Citation: HAN Xiaoqian, LIN Yunyun, LI Zhen, LIU Wenhua, SHI Ningning, WANG Nong. Preparation and Application of Novel Bonded L-Valine and L-Alanine Derived Chiral Stationary Phases[J]. Chinese Journal of Applied Chemistry, ;2018, 35(1): 68-74. doi: 10.11944/j.issn.1000-0518.2018.01.170030 shu

Preparation and Application of Novel Bonded L-Valine and L-Alanine Derived Chiral Stationary Phases

College of Chemical and Biological Engineering, Lanzhou Jiaotong University, Lanzhou 730070, China

Corresponding author: HAN Xiaoqian, hanxq@mail.lzjtu.cn
Received Date: 12 February 2017
Revised Date: 27 April 2017
Accepted Date: 27 April 2017

Fund Project: Supported by the National Natural Science Foundation of China(No.21462024)National Natural Science Foundation of China 21462024

Figures(6)

Ten novel amino acid derived chiral stationary phases(CSPs), including eight amino acid modified triazine derived CSPs(CSP-1~CSP-8) and two N-p-methylbenzoyl L-amino acid CSPs(CSP-9~CSP-10), were prepared from L-valine and L-alanine. The chiral recognition ability of these CSPs was evaluated for regioisomers of o-, m-, p-nitrophenol and six racemates of naproxen ethyl ester, propiconazole, difenoconazole, tebuconazole, hexaconazole, 1, 1'-bi-2-naphthol, under normal phase mode. The results show that CSP-1~CSP-3 and CSP-6~CSP-8 exhibit good selectivity for three regioisomers of nitrophenol. The CSPs obtained from L-alanine show better enantioselective recognition toward the racemates, which leads to a baseline separation of naproxen ethyl ester on CSP-6. Meanwhile, the binding mode and association energy of L-alanine three-substituted triazine derivative CSP Ⅵ with R or S naproxen ethyl ester were investigated by computational simulation with Gaussian 09 software, and hydrogen bonding was found to be a significant factor on the enantioselective recognition.
- amino acid derivatives,
- chiral stationary phases,
- chiral separation,
- Gaussian 09
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