Efficient enantiomer selective acetylation of 1-methyl-3-phenylpropylamine by Fe3O4-APTES-CS2-lipase magnetic nanoparticles in an alternating magnetic field. Issue 2 (4th March 2022)

• Record Type: Journal Article
• Authors: Dai, Hongqian; Lu, Yuan; Shi, Hanbing; Tang, Lan; Sun, Xingyuan; Ou, Zhimin
• Is Part Of: Biocatalysis and biotransformation. Volume 40:Issue 2(2022)
• Page Start: 107
• Page End: 120
• Publication Date: 2022-03-04
• Subjects: Alternating magnetic field -- Fe3O4-APTES-CS2-lipase -- organic solvents -- resolution of racemic 1-methyl-3-phenylpropylamine -- (R)-N-acetyl-1-methyl-3-amphetamine; Enzymes -- Biotechnology -- Periodicals; Enzymes -- Industrial applications -- Periodicals; Biotransformation (Metabolism) -- Periodicals; 660.63
• DOI: 10.1080/10242422.2021.1884230
• Languages: English
• ISSNs: 1024-2422

Abstract

Abstract: Fe3 O4 magnetic nanoparticles were prepared by chemical co-precipitation and modified with 3-aminopropyltriethoxysilane (APTES) and CS2 to form Fe3 O4 -APTES-CS2 magnetic carriers. Magnetically immobilized enzymes are attractive owing to their potential applications in many biological fields. When an alternating magnetic field is applied, the magnetic nanoparticles experience a force in the direction of the field, and the magnetic moments of the magnetic nanoparticles are apt to align in the direction of the field. Thus, magnetic nanoparticles behave like microscopic stirrers. The optimal reaction conditions of the acylation reaction using Fe3 O4 -APTES-CS2 -lipase were 200 mmol/L 1-methyl-3-amphetamine, 100 mg immobilized lipase, 200 μL ethyl acetate, 12.6 × g rotating speed, 40 °C, and 5 days in the shaker. The conversion and enantiomeric excess of R-2a reached a maximum of 36.8% and 98.5%, respectively. 1-Methyl-3-phenylpropylamine was resolved using Fe3 O4 -APTES-CS2 -lipase in an alternating magnetic field. The optimal magnetic field frequency and magnetic field intensity were determined to be 500 Hz and 12 Gs, respectively. The conversion and enantiomeric excess of R-2a reached a maximum of 40.3% and 98.5%, respectively. The results revealed that conversion under a magnetic field was significantly higher than that without a magnetic field. Highly optically active (R)-N-acetyl-1-methyl-3-amphetamine can be obtained via an efficient resolution of racemic 1-methyl-3-phenylpropylamine with immobilized lipase magnetic nanoparticles as a catalyst and ethyl acetate as an acyl donor in organic solvents in an alternating magnetic field.