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dc.creatorJovanović, Predrag
dc.creatorJeremić, Sanja
dc.creatorĐokić, Lidija
dc.creatorSavić, Vladimir
dc.creatorRadivojević, Jelena
dc.creatorMaslak, Veselin
dc.creatorIvković, Branka
dc.creatorVasiljević, Branka
dc.creatorNikodinović-Runić, Jasmina
dc.date.accessioned2019-09-02T11:41:36Z
dc.date.available2019-09-02T11:41:36Z
dc.date.issued2014
dc.identifier.issn0141-0229
dc.identifier.urihttps://farfar.pharmacy.bg.ac.rs/handle/123456789/2202
dc.description.abstractChemoselective 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.en
dc.publisherElsevier Science Inc, New York
dc.relationinfo:eu-repo/grantAgreement/MESTD/Basic Research (BR or ON)/173048/RS//
dc.rightsrestrictedAccess
dc.sourceEnzyme and Microbial Technology
dc.subjectEscherichia coli BL21(DE3)en
dc.subjectBiotransformationen
dc.subjectNitroalkene reductionen
dc.subjectNitrostyreneen
dc.subjectC=C reductionen
dc.titleChemoselective biocatalytic reduction of conjugated nitroalkenes: New application for an Escherichia coli BL21(DE3) expression strainen
dc.typearticle
dc.rights.licenseARR
dcterms.abstractЈеремић, Сања; Ивковић, Бранка; Радивојевић, Јелена; Никодиновић-Рунић, Јасмина; Ђокић, Лидија; Јовановић, Предраг; Васиљевић, Бранка; Маслак, Веселин; Савић, Владимир;
dc.citation.volume60
dc.citation.spage16
dc.citation.epage23
dc.citation.other60: 16-23
dc.citation.rankM22
dc.identifier.wos000337014300003
dc.identifier.doi10.1016/j.enzmictec.2014.03.010
dc.identifier.pmid24835095
dc.identifier.scopus2-s2.0-84903370994
dc.identifier.rcubconv_3094
dc.type.versionpublishedVersion


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