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Direct enantioseparation of mandelic acid by high-performance liquid chromatography using a phenyl column precoated with a small amount of cyclodextrin additive in a mobile phase.
Chirality ( IF 2 ) Pub Date : 2020-04-28 , DOI: 10.1002/chir.23228
Yuri Watanabe 1 , Ikko Mikami 1 , Atsushi Yamamoto 2 , Sen-Ichi Aizawa 3 , Atsushi Taga 4 , Naoki Mochizuki 5 , Yoshimi Ishihara 1 , Shuji Kodama 1
Affiliation  

Direct enantioseparation of mandelic acid by high‐performance liquid chromatography (HPLC) with a reversed phase column and a mobile phase containing a small amount of hydroxylpropyl‐β‐cyclodextrin (HP‐β‐CD) was studied as an efficient method for saving consumption of the CD additive. As a result, it was proposed that racemic mandelic acid can be analyzed with a phenyl column by using a mobile phase composed of 10 mM ammonium acetate buffer (pH 4.2) and 0.02% (w/v) HP‐β‐CD at a flow rate of 1.0 mL/min at 40°C after the passage of 10 mM ammonium acetate buffer (pH 4.2) containing 0.1% (w/v) HP‐β‐CD as a precoating mobile phase for 60 min. It is suggested that HP‐β‐CD is bound with a phenyl group on the surface of the stationary phase to allow a phenyl column to act as a transient chiral column, and injected mandelic acid can form the ternary complex with the adsorbed HP‐β‐CD. The longer retention time of D‐mandelic acid than the L‐isomer for HPLC can be explained from the higher stability of the HP‐β‐CD complex with D‐mandelic acid, which was confirmed by CE experiment with HP‐β‐CD as a selector. The efficiency of a phenyl column compared with other stationary phases was also discussed.

中文翻译:

高效液相色谱法使用在流动相中预涂了少量环糊精添加剂的苯基柱,通过高效液相色谱法直接对映体分离扁桃酸。

高效液相色谱法(HPLC)反相色谱柱和含有少量羟丙基-β-环糊精(HP-β-CD)的流动相直接对映体分离扁桃酸是一种有效的节约方法CD添加剂。因此,有人提出,可以使用由10 mM醋酸铵缓冲液(pH 4.2)和0.02%(w / v)HP-β-CD组成的流动相,用苯基柱分析外消旋扁桃酸。含有0.1%(w / v)HP-β-CD的10 mM醋酸铵缓冲液(pH 4.2)作为预涂层流动相通过60分钟后,在40°C时的流速为1.0 mL / min。建议将HP-β-CD与固定相表面上的苯基键合,以使苯基柱充当瞬时手性柱,注入的扁桃酸可与吸附的HP-β-CD形成三元复合物。D-扁桃酸与HPLC的L-异构体相比保留时间更长,这可以用HP-β-CD与D-扁桃酸的复合物更高的稳定性来解释,这是通过CE-HP-β-CD的CE实验证实的。选择器。还讨论了苯基柱与其他固定相相比的效率。
更新日期:2020-04-28
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