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

(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 dr...

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Detalles Bibliográficos
Autores principales: Wang, Feng, Zhang, Hong, Wang, Jiaxin, Chen, Ge, Fang, Xuedong, Wang, Zhi, Wang, Lei
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2012
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6268847/
https://www.ncbi.nlm.nih.gov/pubmed/22964502
http://dx.doi.org/10.3390/molecules170910864
Descripción
Sumario:(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).