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

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.

Synthesis, lipase catalyzed kinetic resolution, and determination of the absolute configuration of enantiomers of the Morita-Baylis-Hillman adduct 3-hydroxy-2-methylenebutanenitrile

“…Adduct 1(RS) was also used to study nitrile hydrolase activity of Rhodococcus erythropolis SET1. 26 The yield of recovered nitrile and reaction time were satisfactory (42% and 48 h respectively); ee was moderate (76.5%). The configuration of the stereogenic secondary carbinol center was assigned only tentatively (R), and the specific rotatory power also was not determined.…”

The Application of Biocatalysis in the Preparation and Resolution of Morita‐Baylis‐Hillman Adducts and Their Derivatives

“…More recently Lennon and co‐workers [93] evaluated the nitrile‐hydrolysing potential of Rhodococcus erythropolis SET1, a novel nitrile hydrolysing bacterial isolate. A total of 34 β‐hydroxynitriles were tested as substrates, 14 of which were MBH adducts ( 30 , Figure 4).…”

Asymmetric Hydrogenation of β-Aryloxy/Alkoxy Cinnamic Nitriles and Esters

“…Because of their significance in chemical synthesis, great efforts have been devoted to the development of efficient approaches to chiral β-oxy-functionalized nitriles . To the best of our knowledge, however, as one of the most atom-economic, environmentally friendly, and efficient methods for the synthesis of chiral β-oxy-functionalized nitriles, asymmetric hydrogenation of β-aryloxy or alkoxy cinnamic nitriles has not been explored so far despite the fact that some exciting results of asymmetric hydrogenation of vinyl ethers, unsaturated nitriles, and α- or β-aryloxy/alkoxy acrylic acids including their corresponding esters have been successfully reported .…”