Ultrasound Irradiation Promoted Enzymatic Transesterification of (R/S)-1-Chloro-3-(1-naphthyloxy)-2-propanol

Molecules

Feng Wang¹  Hong Zhang¹  Jiaxin Wang¹  Ge Chen¹  Xuedong Fang¹  Zhi Wang¹ 

[1] ¹Center of General Surgery, the Second Hospital of Jilin University, Changchun 130041, China ²Key Laboratory of Molecular Enzymology and Engineering of Ministry of Education, College of Life Sciences, Jilin University, Changchun 130023, China

关键词: propranolol;    1-chloro-3-(1-naphthyloxy)-2-propanol;    lipase;    transesterification;    ultrasound;   

DOI  :  10.3390/molecules170910864

来源: mdpi

【 摘 要 】

(R)-1-Chloro-3-(1-naphthyloxy)-2-propanol (3), which is the key intermediate of (S)-propranolol, was successfully prepared via enantioselective transesterification catalyzed by lipase under ultrasound irradiation. Compared with conventional shaking, the enzyme activity and enantioselectivity were dramatically increased under ultrasound exposure. Effects of various reaction conditions on the synthetic activity of enzyme as well as enantioselectivity, including the type of enzyme, ultrasound power, solvent, acyl donor, temperature and substrate molar ratio, were investigated. Pseudomonas sp. lipase (PSL) showed an excellent catalytic performance under optimum conditions (enzyme activity: 78.3 ± 3.2 μmol·g⁻¹·min⁻¹, E value: 98 ± 6).

【 授权许可】

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This is an open access article distributed under the Creative Commons Attribution License (CC BY) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.