猪胰脂肪酶催化外消旋P-手性α-羟基磷酸酯类化合物的动力学拆分

doi:10.6023/cjoc202212005

摘要/Abstract

酶催化具有高效、高选择性以及反应条件温和等优点, 已经成为有机合成领域的重要方法. 研究了P-手性α-羟基磷(膦)酸酯类化合物的合成方法. 在猪胰脂肪酶的催化作用下, 外消旋α-羟基磷(膦)酸酯与乙酸乙烯酯之间能够顺利地发生酯交换反应, 以高达49%的产率和83%的ee值得到相应的手性产物, 且该反应在非常温和的条件下就能够进行. 同时, 在计算机的辅助下建立了酶-底物之间的结合模型, 通过对接的方法揭示了反应中酶催化对映选择性的机理.

关键词: 生物催化, 动力学拆分, 羟基磷酸酯, 猪胰脂肪酶

The development of enzyme-catalyzed methods for the synthesis of P-chiral phosphine derivatives has important implications. Herein this work presents a direct biocatalytic transesterification of racemic α-hydroxyphosphonates and vinyl acetate, which provides a rapid access to P-chiral hydroxymethylphosphonates. Catalyzed by lipase from porcine pancreas (PPL), which is commercially available, the reactions proceed efficiently with a wide array of reaction partners to deliver various tertiary phosphine oxides in up to 49% yield and 83% ee under very mild conditions. The enzyme-substrate binding mode was established and the high enantioselectivity of PPL was revealed through docking simulations.

Key words: biocatalytic, kinetic resolution, hydroxymethylphosphonates, lipase from porcine pancreas

引用此文

胡慧娟, 闫巧丽, 卢晓刚, 杨启帆, 裴承新, 王红梅, 高润利. 猪胰脂肪酶催化外消旋P-手性α-羟基磷酸酯类化合物的动力学拆分[J]. 有机化学, 2023, 43(8): 2815-2825.

Huijuan Hu, Qiaoli Yan, Xiaogang Lu, Qifan Yang, Chengxin Pei, Hongmei Wang, Runli Gao. Kinetic Resolution of Racemic P-Chiral α-Hydroxymethylphos-phonates Catalyzed by Lipase from Porcine Pancreas[J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2815-2825.

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