Abstract：
:A novel whole cell system based on recombinantly expressed 4-oxalocrotonate tautomerase (4-OT) was developed and shown to be an effective biocatalyst for the asymmetric Michael addition of acetaldehyde to β-nitrostyrenes. Optimal ratio of substrates (2mM β-nitrostyrenes and 20mM acetaldehyde) and biocatalyst of 5 g of cell dry weight of biocatalyst per liter was determined. Through further bioprocess improvement by sequential addition of substrate 10mM nitrostyrene biotransformation was achieved within 150 min. Excellent enantioselectivity (>99% ee) and product yields of up to 60% were obtained with β-nitrostyrene substrate. The biotransformation product, 4-nitro-3-phenyl-butanal, was isolated from aqueous media and further transformed into the corresponding amino alcohol. The biocatalyst exhibited lower reaction rates with p-Cl-, o-Cl- and p-F-β-nitrostyrenes with product yields of 38%, 51%, 31% and ee values of 84%, 88% and 94% respectively. The importance of the terminal proline of 4-OT was confirmed by two proline enriched variants and homology modeling.
journal_name
Bioresour Technoljournal_title
Bioresource technologyauthors
Narancic T,Radivojevic J,Jovanovic P,Francuski D,Bigovic M,Maslak V,Savic V,Vasiljevic B,O'Connor KE,Nikodinovic-Runic Jdoi
10.1016/j.biortech.2013.05.074subject
Has Abstractpub_date
2013-08-01 00:00:00pages
462-8eissn
0960-8524issn
1873-2976pii
S0960-8524(13)00834-1journal_volume
142pub_type
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