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

被引:5
作者
Milovanovic, Jelena [1 ]
Gunduz, Miyase Gozde [2 ]
Zerva, Anastasia [3 ]
Petkovic, Milos [4 ]
Beskoski, Vladimir [5 ]
Thomaidis, Nikolaos S. [6 ]
Topakas, Evangelos [3 ]
Nikodinovic-Runic, Jasmina [1 ]
机构
[1] Univ Belgrade, Inst Mol Genet & Genet Engn, Vojvode Stepe 444a, Belgrade 11221, Serbia
[2] Hacettepe Univ, Fac Pharm, Dept Pharmaceut Chem, TR-06100 Ankara, Turkey
[3] Natl Tech Univ Athens, Sch Chem Engn, Biotechnol Lab, Ind Biotechnol & Biocatalysis Grp, 5 Iroon Polytech Str,Zografou Campus, Athens 15780, Greece
[4] Univ Belgrade, Fac Pharm, Vojvode Stepe 450, Belgrade 11221, Serbia
[5] Univ Belgrade, Fac Chem, Studentski trg 16, Belgrade 11158, Serbia
[6] Natl & Kapodistrian Univ Athens, Dept Chem, Analyt Chem Lab, Panepistimioupolis Zografou, Athens 15771, Greece
关键词
dihydropyridine; hexahydroquinoline; acridinedione; laccase; biotransformation; POLYCYCLIC AROMATIC-HYDROCARBONS; HANTZSCH 1,4-DIHYDROPYRIDINES; MULTICOPPER OXIDASE; CATALYZED OXIDATION; COTA LACCASE; REDOX; SPECIFICITY; PYRIDINES; SYSTEMS;
D O I
10.3390/catal11060727
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
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.
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页数:15
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