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Citation: WANG Baocun, BAO Minghui, LIN Sufei, MA Jieyu, TANG Shouwan. Preparation and chiral recognition of heterosubstituted amylose derivatives-based chiral stationary phases[J]. Chinese Journal of Chromatography, ;2017, 35(6): 572-577. doi: 10.3724/SP.J.1123.2017.02011 shu

Preparation and chiral recognition of heterosubstituted amylose derivatives-based chiral stationary phases

College of Pharmaceutical and Chemical Engineering, Taizhou University, Taizhou 318000, China

Received Date: 13 February 2017

Fund Project: Zhejiang College Students' Science and Technology Innovation Project (Xinmiao Talents Program) (No. 2016R430020).

Two novel amylose derivatives, namely amylose 2-benzoate-3-(4-methylphenylcarbamate)-6-(3,5-dichlorophenylcarbamate) and amylose 2-benzoate-3-(3,5-dichlorophenylcarbamate)-6-(4-methylphenylcarbamate), were prepared utilizing a serial regioselective process. After coated onto aminopropyl silica gel, they were utilized as chiral stationary phases (CSPs) for high performance liquid chromatography. Investigations indicated that the CSPs exhibited characteristic chiral recognition and their chiral recognition abilities were much higher than those of amylose tris(3,5-dichlorophenylcarbamate) (ADCPC), a homosubstituted derivative. The nature and position of the substituents at 3-, and 6-positions of a glucose unit had great influence on the chiral resolution abilities of the amylose derivatives. Some chiral compounds which were not effectively resolved on the commercial column Chiralpak AD were effectively separated on the new CSPs. Moreover, with all the eight tested racemates resolved, amylose 2-benzoate-3-(4-methylphenylcarbamate)-6-(3,5-dichlorophenylcarbamate) exhibited relatively high chiral recognition and might be a potential useful CSP.
- high performance liquid chromatography (HPLC),
- chiral stationary phase (CSP),
- amylose derivative,
- chiral separation,
- polysaccharide
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