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A Laccase Heterogeneous Magnetic Fibrous Silica‐Based Biocatalyst for Green and One‐Pot Cascade Synthesis of Chromene Derivatives
Author(s) -
MogharabiManzari Mehdi,
Ghahremani Mohammad Hossein,
Sedaghat Tabassom,
Shayan Fatemeh,
Faramarzi Mohammad Ali
Publication year - 2019
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201801784
Subject(s) - laccase , chemistry , biocatalysis , catalysis , one pot synthesis , nuclear chemistry , green chemistry , magnetic nanoparticles , heterogeneous catalysis , scanning electron microscope , redox , nanoparticle , organic chemistry , chemical engineering , reaction mechanism , enzyme , physics , quantum mechanics , engineering
Green cascade approaches, which utilize sustainable and recyclable heterogeneous biocatalysts, can be used in the catalysis of multicomponent organic reactions to synthesize biologically important substances. Three magnetic nanoparticles, iron (II, III) oxide, cobalt ferrite, and nickel ferrite, were prepared by co‐precipitation and functionalized with fibrous silica (KCC‐1), and characterized by scanning electron microscopy (SEM), X‐ray diffraction (XRD), and vibrating sample magnetometry (VSM). Laccase immobilized on CoFe 2 O 4 ‐KCC‐1 was used as a heterogeneous biocatalyst for green and one‐pot cascade synthesis of 2‐amino‐5‐oxo‐4‐aryl‐4 H ,5 H ‐pyrano[3,2‐ c ]chromene‐3‐carbonitriles. The reaction was performed in the presence of 2,2,6,6‐tetramethylpiperidine‐1‐oxyl (TEMPO) as a synthetic redox mediator. The optimum reaction conditions were found to be as immobilized laccase (100 mg, 95 U) and TEMPO (2 mol‐%) in a 100 m m sodium citrate buffer (pH 4.5), 40 °C, and incubation time 17 h. About 80 % of initial activity of the immobilized laccase was retained after 15 independent runs.