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Faber, K. et al.: 2015 Science of Synthesis: Biocatalysis in Organic Synthesis DOI: 10.1055/sos-SD-216-00001
Biocatalysis in Organic Synthesis 3

3.1 Dihydroxylation of Aromatics and Alkenes

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Book

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

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

2015 © 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

The use of ring-hydroxylating dioxygenase enzymes for the biotransformation of aromatic hydrocarbons, alkenes, and phenols to give chiral cis-dihydrodiol metabolites is of significant potential for the preparation of chiral precursors for organic synthesis. Many products are produced with high enantiomeric excess, and a wide number of biotransformations have been studied. This type of biotransformation is typically used to convert readily available starting materials into single enantiomer bioproducts in a single step. The enzymes are multicomponent systems comprising two or more protein subunits. Furthermore, there is a requirement for reducing equivalents (e.g., NADH) and therefore whole-cell biocatalysts are used, either as wild-type strains, mutants, or clones. Recently, there have been significant developments in the use of molecular biology methods to improve these biocatalysts. This review covers the approaches employed to perform specific types of biotransformation, namely arene, alkene, and phenol hydroxylation.

Key words

biocatalysis - chiral pool - dihydroxylation - enzyme catalysis - diols - phenols
 
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