Jeremić, Sanja

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orcid::0000-0002-6661-385X
  • Jeremić, Sanja (4)

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Chemical characterization and antimicrobial activity of Juglans nigra L. nut and green husk

Rajković, Katarina; Drobac, Milica; Milić, Petar; Vučić, Vesna; Arsić, Aleksandra; Perić, Mirjana; Radunović, Milena; Jeremić, Sanja; Arsenijević, Jelena

(Serbian Chemical Society, 2023)

TY  - JOUR
AU  - Rajković, Katarina
AU  - Drobac, Milica
AU  - Milić, Petar
AU  - Vučić, Vesna
AU  - Arsić, Aleksandra
AU  - Perić, Mirjana
AU  - Radunović, Milena
AU  - Jeremić, Sanja
AU  - Arsenijević, Jelena
PY  - 2023
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/5035
AB  - Juglans nigra (Black walnut) is a source of health-supporting biologically active compounds used in traditional medicine. The investigation of bioactive compounds in black walnut could lead to its broader application, as well as to the application of its by-products. Therefore, this study aimed to characterize J. nigra nut and green husk based on chemical analysis of their petroleum ether and ethanol extracts obtained by ultrasonic and reflux extraction methods, respectively. Different extract fractions were tested for their antimicrobial activities using Gram-negative bacteria (Escherichia coli, Pseudomonas aeruginosa), Gram-positive bacteria (Enterococcus faecalis, Staphylococcus aureus) and yeast (reference strain and clinical isolates of Candida albicans). The ethanol extracts analysis, performed by high performance liquid chromatography, singled out the ellagic acid as the most dominant compound in nut ((55.0±1.3)×10-3 kg m-3) and green husk ((114.1±0.5)×10-3 kg m-3) extracts. Non-polar compounds were evaluated using gas chromatography analysis of petroleum ether extracts. Juglans nigra nut and green husk contained two saturated fatty acids, palmitic acid (C16:0) and stearic acid (C18:0), then, monounsaturated fatty acids, palmitoleic (C16:1n-7), oleic (C18:1n-9) and vaccenic acid (C18:1n-7), as well as polyunsaturated fatty acids, linoleic (C18:2n-6), γ-linolenic (C18:3n-6) and α-linolenic (C18:3n-3) acids. Ethanol extracts of both J. nigra nut and green husk showed antimicrobial activity against C. albicans, which is the most common cause of yeast infections.
AB  - Juglans nigra (црниорах) каоизворбиолошкиактивнихједињењасекористиутра-диционалнојмедицини. Истраживањебиоактивнихједињењаприсутнихуцрноморахуможедовестидоширеприменењеговихпроизвода. ЗатоовастудијаимазациљдаокарактеришеорашастплодизеленуљускуЈ. nigra наосновухемијскеанализењиховихпетролетарскихиетанолнихекстраката, добијенихултразвучнимирефлуксметодамаекстракције. Антимикробнаактивностразличитихфракцијаекстрактајетестиранако-ришћењемГрам-негативнихбактерија (Escherichia  coli, Pseudomonas  aeruginosa), Грам- -позитивнихбактерија (Enterococcus  faecalis, Staphylococcus  aureus) иквасница (рефе-рентнисојиклиничкиизолатиCandida  albicans). Анализатечномхроматографијомвисокихперформанси, издвојилајеелагинскукиселинукаонајдоминантнијеједињењеуетанолнимекстрактимаорашастогплода ((55,0±1,3)×10-3   kg   m-3) изеленељуске((114,1±0,5)×10-3 g m-3). Неполарнаједињењасуодређенаприменомгаснехроматогра-фскеанализепетролетарскихекстракта. Орашастплодизеленаљускасадржедвезаси-ћенемаснекиселине, палмитинску (C16:0) истеаринскукиселину (C18:0), затиммоно-незасићенемаснекиселине, палмитолеинску  (C16:1n-7),  олеинску  (C18:1n-9)  ивак-ценскукиселину (C18:1n-7), каоиполинезасићенемаснекиселине, линолну (C18:2n-6), γ-линоленску (C18:3n-6) иα-линоленску (C18: 3n-3) киселину. Етанолниекстрактиора-шастогплодаизеленељускепоказалисуантимикробнуактивностнa сојевимаC.  albi-cansкојајенајчешћиузрочникгљивичнихинфекција.
PB  - Serbian Chemical Society
T2  - Journal of the Serbian Chemical Society
T1  - Chemical characterization and antimicrobial activity of Juglans nigra L. nut and green husk
T1  - Хемијска карактеризација и антимикробна активност орашастог плода и зелене љуске Juglans nigra L.
VL  - 88
IS  - 6
SP  - 603
EP  - 614
DO  - 10.2298/JSC230210024R
ER  - 
@article{
author = "Rajković, Katarina and Drobac, Milica and Milić, Petar and Vučić, Vesna and Arsić, Aleksandra and Perić, Mirjana and Radunović, Milena and Jeremić, Sanja and Arsenijević, Jelena",
year = "2023",
abstract = "Juglans nigra (Black walnut) is a source of health-supporting biologically active compounds used in traditional medicine. The investigation of bioactive compounds in black walnut could lead to its broader application, as well as to the application of its by-products. Therefore, this study aimed to characterize J. nigra nut and green husk based on chemical analysis of their petroleum ether and ethanol extracts obtained by ultrasonic and reflux extraction methods, respectively. Different extract fractions were tested for their antimicrobial activities using Gram-negative bacteria (Escherichia coli, Pseudomonas aeruginosa), Gram-positive bacteria (Enterococcus faecalis, Staphylococcus aureus) and yeast (reference strain and clinical isolates of Candida albicans). The ethanol extracts analysis, performed by high performance liquid chromatography, singled out the ellagic acid as the most dominant compound in nut ((55.0±1.3)×10-3 kg m-3) and green husk ((114.1±0.5)×10-3 kg m-3) extracts. Non-polar compounds were evaluated using gas chromatography analysis of petroleum ether extracts. Juglans nigra nut and green husk contained two saturated fatty acids, palmitic acid (C16:0) and stearic acid (C18:0), then, monounsaturated fatty acids, palmitoleic (C16:1n-7), oleic (C18:1n-9) and vaccenic acid (C18:1n-7), as well as polyunsaturated fatty acids, linoleic (C18:2n-6), γ-linolenic (C18:3n-6) and α-linolenic (C18:3n-3) acids. Ethanol extracts of both J. nigra nut and green husk showed antimicrobial activity against C. albicans, which is the most common cause of yeast infections., Juglans nigra (црниорах) каоизворбиолошкиактивнихједињењасекористиутра-диционалнојмедицини. Истраживањебиоактивнихједињењаприсутнихуцрноморахуможедовестидоширеприменењеговихпроизвода. ЗатоовастудијаимазациљдаокарактеришеорашастплодизеленуљускуЈ. nigra наосновухемијскеанализењиховихпетролетарскихиетанолнихекстраката, добијенихултразвучнимирефлуксметодамаекстракције. Антимикробнаактивностразличитихфракцијаекстрактајетестиранако-ришћењемГрам-негативнихбактерија (Escherichia  coli, Pseudomonas  aeruginosa), Грам- -позитивнихбактерија (Enterococcus  faecalis, Staphylococcus  aureus) иквасница (рефе-рентнисојиклиничкиизолатиCandida  albicans). Анализатечномхроматографијомвисокихперформанси, издвојилајеелагинскукиселинукаонајдоминантнијеједињењеуетанолнимекстрактимаорашастогплода ((55,0±1,3)×10-3   kg   m-3) изеленељуске((114,1±0,5)×10-3 g m-3). Неполарнаједињењасуодређенаприменомгаснехроматогра-фскеанализепетролетарскихекстракта. Орашастплодизеленаљускасадржедвезаси-ћенемаснекиселине, палмитинску (C16:0) истеаринскукиселину (C18:0), затиммоно-незасићенемаснекиселине, палмитолеинску  (C16:1n-7),  олеинску  (C18:1n-9)  ивак-ценскукиселину (C18:1n-7), каоиполинезасићенемаснекиселине, линолну (C18:2n-6), γ-линоленску (C18:3n-6) иα-линоленску (C18: 3n-3) киселину. Етанолниекстрактиора-шастогплодаизеленељускепоказалисуантимикробнуактивностнa сојевимаC.  albi-cansкојајенајчешћиузрочникгљивичнихинфекција.",
publisher = "Serbian Chemical Society",
journal = "Journal of the Serbian Chemical Society",
title = "Chemical characterization and antimicrobial activity of Juglans nigra L. nut and green husk, Хемијска карактеризација и антимикробна активност орашастог плода и зелене љуске Juglans nigra L.",
volume = "88",
number = "6",
pages = "603-614",
doi = "10.2298/JSC230210024R"
}
Rajković, K., Drobac, M., Milić, P., Vučić, V., Arsić, A., Perić, M., Radunović, M., Jeremić, S.,& Arsenijević, J.. (2023). Chemical characterization and antimicrobial activity of Juglans nigra L. nut and green husk. in Journal of the Serbian Chemical Society
Serbian Chemical Society., 88(6), 603-614.
https://doi.org/10.2298/JSC230210024R
Rajković K, Drobac M, Milić P, Vučić V, Arsić A, Perić M, Radunović M, Jeremić S, Arsenijević J. Chemical characterization and antimicrobial activity of Juglans nigra L. nut and green husk. in Journal of the Serbian Chemical Society. 2023;88(6):603-614.
doi:10.2298/JSC230210024R .
Rajković, Katarina, Drobac, Milica, Milić, Petar, Vučić, Vesna, Arsić, Aleksandra, Perić, Mirjana, Radunović, Milena, Jeremić, Sanja, Arsenijević, Jelena, "Chemical characterization and antimicrobial activity of Juglans nigra L. nut and green husk" in Journal of the Serbian Chemical Society, 88, no. 6 (2023):603-614,
https://doi.org/10.2298/JSC230210024R . .

Optimization of extraction yield and chemical characterization of optimal extract from Juglans nigra L. leaves

Rajković, Katarina M; Vasić, Marijana; Drobac, Milica; Mutić, Jelena; Jeremić, Sanja; Simić, Valentina; Stanković, Jovan

(Elsevier, 2020)

TY  - JOUR
AU  - Rajković, Katarina M
AU  - Vasić, Marijana
AU  - Drobac, Milica
AU  - Mutić, Jelena
AU  - Jeremić, Sanja
AU  - Simić, Valentina
AU  - Stanković, Jovan
PY  - 2020
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/3604
AB  - The extraction yield of Juglans nigra L. leaves was assessed at different ethanol concen-trations (0–96% (v/v)) and solvent-to-solid ratios (5–20 kg kg−1). The response surfacemethodology (RSM) and artificial neural network with genetic algorithms (ANN-GA) weredeveloped to optimize the extraction variables. The RSM and ANN-GA models determined50% (v/v) ethanol concentration and 20 kg kg−1solvent-to-solid ratio as optimal conditions,ensuring an extraction yield of 27.69 and 27.19 g 100 g−1of dry leaves. The phenolic com-pounds in optimal extract were quantified: 3-O-caffeoylquinic acid (2.27 mg g−1of dry leaves),quercetin-3-O-galactoside (10.99 mg g−1of dry leaves) and quercetin-3-O-rhamnoside (15.07mg g−1of dry leaves) using high-performance liquid chromatography (HPLC). The mineralsin optimal extract were quantified: macro-elements (the relative order by content was: K> Mg > Ca) using inductively coupled plasma optical emission spectrometry (ICP-OES) andmicro-elements (the relative order by content was: Zn > Rb > Mn > I>Sr > Ni > Cu > Co >V > Ag > Se) using inductively coupled plasma mass spectrometry (ICP-MS). The extrac-tion coefficients for minerals were determined and were highest for K (64.3%) and I (53.5%).Optimization of extraction process resulted in high extraction yield from J. nigra leaves andoptimal extract containing different phytochemical compounds.
PB  - Elsevier
T2  - Chemical Engineering Research and Design
T1  - Optimization of extraction yield and chemical characterization of optimal extract from Juglans nigra L. leaves
VL  - 157
SP  - 25
EP  - 33
DO  - doi.org/10.1016/j.cherd.2020.03.002
ER  - 
@article{
author = "Rajković, Katarina M and Vasić, Marijana and Drobac, Milica and Mutić, Jelena and Jeremić, Sanja and Simić, Valentina and Stanković, Jovan",
year = "2020",
abstract = "The extraction yield of Juglans nigra L. leaves was assessed at different ethanol concen-trations (0–96% (v/v)) and solvent-to-solid ratios (5–20 kg kg−1). The response surfacemethodology (RSM) and artificial neural network with genetic algorithms (ANN-GA) weredeveloped to optimize the extraction variables. The RSM and ANN-GA models determined50% (v/v) ethanol concentration and 20 kg kg−1solvent-to-solid ratio as optimal conditions,ensuring an extraction yield of 27.69 and 27.19 g 100 g−1of dry leaves. The phenolic com-pounds in optimal extract were quantified: 3-O-caffeoylquinic acid (2.27 mg g−1of dry leaves),quercetin-3-O-galactoside (10.99 mg g−1of dry leaves) and quercetin-3-O-rhamnoside (15.07mg g−1of dry leaves) using high-performance liquid chromatography (HPLC). The mineralsin optimal extract were quantified: macro-elements (the relative order by content was: K> Mg > Ca) using inductively coupled plasma optical emission spectrometry (ICP-OES) andmicro-elements (the relative order by content was: Zn > Rb > Mn > I>Sr > Ni > Cu > Co >V > Ag > Se) using inductively coupled plasma mass spectrometry (ICP-MS). The extrac-tion coefficients for minerals were determined and were highest for K (64.3%) and I (53.5%).Optimization of extraction process resulted in high extraction yield from J. nigra leaves andoptimal extract containing different phytochemical compounds.",
publisher = "Elsevier",
journal = "Chemical Engineering Research and Design",
title = "Optimization of extraction yield and chemical characterization of optimal extract from Juglans nigra L. leaves",
volume = "157",
pages = "25-33",
doi = "doi.org/10.1016/j.cherd.2020.03.002"
}
Rajković, K. M., Vasić, M., Drobac, M., Mutić, J., Jeremić, S., Simić, V.,& Stanković, J.. (2020). Optimization of extraction yield and chemical characterization of optimal extract from Juglans nigra L. leaves. in Chemical Engineering Research and Design
Elsevier., 157, 25-33.
https://doi.org/doi.org/10.1016/j.cherd.2020.03.002
Rajković KM, Vasić M, Drobac M, Mutić J, Jeremić S, Simić V, Stanković J. Optimization of extraction yield and chemical characterization of optimal extract from Juglans nigra L. leaves. in Chemical Engineering Research and Design. 2020;157:25-33.
doi:doi.org/10.1016/j.cherd.2020.03.002 .
Rajković, Katarina M, Vasić, Marijana, Drobac, Milica, Mutić, Jelena, Jeremić, Sanja, Simić, Valentina, Stanković, Jovan, "Optimization of extraction yield and chemical characterization of optimal extract from Juglans nigra L. leaves" in Chemical Engineering Research and Design, 157 (2020):25-33,
https://doi.org/doi.org/10.1016/j.cherd.2020.03.002 . .
3
10

Poly (epsilon-caprolactone) microspheres for prolonged release of selenium nanoparticles

Filipović, Nenad; Veselinovic, Ljiljana; Ražić, Slavica; Jeremić, Sanja; Filipić, Metka; Zegura, Bojana; Tomic, Sergej; Čolić, Miodrag; Stevanović, Magdalena

(Elsevier Science BV, Amsterdam, 2019)

TY  - JOUR
AU  - Filipović, Nenad
AU  - Veselinovic, Ljiljana
AU  - Ražić, Slavica
AU  - Jeremić, Sanja
AU  - Filipić, Metka
AU  - Zegura, Bojana
AU  - Tomic, Sergej
AU  - Čolić, Miodrag
AU  - Stevanović, Magdalena
PY  - 2019
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/3328
AB  - Poly (e-caprolactone) (PCL) microspheres as a carrier for sustained release of antibacterial agent, selenium nanoparticles (SeNPs), were developed. The obtained PCL/SeNPs microspheres were in the range 1-4 mu m with the encapsulation efficiency of about 90%. The degradation process and release behavior of SeNPs from PCL microspheres were investigated in five different degradation media: phosphate buffer solution (PBS), a solution of lipase isolated from the porcine pancreas in PBS, 0.1 M hydrochloric acid (HCl), Pseudomonas aeruginosa PAO1 cell-free extract in PBS and implant fluid (exudate) from the subcutaneously implanted sterile polyvinyl sponges which induce a foreign-body inflammatory reaction. The samples were thoroughly characterized by SEM, TEM, FTIR, XRD, PSA, DSC, confocal microscopy, and ICP-OES techniques. Under physiological conditions at neutral pH, a very slow release of SeNPs occurred (3 and 8% in the case of PBS or PBS + lipase, respectively and after 660 days), while in the acidic environment their presence was not detected. On the other hand, the release in the medium with bacterial extract was much more pronounced, even after 24 h (13%). After 7 days, the concentration of SeNPs reached a maximum of around 30%. Also, 37% of SeNPs have been released after 11 days of incubation of PCL/SeNPs in the implant exudate. These results suggest that the release of SeNPs from PCL was triggered by Pseudomonas aeruginosa PAO1 bacterium as well as by foreign body inflammatory reaction to implant. Furthermore, PCL/SeNPs microspheres were investigated in terms of their biocompatibility. For this purpose, cytotoxicity, the formation of reactive oxygen species (ROS), and genotoxicity were evaluated on HepG2 cell line. The interaction of PCL/SeNPs with phagocytic cell line (Raw 264.7 macrophages) was monitored as well. It was found that the microspheres in investigated concentration range had no acute cytotoxic effects. Finally, SeNPs, as well as PCL/SeNPs, showed a considerable antibacterial activity against Gram-positive bacteria: Staphylococcus aureus (ATCC 25923) and Staphylococcus epidermidis (ATCC 1228). These results suggest that PCL/SeNPs-based system could be an attractive platform for a prolonged prevention of infections accompanying implants.
PB  - Elsevier Science BV, Amsterdam
T2  - Materials Science & Engineering C: Materials for Biological Applications
T1  - Poly (epsilon-caprolactone) microspheres for prolonged release of selenium nanoparticles
VL  - 96
SP  - 776
EP  - 789
DO  - 10.1016/j.msec.2018.11.073
ER  - 
@article{
author = "Filipović, Nenad and Veselinovic, Ljiljana and Ražić, Slavica and Jeremić, Sanja and Filipić, Metka and Zegura, Bojana and Tomic, Sergej and Čolić, Miodrag and Stevanović, Magdalena",
year = "2019",
abstract = "Poly (e-caprolactone) (PCL) microspheres as a carrier for sustained release of antibacterial agent, selenium nanoparticles (SeNPs), were developed. The obtained PCL/SeNPs microspheres were in the range 1-4 mu m with the encapsulation efficiency of about 90%. The degradation process and release behavior of SeNPs from PCL microspheres were investigated in five different degradation media: phosphate buffer solution (PBS), a solution of lipase isolated from the porcine pancreas in PBS, 0.1 M hydrochloric acid (HCl), Pseudomonas aeruginosa PAO1 cell-free extract in PBS and implant fluid (exudate) from the subcutaneously implanted sterile polyvinyl sponges which induce a foreign-body inflammatory reaction. The samples were thoroughly characterized by SEM, TEM, FTIR, XRD, PSA, DSC, confocal microscopy, and ICP-OES techniques. Under physiological conditions at neutral pH, a very slow release of SeNPs occurred (3 and 8% in the case of PBS or PBS + lipase, respectively and after 660 days), while in the acidic environment their presence was not detected. On the other hand, the release in the medium with bacterial extract was much more pronounced, even after 24 h (13%). After 7 days, the concentration of SeNPs reached a maximum of around 30%. Also, 37% of SeNPs have been released after 11 days of incubation of PCL/SeNPs in the implant exudate. These results suggest that the release of SeNPs from PCL was triggered by Pseudomonas aeruginosa PAO1 bacterium as well as by foreign body inflammatory reaction to implant. Furthermore, PCL/SeNPs microspheres were investigated in terms of their biocompatibility. For this purpose, cytotoxicity, the formation of reactive oxygen species (ROS), and genotoxicity were evaluated on HepG2 cell line. The interaction of PCL/SeNPs with phagocytic cell line (Raw 264.7 macrophages) was monitored as well. It was found that the microspheres in investigated concentration range had no acute cytotoxic effects. Finally, SeNPs, as well as PCL/SeNPs, showed a considerable antibacterial activity against Gram-positive bacteria: Staphylococcus aureus (ATCC 25923) and Staphylococcus epidermidis (ATCC 1228). These results suggest that PCL/SeNPs-based system could be an attractive platform for a prolonged prevention of infections accompanying implants.",
publisher = "Elsevier Science BV, Amsterdam",
journal = "Materials Science & Engineering C: Materials for Biological Applications",
title = "Poly (epsilon-caprolactone) microspheres for prolonged release of selenium nanoparticles",
volume = "96",
pages = "776-789",
doi = "10.1016/j.msec.2018.11.073"
}
Filipović, N., Veselinovic, L., Ražić, S., Jeremić, S., Filipić, M., Zegura, B., Tomic, S., Čolić, M.,& Stevanović, M.. (2019). Poly (epsilon-caprolactone) microspheres for prolonged release of selenium nanoparticles. in Materials Science & Engineering C: Materials for Biological Applications
Elsevier Science BV, Amsterdam., 96, 776-789.
https://doi.org/10.1016/j.msec.2018.11.073
Filipović N, Veselinovic L, Ražić S, Jeremić S, Filipić M, Zegura B, Tomic S, Čolić M, Stevanović M. Poly (epsilon-caprolactone) microspheres for prolonged release of selenium nanoparticles. in Materials Science & Engineering C: Materials for Biological Applications. 2019;96:776-789.
doi:10.1016/j.msec.2018.11.073 .
Filipović, Nenad, Veselinovic, Ljiljana, Ražić, Slavica, Jeremić, Sanja, Filipić, Metka, Zegura, Bojana, Tomic, Sergej, Čolić, Miodrag, Stevanović, Magdalena, "Poly (epsilon-caprolactone) microspheres for prolonged release of selenium nanoparticles" in Materials Science & Engineering C: Materials for Biological Applications, 96 (2019):776-789,
https://doi.org/10.1016/j.msec.2018.11.073 . .
1
23
13
23

Chemoselective biocatalytic reduction of conjugated nitroalkenes: New application for an Escherichia coli BL21(DE3) expression strain

Jovanović, Predrag; Jeremić, Sanja; Đokić, Lidija; Savić, Vladimir; Radivojević, Jelena; Maslak, Veselin; Ivković, Branka; Vasiljević, Branka; Nikodinović-Runić, Jasmina

(Elsevier Science Inc, New York, 2014)

TY  - JOUR
AU  - Jovanović, Predrag
AU  - Jeremić, Sanja
AU  - Đokić, Lidija
AU  - Savić, Vladimir
AU  - Radivojević, Jelena
AU  - Maslak, Veselin
AU  - Ivković, Branka
AU  - Vasiljević, Branka
AU  - Nikodinović-Runić, Jasmina
PY  - 2014
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/2202
AB  - Chemoselective reduction of activated carbon-carbon double bond in conjugated nitroalkenes was achieved using Escherichia coli BL21(DE3) whole cells. Nine different substrates have been used furnishing the reduced products in moderate to good yields. 1-Nitro-4-phenyl-1,3-butadiene and (2-nitro-1-propenyl)benzene were successfully biotransformed with corresponding product yields of 54% and 45% respectively. Using this simple and environmentally friendly system 2-(2-nitropropyl)pyridine and 2-(2-nitropropyl)naphthalene were synthesized and characterized for the first time. High substrate conversion efficiency was coupled with low enantioselectivity, however 29% enantiomeric excess was detected in the case of 2-(2-nitropropyl)pyridine. It was shown that electronic properties of the aromatic ring, which affected polarity of the double bond, were not highly influential factors in the reduction process, but the presence of the nitro functionality was essential for the reaction to proceed. 1-Phenyl-4-nitro-1,3-butadiene could not be biotransformed by whole cells of Pseudomonas putida KT2440 or Bacillus subtilis 168 while it was successfully reduced by E. coli DH5 alpha but with lower efficiency in comparison to E. coli BL21(DE3). Knockout mutant affected in nemA gene coding for N-ethylmaleimide reductase (BL21 Delta nemA) could still catalyze bioreductions suggesting multiple active reductases within E. coli BL21(DE3) biocatalyst. The described biocatalytic reduction of substituted nitroalkenes provides an efficient route for the preparation of the corresponding nitroalkanes and introduces the new application of the strain traditionally utilized for recombinant protein expression.
PB  - Elsevier Science Inc, New York
T2  - Enzyme and Microbial Technology
T1  - Chemoselective biocatalytic reduction of conjugated nitroalkenes: New application for an Escherichia coli BL21(DE3) expression strain
VL  - 60
SP  - 16
EP  - 23
DO  - 10.1016/j.enzmictec.2014.03.010
ER  - 
@article{
author = "Jovanović, Predrag and Jeremić, Sanja and Đokić, Lidija and Savić, Vladimir and Radivojević, Jelena and Maslak, Veselin and Ivković, Branka and Vasiljević, Branka and Nikodinović-Runić, Jasmina",
year = "2014",
abstract = "Chemoselective reduction of activated carbon-carbon double bond in conjugated nitroalkenes was achieved using Escherichia coli BL21(DE3) whole cells. Nine different substrates have been used furnishing the reduced products in moderate to good yields. 1-Nitro-4-phenyl-1,3-butadiene and (2-nitro-1-propenyl)benzene were successfully biotransformed with corresponding product yields of 54% and 45% respectively. Using this simple and environmentally friendly system 2-(2-nitropropyl)pyridine and 2-(2-nitropropyl)naphthalene were synthesized and characterized for the first time. High substrate conversion efficiency was coupled with low enantioselectivity, however 29% enantiomeric excess was detected in the case of 2-(2-nitropropyl)pyridine. It was shown that electronic properties of the aromatic ring, which affected polarity of the double bond, were not highly influential factors in the reduction process, but the presence of the nitro functionality was essential for the reaction to proceed. 1-Phenyl-4-nitro-1,3-butadiene could not be biotransformed by whole cells of Pseudomonas putida KT2440 or Bacillus subtilis 168 while it was successfully reduced by E. coli DH5 alpha but with lower efficiency in comparison to E. coli BL21(DE3). Knockout mutant affected in nemA gene coding for N-ethylmaleimide reductase (BL21 Delta nemA) could still catalyze bioreductions suggesting multiple active reductases within E. coli BL21(DE3) biocatalyst. The described biocatalytic reduction of substituted nitroalkenes provides an efficient route for the preparation of the corresponding nitroalkanes and introduces the new application of the strain traditionally utilized for recombinant protein expression.",
publisher = "Elsevier Science Inc, New York",
journal = "Enzyme and Microbial Technology",
title = "Chemoselective biocatalytic reduction of conjugated nitroalkenes: New application for an Escherichia coli BL21(DE3) expression strain",
volume = "60",
pages = "16-23",
doi = "10.1016/j.enzmictec.2014.03.010"
}
Jovanović, P., Jeremić, S., Đokić, L., Savić, V., Radivojević, J., Maslak, V., Ivković, B., Vasiljević, B.,& Nikodinović-Runić, J.. (2014). Chemoselective biocatalytic reduction of conjugated nitroalkenes: New application for an Escherichia coli BL21(DE3) expression strain. in Enzyme and Microbial Technology
Elsevier Science Inc, New York., 60, 16-23.
https://doi.org/10.1016/j.enzmictec.2014.03.010
Jovanović P, Jeremić S, Đokić L, Savić V, Radivojević J, Maslak V, Ivković B, Vasiljević B, Nikodinović-Runić J. Chemoselective biocatalytic reduction of conjugated nitroalkenes: New application for an Escherichia coli BL21(DE3) expression strain. in Enzyme and Microbial Technology. 2014;60:16-23.
doi:10.1016/j.enzmictec.2014.03.010 .
Jovanović, Predrag, Jeremić, Sanja, Đokić, Lidija, Savić, Vladimir, Radivojević, Jelena, Maslak, Veselin, Ivković, Branka, Vasiljević, Branka, Nikodinović-Runić, Jasmina, "Chemoselective biocatalytic reduction of conjugated nitroalkenes: New application for an Escherichia coli BL21(DE3) expression strain" in Enzyme and Microbial Technology, 60 (2014):16-23,
https://doi.org/10.1016/j.enzmictec.2014.03.010 . .
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