Substrate evaluation of rhodococcus erythropolis SET1, a nitrile hydrolysing bacterium, demonstrating dual activity strongly dependent on nitrile sub-structure

Coady, T.M. and Coffey, L.V. and O'Reilly, C. and Lennon, C.M. (2015) Substrate evaluation of rhodococcus erythropolis SET1, a nitrile hydrolysing bacterium, demonstrating dual activity strongly dependent on nitrile sub-structure. European Journal of Organic Chemistry, 2015 (5). pp. 1108-1116. ISSN 1434-193X

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Abstract

Assessment of Rhodococcus erythropolis SET1, a novel nitrile hydrolysing bacterial isolate, has been undertaken with 34 nitriles, 33 chiral and 1 prochiral. These substrates consist primarily of β-hydroxy nitriles with varying alkyl and aryl groups at the β position and containing in several compounds different substituents α to the nitrile. In the case of β-hydroxy nitriles without substitution at the α position, acids were the major products obtained, along with recovered nitrile after biotransformation, as a result of suspected nitrilase activity of the isolate. Unexpectedly, amides were found to be the major hydrolysis product when the β-hydroxy nitriles possessed a vinyl group at this position. To probe this behaviour further, additional related substrates were evaluated containing electron-withdrawing groups at the α position, and amide was also observed upon biotransformation in the presence of SET1. Therefore this novel isolate has also demonstrated NHase activity with nitriles that appears to be substrate-dependent.

Item Type:	Article
Additional Information:	Publisher Copyright: © 2015 Wiley-VCH Verlag GmbH & Co. KGaA , Weinheim.
Uncontrolled Keywords:	/dk/atira/pure/subjectarea/asjc/1600/1606
Departments or Groups:
Depositing User:	Admin SSL
Date Deposited:	19 Oct 2022 23:09
Last Modified:	07 Jun 2023 18:45
URI:	http://repository-testing.wit.ie/id/eprint/4357

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