Nitrilase-Catalyzed Selective Hydrolysis of Dinitriles and Green Access to the Cyanocarboxylic Acids of Pharmaceutical Importance

• Published in: Advanced synthesis & catalysis Vol. 349; no. 10; pp. 1667 - 1670
• Main Authors: Zhu, Dunming, Mukherjee, Chandrani, Biehl, Edward R., Hua, Ling
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 02-07-2007; WILEY‐VCH Verlag
• Subjects: cyanocarboxylic acids; dinitriles; enzyme catalysis; hydrolysis; nitrilase
• ISSN: 1615-4150; 1615-4169
• DOI: 10.1002/adsc.200700067

To further explore its synthetic applications, the nitrilase bll6402 from Bradyrhizobium japonicum strain USDA110 has been examined toward the hydrolysis of various dinitriles. It has been found that nitrilase bll6402 effectively hydrolyzed α,ω‐dinitriles to ω‐cyanocarboxylic acids, and the selectivity was independent of the substrate chain length. This feature is distinct from all the known nitrilases of various sources. Nitrilase bll6402 was thus applied to the synthesis of 1‐cyanocycloalkaneacetic acids, the useful precursors for the synthesis of gabapentin and its analogues.