Probing the enantioselectivity of a diverse group of purified cobalt-centred nitrile hydratases

van Pelt, Sander, Zhang, Meng, Otten, Linda, Holt, J., Sorokin, Dimitry, van Rantwijk, Fred, Black, Gary, Perry, Justin and Sheldon, Roger (2011) Probing the enantioselectivity of a diverse group of purified cobalt-centred nitrile hydratases. Organic and Biomolecular Chemistry, 9 (8). pp. 3011-3019. ISSN 1477-0520

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Official URL: http://dx.doi.org/10.1039/C0OB01067G

Abstract

In this study a diverse range of purified cobalt containing nitrile hydratases (NHases, EC 4.2.1.84) from Rhodopseudomonas palustris HaA2 (HaA2), Rhodopseudomonas palustris CGA009 (009), Sinorhizobium meliloti 1021 (1021), and Nitriliruptor alkaliphilus (iso2), were screened for the first time for their enantioselectivity towards a broad range of chiral nitriles. Enantiomeric ratios of >100 were found for the NHases from HaA2 and CGA009 on 2-phenylpropionitrile. In contrast, the Fe-containing NHase from the well-characterized Rhodococcus erythropolis AJ270 (AJ270) was practically aselective with a range of different α-phenylacetonitriles. In general, at least one bulky group in close proximity to the α-position of the chiral nitriles seemed to be necessary for enantioselectivity with all NHases tested. Nitrile groups attached to a quaternary carbon atom were only reluctantly accepted and showed no selectivity. Enantiomeric ratios of 80 and >100 for AJ270 and iso2, respectively, were found for the pharmaceutical intermediate naproxennitrile, and 3-(1-cyanoethyl)benzoic acid was hydrated to the corresponding amide by iso2 with an enantiomeric ratio of >100.

Item Type: Article
Subjects: C700 Molecular Biology, Biophysics and Biochemistry
F100 Chemistry
Department: Faculties > Health and Life Sciences > School of Life Sciences > Applied Sciences
Depositing User: Ay Okpokam
Date Deposited: 16 Dec 2011 09:25
Last Modified: 10 Aug 2015 11:40
URI: http://nrl.northumbria.ac.uk/id/eprint/4204

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