3.3.1 Oxidation Using Dehydrogenases

F. Hollmann

doi:10.1055/sos-SD-216-00039

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Faber, K. et al.: 2015 Science of Synthesis: Biocatalysis in Organic Synthesis 3 DOI: 10.1055/sos-SD-216-00039

Biocatalysis in Organic Synthesis 3

3.3.1 Oxidation Using Dehydrogenases

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

Authors: Allen, C. C. R.; de Gonzalo, G.; Ellinger, J. J.; Ewing, T. A.; Faber, K.; Fernández-Lucas, J.; Flynn, C. M.; Fraaije, M. W.; García-Junceda, E.; Garrabou, X.; Gkotsi, D. S.; Glueck, S. M.; Goss, R. J. M.; Grogan, G.; Gröger, H.; Grüschow, S.; Hammer, S. C.; Hauer, B.; Herter, S.; Hilvert, D.; Hollmann, F.; Hormigo, D.; Hummel, W.; Molla, G.; Nestl, B. M.; Nolte, J. C.; Obexer, R.; Oroz-Guinea, I.; Patel, R. N.; Pollegioni, L.; Quin, M. B.; Schmidt-Dannert, C.; Smith, D. R. M.; Turner, N. J.; Urlacher, V. B.; van Berkel, W. J. H.; Woodley, J. M.

Title: Biocatalysis in Organic Synthesis 3

Print ISBN: 9783131746610; Online ISBN: 9783131974914; Book DOI: 10.1055/b-003-125814

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

Subjects: Organic Chemistry

Science of Synthesis Reference Libraries

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Title: Science of Synthesis

DOI: 10.1055/b-00000101

Type: Multivolume Edition

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Abstract

The use of alcohol dehydrogenases has a number of advantages over traditional chemical methods for the oxidation of alcohols. These include the mild reaction conditions, the avoidance of tedious protecting-group strategies, and the high regio- and chemoselectivites. This review highlights the most important alcohol dehydrogenases used for biocatalysis and discusses the systems used for cofactor regeneration when employing these enzymes. The oxidation of primary alcohols to aldehydes and further to carboxylic acids is presented, along with examples of subsequent cascade reactions (e.g., oxidation–lactonization of diols). The oxidation of secondary alcohols to ketones, including the application of this reaction in kinetic resolutions and deracemizations, is also described.

Key words

alcohol dehydrogenases - oxidation - alcohols - aldehydes - ketones - carboxylic acids - cofactor regeneration - kinetic resolution - deracemization

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