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Issue 105, 2014
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Synthesis of γ-nitroaldehydes containing quaternary carbon in the α-position using a 4-oxalocrotonate tautomerase whole-cell biocatalyst

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Abstract

Synthesis of γ-nitroaldehydes from branched chain aldehydes and a range of α,β-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 γ-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 α,α-substituted γ-nitroaldehydes was compared to the organocatalytic approach involving the lithium salt of phenylalanine as a catalyst. As the resulting γ-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.

Graphical abstract: Synthesis of γ-nitroaldehydes containing quaternary carbon in the α-position using a 4-oxalocrotonate tautomerase whole-cell biocatalyst

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The article was received on 09 Jun 2014, accepted on 04 Nov 2014 and first published on 06 Nov 2014


Article type: Paper
DOI: 10.1039/C4RA05517A
Author version available: Download Author version (PDF)
Citation: RSC Adv., 2014,4, 60502-60510
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    Synthesis of γ-nitroaldehydes containing quaternary carbon in the α-position using a 4-oxalocrotonate tautomerase whole-cell biocatalyst

    J. Radivojevic, G. Minovska, L. Senerovic, K. O'Connor, P. Jovanovic, V. Savic, Z. Tokic-Vujosevic, J. Nikodinovic-Runic and V. Maslak, RSC Adv., 2014, 4, 60502
    DOI: 10.1039/C4RA05517A

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