ASYMMETRIC SULFOXIDATION OF ALBENDAZOLE TO RICOBENDAZOLE BY FUNGI: EFFECT OF pH
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%).
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Sociedade Brasileira de Química
2015
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oai:scielo:S0100-404220150007009442015-09-21ASYMMETRIC SULFOXIDATION OF ALBENDAZOLE TO RICOBENDAZOLE BY FUNGI: EFFECT OF pHBarth,ThiagoHilário,Viviane C.Rocha,Bruno A.Furtado,Niege A. J. C.Pupo,Mônica T.Oliveira,Anderson R. M. de albendazole ricobendazole enantiomeric excess pH stereoselective fungal transformation 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%).info:eu-repo/semantics/openAccessSociedade Brasileira de QuímicaQuímica Nova v.38 n.7 20152015-08-01info:eu-repo/semantics/articletext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0100-40422015000700944en10.5935/0100-4042.20150102 |
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Barth,Thiago Hilário,Viviane C. Rocha,Bruno A. Furtado,Niege A. J. C. Pupo,Mônica T. Oliveira,Anderson R. M. de |
spellingShingle |
Barth,Thiago Hilário,Viviane C. Rocha,Bruno A. Furtado,Niege A. J. C. Pupo,Mônica T. Oliveira,Anderson R. M. de ASYMMETRIC SULFOXIDATION OF ALBENDAZOLE TO RICOBENDAZOLE BY FUNGI: EFFECT OF pH |
author_facet |
Barth,Thiago Hilário,Viviane C. Rocha,Bruno A. Furtado,Niege A. J. C. Pupo,Mônica T. Oliveira,Anderson R. M. de |
author_sort |
Barth,Thiago |
title |
ASYMMETRIC SULFOXIDATION OF ALBENDAZOLE TO RICOBENDAZOLE BY FUNGI: EFFECT OF pH |
title_short |
ASYMMETRIC SULFOXIDATION OF ALBENDAZOLE TO RICOBENDAZOLE BY FUNGI: EFFECT OF pH |
title_full |
ASYMMETRIC SULFOXIDATION OF ALBENDAZOLE TO RICOBENDAZOLE BY FUNGI: EFFECT OF pH |
title_fullStr |
ASYMMETRIC SULFOXIDATION OF ALBENDAZOLE TO RICOBENDAZOLE BY FUNGI: EFFECT OF pH |
title_full_unstemmed |
ASYMMETRIC SULFOXIDATION OF ALBENDAZOLE TO RICOBENDAZOLE BY FUNGI: EFFECT OF pH |
title_sort |
asymmetric sulfoxidation of albendazole to ricobendazole by fungi: effect of ph |
description |
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%). |
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Sociedade Brasileira de Química |
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2015 |
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http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0100-40422015000700944 |
work_keys_str_mv |
AT barththiago asymmetricsulfoxidationofalbendazoletoricobendazolebyfungieffectofph AT hilariovivianec asymmetricsulfoxidationofalbendazoletoricobendazolebyfungieffectofph AT rochabrunoa asymmetricsulfoxidationofalbendazoletoricobendazolebyfungieffectofph AT furtadoniegeajc asymmetricsulfoxidationofalbendazoletoricobendazolebyfungieffectofph AT pupomonicat asymmetricsulfoxidationofalbendazoletoricobendazolebyfungieffectofph AT oliveiraandersonrmde asymmetricsulfoxidationofalbendazoletoricobendazolebyfungieffectofph |
_version_ |
1756387605025390592 |