Nitriles microbial transformations

Nagasawa, T. and Yamada, H. (1989) Microbial transformation of nitriles. TIBTECH, 7, 153-158. 

Winkler, M., Martinkova, L., KnaU, A.C., et al. 2005. Synthesis and microbial transformation of P-amino nitriles. Tetrahedron, 61 4249-60. 

T. Nagasawa and H. Yamada, Microbial transformation of nitriles, Trans. Biotechnd., 7 153 (1989). 

The microbial transformations of nitriles have been extensively studied especially the... 

Synthesis and microbial transformation of p-amino nitriles. Tetrahedron, 61,... 

Enantioselective transformations of several cyclopropane or oxirane-containing nitriles were studied using nitrile-transforming enzymes [78]. Microbial Rhodococcus sp. whole cells containing a nitrile hydratase/amidase system hydrolyzed a number... 

De Raddt A et al. (1992) Microbial reagents in organic synthesis—microbial and enzymatic transformation of nitriles. In Servi S (ed) NATO ASI Series C, vol 381. Kluwer, Dordrecht, pp 209-253... 

Increasing interest has been directed to the microbial synthesis of chiral compounds that would not be readily accessible by chemical synthesis, and a few examples are given to illustrate the diversity of reactions that have been examined the stereoselective hydrolysis of nitriles to carboxylic acids has already been noted. Both by microbiological reactions and by combinations of microbiological transformation of aromatic compounds followed by designed chemical transformation (see Chapter 4, Section 4.2.3) have been used. Illustrations of both will be given. 

In addition to hydrolysis, nerve agents may be transformed in soil by microbial degradation via 0-dealkylation and C-dealkylation with resulting toxic products (Morrill et al. 1985). GA can also be biodegraded via nitrile hydrolysis, resulting in a nontoxic compound N-dealkylation results in a compound that is... 

The microbial hydrolysis of nitriles to amides or carboxylic acids often does not proceed with high enantioselectivity, but it offers a valuable and mild alternative method to the harsh reaction conditions usually required for this conversion using traditional methodology. As a consequence, it has proven to be a very useful and competitive method in the chemoselective transformation of nitriles on an industrial scale. 

The synthesis of AAm by enzymatic transformation is attracting increasing attention. Microbial nitrile hydratase converts nitriles into AAm. This method has been applied to the industrial kiloton-scale production of AAms [378]. 

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