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Synthesis of gamma-nitroaldehydes containing quaternary carbon in the alpha-position using a 4-oxalocrotonate tautomerase whole-cell biocatalyst
dc.creator | Radivojević, Jelena | |
dc.creator | Minovska, Gordana | |
dc.creator | Šenerović, Lidija | |
dc.creator | O'Connor, Kevin E. | |
dc.creator | Jovanović, Predrag M. | |
dc.creator | Savić, Vladimir | |
dc.creator | Tokić-Vujošević, Zorana | |
dc.creator | Nikodinović-Runić, Jasmina | |
dc.creator | Maslak, Veselin | |
dc.date.accessioned | 2018-11-22T00:29:39Z | |
dc.date.available | 2018-11-22T00:29:39Z | |
dc.date.issued | 2014 | |
dc.identifier.issn | 2046-2069 | |
dc.identifier.uri | https://cherry.chem.bg.ac.rs/handle/123456789/1883 | |
dc.description.abstract | Synthesis of gamma-nitroaldehydes from branched chain aldehydes and a range of alpha,beta-unsaturated nitroalkenes was achieved by a whole-cell biocatalytic reaction using 4-oxalocrotonate tautomerase as catalyst. Under mild conditions, cyclic and acyclic branched aldehydes were converted into synthetically valuable quaternary carbon containing gamma-nitroaldehydes. The yields of the desired products were influenced by reaction condition parameters such as organic solvent, temperature and pH. The whole-cell biocatalytic approach to the generation of alpha,alpha-substituted gamma-nitroaldehydes was compared to the organocatalytic approach involving the lithium salt of phenylalanine as a catalyst. As the resulting gamma-nitroaldehydes exhibited moderate antifungal activity and mild in vitro cytotoxicity against human fibroblasts (0.2-0.4 mM) they could further be examined as potentially useful pharmaceutical synthons. | en |
dc.publisher | Royal Soc Chemistry, Cambridge | |
dc.relation | info:eu-repo/grantAgreement/MESTD/Basic Research (BR or ON)/173048/RS// | |
dc.relation | info:eu-repo/grantAgreement/MESTD/Basic Research (BR or ON)/172002/RS// | |
dc.rights | restrictedAccess | |
dc.source | RSC Advances | |
dc.title | Synthesis of gamma-nitroaldehydes containing quaternary carbon in the alpha-position using a 4-oxalocrotonate tautomerase whole-cell biocatalyst | en |
dc.type | article | |
dc.rights.license | ARR | |
dcterms.abstract | Радивојевиц, Јелена; Миновска, Гордана; Јовановиц, Предраг; Сенеровиц, Лидија; О'Цоннор, Кевин; Маслак, Веселин; Никодиновић-Рунић, Јасмина; Токиц-Вујосевиц, Зорана; Савиц, Владимир; | |
dc.citation.volume | 4 | |
dc.citation.issue | 105 | |
dc.citation.spage | 60502 | |
dc.citation.epage | 60510 | |
dc.identifier.wos | 000345655600010 | |
dc.identifier.doi | 10.1039/c4ra05517a | |
dc.citation.other | 4(105): 60502-60510 | |
dc.citation.rank | M21 | |
dc.type.version | publishedVersion | |
dc.identifier.scopus | 2-s2.0-84937196259 |