These authors contributed equally to this work.
Promiscuous Catalysis of Asymmetric Michael-Type Additions of Linear Aldehydes to β-Nitrostyrene by the Proline-Based Enzyme 4-Oxalocrotonate Tautomerase
Article first published online: 9 JAN 2013
Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Volume 14, Issue 2, pages 191–194, January 21, 2013
How to Cite
Miao, Y., Geertsema, E. M., Tepper, P. G., Zandvoort, E. and Poelarends, G. J. (2013), Promiscuous Catalysis of Asymmetric Michael-Type Additions of Linear Aldehydes to β-Nitrostyrene by the Proline-Based Enzyme 4-Oxalocrotonate Tautomerase. ChemBioChem, 14: 191–194. doi: 10.1002/cbic.201200676
- Issue published online: 17 JAN 2013
- Article first published online: 9 JAN 2013
- Manuscript Received: 29 OCT 2012
- European Research Council. Grant Number: 242293
- catalytic promiscuity;
- Michael addition;
Exploiting catalytic promiscuity: The proline-based enzyme 4-oxalocrotonate tautomerase (4-OT) promiscuously catalyzes asymmetric Michael-type additions of linear aldehydes—ranging from acetaldehyde to octanal—to trans-β-nitrostyrene in aqueous solvent. The presence of 1.4 mol % of 4-OT effected formation of the anticipated γ-nitroaldehydes in fair to good yields with dr values of up to 93:7 and ee values of up to 81 %.