2003Journal of Synthetic Organic Chemistry JapanOpen access

Biocatalyst Process: Enzymatic Transformation of Nitrile Compounds and The Application

Koichiro Ryuno, Tetsuji Nakamura

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Abstract

The application of enzymes to an organic synthesis is one of the most useful and practical methods for the production of nitriles, amides and carboxylic acids. There are two different enzymatic pathway for the degradation of nitrile compounds. One is two step degradation involving nitrile hydratase and amidase, via an amide as an intermediate. The other is the direct hydrolysis of nitriles to the corresponding acids and ammonia, catalyzed by nitrilase. Some of the nitrilases are capable of hydrolyzing nitriles stereospecifically. Rhodococcus sp. N-774 was the first strain that was put into commercial use to produce acrylamide from acrylonitrile. Rhodococcus rhodochrous J-1 exhibits a magnitude of order higher productivity than strain N-774. The enzymatic transformation process to produce R-mandelic acid using a R-specific nitrilase has been commercialized by our company. In this article are introduced novel processes for enzymatic production of acrylamide, R-mandelic acid and other compounds.

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The application of enzymes to an organic synthesis is one of the most useful and practical methods for the production of nitriles, amides and carboxylic acids. There are two different enzymatic pathway for the degradation of nitrile compounds. One is two step degradation involving nitrile hydratase and amidase, via an amide as an intermediate. The other is the direct hydrolysis of nitriles to the corresponding acids and ammonia, catalyzed by nitrilase. Some of the nitrilases are capable of hydrolyzing nitriles stereospecifically. Rhodococcus sp. N-774 was the first strain that was put into commercial use to produce acrylamide from acrylonitrile. Rhodococcus rhodochrous J-1 exhibits a magnitude of order higher productivity than strain N-774. The enzymatic transformation process to produce R-mandelic acid using a R-specific nitrilase has been commercialized by our company. In this article are introduced novel processes for enzymatic production of acrylamide, R-mandelic acid and other compounds.

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Available abstract

The application of enzymes to an organic synthesis is one of the most useful and practical methods for the production of nitriles, amides and carboxylic acids. There are two different enzymatic pathway for the degradation of nitrile compounds. One is two step degradation involving nitrile hydratase and amidase, via an amide as an intermediate. The other is the direct hydrolysis of nitriles to the corresponding acids and ammonia, catalyzed by nitrilase. Some of the nitrilases are capable of hydrolyzing nitriles stereospecifically. Rhodococcus sp. N-774 was the first strain that was put into commercial use to produce acrylamide from acrylonitrile. Rhodococcus rhodochrous J-1 exhibits a magnitude of order higher productivity than strain N-774. The enzymatic transformation process to produce R-mandelic acid using a R-specific nitrilase has been commercialized by our company. In this article are introduced novel processes for enzymatic production of acrylamide, R-mandelic acid and other compounds.

Key concepts: Nitrilase, Nitrile hydratase, Amidase, Mandelic acid, Rhodococcus rhodochrous, Chemistry, Nitrile, Acrylonitrile

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