Hydrolysis of ibuprofen nitrile and ibuprofen amide and deracemisation of ibuprofen using Nocardia corallina B-276

Ricardo Lievano; Herminia Inés Pérez; Norberto Manjarrez; Aida Solís; Myrna Solís-Oba

doi:10.3390/molecules17033148

Hydrolysis of ibuprofen nitrile and ibuprofen amide and deracemisation of ibuprofen using Nocardia corallina B-276

Ricardo Lievano, Herminia Inés Pérez, Norberto Manjarrez, Aida Solís, Myrna Solís-Oba

Centro de Investigación en Biotecnología Aplicada (CIBA), Unidad Tlaxcala

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8 Scopus citations

Abstract

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.

Original language	English
Pages (from-to)	3148-3154
Number of pages	7
Journal	Molecules
Volume	17
Issue number	3
DOIs	https://doi.org/10.3390/molecules17033148
State	Published - Mar 2012

Keywords

Amidase
Deracemisation
Ibuprofen
Nitrile hydratase
Nocardia corallina

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10.3390/molecules17033148

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title = "Hydrolysis of ibuprofen nitrile and ibuprofen amide and deracemisation of ibuprofen using Nocardia corallina B-276",

abstract = "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.",

keywords = "Amidase, Deracemisation, Ibuprofen, Nitrile hydratase, Nocardia corallina",

author = "Ricardo Lievano and P{\'e}rez, {Herminia In{\'e}s} and Norberto Manjarrez and Aida Sol{\'i}s and Myrna Sol{\'i}s-Oba",

year = "2012",

month = mar,

doi = "10.3390/molecules17033148",

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T1 - Hydrolysis of ibuprofen nitrile and ibuprofen amide and deracemisation of ibuprofen using Nocardia corallina B-276

AU - Lievano, Ricardo

AU - Pérez, Herminia Inés

AU - Manjarrez, Norberto

AU - Solís, Aida

AU - Solís-Oba, Myrna

PY - 2012/3

Y1 - 2012/3

N2 - 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.

AB - 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.

KW - Amidase

KW - Deracemisation

KW - Ibuprofen

KW - Nitrile hydratase

KW - Nocardia corallina

UR - http://www.scopus.com/inward/record.url?scp=84858982077&partnerID=8YFLogxK

U2 - 10.3390/molecules17033148

DO - 10.3390/molecules17033148

M3 - Artículo

C2 - 22410421

SN - 1420-3049

VL - 17

SP - 3148

EP - 3154

JO - Molecules

JF - Molecules

IS - 3

ER -

Hydrolysis of ibuprofen nitrile and ibuprofen amide and deracemisation of ibuprofen using Nocardia corallina B-276

Abstract

Keywords

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