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Development of on-site chiral switching micro columns

现场手性开关微柱的开发

基本信息

批准号：
14540562
负责人：
NAKAGAMA Tatsuro
金额：
$ 1.92万
依托单位：
Tokyo Metropolitan University
依托单位国家：
日本
项目类别：
Grant-in-Aid for Scientific Research (C)
财政年份：
2002
资助国家：
日本
起止时间：
2002 至 2003
项目状态：
已结题

来源：
https://kaken.nii.ac.jp/grant/KAKENHI-PROJECT-14540562/
关键词：
micro liquid chromatography enantiomer separation photo-responsive stationary phase azobenzene 光応答

项目摘要

Recently, the racemization of optically-active and bioactive compounds or the role of D-amino acids etc. in vivo have been cleared. Additionally, the importance of chiral separation is increasing because the measurement of optical purity of chiral drug substances becomes important due to the side-effect problem etc., Meanwhile, the downsizing analytical devices are rapidly advanced. Only the separation system in the downsizing device is hardly improved because, in most case, the separation and flow systems are integrated in the same system.In this study, A micro column that is able to change the elution order of enantiomers by photo-irradiation was developed.Two photo-responsive chiral stationary phases (CSP(1) and CSP(2)) with an azobenzene moiety were prepared using D-and L-valine, respectively. Prepared stationary phases were continuously packed into a UV-permeable polymer-coated fused silica capillary tubing (100 mm, i.d.) with 20 cm of length, respectively, and used as a micro column. When 3,5-dinitrobenzoyl-D,L-leucine isopropyl ester and 3,5-dinitrobenzoyl-D,L-alanine methyl ester were used as test samples, the samples were eluted in this order, D-form and L-form, after a UV light was irradiated to only the part of CSP(1) in the column. Continuously, when a UV light was irradiated to the part of CSP(2) after a visible light was done to the CSP(1), the elution order became L-form and D-form. It can be seen that the reversible change in the retention order was caused by the reduction of the enantio-of the enantio-selectivity of the stationary phase by the UV light irradiation.

最近，光学活性和生物活性化合物的外消旋化或D-氨基酸等在体内的作用已被清除。此外，由于手性药物的光学纯度的测量由于副作用问题等而变得重要，因此手性分离的重要性正在增加，与此同时，小型化的分析装置正在迅速发展。本研究开发了一种能够通过光照射改变对映体洗脱顺序的微柱，并分别以D-和L-缬氨酸为原料制备了两种含偶氮苯结构的光响应手性固定相（CSP（1）和CSP（2））。将制备的固定相连续填充到UV可渗透的聚合物涂覆的熔融石英毛细管（100 mm，i.d.）长度分别为20 cm，并用作微柱。当使用3，5-二硝基苯甲酰基-D，L-亮氨酸异丙酯和3，5-二硝基苯甲酰基-D，L-丙氨酸甲酯作为测试样品时，在UV光仅照射到柱中CSP（1）的部分之后，以D-型和L-型的顺序洗脱样品。连续地，当在对CSP（1）进行可见光照射之后对CSP（2）的部分照射UV光时，洗脱顺序变为L-型和D-型。可以看出，保留顺序的可逆变化是由紫外光照射降低固定相的对映选择性引起的。