Chiral stationary phases based on chitosan bis(4-methylphenylcarbamate)-(alkoxyformamide)
Chiral stationary phases based on chitosan bis(4-methylphenylcarbamate)-(alkoxyformamide)
复制标题
基于壳聚糖双(4-甲基苯基氨基甲酸酯)-(烷氧基甲酰胺)的手性固定相
DOI：
10.1002/jssc.201600680
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发表时间：
2016-10-01
影响因子：
3.1
通讯作者：
Bai, Zheng-Wu
中科院分区：
文献类型：
--
作者：
Feng, Zi-Wei;Chen, Wei;Bai, Zheng-Wu
选择高度N-脱乙酰壳聚糖作为天然手性源合成手性固定相选择剂。因此，壳聚糖首先被不同的氯甲酸烷基酯酰化，得到壳聚糖烷氧基甲酰胺，然后这些产物与4-甲基苯基异氰酸酯进一步衍生，得到壳聚糖双（4-甲基苯基氨基甲酸酯）-（烷氧基甲酰胺）。将这些衍生物涂敷在3-氨丙基硅胶上制备了一系列手性固定相。衍生物在手性固定相上的含量接近20%（重量）。壳聚糖双（4-甲基苯基氨基甲酸酯）-（乙氧基甲酰胺）和壳聚糖双（4-甲基苯基氨基甲酸酯）-（异丙氧基甲酰胺）手性固定相的拆分效果优于壳聚糖双（4-甲基苯基氨基甲酸酯）-（正戊氧基甲酰胺）和壳聚糖双（4-甲基苯基氨基甲酸酯）-（苄氧基甲酰胺）手性固定相。研究了壳聚糖双（4-甲基苯基氨基甲酸酯）-（乙氧基甲酰胺）手性固定相对有机溶剂的耐受性，结果表明，该固定相可在100%乙酸乙酯和100%氯仿移动的中工作。由于所合成的手性选择剂不溶于许多常见的有机溶剂，因此与传统的纤维素和直链淀粉衍生物的涂层型手性固定相相比，相应的手性固定相可用于更宽范围的移动的流动相。
Highly N-deacetylated chitosan was chosen as a natural chiral origin for the synthesis of the selectors of chiral stationary phases. Therefore, chitosan was firstly acylated by various alkyl chloroformates yielding chitosan alkoxyformamides, and then these resulting products were further derivatized with 4-methylphenyl isocyanate to afford chitosan bis(4-methylphenylcarbamate)-(alkoxyformamide). A series of chiral stationary phases was prepared by coating these derivatives on 3-aminopropyl silica gel. The content of the derivatives on the chiral stationary phases was nearly 20% by weight. The chiral stationary phases prepared from chitosan bis(4-methylphenylcarbamate)-(ethoxyformamide) and chitosan bis(4-methylphenylcarbamate)-(isopropoxyformamide) comparatively showed better enantioseparation capability than those prepared from chitosan bis(4-methylphenylcarbamate)-(n-pentoxyformamide) and chitosan bis(4-methylphenylcarbamate)-(benzoxyformamide). The tolerance against organic solvents of the chiral stationary phase of chitosan bis(4methylphenylcarbamate)-(ethoxyformamide) was investigated, and the results revealed that this phase can work in 100% ethyl acetate and 100% chloroform mobile phases. Because as-synthesized chiral selectors did not dissolve in many common organic solvents, the corresponding chiral stationary phases can be utilized in a wider range of mobile phases in comparison with conventional coating type chiral stationary phases of cellulose and amylose derivatives.