2021
DOI: 10.3390/catal11111287
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Gordonia hydrophobica Nitrile Hydratase for Amide Preparation from Nitriles

Abstract: The active pharmaceutical ingredient levetiracetam has anticonvulsant properties and is used to treat epilepsies. Herein, we describe the enantioselective preparation of the levetiracetam precursor 2-(pyrrolidine-1-yl)butanamide by enzymatic dynamic kinetic resolution with a nitrile hydratase enzyme. A rare representative of the family of iron-dependent nitrile hydratases from Gordonia hydrophobica (GhNHase) was evaluated for its potential to form 2-(pyrrolidine-1-yl)butanamide in enantioenriched form from the… Show more

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Cited by 2 publications
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“…Nitrile hydratase was the first functional enzyme to be studied in B. smithii and can be applied as a biocatalyst for the synthesis of organic substances (amino acids, amides, carboxylic acids, and their derivatives), facilitating the development of biodegradable plastics, pharmaceuticals, and vitamins (Grill et al., 2021; Hourai et al., 2005; Pawar & Yadav, 2014). Takashima published a patent in 1996 for the isolation of a nitrile hydratase–producing strain of B. smithii from hot springs, later named B. smithii SC‐J05‐1 (patent number: JP3763157B2/JPH09248188A), and published the corresponding paper in 1998 (Takashima et al., 1998).…”
Section: Application Status and Concernsmentioning
confidence: 99%
“…Nitrile hydratase was the first functional enzyme to be studied in B. smithii and can be applied as a biocatalyst for the synthesis of organic substances (amino acids, amides, carboxylic acids, and their derivatives), facilitating the development of biodegradable plastics, pharmaceuticals, and vitamins (Grill et al., 2021; Hourai et al., 2005; Pawar & Yadav, 2014). Takashima published a patent in 1996 for the isolation of a nitrile hydratase–producing strain of B. smithii from hot springs, later named B. smithii SC‐J05‐1 (patent number: JP3763157B2/JPH09248188A), and published the corresponding paper in 1998 (Takashima et al., 1998).…”
Section: Application Status and Concernsmentioning
confidence: 99%
“…Nitrile hydratase is a biocatalytic enzyme that is commonly used to synthesize acrylamide from acrylonitrile [26,27]. Grill et al [28] investigated a new nitrile hydratase, Gordonia hydrophobica nitrile hydratase (GhNHase), which was produced in Escherichia coli and applied as a cell-free extract (CFE). An enzymatic dynamic kinetic resolution with GhNHase was employed to prepare the precursor of API levetiracetam, 2-(pyrrolidine-1-yl) butanamide, via enantioselective.…”
mentioning
confidence: 99%