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Nitrilase‐Catalyzed Selective Hydrolysis of Dinitriles and Green Access to the Cyanocarboxylic Acids of Pharmaceutical Importance
Author(s) -
Zhu Dunming,
Mukherjee Chandrani,
Biehl Edward R.,
Hua Ling
Publication year - 2007
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200700067
Subject(s) - nitrilase , chemistry , hydrolysis , selectivity , catalysis , substrate (aquarium) , organic chemistry , combinatorial chemistry , oceanography , geology
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.