Selective hydrolysis of nitriles under mild conditions by an enzyme.

✍ Scribed by Mark A. Cohen; Janette Sawden; Nicholas J. Turner

• Book ID: 104228578
• Publisher: Elsevier Science
• Year: 1990
• Tongue: French
• Weight: 247 KB
• Volume: 31
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)97285-x

✦ Synopsis

Abetract: A wide range of aromatic/aliphatic nitriles and dinitriles have been selectively hydrolysed using a commercially available enzyme preparation from a Rhodococcus sp.

Nitrile containing compounds are useful intermediates in organic synthesis owing to their ease of preparation uio a number of methods.

These include addition of cyanide ion (or its equivalent) to alkyl halidee,l the reaction of aryl halides and copper cyanide,2 dehydration of amides,3reaction of ketones with tosylmethyl isocyanide,4and the Sandmeyer reaction5 The ability of enzymes to hydrolyse nitriles is well known,6 selective hydrolysis has been demonstrated in some instances7 and the mechanism of some of these enzymes has been extensively studied. 8 Two distinct pathway B have been recognised,6b namely the atepwise conversion of nitriles to amides (r&r a hydratase) followed by hydrolysis of the amide to a carboxylic acid (via an amidase) (Eqn. l), or the direct conversion of nitriles to carboxylic acids (via a nitiilase) (Eqn. 2).

RCN ~RCCNI-Iz LRCCzH nitrile hydratase amidase

Eqn. 1