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Ultrasound Irradiation Promoted Enzymatic Transesterification of (R/S)-1-Chloro-3-(1-naphthyloxy)-2-propanol
Center of General Surgery, the Second Hospital of Jilin University, Changchun 130041, China
Key Laboratory of Molecular Enzymology and Engineering of Ministry of Education, College of Life Sciences, Jilin University, Changchun 130023, China
* Authors to whom correspondence should be addressed.
Received: 15 June 2012; in revised form: 13 August 2012 / Accepted: 4 September 2012 / Published: 10 September 2012
Abstract: (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).
Keywords: propranolol; 1-chloro-3-(1-naphthyloxy)-2-propanol; lipase; transesterification; ultrasound
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MDPI and ACS Style
Wang, F.; Zhang, H.; Wang, J.; Chen, G.; Fang, X.; Wang, Z.; Wang, L. Ultrasound Irradiation Promoted Enzymatic Transesterification of (R/S)-1-Chloro-3-(1-naphthyloxy)-2-propanol. Molecules 2012, 17, 10864-10874.
Wang F, Zhang H, Wang J, Chen G, Fang X, Wang Z, Wang L. Ultrasound Irradiation Promoted Enzymatic Transesterification of (R/S)-1-Chloro-3-(1-naphthyloxy)-2-propanol. Molecules. 2012; 17(9):10864-10874.
Wang, Feng; Zhang, Hong; Wang, Jiaxin; Chen, Ge; Fang, Xuedong; Wang, Zhi; Wang, Lei. 2012. "Ultrasound Irradiation Promoted Enzymatic Transesterification of (R/S)-1-Chloro-3-(1-naphthyloxy)-2-propanol." Molecules 17, no. 9: 10864-10874.