Chiral recognition ability of amylose derivatives bearing regioselectively different carbamate pendants at 2,3-and 6-positions
Chiral recognition ability of amylose derivatives bearing regioselectively different carbamate pendants at 2,3-and 6-positions
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在 2,3-和 6-位带有区域选择性不同氨基甲酸酯侧链的直链淀粉衍生物的手性识别能力。
DOI：
10.1016/j.carbpol.2019.03.052
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发表时间：
2019-08-15
影响因子：
11.2
通讯作者：
Okamoto, Yoshio
中科院分区：
文献类型：
--
作者：
Dai, Xiao;Bi, Wanying;Okamoto, Yoshio
通过6位保护和脱保护，合成了7个在葡萄糖单元的2，3-和6-位上带有两个区域选择性氨基甲酸酯侧基的直链淀粉衍生物。将所得衍生物作为高效液相色谱手性固定相，考察了其对映体的识别能力。每个衍生物都有自己的特征识别能力，这取决于在三个位置的氨基甲酸酯侧基的排列。侧基上取代基的性质、位置和数目对该类衍生物的手性识别能力有重要影响。大多数直链淀粉衍生物对外消旋体具有较好的对映选择性，其中2-和3-位带有吸电子对氯苯氨基甲酸酯的直链淀粉衍生物具有较好的手性识别能力。一些外消旋体可以更好地解决与不同的侧基的直链淀粉衍生物比Chiralpak AD，一个最强大的商业可用的手性柱衍生自直链淀粉三（3，5-二甲基苯基氨基甲酸酯）。
Seven amylose derivatives bearing two regioselective carbamate pendants at 2,3- and 6-positions of a glucose unit were synthesized through protection and deprotection at the 6-position. The chiral recognition abilities of the obtained derivatives were evaluated as the chiral stationary phases (CSPs) for high-performance liquid chromatography (HPLC). Each derivative had its own characteristic recognition ability depending on the arrangement of carbamate pendants at the three positions. The nature, position and number of the substituents on the aromatic moieties of pendants play a significant role on the chiral recognition ability of these derivatives. Most amylose derivatives exhibit good enantioselectivity for the racemates in this study, and those bearing electron-withdrawing para-chlorophenylcarbamates at 2- and 3-positions possessed relatively better chiral recognition than others. Some racemates could be better resolved on the amylose derivatives with different pendants than on Chiralpak AD, one of the most powerful commercially available chiral columns derived from amylose tris(3,5-dimethylphenylcarbamate).