Asymmetric Synthesis of Aliphatic 2‐Hydroxy Ketones by Enzymatic Carboligation of Aldehydes
- 1 June 2007
- journal article
- research article
- Published by Wiley in European Journal of Organic Chemistry
- Vol. 2007 (18) , 2940-2944
- https://doi.org/10.1002/ejoc.200600876
Abstract
Benzaldehyde lyase (BAL) and benzoylformate decarboxylase (BFD) catalyse the asymmetric ligation of aliphatic aldehydes to afford enantiomerically enriched 2‐hydroxy ketones. Carboligation of linear aldehydes with both enzymes results in high levels of conversion and in enantioselectivities of up to 80 % ee. In cases involving branched aliphatic aldehydes, BAL enables the carboligation of 3‐methylbutanal with a high level of conversion and an enantioselectivity of 89 % ee.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)Keywords
This publication has 27 references indexed in Scilit:
- Synthesis with good enantiomeric excess of both enantiomers of α-ketols and acetolactates by two thiamin diphosphate-dependent decarboxylasesBioorganic Chemistry, 2006
- A new perspective on thiamine catalysisCurrent Opinion in Biotechnology, 2004
- A New Route to Protected Acyloins and Their Enzymatic Resolution with LipasesEuropean Journal of Organic Chemistry, 2004
- Alteration of the Substrate Specificity of Benzoylformate Decarboxylase from Pseudomonas putida by Directed EvolutionChemBioChem, 2003
- Chemoenzymatic Synthesis of Aroma Active 5,6-Dihydro- and Tetrahydropyrazines from Aliphatic Acyloins Produced by Baker's YeastJournal of Agricultural and Food Chemistry, 2003
- Thiamin-Diphosphate-Dependent Enzymes: New Aspects of Asymmetric C-C Bond FormationChemistry – A European Journal, 2002
- The reduction of α-silyloxy ketones using phenyldimethylsilyllithiumJournal of the Chemical Society, Perkin Transactions 1, 1998
- Microbiological Reduction Ofcarbonyl Groupings: Preparation of Stereoisomers Acyclic Chiral α-DiolsBiocatalysis, 1992
- Studies on pyruvate decarboxylase: acyloin formation from aliphatic, aromatic and heterocyclic aldehydesJournal of the Chemical Society, Perkin Transactions 1, 1991
- Acetoin and Phenylacetylcarbinol Formation by the Pyruvate Decarboxylases ofZymomonas MobilisandSaccharomyces CarlsbergensisStephanie Bringer-MeyerBiocatalysis, 1988