2.1.4 Enzymatic Carboxylation and Decarboxylation

R. Lewin; M. L. Thompson; J. Micklefield

doi:10.1055/sos-SD-215-00069

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Faber, K. et al.: 2015 Science of Synthesis: Biocatalysis Organic Synthesis 2 DOI: 10.1055/sos-SD-215-00069

Biocatalysis in Organic Synthesis 2

2.1.4 Enzymatic Carboxylation and Decarboxylation

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

Authors: Au, S. K.; Bartsch, S.; Beecher, D.; Boffi, A.; Bommarius, A. S.; Bonamore, A.; Brown, G.; Busto, E.; Clapés, P.; Faber, K.; Fischereder, E.-M.; France, S. P.; Fuchs, C. S.; Geertsema, E. M.; Glieder, A.; Gruber-Khadjawi, M.; Hall, M.; Hanefeld, U.; Hussain, S.; Ilari, A.; Janssen, D. B.; Kaluđerović, G. N.; Kroutil, W.; Lamm, A. S.; Leipold, F.; Lewin, R.; Li, A. T.; Li, Z.; Majerić Elenkov, M.; Micklefield, J.; Moody, T. S.; Mix, S.; Müller, M.; Poelarends, G. J.; Pohl, M.; Pressnitz, D.; Resch, V.; Richter, N.; Rosazza, J. P. N.; Schreckenbach, H. F.; Simon, R. C.; Steiner, K.; Szymański, W.; Thompson, M. L.; Turner, N. J.; Venkitasubramanian, P.; Vogel, A.; Wechsler, C.; Wessjohann, L. A.; Wohlgemuth, R.

Title: Biocatalysis Organic Synthesis 2

Print ISBN: 9783131741615; Online ISBN: 9783131975317; Book DOI: 10.1055/b-003-125813

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

Subjects: Organic Chemistry

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Title: Science of Synthesis

DOI: 10.1055/b-00000101

Type: Multivolume Edition

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Abstract

Carboxylation reactions utilizing whole cells or purified carboxylase/decarboxylase enzymes enable the regioselective formation of new C—C bonds under more benign conditions than are typically used in nonenzymatic transformations such as the Kolbe–Schmitt reaction. A wide variety of substrates have been used in enzymatic carboxylation reactions including phenols, styrenes, pyrroles, and indoles.

Enzymatic decarboxylation can be used to transform simple achiral carboxylic acid substrates into more valuable homochiral building blocks through stereoselective C—H or C—C bond formation. For example, arylmalonate decarboxylases catalyze the enantioselective decarboxylative protonation of α-aryl- and α-alkenylmalonic acids under mild conditions and with excellent enantioselectivity. In addition, thiamine diphosphate dependent decarboxylases catalyze C—C bond formation with a broad range of α-keto acid and aldehyde substrates to produce homochiral α-hydroxy ketones.

Key words

carboxylation - Kolbe–Schmitt reaction - regioselectivity - whole-cell reaction - C—C bond formation - enantioselectivity - decarboxylation - arylmalonate decarboxylase - malonic acids - stereoselectivity - enantioselective decarboxylative protonation

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