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Faber, K. et al.: 2015 Science of Synthesis, 1: Biocatalysis in Organic Synthesis 1 DOI: 10.1055/sos-SD-214-00188
Biocatalysis in Organic Synthesis 1

1.4.1 Hydrolysis of Nitriles to Amides

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Editors: Faber, K.; Fessner, W.-D.; Turner, N. J.

Authors: Asano, Y.; Babich, L.; Bertau, M.; Cobucci-Ponzano, B.; Díaz-Rodríguez, A.; Engel, U.; Faber, K.; Flitsch, S. L.; Glueck, S. M.; Gotor-Fernández, V.; Green, A. P.; Hall, M.; Hartog, A. F.; Hepworth, L. J.; Hollmann, F.; Jeromin, G. E.; Lauchli, R.; Lavandera, I.; Liese, A.; Martínková, L.; Moracci, M.; Pesci, L.; Rodríguez-Mata, M.; Rozzell, D.; Rudat, J.; Schmidberger, J. W.; Servi, S.; Slomka, C.; Syldatk, C.; Tasnádi, G.; Tessaro, D.; Veselá, A. B.; Voglmeir, J.; Wever, R.

Title: Biocatalysis in Organic Synthesis 1

Print ISBN: 9783131741318; Online ISBN: 9783131975218; Book DOI: 10.1055/b-003-125815

1st edition © 2015. Thieme. All rights reserved.
Georg Thieme Verlag KG, Stuttgart

Subjects: Organic Chemistry

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Parent publication

Title: Science of Synthesis

DOI: 10.1055/b-00000101

Type: Multivolume Edition

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Abstract

Nitrile hydratase (NHase; EC 4.2.1.84) catalyzes the hydration of nitriles to form amides. The reaction catalyzed by nitrile hydratase is strikingly fast and versatile and a wide range of nitriles, including aromatic and arylalkyl nitriles, α- and β-substituted nitriles, and aminonitriles can be hydrated to the corresponding amides. Although nitrile hydratase generally has low stereoselectivity, its use in conjunction with highly stereospecific amidases provides a valuable route for the stereoselective synthesis of carboxylic acids. The powerful nature of nitrile hydratase has had a huge impact on the progress of applied microbiology, enzyme engineering, and enzyme-catalyzed organic synthesis. The best-known applications of nitrile hydratase on an industrial scale are the production of acrylamide and nicotinamide from acrylonitrile and pyridine-3-carbonitrile, respectively.

This chapter provides an overview of the current scope of nitrile hydratase mediated reactions and focuses on whole-cell biotransformations.

Key words

nitriles - amides - nitrile hydratase - hydrolysis - hydration - chemoselectivity - carboxylic acids - kinetic resolution - desymmetrization - whole-cell biotransformations - aldoxime–nitrile pathway
 
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