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.
Highlights
Ibuprofen, (±)-2-(4-isobutylphenyl)propanoic acid, is one of the most well-known non-steroidal anti-inflammatory agents
We were interested in evaluating the use of N. corallina to biocatalyse the enantioselective hydrolysis of racemic ibuprofen nitrile [2-(4-isobutylphenyl)propanenitrile, 1], to optically active ibuprofen amide [2-(4-isobutylphenyl)propanamide, 2] a prodrug [7,8], and to investigate whether this microorganism has the ability to hydrolyse amide 2 to optically active ibuprofen (3) (Scheme 1)
N. corallina B-276 (Scheme 1): Method A, with the cells suspended in the culture media, in a 3-L
Summary
Ibuprofen, (±)-2-(4-isobutylphenyl)propanoic acid, is one of the most well-known non-steroidal anti-inflammatory agents. It is noteworthy that the laboratory of Ohta, in 1991, was the first group to report the enzymatic hydrolysis of 2-substituted nitriles to give optically active 2-arylalkanoic acids [6]. Based on these reports, we were interested in evaluating the use of N. corallina to biocatalyse the enantioselective hydrolysis of racemic ibuprofen nitrile [2-(4-isobutylphenyl)propanenitrile, 1], to optically active ibuprofen amide [2-(4-isobutylphenyl)propanamide, 2] a prodrug [7,8], and to investigate whether this microorganism has the ability to hydrolyse amide 2 to optically active ibuprofen (3) (Scheme 1). Biotransformation of ibuprofen nitrile 1 to ibuprofen amide 2 and ibuprofen 3 using Nocardia corallina B-276
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