Substrate Evaluation of Rhodococcus erythropolis SET1, a Nitrile Hydrolysing Bacterium, Demonstrating Dual Activity Strongly Dependent on Nitrile Sub-Structure

作者：Coady Tracey M; Coffey Lee V; O'Reilly Catherine; Lennon Claire M^*

来源：European Journal of Organic Chemistry, 2015, 2015(5): 1108-1116.

DOI：10.1002/ejoc.201403201

• Biotransformations
• Enzyme catalysis
• Reaction mechanisms
• Nitriles

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 beta-hydroxy nitriles with varying alkyl and aryl groups at the beta position and containing in several compounds different substituents alpha to the nitrile. In the case of beta-hydroxy nitriles without substitution at the alpha 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 beta-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 alpha 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.

• 出版日期2015-2