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...

Full description

Bibliographic Details
Main Authors: Myrna Solís-Oba, Norberto Manjarrez, Aida Solís, Ricardo Lievano, Herminia Inés Pérez
Format: Article
Language:English
Published: MDPI AG 2012-03-01
Series:Molecules
Subjects:
Online Access:http://www.mdpi.com/1420-3049/17/3/3148/
_version_ 1818307331449946112
author Myrna Solís-Oba
Norberto Manjarrez
Aida Solís
Ricardo Lievano
Herminia Inés Pérez
author_facet Myrna Solís-Oba
Norberto Manjarrez
Aida Solís
Ricardo Lievano
Herminia Inés Pérez
author_sort Myrna Solís-Oba
collection DOAJ
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.
first_indexed 2024-12-13T06:56:41Z
format Article
id doaj.art-bbe14da6513543aaa07cb015d061f78b
institution Directory Open Access Journal
issn 1420-3049
language English
last_indexed 2024-12-13T06:56:41Z
publishDate 2012-03-01
publisher MDPI AG
record_format Article
series Molecules
spelling doaj.art-bbe14da6513543aaa07cb015d061f78b2022-12-21T23:56:01ZengMDPI AGMolecules1420-30492012-03-011733148315410.3390/molecules17033148Hydrolysis of Ibuprofen Nitrile and Ibuprofen Amide and Deracemisation of Ibuprofen Using Nocardia corallina B-276Myrna Solís-ObaNorberto ManjarrezAida SolísRicardo LievanoHerminia Inés PérezA 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.http://www.mdpi.com/1420-3049/17/3/3148/Nocardia corallinaderacemisationibuprofennitrile hydrataseamidase
spellingShingle Myrna Solís-Oba
Norberto Manjarrez
Aida Solís
Ricardo Lievano
Herminia Inés Pérez
Hydrolysis of Ibuprofen Nitrile and Ibuprofen Amide and Deracemisation of Ibuprofen Using Nocardia corallina B-276
Molecules
Nocardia corallina
deracemisation
ibuprofen
nitrile hydratase
amidase
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 Nocardia corallina
deracemisation
ibuprofen
nitrile hydratase
amidase
url http://www.mdpi.com/1420-3049/17/3/3148/
work_keys_str_mv AT myrnasolisoba hydrolysisofibuprofennitrileandibuprofenamideandderacemisationofibuprofenusingnocardiacorallinab276
AT norbertomanjarrez hydrolysisofibuprofennitrileandibuprofenamideandderacemisationofibuprofenusingnocardiacorallinab276
AT aidasolis hydrolysisofibuprofennitrileandibuprofenamideandderacemisationofibuprofenusingnocardiacorallinab276
AT ricardolievano hydrolysisofibuprofennitrileandibuprofenamideandderacemisationofibuprofenusingnocardiacorallinab276
AT herminiainesperez hydrolysisofibuprofennitrileandibuprofenamideandderacemisationofibuprofenusingnocardiacorallinab276