CHIRAL SEPARATIONS USING CARBOHYDRATE BONDED PHASES

使用碳水化合物键合相进行手性分离

• 批准号: 3468933
• 负责人: Apryll M Stalcup
• 金额: $ 7.94万
• 依托单位: UNIVERSITY OF HAWAII AT MANOA
• 依托单位国家: 美国
• 财政年份: 1992
• 资助国家: 美国
• 起止时间: 1992-08-05 至 1997-07-31
• 项目状态: 已结题
• 来源: https://reporter.nih.gov/project-details/3468933
• 关键词: chemical binding; ligands; liquid chromatography; method development; oligosaccharides; physical separation; stereoisomer

In many cases, optical isomers, including many compounds of pharmaceutical interest, are known to exhibit very different bioactivities as well as biotoxicities. Traditionally, the separation of optical isomers has been considered among the most difficult of all separations. Indeed, many optical isomers remain unresolvable using currently available techniques. Carbohydrate-based phases, including derivatized and underivatized cyclodextrins, cellulosic and amylosic phases have been shown to be effective for the liquid chromatographic resolution of some optical isomers. The enantioselectivity of chiral stationary phases based on small carbohydrate bonded ligands will be studied. Derivatized carbohydrate- based bonded phases will be prepared which incorporate various types of functionalities known to be important in chiral recognition processes. The resultant sorbents will be evaluated as chromatographic chiral stationary phases. Retention as well as chiral recognition mechanisms will be explored by judicious choice of analyte and derivative structural features. Results will be compared to results obtained on the various phases synthesized as part of this project as well as with results obtained on other carbohydrate-derived chirally selective stationary phases. The proposed work will provide important information regarding the chiral recognition mechanism(s) of these new bonded phases. In addition, it is anticipated that these new phases may also provide some insight into the chiral recognition mechanisms of other carbohydrate-based phases such as the cellulosic and amylosic phases. Understanding the mechanisms responsible for chiral recognition is fundamental to the intelligent design and application of new methodologies for the separation of optical isomers.

在许多情况下，光学异构体，包括药物组合物的许多化合物， 感兴趣，已知表现出非常不同的生物活性， 生物毒性 传统上，光学异构体的分离已经被 被认为是所有分离中最困难的。 事实上许多 旋光异构体仍然不能使用目前可用的技术来解析。 碳水化合物基相，包括衍生化和未衍生化相 环糊精、纤维素和直链淀粉相已被证明是 有效的液相色谱分离的一些光学 异构体 小分子手性固定相的对映选择性 将研究碳水化合物键合的配体。 衍生碳水化合物- 基粘结相将被制备， 已知在手性识别过程中重要的官能团。 的 所得吸附剂将作为色谱手性固定相进行评价 阶段。 保留以及手性识别机制将是 通过分析物和衍生物结构特征的明智选择来探索。 结果将与各个阶段的结果进行比较 作为该项目的一部分，以及 其它碳水化合物衍生的手性选择性固定相。 拟议的工作将提供有关手性的重要信息 这些新键合相的识别机制。 此外还 预计这些新的阶段也可能提供一些见解， 其他碳水化合物基相的手性识别机制， 纤维素和淀粉相。 了解机制 负责手性识别是智能设计的基础 以及光学异构体分离新方法的应用。