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

doi:10.3724/SP.J.1123.2017.02011

Abstract

Abstract:

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.

Key words: amylose derivative, chiral separation, chiral stationary phase (CSP), high performance liquid chromatography (HPLC), polysaccharide

CLC Number:

O658

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.

References

[1] Ward T J, Ward K D. Anal Chem, 2012, 84(2): 626
[2] Jin Z L, Hu F F, Wang Y B, et al. Chinese Journal of Chromatography, 2011, 29(11): 1087 金召磊, 胡芳芳, 汪一波, 等. 色谱, 2011, 29(11): 1087
[3] Luo A, Wan Q, Fan H J, et al. Chinese Journal of Chromatography, 2014, 32(9): 1013 罗安, 万强, 范华均, 等. 色谱, 2014, 32 (9): 1013
[4] Wang M. Chinese Journal of Chromatography, 2014, 32(2): 198 王敏. 色谱, 2014, 32(2): 198
[5] Peluso P, Mamane V, Cossu S. Chirality, 2015, 27(10): 667
[6] Kurka O, Kucera L, Bednar P. J Sep Sci, 2016, 39(14): 2736
[7] Li D Y, Wu X, Hao F L, et al. Chinese Journal of Chromatography, 2016, 34(1): 80 李冬艳, 吴锡, 郝芳丽, 等. 色谱, 2016, 34(1): 80
[8] Li L Q, Fan J, Zhang J, et al. Chinese Journal of Chromatography, 2016, 34(1): 107 李丽群, 范军, 张晶, 等. 色谱, 2016, 34(1): 108
[9] Kaida Y, Okamoto Y. Bull Chem Soc Jpn, 1993, 66(8): 2225
[10] Qu H T, Li J Q, Shen J, et al. Chinese Journal of Analytical Chemistry, 2011, 39(4): 461 屈海涛, 李峻青, 沈军, 等. 分析化学, 2011, 39(4): 461
[11] Tang S W, Li X F, Wang F, et al. Chirality, 2012, 24(2): 167
[12] Shen J, Liu S Y, Zhao Y Q, et al. Acta Polymerica Sinina, 2013(3): 293 沈军, 刘双燕, 赵勇强, 等. 高分子学报, 2013(3): 293
[13] Shen J, Li G, Yang Z Z, et al. J Chromatogr A, 2016, 1467: 199
[14] Dicke R. Cellulose, 2004, 11(2): 255
[15] Kondo S, Yamamoto C, Kamigaito M, et al. Chem Lett, 2008, 37(5): 558
[16] Shen J, Ikai T, Okamoto Y. J Chromatogr A, 2010, 1217: 1041
[17] Sun B S, Li X F, Jin Z L, et al. Chromatographia, 2012, 75(23/24): 1347
[18] Xu H Y, Tang S W, Pan F Y, et al. Science Technology and Engineering, 2015(3): 5 徐红月, 唐守万, 潘富友, 等. 科学技术与工程, 2015(3): 5
[19] Shen J, Li G, Li P, et al. Chinese Journal of Chromatography, 2016, 34(1): 50 沈军, 李庚, 李平, 等. 色谱, 2016, 34(1): 50
[20] Okamoto Y, Aburatani R, Fukumoto T, et al. Chem Lett, 1987, 16(9): 1857