TY  - JOUR
AU  - Cvijetić, Ilija
AU  - Bigović, Miljan
AU  - Ristivojević, Petar
AU  - Vitorović-Todorović, Maja D.
AU  - Zloh, Mire
AU  - Milojković-Opsenica, Dušanka
PY  - 2021
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/4534
AB  - Humulones and iso-humulones are potent natural antioxidants found in beer. In this study, density functional theory (DFT) method was applied for elucidating the structure-antioxidant activity relationship and molecular mechanism of antioxidant activity of eight bioactive humulones previously identified in different beer samples: isoxanthohumol, (R)- and (S)-adhumulone, cis- and trans-iso-adhumulone, cis- and trans-iso-n-humulone, and desdimethyl-octahydro-iso-cohumulone. The calculated bond dissociation enthalpies (BDEs) suggest that desdimethyl-octahydro-iso-cohumulone was the most potent compound with BDEs 5.1 and 23.9 kJ/mol lower compared to the values for resveratrol in gas phase and water, respectively. The enolic –OH is the most reactive site for hydrogen atom transfer (HAT). The presence of β-keto group with respect to enolic –OH diminishes the HAT potency via the formation of a strong intramolecular hydrogen bond. Another common antioxidant mechanism, single electron transfer followed by proton transfer (SET-PT), is only feasible for isoxanthohumol. The results of this study indicate a strong correlation between the increased antioxidant activity of beer products and the higher content of reduced iso-α-acids.
PB  - Springer
T2  - Structural Chemistry
T1  - DFT study of the radical scavenging activity of isoxanthohumol, humulones (α-acids), and iso-α-acids from beer
VL  - 32
SP  - 2051
EP  - 2059
DO  - 10.1007/s11224-021-01780-4
ER  - 

@article{
author = "Cvijetić, Ilija and Bigović, Miljan and Ristivojević, Petar and Vitorović-Todorović, Maja D. and Zloh, Mire and Milojković-Opsenica, Dušanka",
year = "2021",
abstract = "Humulones and iso-humulones are potent natural antioxidants found in beer. In this study, density functional theory (DFT) method was applied for elucidating the structure-antioxidant activity relationship and molecular mechanism of antioxidant activity of eight bioactive humulones previously identified in different beer samples: isoxanthohumol, (R)- and (S)-adhumulone, cis- and trans-iso-adhumulone, cis- and trans-iso-n-humulone, and desdimethyl-octahydro-iso-cohumulone. The calculated bond dissociation enthalpies (BDEs) suggest that desdimethyl-octahydro-iso-cohumulone was the most potent compound with BDEs 5.1 and 23.9 kJ/mol lower compared to the values for resveratrol in gas phase and water, respectively. The enolic –OH is the most reactive site for hydrogen atom transfer (HAT). The presence of β-keto group with respect to enolic –OH diminishes the HAT potency via the formation of a strong intramolecular hydrogen bond. Another common antioxidant mechanism, single electron transfer followed by proton transfer (SET-PT), is only feasible for isoxanthohumol. The results of this study indicate a strong correlation between the increased antioxidant activity of beer products and the higher content of reduced iso-α-acids.",
publisher = "Springer",
journal = "Structural Chemistry",
title = "DFT study of the radical scavenging activity of isoxanthohumol, humulones (α-acids), and iso-α-acids from beer",
volume = "32",
pages = "2051-2059",
doi = "10.1007/s11224-021-01780-4"
}

Cvijetić, I., Bigović, M., Ristivojević, P., Vitorović-Todorović, M. D., Zloh, M.,& Milojković-Opsenica, D.. (2021). DFT study of the radical scavenging activity of isoxanthohumol, humulones (α-acids), and iso-α-acids from beer. in Structural Chemistry
Springer., 32, 2051-2059.
https://doi.org/10.1007/s11224-021-01780-4

Cvijetić I, Bigović M, Ristivojević P, Vitorović-Todorović MD, Zloh M, Milojković-Opsenica D. DFT study of the radical scavenging activity of isoxanthohumol, humulones (α-acids), and iso-α-acids from beer. in Structural Chemistry. 2021;32:2051-2059.
doi:10.1007/s11224-021-01780-4 .

Cvijetić, Ilija, Bigović, Miljan, Ristivojević, Petar, Vitorović-Todorović, Maja D., Zloh, Mire, Milojković-Opsenica, Dušanka, "DFT study of the radical scavenging activity of isoxanthohumol, humulones (α-acids), and iso-α-acids from beer" in Structural Chemistry, 32 (2021):2051-2059,
https://doi.org/10.1007/s11224-021-01780-4 . .

TY  - DATA
AU  - Milošević, Milena D.
AU  - Prlainović, Nevena Z.
AU  - Milčić, Miloš K.
AU  - Nikolić, Vesna
AU  - Božić, Aleksandra R.
AU  - Bigović, Miljan
AU  - Marinković, Aleksandar
PY  - 2018
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3255
PB  - Springer, New York
T2  - Journal of the Iranian Chemical Society
T1  - Supplementary material for the article: Milošević, M. D.; Prlainović, N. Ž.; Milčić, M.; Nikolić, V.; Božić, A.; Bigović, M.; Marinković, A. D. Solvent, Structural, Quantum Chemical Study and Antioxidative Activity of Symmetrical 1-Methyl-2,6-Bis[2-(Substituted Phenyl)Ethenyl]Pyridinium Iodides. Journal of the Iranian Chemical Society 2018, 15 (11), 2483–2501. https://doi.org/10.1007/s13738-018-1437-5
UR  - https://hdl.handle.net/21.15107/rcub_cherry_3255
ER  - 

@misc{
author = "Milošević, Milena D. and Prlainović, Nevena Z. and Milčić, Miloš K. and Nikolić, Vesna and Božić, Aleksandra R. and Bigović, Miljan and Marinković, Aleksandar",
year = "2018",
publisher = "Springer, New York",
journal = "Journal of the Iranian Chemical Society",
title = "Supplementary material for the article: Milošević, M. D.; Prlainović, N. Ž.; Milčić, M.; Nikolić, V.; Božić, A.; Bigović, M.; Marinković, A. D. Solvent, Structural, Quantum Chemical Study and Antioxidative Activity of Symmetrical 1-Methyl-2,6-Bis[2-(Substituted Phenyl)Ethenyl]Pyridinium Iodides. Journal of the Iranian Chemical Society 2018, 15 (11), 2483–2501. https://doi.org/10.1007/s13738-018-1437-5",
url = "https://hdl.handle.net/21.15107/rcub_cherry_3255"
}

Milošević, M. D., Prlainović, N. Z., Milčić, M. K., Nikolić, V., Božić, A. R., Bigović, M.,& Marinković, A.. (2018). Supplementary material for the article: Milošević, M. D.; Prlainović, N. Ž.; Milčić, M.; Nikolić, V.; Božić, A.; Bigović, M.; Marinković, A. D. Solvent, Structural, Quantum Chemical Study and Antioxidative Activity of Symmetrical 1-Methyl-2,6-Bis[2-(Substituted Phenyl)Ethenyl]Pyridinium Iodides. Journal of the Iranian Chemical Society 2018, 15 (11), 2483–2501. https://doi.org/10.1007/s13738-018-1437-5. in Journal of the Iranian Chemical Society
Springer, New York..
https://hdl.handle.net/21.15107/rcub_cherry_3255

Milošević MD, Prlainović NZ, Milčić MK, Nikolić V, Božić AR, Bigović M, Marinković A. Supplementary material for the article: Milošević, M. D.; Prlainović, N. Ž.; Milčić, M.; Nikolić, V.; Božić, A.; Bigović, M.; Marinković, A. D. Solvent, Structural, Quantum Chemical Study and Antioxidative Activity of Symmetrical 1-Methyl-2,6-Bis[2-(Substituted Phenyl)Ethenyl]Pyridinium Iodides. Journal of the Iranian Chemical Society 2018, 15 (11), 2483–2501. https://doi.org/10.1007/s13738-018-1437-5. in Journal of the Iranian Chemical Society. 2018;.
https://hdl.handle.net/21.15107/rcub_cherry_3255 .

Milošević, Milena D., Prlainović, Nevena Z., Milčić, Miloš K., Nikolić, Vesna, Božić, Aleksandra R., Bigović, Miljan, Marinković, Aleksandar, "Supplementary material for the article: Milošević, M. D.; Prlainović, N. Ž.; Milčić, M.; Nikolić, V.; Božić, A.; Bigović, M.; Marinković, A. D. Solvent, Structural, Quantum Chemical Study and Antioxidative Activity of Symmetrical 1-Methyl-2,6-Bis[2-(Substituted Phenyl)Ethenyl]Pyridinium Iodides. Journal of the Iranian Chemical Society 2018, 15 (11), 2483–2501. https://doi.org/10.1007/s13738-018-1437-5" in Journal of the Iranian Chemical Society (2018),
https://hdl.handle.net/21.15107/rcub_cherry_3255 .

TY  - JOUR
AU  - Milošević, Milena D.
AU  - Prlainović, Nevena Z.
AU  - Milčić, Miloš K.
AU  - Nikolić, Vesna
AU  - Božić, Aleksandra R.
AU  - Bigović, Miljan
AU  - Marinković, Aleksandar
PY  - 2018
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/2216
AB  - 15 symmetric 1-methyl-2,6-bis[2-(substituted phenyl)ethenyl]pyridinium iodides were synthesized in this work. Their structures were characterized using IR, H-1 and C-13 NMR, and UV-Vis spectroscopy. DFT calculations indicated that s-trans/s-trans conformation prevail in all compounds. The effects of specific and non-specific solvent-solute interactions on the UV-Vis absorption maxima shifts were evaluated using linear solvation-free energy relationships (LSER), i.e., Kamlet-Taft and Catalan models. A linear free energy relationship (LFER) in the form of single substituent parameter equations (SSP) was used to postulate quantitative structure-property relations of substituent effect on NMR data. TD-DFT results showed dependence of electronic transition on the substituent effects. The push-pull character of these compounds was analyzed by differences in C-13 chemical shift of the ethylenic double bond in 2- and 6-positions of cross-conjugated with pyridinum central ring. Also, the quotient of the occupations for the bonding pi and anti-bonding pi* orbitals of this bond was considered. Good correlations of the selected parameter between double bond lengths with pi*/pi and C-13 chemical shift differences of the bridging group proved them to be adequate descriptor of push-pull character. Synthesized compounds were screened for the antioxidant activity, using 1,1-diphenyl-2-picrylhydrazyl (DPPH) and 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) radical methods, and results demonstrated moderate antioxidant potential.
PB  - Springer, New York
T2  - Journal of the Iranian Chemical Society
T1  - Solvent, structural, quantum chemical study and antioxidative activity of symmetrical 1-methyl-2,6-bis[2-(substituted phenyl)ethenyl]pyridinium iodides
VL  - 15
IS  - 11
SP  - 2483
EP  - 2501
DO  - 10.1007/s13738-018-1437-5
ER  - 

@article{
author = "Milošević, Milena D. and Prlainović, Nevena Z. and Milčić, Miloš K. and Nikolić, Vesna and Božić, Aleksandra R. and Bigović, Miljan and Marinković, Aleksandar",
year = "2018",
abstract = "15 symmetric 1-methyl-2,6-bis[2-(substituted phenyl)ethenyl]pyridinium iodides were synthesized in this work. Their structures were characterized using IR, H-1 and C-13 NMR, and UV-Vis spectroscopy. DFT calculations indicated that s-trans/s-trans conformation prevail in all compounds. The effects of specific and non-specific solvent-solute interactions on the UV-Vis absorption maxima shifts were evaluated using linear solvation-free energy relationships (LSER), i.e., Kamlet-Taft and Catalan models. A linear free energy relationship (LFER) in the form of single substituent parameter equations (SSP) was used to postulate quantitative structure-property relations of substituent effect on NMR data. TD-DFT results showed dependence of electronic transition on the substituent effects. The push-pull character of these compounds was analyzed by differences in C-13 chemical shift of the ethylenic double bond in 2- and 6-positions of cross-conjugated with pyridinum central ring. Also, the quotient of the occupations for the bonding pi and anti-bonding pi* orbitals of this bond was considered. Good correlations of the selected parameter between double bond lengths with pi*/pi and C-13 chemical shift differences of the bridging group proved them to be adequate descriptor of push-pull character. Synthesized compounds were screened for the antioxidant activity, using 1,1-diphenyl-2-picrylhydrazyl (DPPH) and 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) radical methods, and results demonstrated moderate antioxidant potential.",
publisher = "Springer, New York",
journal = "Journal of the Iranian Chemical Society",
title = "Solvent, structural, quantum chemical study and antioxidative activity of symmetrical 1-methyl-2,6-bis[2-(substituted phenyl)ethenyl]pyridinium iodides",
volume = "15",
number = "11",
pages = "2483-2501",
doi = "10.1007/s13738-018-1437-5"
}

Milošević, M. D., Prlainović, N. Z., Milčić, M. K., Nikolić, V., Božić, A. R., Bigović, M.,& Marinković, A.. (2018). Solvent, structural, quantum chemical study and antioxidative activity of symmetrical 1-methyl-2,6-bis[2-(substituted phenyl)ethenyl]pyridinium iodides. in Journal of the Iranian Chemical Society
Springer, New York., 15(11), 2483-2501.
https://doi.org/10.1007/s13738-018-1437-5

Milošević MD, Prlainović NZ, Milčić MK, Nikolić V, Božić AR, Bigović M, Marinković A. Solvent, structural, quantum chemical study and antioxidative activity of symmetrical 1-methyl-2,6-bis[2-(substituted phenyl)ethenyl]pyridinium iodides. in Journal of the Iranian Chemical Society. 2018;15(11):2483-2501.
doi:10.1007/s13738-018-1437-5 .

Milošević, Milena D., Prlainović, Nevena Z., Milčić, Miloš K., Nikolić, Vesna, Božić, Aleksandra R., Bigović, Miljan, Marinković, Aleksandar, "Solvent, structural, quantum chemical study and antioxidative activity of symmetrical 1-methyl-2,6-bis[2-(substituted phenyl)ethenyl]pyridinium iodides" in Journal of the Iranian Chemical Society, 15, no. 11 (2018):2483-2501,
https://doi.org/10.1007/s13738-018-1437-5 . .

TY  - DATA
AU  - Bigović, Miljan
AU  - Škaro, Sanja
AU  - Maslak, Veselin
AU  - Saičić, Radomir
PY  - 2013
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3493
PB  - Pergamon-Elsevier Science Ltd, Oxford
T2  - Tetrahedron Letters
T1  - Supplementary data for article: Bigović, M.; Skaro, S.; Maslak, V.; Saičić, R. Expanding the Scope of the Indium-Promoted Allylation Reaction: 4-(Bromomethyl)-1,3-Dioxol-2-One as a Synthetic Equivalent of a 3-Arylhydroxyacetone Enolate. Tetrahedron Letters 2013, 54 (48), 6624–6626. https://doi.org/10.1016/j.tetlet.2013.09.115eaction: 4-(bromomethyl)-1,3-dioxol-2-one as a synthetic equivalent of a 3-arylhydroxyacetone enolate
UR  - https://hdl.handle.net/21.15107/rcub_cherry_3493
ER  - 

@misc{
author = "Bigović, Miljan and Škaro, Sanja and Maslak, Veselin and Saičić, Radomir",
year = "2013",
publisher = "Pergamon-Elsevier Science Ltd, Oxford",
journal = "Tetrahedron Letters",
title = "Supplementary data for article: Bigović, M.; Skaro, S.; Maslak, V.; Saičić, R. Expanding the Scope of the Indium-Promoted Allylation Reaction: 4-(Bromomethyl)-1,3-Dioxol-2-One as a Synthetic Equivalent of a 3-Arylhydroxyacetone Enolate. Tetrahedron Letters 2013, 54 (48), 6624–6626. https://doi.org/10.1016/j.tetlet.2013.09.115eaction: 4-(bromomethyl)-1,3-dioxol-2-one as a synthetic equivalent of a 3-arylhydroxyacetone enolate",
url = "https://hdl.handle.net/21.15107/rcub_cherry_3493"
}

Bigović, M., Škaro, S., Maslak, V.,& Saičić, R.. (2013). Supplementary data for article: Bigović, M.; Skaro, S.; Maslak, V.; Saičić, R. Expanding the Scope of the Indium-Promoted Allylation Reaction: 4-(Bromomethyl)-1,3-Dioxol-2-One as a Synthetic Equivalent of a 3-Arylhydroxyacetone Enolate. Tetrahedron Letters 2013, 54 (48), 6624–6626. https://doi.org/10.1016/j.tetlet.2013.09.115eaction: 4-(bromomethyl)-1,3-dioxol-2-one as a synthetic equivalent of a 3-arylhydroxyacetone enolate. in Tetrahedron Letters
Pergamon-Elsevier Science Ltd, Oxford..
https://hdl.handle.net/21.15107/rcub_cherry_3493

Bigović M, Škaro S, Maslak V, Saičić R. Supplementary data for article: Bigović, M.; Skaro, S.; Maslak, V.; Saičić, R. Expanding the Scope of the Indium-Promoted Allylation Reaction: 4-(Bromomethyl)-1,3-Dioxol-2-One as a Synthetic Equivalent of a 3-Arylhydroxyacetone Enolate. Tetrahedron Letters 2013, 54 (48), 6624–6626. https://doi.org/10.1016/j.tetlet.2013.09.115eaction: 4-(bromomethyl)-1,3-dioxol-2-one as a synthetic equivalent of a 3-arylhydroxyacetone enolate. in Tetrahedron Letters. 2013;.
https://hdl.handle.net/21.15107/rcub_cherry_3493 .

Bigović, Miljan, Škaro, Sanja, Maslak, Veselin, Saičić, Radomir, "Supplementary data for article: Bigović, M.; Skaro, S.; Maslak, V.; Saičić, R. Expanding the Scope of the Indium-Promoted Allylation Reaction: 4-(Bromomethyl)-1,3-Dioxol-2-One as a Synthetic Equivalent of a 3-Arylhydroxyacetone Enolate. Tetrahedron Letters 2013, 54 (48), 6624–6626. https://doi.org/10.1016/j.tetlet.2013.09.115eaction: 4-(bromomethyl)-1,3-dioxol-2-one as a synthetic equivalent of a 3-arylhydroxyacetone enolate" in Tetrahedron Letters (2013),
https://hdl.handle.net/21.15107/rcub_cherry_3493 .

TY  - DATA
AU  - Narančić, Tanja
AU  - Kadivojević, Jelena
AU  - Jovanović, Predrag M.
AU  - Francuski, Đorđe
AU  - Bigović, Miljan
AU  - Maslak, Veselin
AU  - Savić, Vladimir
AU  - Vasiljević, Branka
AU  - O'Connor, Kevin E.
AU  - Nikodinović-Runić, Jasmina
PY  - 2013
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3499
PB  - Elsevier Sci Ltd, Oxford
T2  - Bioresource Technology
T1  - Supplementary data for article: Narančić, T.; Kadivojevic, J.; Jovanovic, P.; Francuski, D.; Bigović, M.; Maslak, V.; Savić, V.; Vasiljević, B.; O’Connor, K. E.; Nikodinović-Runić, J. Highly Efficient Michael-Type Addition of Acetaldehyde to Beta-Nitrostyrenes by Whole Resting Cells of Escherichia Coli Expressing 4-Oxalocrotonate Tautomerase. Bioresource Technology 2013, 142, 462–468. https://doi.org/10.1016/j.biortech.2013.05.074
UR  - https://hdl.handle.net/21.15107/rcub_cherry_3499
ER  - 

@misc{
author = "Narančić, Tanja and Kadivojević, Jelena and Jovanović, Predrag M. and Francuski, Đorđe and Bigović, Miljan and Maslak, Veselin and Savić, Vladimir and Vasiljević, Branka and O'Connor, Kevin E. and Nikodinović-Runić, Jasmina",
year = "2013",
publisher = "Elsevier Sci Ltd, Oxford",
journal = "Bioresource Technology",
title = "Supplementary data for article: Narančić, T.; Kadivojevic, J.; Jovanovic, P.; Francuski, D.; Bigović, M.; Maslak, V.; Savić, V.; Vasiljević, B.; O’Connor, K. E.; Nikodinović-Runić, J. Highly Efficient Michael-Type Addition of Acetaldehyde to Beta-Nitrostyrenes by Whole Resting Cells of Escherichia Coli Expressing 4-Oxalocrotonate Tautomerase. Bioresource Technology 2013, 142, 462–468. https://doi.org/10.1016/j.biortech.2013.05.074",
url = "https://hdl.handle.net/21.15107/rcub_cherry_3499"
}

Narančić, T., Kadivojević, J., Jovanović, P. M., Francuski, Đ., Bigović, M., Maslak, V., Savić, V., Vasiljević, B., O'Connor, K. E.,& Nikodinović-Runić, J.. (2013). Supplementary data for article: Narančić, T.; Kadivojevic, J.; Jovanovic, P.; Francuski, D.; Bigović, M.; Maslak, V.; Savić, V.; Vasiljević, B.; O’Connor, K. E.; Nikodinović-Runić, J. Highly Efficient Michael-Type Addition of Acetaldehyde to Beta-Nitrostyrenes by Whole Resting Cells of Escherichia Coli Expressing 4-Oxalocrotonate Tautomerase. Bioresource Technology 2013, 142, 462–468. https://doi.org/10.1016/j.biortech.2013.05.074. in Bioresource Technology
Elsevier Sci Ltd, Oxford..
https://hdl.handle.net/21.15107/rcub_cherry_3499

Narančić T, Kadivojević J, Jovanović PM, Francuski Đ, Bigović M, Maslak V, Savić V, Vasiljević B, O'Connor KE, Nikodinović-Runić J. Supplementary data for article: Narančić, T.; Kadivojevic, J.; Jovanovic, P.; Francuski, D.; Bigović, M.; Maslak, V.; Savić, V.; Vasiljević, B.; O’Connor, K. E.; Nikodinović-Runić, J. Highly Efficient Michael-Type Addition of Acetaldehyde to Beta-Nitrostyrenes by Whole Resting Cells of Escherichia Coli Expressing 4-Oxalocrotonate Tautomerase. Bioresource Technology 2013, 142, 462–468. https://doi.org/10.1016/j.biortech.2013.05.074. in Bioresource Technology. 2013;.
https://hdl.handle.net/21.15107/rcub_cherry_3499 .

Narančić, Tanja, Kadivojević, Jelena, Jovanović, Predrag M., Francuski, Đorđe, Bigović, Miljan, Maslak, Veselin, Savić, Vladimir, Vasiljević, Branka, O'Connor, Kevin E., Nikodinović-Runić, Jasmina, "Supplementary data for article: Narančić, T.; Kadivojevic, J.; Jovanovic, P.; Francuski, D.; Bigović, M.; Maslak, V.; Savić, V.; Vasiljević, B.; O’Connor, K. E.; Nikodinović-Runić, J. Highly Efficient Michael-Type Addition of Acetaldehyde to Beta-Nitrostyrenes by Whole Resting Cells of Escherichia Coli Expressing 4-Oxalocrotonate Tautomerase. Bioresource Technology 2013, 142, 462–468. https://doi.org/10.1016/j.biortech.2013.05.074" in Bioresource Technology (2013),
https://hdl.handle.net/21.15107/rcub_cherry_3499 .

TY  - JOUR
AU  - Narančić, Tanja
AU  - Kadivojević, Jelena
AU  - Jovanović, Predrag M.
AU  - Francuski, Đorđe
AU  - Bigović, Miljan
AU  - Maslak, Veselin
AU  - Savić, Vladimir
AU  - Vasiljević, Branka
AU  - O'Connor, Kevin E.
AU  - Nikodinović-Runić, Jasmina
PY  - 2013
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/1377
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 ( gt 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 = "Narančić, Tanja and Kadivojević, Jelena and Jovanović, Predrag M. and Francuski, Đorđe and Bigović, Miljan and Maslak, Veselin and Savić, Vladimir and Vasiljević, Branka and O'Connor, Kevin E. 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 ( gt 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"
}

Narančić, T., Kadivojević, J., Jovanović, P. M., Francuski, Đ., Bigović, M., Maslak, V., Savić, V., Vasiljević, B., O'Connor, K. E.,& 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

Narančić T, Kadivojević J, Jovanović PM, Francuski Đ, Bigović M, Maslak V, Savić V, Vasiljević B, O'Connor KE, 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 .

Narančić, Tanja, Kadivojević, Jelena, Jovanović, Predrag M., Francuski, Đorđe, Bigović, Miljan, Maslak, Veselin, Savić, Vladimir, Vasiljević, Branka, O'Connor, Kevin E., 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  - Škaro, Sanja
AU  - Maslak, Veselin
AU  - Saičić, Radomir
PY  - 2013
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/1430
AB  - Cyclic enol carbonates of type 2, obtained via the indium-promoted allylation of aldehydes with 4-(bromomethyl)-1,3-dioxol-2-one, undergo Heck reaction with aryl iodides in the presence of silver trifluoroacetate, to give the corresponding arylated products. Thus, 4-(bromomethyl)-1,3-dioxol-2-one can be considered as a synthetic equivalent of 3-mylhydroxyacetone enolate.
PB  - Pergamon-Elsevier Science Ltd, Oxford
T2  - Tetrahedron Letters
T1  - Expanding the scope of the indium-promoted allylation reaction: 4-(bromomethyl)-1,3-dioxol-2-one as a synthetic equivalent of a 3-arylhydroxyacetone enolate
VL  - 54
IS  - 48
SP  - 6624
EP  - 6626
DO  - 10.1016/j.tetlet.2013.09.115
ER  - 

@article{
author = "Bigović, Miljan and Škaro, Sanja and Maslak, Veselin and Saičić, Radomir",
year = "2013",
abstract = "Cyclic enol carbonates of type 2, obtained via the indium-promoted allylation of aldehydes with 4-(bromomethyl)-1,3-dioxol-2-one, undergo Heck reaction with aryl iodides in the presence of silver trifluoroacetate, to give the corresponding arylated products. Thus, 4-(bromomethyl)-1,3-dioxol-2-one can be considered as a synthetic equivalent of 3-mylhydroxyacetone enolate.",
publisher = "Pergamon-Elsevier Science Ltd, Oxford",
journal = "Tetrahedron Letters",
title = "Expanding the scope of the indium-promoted allylation reaction: 4-(bromomethyl)-1,3-dioxol-2-one as a synthetic equivalent of a 3-arylhydroxyacetone enolate",
volume = "54",
number = "48",
pages = "6624-6626",
doi = "10.1016/j.tetlet.2013.09.115"
}

Bigović, M., Škaro, S., Maslak, V.,& Saičić, R.. (2013). Expanding the scope of the indium-promoted allylation reaction: 4-(bromomethyl)-1,3-dioxol-2-one as a synthetic equivalent of a 3-arylhydroxyacetone enolate. in Tetrahedron Letters
Pergamon-Elsevier Science Ltd, Oxford., 54(48), 6624-6626.
https://doi.org/10.1016/j.tetlet.2013.09.115

Bigović M, Škaro S, Maslak V, Saičić R. Expanding the scope of the indium-promoted allylation reaction: 4-(bromomethyl)-1,3-dioxol-2-one as a synthetic equivalent of a 3-arylhydroxyacetone enolate. in Tetrahedron Letters. 2013;54(48):6624-6626.
doi:10.1016/j.tetlet.2013.09.115 .

Bigović, Miljan, Škaro, Sanja, Maslak, Veselin, Saičić, Radomir, "Expanding the scope of the indium-promoted allylation reaction: 4-(bromomethyl)-1,3-dioxol-2-one as a synthetic equivalent of a 3-arylhydroxyacetone enolate" in Tetrahedron Letters, 54, no. 48 (2013):6624-6626,
https://doi.org/10.1016/j.tetlet.2013.09.115 . .

TY  - DATA
AU  - Bigović, Miljan
AU  - Maslak, Veselin
AU  - Tokić-Vujošević, Zorana
AU  - Divjaković, Vladimir
AU  - Saičić, Radomir
PY  - 2011
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3570
PB  - Amer Chemical Soc, Washington
T2  - Organic Letters
T1  - Supplementary data for article: Bigović, M.; Maslak, V.; Tokic-Vujosevic, Z.; Divjaković, V.; Saičić, R. A Useful Synthetic Equivalent of a Hydroxyacetone Enolate. Organic Letters 2011, 13 (17), 4720–4723. https://doi.org/10.1021/ol2019357
UR  - https://hdl.handle.net/21.15107/rcub_cherry_3570
ER  - 

@misc{
author = "Bigović, Miljan and Maslak, Veselin and Tokić-Vujošević, Zorana and Divjaković, Vladimir and Saičić, Radomir",
year = "2011",
publisher = "Amer Chemical Soc, Washington",
journal = "Organic Letters",
title = "Supplementary data for article: Bigović, M.; Maslak, V.; Tokic-Vujosevic, Z.; Divjaković, V.; Saičić, R. A Useful Synthetic Equivalent of a Hydroxyacetone Enolate. Organic Letters 2011, 13 (17), 4720–4723. https://doi.org/10.1021/ol2019357",
url = "https://hdl.handle.net/21.15107/rcub_cherry_3570"
}

Bigović, M., Maslak, V., Tokić-Vujošević, Z., Divjaković, V.,& Saičić, R.. (2011). Supplementary data for article: Bigović, M.; Maslak, V.; Tokic-Vujosevic, Z.; Divjaković, V.; Saičić, R. A Useful Synthetic Equivalent of a Hydroxyacetone Enolate. Organic Letters 2011, 13 (17), 4720–4723. https://doi.org/10.1021/ol2019357. in Organic Letters
Amer Chemical Soc, Washington..
https://hdl.handle.net/21.15107/rcub_cherry_3570

Bigović M, Maslak V, Tokić-Vujošević Z, Divjaković V, Saičić R. Supplementary data for article: Bigović, M.; Maslak, V.; Tokic-Vujosevic, Z.; Divjaković, V.; Saičić, R. A Useful Synthetic Equivalent of a Hydroxyacetone Enolate. Organic Letters 2011, 13 (17), 4720–4723. https://doi.org/10.1021/ol2019357. in Organic Letters. 2011;.
https://hdl.handle.net/21.15107/rcub_cherry_3570 .

Bigović, Miljan, Maslak, Veselin, Tokić-Vujošević, Zorana, Divjaković, Vladimir, Saičić, Radomir, "Supplementary data for article: Bigović, M.; Maslak, V.; Tokic-Vujosevic, Z.; Divjaković, V.; Saičić, R. A Useful Synthetic Equivalent of a Hydroxyacetone Enolate. Organic Letters 2011, 13 (17), 4720–4723. https://doi.org/10.1021/ol2019357" in Organic Letters (2011),
https://hdl.handle.net/21.15107/rcub_cherry_3570 .

TY  - JOUR
AU  - Bigović, Miljan
AU  - Maslak, Veselin
AU  - Tokić-Vujošević, Zorana
AU  - Divjaković, Vladimir
AU  - Saičić, Radomir
PY  - 2011
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/1194
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",
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.. (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 R. 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, "A Useful Synthetic Equivalent of a Hydroxyacetone Enolate" in Organic Letters, 13, no. 17 (2011):4720-4723,
https://doi.org/10.1021/ol2019357 . .