Enzyme-catalysed Hydrolysis of Amides

The hydrolysis of amides is not limited to the industrial synthesis of enantio-pure amino acids. Lonza has developed routes towards (S)-pipecolic acid and (R)- and (S)-piperazine-2-carboxylic acid that are based on amidases [93, 94]. 

For the synthesis of the Glaxo anti-HIV drug abacavir (ziagen) a chiral cyclo-pentene derivative was needed. At Glaxo the application of savinase, a cheap en- 

B the Lonza route towards the chiral abacavir building block. 

In general the hydrolysis of amides is performed as a kinetic resolution and not as a dynamic kinetic resolution. It is applied industrially [96] but in most cases the industrial kinetic resolution of amines, as performed for instance by BASF, is an acylation of racemic amines [38], rather than the hydrolysis of racemic amides. For the acylation of amines many different acyl donors [27] and enzymes can be used, including lipases (or a review see [97]). 

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The enzyme-catalysed hydrolysis of amides and lactams is well known. The enzyme lipolase has been used to resolve a series of bicyclic p-lactams (Scheme 4.12) [22]. 

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