Does local chain conformation affect the chiral recognition ability of an amylose derivative? Comparison between linear and cyclic amylose tris(3,5-dimethylphenylcarbamate)
Does local chain conformation affect the chiral recognition ability of an amylose derivative? Comparison between linear and cyclic amylose tris(3,5-dimethylphenylcarbamate)
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局部链构象是否影响直链淀粉衍生物的手性识别能力？
DOI：
10.1016/j.chroma.2019.04.019
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发表时间：
2019
影响因子：
4.1
通讯作者：
Terao Ken
中科院分区：
文献类型：
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作者：
Ryoki Akiyuki;Kimura Yuto;Kitamura Shinichi;Maeda Katsuhiro;Terao Ken
以3个环直链淀粉三（3,5-二甲基苯基氨基甲酸酯）（cADMPC）样品和3个线性ADMPC样品为原料，分别制备了19 ~ 91 kg mol−1和25 ~ 90 kg mol−1的包覆型手性固定相，用于高效液相色谱（HPLC）。与使用正己烷和2-丙醇混合洗脱液的ADMPC相比，用cADMPC制备的csp具有明显不同的手性分离能力。局部构象对手性分离起着重要的作用，因为与ADMPC相比，cADMPC在稀溶液中的局部螺旋结构得到了扩展。以3-（三乙氧基硅基）丙基氨基甲酸酯为连接物（ADMPCi和cADMPCi），酶解合成线性和环状直链淀粉样品制备固定化型csp，其分子量在18 ~ 130 kg mol−1之间。当我们选择相当高的连接物含量时，cADMPCi的csp与ADMPCi的csp相当接近。这表明ADMPCi和cADMPCi在固定相的局部构象是相似的，因为它们在聚合物链上有多个点与其他聚合物链交联。
Coated-type chiral stationary phases (CSPs) for high-performance liquid chromatography (HPLC) were prepared from three cyclic amylose tris(3,5-dimethylphenylcarbamate) (cADMPC) samples, of which weight-average molar mass (Mw) ranges from 19 to 91 kg mol−1, and from three linear ADMPC samples ranging inMwfrom 25 to 90 kg mol−1. CSPs made of cADMPC showed appreciably different chiral separation ability comparing with those for ADMPC with a mixed eluent ofn-hexane and 2-propanol. Local conformation plays an important role for the chiral separation taking into account that the local helical structure of cADMPC in dilute solution is extended comparing with ADMPC. Immobilized-type CSPs were also prepared from enzymatically synthesized linear and cyclic amylose samples with 3-(triethoxysilyl)propylcarbamate linkers (ADMPCi and cADMPCi) of whichMw’s are in the range from 18 to 130 kg mol−1. When we choose quite high linker contents, CSPs of cADMPCi were fairly close to those of ADMPCi. This suggests that local conformations of ADMPCi and cADMPCi are similar in the stationary phase since they are crosslinked to the other polymer chains with multiple points on the polymer chain.