capping of unreacted mercapto groups on silica gel. The CSP is chemically bonded to the silica and can be used in the normal-phase mode, reversed-phase mode, and with halogenated solvents mobile phases, if desired. The chromatographic performance of the CSP was evaluated with enantioseparation of the 3,5-dinitrobenzoyl )DNB) derivatives of some amino acids.

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