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Industrial Biotransformations

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Nitrilase / Hydroxylase<br />

Agrobacterium sp.<br />

Fig. 3.5.5.1 / 1.5.1.13 – 1<br />

1) Reaction conditions<br />

[1]: 0.29 M, 30 g · L –1 [105.1 g · mol –1 ]<br />

pH: 6.0–8.0<br />

T: 15 °C – 45 °C<br />

medium: aqueous<br />

reaction type: N-bond hydrolysis (nitrile hydrolysis)<br />

catalyst: suspended, living whole cells<br />

enzyme: E1: nitrilase (nitrile aminohydrolase) and E2: hydroxylase (nicotinate dehydrogenase)<br />

(EC 1.5.1.13)<br />

strain: Agrobacterium sp. DSM 6336 (E1 + E2)<br />

CAS (enzyme): E1: [9024–90–2] / E2: [9059-03–4]<br />

2) Remarks<br />

EC 3.5.5.1 / 1.5.1.13<br />

● In contrast to the biotransformation the chemical synthesis of 5-substituted pyrazine-2-carboxylic<br />

acid leads to a mixture of 5- and 6-substituted pyrazinecarboxylic acids and requires<br />

multiple steps.<br />

● Although the reaction sequence of growth and biotransformation are pretty similar, the cells<br />

grown on 2-cyanopyridine are much more active due to an optimized expression of the hydroxylase.<br />

Additonally, the degradation pathway in case of 2-cyanopyrazine can be stopped.<br />

430

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