摘要
为了响应合成药物化学领域的研究的突破,基于使用手性固定相(CSP)的对映选择性色谱法被认为是合成化合物对映体纯度的分析测定的选择性选择。与最初的怀疑相反,制备规模应用程序正在越来越多地被认为是生物活性化合物的纯对映异构体的对映选择性合成的有力替代。由于开发了高效的CSP,所以液相色谱方法的成功越来越多,这使得几乎所有化学类别的手性化合物都能进行对映体分析。然而,只有少数CSP真正适合于制备规模应用,因为负载能力是准备大型对等分离的主要关注点。基于纤维素和直链淀粉的CSP具有最高的负载能力和对映体功率,这使得这些CSP成为最通用的并且适用于所有适用的洗脱模式(反相,正相和极 - 有机或非极性)的制备规模应用 极性离子洗脱液)。然而,在这方面也已经成功地使用了其他类型的CSP(刷型相,聚丙烯酰胺和交联的二烯丙基三聚酰胺相以及环糊精和含糖相的相)。 在没有已知的对映体纯度参考标准的情况下,存在用于确定有机化合物的绝对构型的几种工具方法。 最广为人知的是X射线晶体学,其次是光学方法[例如电子和振动圆二色性(分别为ECD和VCD)]和核磁共振(NMR)光谱。 所有这些方面将予以审查对待。
关键词: 实验室规模制备方法,高效液相色谱(HPLC),外消旋法,商业手性固定相,药学上相关的化合物,绝对构型。
图形摘要
Current Medicinal Chemistry
Title:Laboratory-Scale Preparative Enantioseparations of Pharmaceutically Relevant Compounds on Commercially Available Chiral Stationary Phases for HPLC
Volume: 24 Issue: 8
关键词: 实验室规模制备方法,高效液相色谱(HPLC),外消旋法,商业手性固定相,药学上相关的化合物,绝对构型。
摘要: In response to the outburst of research in the field of synthetic medicinal chemistry, enantioselective chromatography methods based on the use of chiral stationary phases (CSPs) found immediate acceptance as the elective choice for the analytical determinations of the enantiomeric purity of synthetic compounds. In contrast to an initial scepticism, also the preparative-scale applications are gaining increasing recognition as a powerful alternative to enantioselective synthesis for the supply of pure enantiomers of bioactive compounds. The increasing success of liquid chromatography methods has been made possible thanks to the development of highly efficient CSPs allowing the enantioresolution of practically all the chemical classes of chiral compounds. However, only few CSPs are really suitable for preparative- scale applications, being the loading capacity is the major concern for preparativescale enantioseparations. The cellulose- and amylose-based CSPs present the highest loading capacity and enantiodiscrimination power, which makes these CSPs the most versatile and applicable for preparative-scale applications in all the applicable elution modes (reversedphase, normal-phase, and with polar-organic or polar-ionic eluents). However, also other types of CSPs have been successfully employed at this regard (brush-type phases, polyacrylamide and cross-linked di-allyltartardiamide phases as well as cyclodextrin, and glycopeptide containing phases).
Several instrumental methods exist for the determination of the absolute configuration of organic compounds in absence of known enantiopure reference standards. The most widely known are X-ray crystallography, followed by chirooptical methods [e.g., electronic and vibrational circular dichroism (ECD and VCD, respectively)] and nuclear magnetic resonance (NMR) spectroscopy. All these aspects will be treated in the review.Export Options
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Cite this article as:
Laboratory-Scale Preparative Enantioseparations of Pharmaceutically Relevant Compounds on Commercially Available Chiral Stationary Phases for HPLC, Current Medicinal Chemistry 2017; 24 (8) . https://dx.doi.org/10.2174/0929867323666160907111107
DOI https://dx.doi.org/10.2174/0929867323666160907111107 |
Print ISSN 0929-8673 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-533X |
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