Nitrile Hydratase Activity of Nitrilases

The formation of amides during nitrilase reactions was observed as early as 1964 

2 Davies, S.G., Ichihara, O., Lenoir, I. and Walters, I.A.S. (1994) Journal of the Chemical Society-Perlan Transactions, 1, 1411-1415. 

4 Juaristi, E. (ed.) (1997) Enantiosdective Synthesis cf -Amino Acids, Wiley-VCH Verlag GmbH, Weinheim. 

15 Nazabadioko, S., Perez, R.J., Brieva, R. and Gotor, V. (1998) Tetrahedron Asymmetry, 9,1597 1604 and references therein. 

16 Eichhom, E., Roduit, J.-P., Shaw, N., Heinzmann, K. and Kiener, A. (1997) Tetrahedron Asymmetry, 8, 2533-2536 and references therein. 

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Not surprisingly, some nitrilase reactions were accompanied by the formation of the corresponding amides, such as pipecolic amide 12b (up to 10%) and pyrrolidine-3-carbo3amide 10b (for a discussion of nitrile hydratase activity of nitrilases see Section 15.3.3). 

However, the rise of more sophisticated analytical techniques has triggered communications on this subject substantially in recent times. This nitrile hydratase activity of nitrilases was frequently observed when substrates activated in the a-position to the nitrile group were used [45, 46]. Most recently, a study appeared on this subject suggesting a mechanistic rationale of amide formation [47]. 

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