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Synfacts 2010(5): 0593-0593
DOI: 10.1055/s-0029-1219755
DOI: 10.1055/s-0029-1219755
Organo- and Biocatalysis
© Georg Thieme Verlag
Stuttgart ˙ New York
Enzyme-Catalyzed Carboligations by Thiamine Diphosphate Dependent YerE
P. Lehwald, M. Richter, C. Röhr, H.-W. Liu, M. Müller*
Albert-Ludwigs-Universität Freiburg, Germany; Empa-Swiss Federal Laboratories for Materials Testing and Research, St. Gallen, Switzerland; University of Texas at Austin, USA
Further Information
Publication History
Publication Date:
22 April 2010 (online)
Significance
An enzyme-catalyzed decarboxylative benzoin reaction of pyruvate with various aldehydes and ketones is described. The utilized flavoenzyme YerE, a thiamine diphosphate (ThDP) dependent biocatalyst expressed from Escherichia coli, delivered the desired tertiary alcohols and phenylacetylcarbinol derivatives smoothly. The activation mode of ThDP-based enzymes is assumed and widely accepted as occurring via the decarboxylative formation of an activated acetaldehyde species which undergoes a carboligation to ketones or aldehydes, respectively (see also: M. Pohl, B. Lingen, M. Müller Chem. Eur. J. 2002, 8, 5288-5295).