Biocatalytic Racemization of (Hetero)Aryl-aliphatic α-Hydroxycarboxylic Acids by Lactobacillus spp. Proceeds via an Oxidation–Reduction Sequence
✍ Scribed by Bettina M. Nestl; Silvia M. Glueck; Melanie Hall; Wolfgang Kroutil; Rainer Stuermer; Bernhard Hauer; Kurt Faber
- Publisher
- John Wiley and Sons
- Year
- 2006
- Tongue
- English
- Weight
- 109 KB
- Volume
- 2006
- Category
- Article
- ISSN
- 1434-193X
No coin nor oath required. For personal study only.
✦ Synopsis
Abstract
The biocatalytic racemization of a range of (hetero)aryl‐ and (di)aryl‐aliphatic α‐hydroxycarboxylic acids has been achieved by using whole resting cells of Lactobacillus spp. The essentially mild (physiological) reaction conditions ensure the suppression of undesired side reactions, such as elimination, decomposition or condensation. Cofactor/inhibitor studies using a cell‐free extract of Lactobacillus paracasei DSM 20207 reveal that the addition of redox cofactors (NAD^+^/NADH) leads to a distinct increase in the racemization rate, while strong inhibition is observed in the presence of Thio‐NAD^+^, which suggests that the racemization proceeds by an oxidation–reduction sequence rather than involvement of a “racemase” enzyme. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)