Efficient synthesis of Guanfu base G via highly regioselective lipase-catalyzed acylation in non-aqueous phase

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• 作者：Ye Xia^a ; Ji-Hua Liu^a ; ^{jihualiu88@163.com} ; Jing-Han Liu^c ; Bo-Yang Yu^b ; ^{boyangyu59@163.com}
• 关键词：Guanfu base G ; Vinyl acetate ; Lipases ; Acylation
• 刊名：Bioorganic and Medicinal Chemistry Letters
• 出版年：2012
• 期刊代码：10_0960894x
• 类别：ch
• 出版时间：1 May, 2012
• 卷：22
• 期：9
• 页码：3100-3103
• 文件大小：441 K

摘要

Lipase-catalyzed acylation of Guanfu alcohol-amine (GFAA) with vinyl acetate (VA) was performed in non-aqueous system for the preparation of Guanfu base G (GFG), a plant-originated alkaloid with significant antiarrhythmic activity. Among the eight lipases from different origins, Novozym 435 was found to be the best biocatalyst. The most suitable molecular sieve amount, substrate concentration, molar ratio of VA to GFAA, enzyme amount and reaction temperature were proved to be 40 mg/mL, 6 渭mol/mL, 10:1, 2 mg/mL and 50 掳C, respectively. A maximum GFG yield of 37.4%was achieved under the selected conditions with methanol served as the optimal reaction medium. The structure of the acetylated product was elucidated by ¹H NMR and ¹³C NMR analysis.