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Molecules 2012, 17(3), 3148-3154; doi:10.3390/molecules17033148
Article

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

1, 1,* , 1, 1 and 2
1 Departamento de Sistemas Biológicos, Universidad Autónoma Metropolitana Unidad Xochimilco, Calzada del Hueso No. 1100, Col. Villa Quietud, Delegación Coyoacán, C.P. 04960 México, D.F., Mexico 2 Centro de Investigación en Biotecnología Ambiental, Instituto Politécnico Nacional, Carretera Estatal Santa Inés Tecuexcomac-Tepetitla Km 1.5, C.P. 90700, Tlaxcala, Mexico
* Author to whom correspondence should be addressed.
Received: 31 January 2012 / Revised: 6 March 2012 / Accepted: 7 March 2012 / Published: 12 March 2012
(This article belongs to the Section Organic Synthesis)
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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: Nocardia corallina; deracemisation; ibuprofen; nitrile hydratase; amidase Nocardia corallina; deracemisation; ibuprofen; nitrile hydratase; amidase
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).
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Lievano, R.; Pérez, H.I.; Manjarrez, N.; Solís, A.; Solís-Oba, M. Hydrolysis of Ibuprofen Nitrile and Ibuprofen Amide and Deracemisation of Ibuprofen Using Nocardia corallina B-276. Molecules 2012, 17, 3148-3154.

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