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Article

Synthesis and Laccase-Mediated Oxidation of New Condensed 1,4-Dihydropyridine Derivatives

1
Institute of Molecular Genetics and Genetic Engineering, University of Belgrade, Vojvode Stepe 444a, 11221 Belgrade, Serbia
2
Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Hacettepe University, Sıhhiye, 06100 Ankara, Turkey
3
Industrial Biotechnology and Biocatalysis Group, Biotechnology Laboratory, School of Chemical Engineering, National Technical University of Athens, 5 Iroon Polytechniou Str., Zografou Campus, 15780 Athens, Greece
4
Faculty of Pharmacy, University of Belgrade, Vojvode Stepe 450, 11221 Belgrade, Serbia
5
Faculty of Chemistry, University of Belgrade, Studentski trg 16, 11158 Belgrade, Serbia
6
Laboratory of Analytical Chemistry, Department of Chemistry, National and Kapodistrian University of Athens, Panepistimioupolis Zografou, 15771 Athens, Greece
*
Author to whom correspondence should be addressed.
Equal contribution.
Academic Editor: Antonio Zuorro
Catalysts 2021, 11(6), 727; https://doi.org/10.3390/catal11060727
Received: 25 May 2021 / Revised: 9 June 2021 / Accepted: 10 June 2021 / Published: 12 June 2021
We describe herein the synthesis and laccase mediated oxidation of six novel 1,4-dihydropyridine (DHP)-based hexahydroquinolines (DHP1-DHP3) and decahydroacridines (DHP4-DHP6). We employed different laccase enzymes with varying redox potential to convert DHP1-DHP3 and DHP4-DHP6 to the corresponding pyridine-containing tetrahydroquinoline and octahydroacridine derivatives, respectively. Intensively coloured products were detected in all biocatalytic reactions using laccase from Trametes versicolor (TvLacc), possibly due to the presence of conjugated chromophores formed in products after oxidation. The NMR assessment confirmed that the oxidation product of DHP1 was its corresponding pyridine-bearing tetrahydroquinoline derivative. Laccase from Bacillus subtillis (BacillusLacc) was the most efficient enzyme for this group of substrates using HPLC assessment. Overall, it could be concluded that DHP2 and DHP5, bearing catecholic structures, were easily oxidized by all tested laccases, while DHP3 and DHP6 containing electron-withdrawing nitro-groups are not readily oxidized by laccases. DHP4 with decahydroacridine moiety consisting of three condensed six-membered rings that contribute not only to the volume but also to the higher redox potential of the substrate rendered this compound not to be biotransformed with any of the mentioned enzymes. Overall, we showed that multiple analytical approaches are needed in order to assess biocatalytical reactions. View Full-Text
Keywords: dihydropyridine; hexahydroquinoline; acridinedione; laccase; biotransformation dihydropyridine; hexahydroquinoline; acridinedione; laccase; biotransformation
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MDPI and ACS Style

Milovanovic, J.; Gündüz, M.G.; Zerva, A.; Petkovic, M.; Beskoski, V.; Thomaidis, N.S.; Topakas, E.; Nikodinovic-Runic, J. Synthesis and Laccase-Mediated Oxidation of New Condensed 1,4-Dihydropyridine Derivatives. Catalysts 2021, 11, 727. https://doi.org/10.3390/catal11060727

AMA Style

Milovanovic J, Gündüz MG, Zerva A, Petkovic M, Beskoski V, Thomaidis NS, Topakas E, Nikodinovic-Runic J. Synthesis and Laccase-Mediated Oxidation of New Condensed 1,4-Dihydropyridine Derivatives. Catalysts. 2021; 11(6):727. https://doi.org/10.3390/catal11060727

Chicago/Turabian Style

Milovanovic, Jelena, Miyase G. Gündüz, Anastasia Zerva, Milos Petkovic, Vladimir Beskoski, Nikolaos S. Thomaidis, Evangelos Topakas, and Jasmina Nikodinovic-Runic. 2021. "Synthesis and Laccase-Mediated Oxidation of New Condensed 1,4-Dihydropyridine Derivatives" Catalysts 11, no. 6: 727. https://doi.org/10.3390/catal11060727

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