High-performance liquid chromatographic separation of enantiomers and diastereomers of 2-methylcyclohexanone thiosemicarbazone, and determination of absolute configuration and configurational stability

被引：45
作者：
Cirilli, R.
Feffetti, R.
La Torre, F.
Secci, D.
Bolasco, A.
Carradori, S.
Pierini, A.
机构：
[1] Ist Super Sanita, Dipartimento Farmaco, I-00161 Rome, Italy
[2] Univ Roma La Sapienza, Dipartimento Studi Chim & Tecnol Sutanze Biolgica, I-00185 Rome, Italy
来源：
JOURNAL OF CHROMATOGRAPHY A | 2007年 / 1172卷 / 02期
关键词：
E-Z isomerization; enantiomerization; deracemization; chiral synthone; chiral separation; Chiralpak IA; ab initio calculations; absolute configuration;
D O I：
10.1016/j.chroma.2007.10.009
中图分类号：
Q5 [生物化学];
学科分类号：
071010 ; 081704 ;
摘要：
Simultaneous HPLC diastereo- and enantioseparations of 2-methylcyclohexanone thiosemicarbazone (2-MCET) were accomplished on coated-and immobilized type poly saccharide-based chiral stationary phases (CSPs). The identification of all stereoisomeric forms and their stereochemistry were achieved by combining theoretical, HPLC and chiroptical data. The stereochemical stability of the target compound was studied by classical off-column and dynamic HPLC kinetic procedures and the influence of different parameters such solvent, TFA concentration and temperature on stereoisomerization process was evaluated. The findings obtained by chromatographic and kinetic experiments were used to develop a simple method to convert the racemic form of 2-MCET into a single enantiomer. (c) 2007 Elsevier B.V. All rights reserved.
引用
收藏
页码：160 / 169
页数：10
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