Ilisz István, Berkecz Róbert, Péter Antal
Department of Inorganic and Analytical Chemistry, University of Szeged, Hungary.
J Sep Sci. 2006 Jul;29(10):1305-21. doi: 10.1002/jssc.200600046.
The search for new and effective chiral selectors capable of separating a wide variety of enantiomeric compounds is an ongoing process. In the past decade, macrocyclic antibiotics have proved to be an exceptionally useful class of chiral selectors for the separation of enantiomers of biological and pharmacological importance by means of HPLC, TLC and electrophoresis. More chiral analytes have been resolved through the use of glycopeptides than with all the other macrocyclic antibiotics combined (ansamycins, thiostrepton, aminoglycosides, etc.). The glycopeptides avoparcin, teicoplanin, ristocetin A and vancomycin have been extensively used as chiral selectors in the form of chiral bonded phases in HPLC, and HPLC stationary phases based on these glycopeptides have been commercialized. Teicoplanin, vancomycin, their analogs and ristocetin A seem to be the most useful glycopeptide HPLC bonded phases for the enantioseparation of proteins and unusal native and derivatized amino acids. In fact, the macrocyclic glycopeptides are to some extent complementary to one another: where partial enantioresolution is obtained with one glycopeptide, there is a high probability that baseline or better separation can be obtained with another. This review sets out to characterize the physicochemical properties of these antibiotics and their application in the enantioseparations of amino acids. The mechanism of separation, the sequence of elution of the stereoisomers and the relation to the absolute configuration are also discussed.
寻找能够分离多种对映体化合物的新型有效手性选择剂是一个持续不断的过程。在过去十年中，大环抗生素已被证明是一类非常有用的手性选择剂，可通过高效液相色谱（HPLC）、薄层色谱（TLC）和电泳分离具有生物学和药理学重要性的对映体。与所有其他大环抗生素（安莎霉素、硫链丝菌素、氨基糖苷类等）的总和相比，通过使用糖肽已拆分出更多的手性分析物。阿伏帕星、替考拉宁、瑞斯托菌素A和万古霉素等糖肽已在HPLC中以手性键合相的形式广泛用作手性选择剂，基于这些糖肽的HPLC固定相已实现商业化。替考拉宁、万古霉素、它们的类似物以及瑞斯托菌素A似乎是用于蛋白质以及天然和衍生化的特殊氨基酸对映体拆分的最有用的糖肽HPLC键合相。事实上，大环糖肽在某种程度上是相互补充的：如果用一种糖肽获得了部分对映体拆分，那么用另一种糖肽很有可能实现基线分离或更好的分离。本综述旨在描述这些抗生素的物理化学性质及其在氨基酸对映体拆分中的应用。还讨论了分离机制、立体异构体的洗脱顺序以及与绝对构型的关系。
