Lipase-Catalyzed Regioselective Monoacetylation of Unsymmetrical 1,5-Primary Diols
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- 作者：Camille Oger ; Zsuzsanna Marton ; Yasmin Brinkmann ; Valrie Bultel-Ponc ; Thierry Durand ; Marianne Graber ; Jean-Marie Galano
- 刊名：Journal of Organic Chemistry
- 出版年：2010
- 出版时间：March 19, 2010
- 年：2010
- 卷：75
- 期：6
- 页码：1892-1897
- 全文大小：846K
- 年卷期：v.75,no.6(March 19, 2010)
- ISSN：1520-6904
文摘
Lipase B from Candida antarctica (CALB) has been selected as the most suitable enzyme to catalyze the regioselective monoacetylation of 1,5-diol isoprostane intermediate, using vinyl acetate as an acyl transfer reagent in THF. We next applied this reaction on linear 2-substituted, 2,2′-disubstituted-1,5-pentanediols, and cyclic 2,3-disubstituted-1,5-pentanediols. To rationalize the regioselectivity observed, molecular docking simulations were performed.