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Highly efficient Michael-type addition of acetaldehyde to beta-nitrostyrenes by whole resting cells of Escherichia coli expressing 4-oxalocrotonate tautomerase

Authorized Users Only
2013
Authors
Narancić, Tanja
Kadivojević, Jelena
Jovanović, Predrag
Francuski, Đorđe
Bigović, Miljan
Maslak, Veselin
Savić, Vladimir
Vasiljević, Branka
O'Connor, Kevin
Nikodinović-Runić, Jasmina
Article (Published version)
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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 beta-nitrostyrenes. Optimal ratio of substrates (2 mM beta-nitrostyrenes and 20 mM 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 10 mM nitrostyrene biotransformation was achieved within 150 min. Excellent enantioselectivity (>99% ee) and product yields of up to 60% were obtained with beta-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-beta-nitrostyrenes with product yields of 38%, 51%, 31% and ee values of 84%, 88% and 94% respectively. The importance of the termi...nal,proline of 4-UT was confirmed by two proline enriched variants and homology modeling.

Keywords:
Biocatalyst / Michael addition / Nitrostyrene / 4-Oxalocrotonate tautomerase / Whole cell
Source:
Bioresource Technology, 2013, 142, 462-468
Publisher:
  • Elsevier Sci Ltd, Oxford
Projects:
  • Microbial diversity study and characterization of beneficial environmental microorganisms (RS-173048)

DOI: 10.1016/j.biortech.2013.05.074

ISSN: 0960-8524

PubMed: 23759430

WoS: 000322292800061

Scopus: 2-s2.0-84879283087
[ Google Scholar ]
15
17
URI
http://farfar.pharmacy.bg.ac.rs/handle/123456789/1960
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  • Radovi istraživača / Researchers’ publications
Institution
Pharmacy

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