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• 54529-88-3 3-acetoxy-butyronitrile 

Relevant academic research and scientific papers

Crown ethers as regulators of enzymatic reactions: Enhanced reaction rate and enantioselectivity in lipase-catalyzed hydrolysis of 2-cyano-1-methylethyl acetate

Both reaction rate and enantioselectivity in lipase-catalyzed hydrolysis of 2-cyano-1-methylethyl acetate were significantly changed by addition of some crown ethers. Although various crown ethers accelerated the reaction rate, the enantioselectivity greatly depended on the nature of each one. Among 27 crown ethers and 5 polyethers tested, benzo-crown, armed azacrown, and thiacrown ethers offered high enantioselectivity of the lipase-catalyzed hydrolysis. Hydrophobicity and chirality of the crown ether did not affect the hydrolysis behavior, but its concentration greatly influenced enantioselectivity. Two hundred fifty or more times the crown ether, molarity based on the enzyme, was required to attain satisfactorily high reaction rate and enantioselectivity.

Thiacrown Ether Technology in Lipase-Catalyzed Reaction: Scope and Limitation for Preparing Optically Active 3-Hydroxyalkanenitriles and Application to Insect Pheromone Synthesis

Both reaction rate and enantioselectivity in Pseudomonas cepacia lipase (PCL)-catalyzed hydrolysis of 3-hydroxyalkanenitrile acetates were significantly changed by the addition of catalytic amounts of thiacrown ether (1,4,8,11-tetrathiacyclotetradecane). Although the reaction rate of various nitriles was accelerated, the enantioselectivity greatly depended on the nature of the substrate. Among 10 substrates tested, thiacrown ether offered highest enantioselectivity in PCL-catalyzed hydrolysis of 1-(cyanomehtyl)propyl acetate. Forty or more times this crown ether, molarity based on the enzyme, was required to attain an acceptably high reaction rate and enantioselectivity. Applying this technology, we succeeded in synthesizing the optically pure attractant pheromone of ant Myrmica scabrinodis (A), (R)-3-octanol and its antipode of (S)-isomer in good overall yields.

Enhanced reaction rate and enantioselectivity in lipase-catalyzed hydrolysis by addition of a crown ether

Both reaction rate and enantioselectivity in a lipase-catalyzed hydrolysis of β-acetoxybutyronitrile were significantly enhanced by addition of hydroxymethyl-12-crown-4.

Enhanced Enantioselectivity of the Lipase-catalyzed Hydrolysis by the Addition of a Catalytic Amount of an Amino Alcohol

L-Methioninol (L-MetOH) was discovered to be an effective additive for improving the enantioselectivity of lipase-catalyzed hydrolysis.It was found that L-MetOH accelerated the enzyme-catalyzed hydrolysis of (R)-3-acetoxybutyronitrile (1) and inhibited that of (S)-1.