Hydrolysis of Ibuprofen Nitrile and Ibuprofen Amide and Deracemisation of Ibuprofen Using Nocardia corallina B-276

A novel application of whole cells of Nocardia corallina B-276 for the deracemisation of ibuprofen is reported. This microorganism successfully hydrolysed ibuprofen nitrile to ibuprofen amide, and ibuprofen amide to ibuprofen, using a suspension of cells in a potassium phosphate buffer solution (0.1...

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Autores principales: Lievano, Ricardo, Pérez, Herminia Inés, Manjarrez, Norberto, Solís, Aida, Solís-Oba, Myrna
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2012
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6268212/
https://www.ncbi.nlm.nih.gov/pubmed/22410421
http://dx.doi.org/10.3390/molecules17033148
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author Lievano, Ricardo
Pérez, Herminia Inés
Manjarrez, Norberto
Solís, Aida
Solís-Oba, Myrna
author_facet Lievano, Ricardo
Pérez, Herminia Inés
Manjarrez, Norberto
Solís, Aida
Solís-Oba, Myrna
author_sort Lievano, Ricardo
collection PubMed
description A novel application of whole cells of Nocardia corallina B-276 for the deracemisation of ibuprofen is reported. This microorganism successfully hydrolysed ibuprofen nitrile to ibuprofen amide, and ibuprofen amide to ibuprofen, using a suspension of cells in a potassium phosphate buffer solution (0.1 M, pH = 7.0). These results can be explained by the presence of NHase and amidase enzymes, but the reactions are not enantioselective and low ee values were obtained. However, (R)-ibuprofen was isolated with >99% ee by a deracemisation process catalysed by N.corallina B-276. This is the first report of this kind of catalysis with this microorganism.
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spelling pubmed-62682122018-12-20 Hydrolysis of Ibuprofen Nitrile and Ibuprofen Amide and Deracemisation of Ibuprofen Using Nocardia corallina B-276 Lievano, Ricardo Pérez, Herminia Inés Manjarrez, Norberto Solís, Aida Solís-Oba, Myrna Molecules Article A novel application of whole cells of Nocardia corallina B-276 for the deracemisation of ibuprofen is reported. This microorganism successfully hydrolysed ibuprofen nitrile to ibuprofen amide, and ibuprofen amide to ibuprofen, using a suspension of cells in a potassium phosphate buffer solution (0.1 M, pH = 7.0). These results can be explained by the presence of NHase and amidase enzymes, but the reactions are not enantioselective and low ee values were obtained. However, (R)-ibuprofen was isolated with >99% ee by a deracemisation process catalysed by N.corallina B-276. This is the first report of this kind of catalysis with this microorganism. MDPI 2012-03-12 /pmc/articles/PMC6268212/ /pubmed/22410421 http://dx.doi.org/10.3390/molecules17033148 Text en © 2012 by the authors; licensee MDPI, Basel, Switzerland. http://creativecommons.org/licenses/by/3.0/ This article is an open-access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/).
spellingShingle Article
Lievano, Ricardo
Pérez, Herminia Inés
Manjarrez, Norberto
Solís, Aida
Solís-Oba, Myrna
Hydrolysis of Ibuprofen Nitrile and Ibuprofen Amide and Deracemisation of Ibuprofen Using Nocardia corallina B-276
title Hydrolysis of Ibuprofen Nitrile and Ibuprofen Amide and Deracemisation of Ibuprofen Using Nocardia corallina B-276
title_full Hydrolysis of Ibuprofen Nitrile and Ibuprofen Amide and Deracemisation of Ibuprofen Using Nocardia corallina B-276
title_fullStr Hydrolysis of Ibuprofen Nitrile and Ibuprofen Amide and Deracemisation of Ibuprofen Using Nocardia corallina B-276
title_full_unstemmed Hydrolysis of Ibuprofen Nitrile and Ibuprofen Amide and Deracemisation of Ibuprofen Using Nocardia corallina B-276
title_short Hydrolysis of Ibuprofen Nitrile and Ibuprofen Amide and Deracemisation of Ibuprofen Using Nocardia corallina B-276
title_sort hydrolysis of ibuprofen nitrile and ibuprofen amide and deracemisation of ibuprofen using nocardia corallina b-276
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6268212/
https://www.ncbi.nlm.nih.gov/pubmed/22410421
http://dx.doi.org/10.3390/molecules17033148
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