Molecules 2012, 17(9), 10864-10874; doi:10.3390/molecules170910864
Article

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

1 Center of General Surgery, the Second Hospital of Jilin University, Changchun 130041, China 2 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
(This article belongs to the Section Organic Synthesis)
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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.

AMA 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(9):10864-10874.

Chicago/Turabian Style

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.

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