Citation: SHEN Jun, LI Geng, LI Ping, YANG Chao, LIU Shuangyan, OKAMOTO Yoshio. Preparation and enantioseparation property of novel amylose-based chiral stationary phases for high performance liquid chromatography[J]. Chinese Journal of Chromatography, ;2016, 34(1): 50-56. doi: 10.3724/SP.J.1123.2015.10015 shu

Preparation and enantioseparation property of novel amylose-based chiral stationary phases for high performance liquid chromatography

SHEN Jun ^1,, ,
LI Geng ¹ ,
LI Ping ¹ ,
YANG Chao ¹ ,
LIU Shuangyan ¹ ,
OKAMOTO Yoshio ^1,2

1.
1. Polymer Materials Research Center, Key Laboratory of Superlight Materials and Surface Technology of Ministry of Education, College of Materials Science and Chemical Engineering, Harbin Engineering University, Harbin 150001, China;
2.
2. Nagoya University, Nagoya 464-8603, Japan

Corresponding author: SHEN Jun,
Received Date: 12 October 2015

Fund Project: 国家自然科学基金项目(21474024,51073046) (21474024,51073046)黑龙江省自然科学基金项目(B2015022) (B2015022)中央高校基本科研业务费专项资金(HEUCFT1009). (HEUCFT1009)

Five new amylose derivatives, namely amylose 2-benzoate-3-(4-chlorophenylcarbamate)-6-(3,5-dimethylphenylcarbamate), amylose 2-benzoate-3-(4-chlorophenylcarbamate)-6-(3,5-dichlorophenylcarbamate), amylose 2-benzoate-3,6-bis(4-chlorophenylcarbamate), amylose 2-(4-chlorobenzoate)-3,6-bis(4-chlorophenylcarbamate) and amylose 2-(4-chlorobenzoate)-3,6-biscyclohexylcarbamate, were synthesized by a series of regioselective process. These derivatives were then coated on the surface of aminopropyl silica gels, and used as chiral stationary phases (CSPs) for high performance liquid chromatography (HPLC). These derivatives were characterized by ¹H-nuclear magnetic resonance (¹H-NMR) and Fourier transform infrared (FT-IR) spectroscopies, and their chiral recognition abilities were evaluated using nine racemates by HPLC. Compared with other amylose derivatives, some racemates were better resolved on the new CSPs. The obtained results indicate that the property and position of substituents at 2-, 3- and 6-positions of glucose unit have great influence on the chiral recognition abilities of the amylose derivatives.
- high performance liquid chromatography (HPLC),
- amylose,
- chiral stationary phases (CSPs),
- benzoates,
- phenylcarbamates,
- enantioseparation,
- chiral recognition
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