1.4.2 Hydrolysis of Nitriles to Carboxylic Acids

L. Martinková; A. B. Veselá

doi:10.1055/sos-SD-214-00194

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Faber, K. et al.: 2015 Science of Synthesis, 1: Biocatalysis in Organic Synthesis 1 DOI: 10.1055/sos-SD-214-00194

Biocatalysis in Organic Synthesis 1

1.4.2 Hydrolysis of Nitriles to Carboxylic Acids

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

Autoren: 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.

Titel: Biocatalysis in Organic Synthesis 1

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

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

Fachgebiete: Organische Chemie

Science of Synthesis Reference Libraries

Übergeordnete Publikation

Titel: Science of Synthesis

DOI: 10.1055/b-00000101

Typ: Mehrbändiges Werk

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Abstract

The synthesis of carboxylic acids from nitriles utilizes two pathways of nitrile biotransformations: direct hydrolysis by nitrilase and bienzymatic hydrolysis by nitrile hydratase and amidase. General procedures consist of using whole cells or isolated enzymes as catalysts in aqueous media with a small fraction of organic cosolvent. These methods afford a number of products that are often difficult to prepare by chemical means such as 3-oxoamides, cyano carboxamides and cyano carboxylic acids, enantiopure 2- and 3-substituted carboxylic acids and carboxamides, and enantiopure (hetero)cyclic carboxylic acids and carboxamides. Stereochemistry is mainly recognized by amidase, but in some cases also by nitrilase and nitrile hydratase. Nitrile hydrolysis has also been employed in chemoenzymatic and multienzymatic methods such as the synthesis of aromatic and heterocyclic amides from aldehydes, the synthesis of enantiopure 2-hydroxy acids from aldehydes, the synthesis of enantiopure 3-hydroxy acids from 3-oxonitriles, and the synthesis of cyclophellitols from benzo-1,4-quinone.

Schlüsselwörter

nitriles - carboxylic acids - carboxamides - aldehydes - nitrilase - nitrile hydratase - amidase - stereochemistry - chemoenzymatic methods - multienzymatic methods

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