TY  - JOUR
AU  - Narancić, Tanja
AU  - Kadivojević, Jelena
AU  - Jovanović, Predrag
AU  - Francuski, Đorđe
AU  - Bigović, Miljan
AU  - Maslak, Veselin
AU  - Savić, Vladimir
AU  - Vasiljević, Branka
AU  - O'Connor, Kevin
AU  - Nikodinović-Runić, Jasmina
PY  - 2013
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/1960
AB  - 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 terminal,proline of 4-UT was confirmed by two proline enriched variants and homology modeling.
PB  - Elsevier Sci Ltd, Oxford
T2  - Bioresource Technology
T1  - Highly efficient Michael-type addition of acetaldehyde to beta-nitrostyrenes by whole resting cells of Escherichia coli expressing 4-oxalocrotonate tautomerase
VL  - 142
SP  - 462
EP  - 468
DO  - 10.1016/j.biortech.2013.05.074
ER  - 

@article{
author = "Narancić, Tanja and Kadivojević, Jelena and Jovanović, Predrag and Francuski, Đorđe and Bigović, Miljan and Maslak, Veselin and Savić, Vladimir and Vasiljević, Branka and O'Connor, Kevin and Nikodinović-Runić, Jasmina",
year = "2013",
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 terminal,proline of 4-UT was confirmed by two proline enriched variants and homology modeling.",
publisher = "Elsevier Sci Ltd, Oxford",
journal = "Bioresource Technology",
title = "Highly efficient Michael-type addition of acetaldehyde to beta-nitrostyrenes by whole resting cells of Escherichia coli expressing 4-oxalocrotonate tautomerase",
volume = "142",
pages = "462-468",
doi = "10.1016/j.biortech.2013.05.074"
}

Narancić, T., Kadivojević, J., Jovanović, P., Francuski, Đ., Bigović, M., Maslak, V., Savić, V., Vasiljević, B., O'Connor, K.,& Nikodinović-Runić, J.. (2013). Highly efficient Michael-type addition of acetaldehyde to beta-nitrostyrenes by whole resting cells of Escherichia coli expressing 4-oxalocrotonate tautomerase. in Bioresource Technology
Elsevier Sci Ltd, Oxford., 142, 462-468.
https://doi.org/10.1016/j.biortech.2013.05.074

Narancić T, Kadivojević J, Jovanović P, Francuski Đ, Bigović M, Maslak V, Savić V, Vasiljević B, O'Connor K, Nikodinović-Runić J. Highly efficient Michael-type addition of acetaldehyde to beta-nitrostyrenes by whole resting cells of Escherichia coli expressing 4-oxalocrotonate tautomerase. in Bioresource Technology. 2013;142:462-468.
doi:10.1016/j.biortech.2013.05.074 .

Narancić, Tanja, Kadivojević, Jelena, Jovanović, Predrag, Francuski, Đorđe, Bigović, Miljan, Maslak, Veselin, Savić, Vladimir, Vasiljević, Branka, O'Connor, Kevin, Nikodinović-Runić, Jasmina, "Highly efficient Michael-type addition of acetaldehyde to beta-nitrostyrenes by whole resting cells of Escherichia coli expressing 4-oxalocrotonate tautomerase" in Bioresource Technology, 142 (2013):462-468,
https://doi.org/10.1016/j.biortech.2013.05.074 . .

TY  - JOUR
AU  - Bigović, Miljan
AU  - Maslak, Veselin
AU  - Tokić-Vujošević, Zorana
AU  - Divjaković, Vladimir
AU  - Saičić, Radomir N.
PY  - 2011
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/1482
AB  - Indium promoted allyiation of carbonyl compounds with 4-(bromomethyl)-1,3-dioxol-2-one diastereoselectively affords and-alpha,beta-dihydroxyketones, protected as enol carbonates. These initial products can be deprotected to free dihydroxyketones or transformed under mild conditions Into the corresponding cyclic carbonates, which constitutes a useful approach to hydroxyacetone aldois.
PB  - Amer Chemical Soc, Washington
T2  - Organic Letters
T1  - A Useful Synthetic Equivalent of a Hydroxyacetone Enolate
VL  - 13
IS  - 17
SP  - 4720
EP  - 4723
DO  - 10.1021/ol2019357
ER  - 

@article{
author = "Bigović, Miljan and Maslak, Veselin and Tokić-Vujošević, Zorana and Divjaković, Vladimir and Saičić, Radomir N.",
year = "2011",
abstract = "Indium promoted allyiation of carbonyl compounds with 4-(bromomethyl)-1,3-dioxol-2-one diastereoselectively affords and-alpha,beta-dihydroxyketones, protected as enol carbonates. These initial products can be deprotected to free dihydroxyketones or transformed under mild conditions Into the corresponding cyclic carbonates, which constitutes a useful approach to hydroxyacetone aldois.",
publisher = "Amer Chemical Soc, Washington",
journal = "Organic Letters",
title = "A Useful Synthetic Equivalent of a Hydroxyacetone Enolate",
volume = "13",
number = "17",
pages = "4720-4723",
doi = "10.1021/ol2019357"
}

Bigović, M., Maslak, V., Tokić-Vujošević, Z., Divjaković, V.,& Saičić, R. N.. (2011). A Useful Synthetic Equivalent of a Hydroxyacetone Enolate. in Organic Letters
Amer Chemical Soc, Washington., 13(17), 4720-4723.
https://doi.org/10.1021/ol2019357

Bigović M, Maslak V, Tokić-Vujošević Z, Divjaković V, Saičić RN. A Useful Synthetic Equivalent of a Hydroxyacetone Enolate. in Organic Letters. 2011;13(17):4720-4723.
doi:10.1021/ol2019357 .

Bigović, Miljan, Maslak, Veselin, Tokić-Vujošević, Zorana, Divjaković, Vladimir, Saičić, Radomir N., "A Useful Synthetic Equivalent of a Hydroxyacetone Enolate" in Organic Letters, 13, no. 17 (2011):4720-4723,
https://doi.org/10.1021/ol2019357 . .