USE OF A MACROCYCLIC ANTIBIOTIC, RIFAMYCIN-B, AND INDIRECT DETECTION FOR THE RESOLUTION OF RACEMIC AMINO-ALCOHOLS BY CE
USE OF A MACROCYCLIC ANTIBIOTIC, RIFAMYCIN-B, AND INDIRECT DETECTION FOR THE RESOLUTION OF RACEMIC AMINO-ALCOHOLS BY CE
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DOI：
10.1021/ac00082a015
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发表时间：
1994-05-15
影响因子：
7.4
通讯作者：
REID, GL
中科院分区：
文献类型：
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作者：
ARMSTRONG, DW;RUNDLETT, K;REID, GL
安莎霉素是一类非常特殊的大环抗生素，其中利福霉素是较知名的成员之一。利福霉素结合并抑制DNA聚合酶。利福霉素B（最容易获得的安莎霉素）带负电荷，并显示与几种手性氨基醇缔合并对映选择性拆分，包括特布他林、异丙肾上腺素、巴美生、间丙肾上腺素、辛尼替林、间苯二胺、沙丁胺醇、肾上腺素、去甲苯二胺、麻黄碱、伪麻黄碱、章鱼胺、去甲肾上腺素、去甲间苯二胺、美托洛尔、阿普洛尔、阿替洛尔和氧烯洛尔。给出了一般利福霉素和特别是利福霉素B的结构和性质的描述。利福霉素B对上述外消旋化合物的络合和手性识别是通过多种相互作用来实现的，其中电荷-电荷、氢键和疏水包合相互作用最可能在含水有机溶剂中占主导地位。在优化毛细管电泳分离条件的基础上，讨论了各种实验因素对手性拆分的影响。由于大多数手性抗生素大环是可电离的，有些柔性，并含有疏水和亲水部分，它们往往会受到溶液环境变化的显著影响。
Ansamycins are a very specific class of macrocyclic antibiotics of which the rifamycins are among the better known members. Rifamycins bind to and inhibit DNA polymerase. Rifamycin B (the most easily obtained ansamycin) is negatively charged and is shown to associate with and enantioselectively resolve several chiral amino alcohols including terbutaline, isoproterenol, bamethan, metaproterenol, synephrine, metanephrine, salbutamol, epinephrine, norphenylephrine, ephedrine, psi-ephedrine, octopamine, norepinephrine, normetanephrine, meteprolol, alprenolol, atenolol, and oxprenolol. A description of the structure and properties of rifamycins, in general, and rifamycin B, in particular, is given. The complexation and chiral recognition of the aforementioned racemic compounds by rifamycin B is afforded by multiple interactions of which charge-charge, hydrogen-bonding, and hydrophobic inclusion interactions most likely dominate in hydroorganic solvents. The effect of various experimental factors on enantiomeric resolution is discussed in terms of optimizing the CE separations. Since most chiral antibiotic macrocycles are ionizable, somewhat flexible, and contain hydrophobic and hydrophilic moieties, they tend to be significantly affected by variations in the solution environment.