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使用大环抗生素的手性分离:综述

Chiral separations using the macrocyclic antibiotics: a review.

作者信息

Ward T J, Farris A B

机构信息

Department of Chemistry, Millsaps College, Jackson, MS 39210, USA.

出版信息

J Chromatogr A. 2001 Jan 12;906(1-2):73-89. doi: 10.1016/s0021-9673(00)00941-9.

DOI:10.1016/s0021-9673(00)00941-9
PMID:11215904
Abstract

The macrocyclic antibiotics have recently gained popularity as chiral selectors in CE, HPLC and TLC. The macrocyclic antibiotics used for chiral separations include the ansamycins, the glycopeptides, and the polypeptide antibiotic thiostrepton. Although not strictly considered macrocyclic antibiotics, the aminoglycosides are antibiotics that have been used for chiral separations in CE. More chiral analytes have been resolved using the glycopeptides than with the other macrocyclic antibiotics combined. The glycopeptides vancomycin, ristocetin A and teicoplanin have been used extensively as chiral selectors in CE, with ristocetin A appearing to be the most useful chiral selector followed by vancomycin and teicoplanin, respectively. The macrocyclic antibiotics have also been used as chiral bonded phases in HPLC, and HPLC stationary phases based on vancomycin, ristocetin A and teicoplanin have been commercialized. Ristocetin A seems to be the most useful glycopeptide HPLC bonded phase, but its greater expense can be a drawback. The macrocyclic antibiotics have been used with micelles to improve efficiency, provide unique selectivity, and extend the range of separations to neutral solutes. Changing the macrocyclic antibiotic used in CE or HPLC can significantly alter the enantioselectivity of the separations. In fact, the glycopeptide antibiotics are complementary to one another, where if a partial enantioresolution is obtained with one glycopeptide, there is a high probability that a baseline or better separation can be obtained with another.

摘要

大环抗生素最近在毛细管电泳(CE)、高效液相色谱(HPLC)和薄层色谱(TLC)中作为手性选择剂受到广泛关注。用于手性分离的大环抗生素包括安莎霉素、糖肽类以及多肽抗生素硫链丝菌素。氨基糖苷类虽然严格来说不属于大环抗生素,但已被用于CE中的手性分离。与其他大环抗生素的总和相比,使用糖肽类已拆分出更多的手性分析物。糖肽类万古霉素、瑞斯托菌素A和替考拉宁已在CE中广泛用作手性选择剂,其中瑞斯托菌素A似乎是最有效的手性选择剂,其次分别是万古霉素和替考拉宁。大环抗生素也已用作HPLC中的手性键合相,基于万古霉素、瑞斯托菌素A和替考拉宁的HPLC固定相已实现商业化。瑞斯托菌素A似乎是最有效的糖肽类HPLC键合相,但其成本较高可能是一个缺点。大环抗生素已与胶束一起使用,以提高效率、提供独特的选择性并将分离范围扩展至中性溶质。改变CE或HPLC中使用的大环抗生素可显著改变分离的对映体选择性。事实上,糖肽类抗生素之间具有互补性,即如果使用一种糖肽类仅获得部分对映体拆分,那么使用另一种糖肽类很有可能实现基线分离或更好的分离。

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