Correlation between conformational feature in solution and chiral separation ability of linear and nonlinear amylose tris(alkylcarbamate)s
Correlation between conformational feature in solution and chiral separation ability of linear and nonlinear amylose tris(alkylcarbamate)s
复制标题
线性和非线性直链淀粉三(烷基氨基甲酸酯)溶液中构象特征与手性分离能力的相关性
DOI：
10.1016/j.polymer.2023.126303
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发表时间：
2023
期刊：
影响因子：
4.6
通讯作者：
K. Terao
中科院分区：
文献类型：
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作者：
Aika Kishimoto;Akiyuki Ryoki;S. Kitamura;K. Terao
以直链、环状和超支化直链淀粉三（正十八烷基氨基甲酸酯）（ATODC）和直链淀粉三（正丁基氨基甲酸酯）（ATBC）为原料，制备了5种固定化手性柱。少量的接头位点，3-（三乙氧基甲硅烷基）丙基氨基甲酸酯，显着降低了ATBC的链尺寸，其中高链刚度是通过位于相邻的糖苷残基上的丁基氨基甲酸酯基团之间的分子内氢键来实现的。对于ATODC没有发现这种现象，ATODC主要是由庞大的侧基硬化的。虽然这两种色谱柱都具有明显的手性识别能力，但分离的外消旋体数量随着侧基体积的减小而减少。因此，侧基的庞大性在手性分离能力中起着确定的作用。此外，在二氧化硅表面上的链的线性度是一个重要的因素的手性分离，因为没有发现由环状ATODC和环状ATBC的手性柱的手性分离。由超支化ATODC制成的手性柱具有介于线性和环状ATODC之间的手性分离能力，支持这一建议。
Five immobilized-type chiral columns were prepared from linear, cyclic, and hyperbranched amylose tris(n-octadecylcarbamate) (ATODC) and amylose tris(n-butylcarbamate) (ATBC). A small amount of the linker site, 3-(triethoxysilyl)propylcarbamate, significantly reduced the chain dimensions of ATBC for which high chain stiffness is attained by intramolecular hydrogen bonding between butylcarbamate groups located on the neighboring glycosidic residue. This phenomenon was not found for ATODC, which is mainly stiffened by bulky side groups. While both columns have appreciable chiral recognition ability, number of separated racemates decreased with decreasing side group bulkiness. The bulkiness of the side groups thus plays a definite role in the chiral separation ability. Furthermore, chain linearity on the silica surface is an important factor for the chiral separation because no substantial chiral separation was found for the chiral columns consisting of cyclic ATODC and cyclic ATBC. The chiral column made of hyperbranched ATODC has an intermediate chiral separation ability between linear and cyclic ATODC, supporting this suggestion.
影响因子：
4.1
作者：
Ikai, Tomoyuki;Yamamoto, Chiyo;Okamoto, Yoshio
通讯作者：
Okamoto, Yoshio
溶液中线性和环状直链淀粉衍生物的分子构象和分子间相互作用
影响因子：
--
作者：
Terao Ken;Ryoki Akiyuki;Kitamura Shinichi;Sato Takahiro
通讯作者：
Sato Takahiro