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Industrial Biotransformations

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78<br />

3 Retrosynthetic Biocatalysis<br />

When cyanohydrins are used, dynamic resolution can be achieved due to the intrinsic<br />

instability of the substrate itself [45].<br />

OH<br />

R CN<br />

R = alkyl, aryl<br />

nitrilase A<br />

nitrilase B<br />

OH<br />

R COOH<br />

OH<br />

R COOH<br />

+<br />

+<br />

OH<br />

R CN<br />

OH<br />

R CN<br />

Polyfunctionalized a-hydroxy acids such as those listed in the scheme can be prepared<br />

by enzymatic Michael type additions to electron deficient alkenes. Both processes have<br />

been commercialized [46].<br />

HO 2C<br />

X<br />

HO2C<br />

X<br />

OH<br />

CO 2H<br />

NH2<br />

CO2H<br />

X = H, Cl, alkyl<br />

fumarase<br />

aspartase<br />

HO 2C<br />

X<br />

HO2C<br />

X<br />

CO2H<br />

CO2H

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