酒石酸衍生化手性固定相的制备及其色谱应用
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摘要
酒石酸是一种天然手性化合物,具有两个羧酸和两个羟基基团的对称结构。酒石酸及其衍生物作为手性拆分试剂对碱性消旋体的拆分有良好的效果,由于其来源广泛,价格低廉,在制药工业使用非常普遍。根据酒石酸及其衍生物良好的手性拆分效果,如果能把酒石酸衍生物通过某种方法键合到硅胶上制备手性固定相,该类固定相将有很好的应用潜力。最近几年,在固定相制备过程中,新型的有机合成方法“点击化学”由于其高效性和选择专一性,在手性固定相制备过程中引入此方法能很好的实现目标功能分子的键合。
本课题根据酒石酸结构的特点,结合先前酒石酸型手性固定相的制备和色谱性能,对酒石酸进行一系列的衍生化--羟基用不同的芳基酰氯保护起来,在羧酸基团引入炔基基团,利用点击化学与叠氮基反应制得手性固定相。在制备过程中,采用了两种合成策略,一种是液-液条件下采用点击化学方法将γ-叠氮基丙基三乙氧基硅烷与含有炔基的酒石酸衍生物反应制得纯的手性硅烷前驱体,一步法键合到硅胶表面；另一种是首先将γ-叠氮基丙基三乙氧基硅烷键合到硅胶表面制得叠氮化硅胶,然后在固-液条件下与含有炔基的酒石酸衍生物反应。两种方法的优缺点用元素分析和红外光谱加以评价,所制得的几种不同衍生化手性固定相被装填成色谱柱,并在正相和反相条件下评价了其色谱性能。
从结果上来看,采用第一种方法能够得到结构确切的手性硅烷前驱体,一步法键合到硅胶上,可确保较高的键合量和制备方法的稳定可靠性；而另一种经典的固-液条件下的点击化学方法并没有实现硅胶表面叠氮基团的完全转化,其合成条件需要进一步的优化。从色谱评价上来看,所制得的几种酒石酸衍生化手性固定相都表现出一定的手性拆分能力,其中用3,5-二甲基苯甲酰基和3,5-二硝基苯甲酰基衍生化的两类手性固定相效果相对较好,而且两者对相同分析底物的拆分存在较大差异。
Tartaric acid is a natural chiral compound with two carboxylic acid and two hydroxyl groups of the symmetrical structure. Tartaric acid and its derivatives as chiral reagents for the separation of basic enantiomers have a good effect. Because of its wide variety of sources and low price, it has used greatly in the pharmaceutical industry. Based on its great chiral separation ability, if tartaric acid and its derivatives could be bonded to silica gel by some way, those stationary phases will have a good application potential in chiral separation. In recent years, new organic synthetic methods "click chemistry" has been greatly used in the preparation process of chiral stationary phases. Because of its high efficiency and specificity, introducing this method in the preparation of CSP could make the target functional molecules bond to silica easily.
In this thesis, according to the characteristics of tartaric acid, the previous chiral stationary phases and chromatographic properties, a series of derivatives of tartaric acid in which hydroxyl groups was protected by different aryl chloride and alkynyl groups was introduced, hoping to use click chemistry reaction with the azide group successfully prepared stationary phase. In the preparation process, two synthetic strategies were applied, one is use click chemistry to make y-azido-propyl triethoxysilane react with alkynyl-tartaric acid derivatives under the liquid-liquid conditions and pure chiral silica precursor was then got, one-step bonding to the silica surface was utilized during this method; the other is bond y-azido-propyl triethoxypropionic silane onto silica first, and then react with tartaric acid derivatives containing alkynyl group under solid-liquid conditions. By elemental analysis and infrared spectroscopy we can evaluate the advantages and disadvantages of both methods. In this paper, we obtained several different stationary phases and evaluated the chromatographic performance under NP and RP modes.
From the results, the first strategy by getting the exact structure of the chiral silica precursor and one-step method bonded to the silica gel has larger amount of chiral selectors bonded and is a stable and reliable preparation method. However, the classic click chemistry under solid-liquid condition has not achieved completely conversion of azide-group on silica, and its further optimization of reaction conditions should be done. From the point of view of chromatographic evaluation, a system of several tartaric acid derived chiral stationary phases showed a certain degree of chiral recognition ability, two types chiral stationary phases derived with 3,5-dimethyl-benzoyl and 3,5-dinitrobenzoyl have better separation ability, and different resolution results for same analytes between the two CSPs were observed.
本课题根据酒石酸结构的特点,结合先前酒石酸型手性固定相的制备和色谱性能,对酒石酸进行一系列的衍生化--羟基用不同的芳基酰氯保护起来,在羧酸基团引入炔基基团,利用点击化学与叠氮基反应制得手性固定相。在制备过程中,采用了两种合成策略,一种是液-液条件下采用点击化学方法将γ-叠氮基丙基三乙氧基硅烷与含有炔基的酒石酸衍生物反应制得纯的手性硅烷前驱体,一步法键合到硅胶表面；另一种是首先将γ-叠氮基丙基三乙氧基硅烷键合到硅胶表面制得叠氮化硅胶,然后在固-液条件下与含有炔基的酒石酸衍生物反应。两种方法的优缺点用元素分析和红外光谱加以评价,所制得的几种不同衍生化手性固定相被装填成色谱柱,并在正相和反相条件下评价了其色谱性能。
从结果上来看,采用第一种方法能够得到结构确切的手性硅烷前驱体,一步法键合到硅胶上,可确保较高的键合量和制备方法的稳定可靠性；而另一种经典的固-液条件下的点击化学方法并没有实现硅胶表面叠氮基团的完全转化,其合成条件需要进一步的优化。从色谱评价上来看,所制得的几种酒石酸衍生化手性固定相都表现出一定的手性拆分能力,其中用3,5-二甲基苯甲酰基和3,5-二硝基苯甲酰基衍生化的两类手性固定相效果相对较好,而且两者对相同分析底物的拆分存在较大差异。
Tartaric acid is a natural chiral compound with two carboxylic acid and two hydroxyl groups of the symmetrical structure. Tartaric acid and its derivatives as chiral reagents for the separation of basic enantiomers have a good effect. Because of its wide variety of sources and low price, it has used greatly in the pharmaceutical industry. Based on its great chiral separation ability, if tartaric acid and its derivatives could be bonded to silica gel by some way, those stationary phases will have a good application potential in chiral separation. In recent years, new organic synthetic methods "click chemistry" has been greatly used in the preparation process of chiral stationary phases. Because of its high efficiency and specificity, introducing this method in the preparation of CSP could make the target functional molecules bond to silica easily.
In this thesis, according to the characteristics of tartaric acid, the previous chiral stationary phases and chromatographic properties, a series of derivatives of tartaric acid in which hydroxyl groups was protected by different aryl chloride and alkynyl groups was introduced, hoping to use click chemistry reaction with the azide group successfully prepared stationary phase. In the preparation process, two synthetic strategies were applied, one is use click chemistry to make y-azido-propyl triethoxysilane react with alkynyl-tartaric acid derivatives under the liquid-liquid conditions and pure chiral silica precursor was then got, one-step bonding to the silica surface was utilized during this method; the other is bond y-azido-propyl triethoxypropionic silane onto silica first, and then react with tartaric acid derivatives containing alkynyl group under solid-liquid conditions. By elemental analysis and infrared spectroscopy we can evaluate the advantages and disadvantages of both methods. In this paper, we obtained several different stationary phases and evaluated the chromatographic performance under NP and RP modes.
From the results, the first strategy by getting the exact structure of the chiral silica precursor and one-step method bonded to the silica gel has larger amount of chiral selectors bonded and is a stable and reliable preparation method. However, the classic click chemistry under solid-liquid condition has not achieved completely conversion of azide-group on silica, and its further optimization of reaction conditions should be done. From the point of view of chromatographic evaluation, a system of several tartaric acid derived chiral stationary phases showed a certain degree of chiral recognition ability, two types chiral stationary phases derived with 3,5-dimethyl-benzoyl and 3,5-dinitrobenzoyl have better separation ability, and different resolution results for same analytes between the two CSPs were observed.
引文
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