Wu Jie, Liu Fei, Wang Shanping, Wang Hongjun, Liu Qing, Song Xinghan, Li Junxiao, Xu Ling, Tan Wen
School of Bioscience and Bioengineering, South China University of Technology; Pre-Incubator for Innovative Drug and Medicine, South China University of Technology; Guangdong Provincial Key Laboratory of Fermentation and Enzyme Engineering, South China University of Technology, Guangzhou, Guangdong, China.
Keypharma Biomedical Inc., Songshan Lake Science & Technology Industry Park, Dongguan, Guangdong, China.
Chirality. 2016 Apr;28(4):306-12. doi: 10.1002/chir.22573. Epub 2016 Jan 25.
In this study an enantioseparation method for rac-bambuterol (5-(2-(tert-butylamino)-1-hydroxyethyl)-1,3-phenylene bis(dimethylcarbamate)) via diastereoisomeric salt formation with o-chloromandelic acid was developed. The enantiomeric excess (ee) values and chemical purities of the desired products were confirmed by high-performance liquid chromatography (HPLC) using chiral stationary phase and reverse-phase HPLC analyses, respectively. The ee values and the chemical purities both exceeded 99%. Animal experiments showed that (R)-bambuterol was a potent inhibitor for histamine-induced asthma reactions. (S)-bambuterol was ineffective in relaxing the airways. Both enantiomers increased heart rates in beagles. Therefore, replacing rac-bambuterol with (R)-bambuterol could be beneficial for asthma patients.
