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MATERIALS SCIENCE FORUM · 2020 · IF 0

Resolution of 1-Methyl-3-Amphetamine by Magnetic Fe3O4-APTES-CS2- Lipase in a Non-Aqueous Solvent

Hong Qian Dai,Yuan Lu,Zhi Hin Ou,Min Xu

Fe3O4-APTES-CS2 was prepared by modification of Fe3O4 with 3-aminopropyltriethoxysilane (APTES) and carbon disulfide (CS2). Lipase was covalently bonded to Fe3O4-APTES-CS2 to obtain the immobilized lipase Fe3O4-APTES-CS2-lipase. The textural characteristic of Fe3O4-APTES-CS2-lipase was assessed by scanning electron microscopy. The optimal immobilization conditions were 2.5 mg/mL lipase, pH 7.0, 35 °C, 3 h. The loading amount of lipase was 119.0 mg/g carrier. The immobilization efficiency reached 57%. (R)-(+)-N-acetyl-1-methyl-3-amphetamine was synthesized by Fe3O4-APTES-CS2-Li- pase. The conversion, enantiomeric excess of (R)-(+)-N-acetyl-1-methyl-3-amphet-a- mine and E value reached 36.8%, 98.5% and 132, respectivel.

研究领域: 化学 · 生物化学 · 材料科学 · 催化

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BIOCATALYSIS AND BIOTRANSFORMATION · 2021 · IF 2.181

Efficient enantiomer selective acetylation of 1-methyl-3-phenylpropylamine by Fe3O4-APTES-CS2-lipase magnetic nanoparticles in an alternating magnetic field

Hongqian Dai,Yuan Lu,Hanbing Shi,Lan Tang,Xingyuan Sun,Zhimin Ou

Fe3O4 magnetic nanoparticles were prepared by chemical co-precipitation and modified with 3-aminopropyltriethoxysilane (APTES) and CS2 to form Fe3O4-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 Fe3O4-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 Fe3O4-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.

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Resolution of 1-Methyl-3-Amphetamine by Magnetic Fe3O4-APTES-CS2- Lipase in a Non-Aqueous Solvent

Efficient enantiomer selective acetylation of 1-methyl-3-phenylpropylamine by Fe3O4-APTES-CS2-lipase magnetic nanoparticles in an alternating magnetic field