Direct high-performance liquid chromatographic enantioseparation of beta-lactam stereoisomers.
Direct high-performance liquid chromatographic enantioseparation of beta-lactam stereoisomers.
复制标题
β-内酰胺立体异构体的直接高效液相色谱对映体分离。
DOI：
10.1002/chir.20149
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发表时间：
2005
期刊：
影响因子：
--
通讯作者：
Armstrong,DanielW
中科院分区：
文献类型：
--
作者：
Peter,Antal;Arki,Anita;Forro,Eniko;Fulop,Ferenc;Armstrong,DanielW
High‐performance liquid chromatographic methods were developed for the separation of the enantiomers of 12 β‐lactams. Direct separations were performed on chiral stationary phases (CSPs) containing cellulose‐tris‐3,5‐dimethylphenyl carbamate (Chiralcel OD‐RH and OD‐H columns), the macrocyclic glycopeptide antibiotic teicoplanin (Chirobiotic T column), or teicoplanin aglycone (Chirobiotic TAG column) as the chiral selector. It was clearly established that, with teicoplanin‐based columns, the teicoplanin aglycone was most often responsible for the enantioseparation of the β‐lactams. The difference in enantioselective free energy between the aglycone CSP and the teicoplanin CSP was in the range between 0.02 and 0.97 kJ mol−1for these β‐lactam stereoisomer separations. The separations were carried out with high selectivity and resolution, and the method was therefore suitable for monitoring of the enantiomeric excess after chiral synthesis. The Chirobiotic and Chiralcel columns appear to be highly complementary to one another. The best separation of this class of β‐lactam compound could be obtained using the Chirobiotic TAG in the polar‐organic mode plus the Chiralcel OD‐H in the normal‐phase mode. The elution sequence was also determined.Chirality 17:193–200, 2005.© 2005 Wiley‐Liss, Inc.
