ASYMMETRIC SULFOXIDATION OF ALBENDAZOLE TO RICOBENDAZOLE BY FUNGI: EFFECT OF pH

Química Nova

Thiago Barth¹  Viviane C. Hilário¹  Bruno A. Rocha¹  Niege A. J. C. Furtado¹  Mônica T. Pupo¹  Anderson R. M. De Oliveira¹ 

关键词: albendazole;    ricobendazole;    enantiomeric excess;    pH;    stereoselective fungal transformation;   

DOI  :  10.5935/0100-4042.20150102

来源: SciELO

【 摘 要 】

Albendazole (ABZ) is an anthelmintic drug used for the treatment of infectious diseases in veterinary and human medicine. This drug is a prochiral drug that after administration, is rapidly oxidized in the pharmacologically active sulfoxide metabolite, which is also known as ricobendazole (ABZSOX). ABZSOX has a stereogenic center and possibly two enantiomers, (+)-ABZSOX and (-)-ABZSOX. In the present work, we investigate the pH effect on the asymmetric stereoselective sulfoxidation of ABZ into ABZSOX by employing the fungi Nigrospora sphaerica, Papulaspora immera Hotson, and Mucor rouxii. The results show a possibility of obtaining the pure enantiomers of the ricobendazole drug using fungi as biocatalytic agents. The three fungi showed a high degree of enantioselectivity expressed by enantiomeric excess. In addition, M. rouxii can be used as an alternative to obtain the (+)-ABZSOX enantiomer (ee 89.8%).

【 授权许可】

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