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

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

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
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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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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MDPI and ACS Style

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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