Abstract Chiral 1-phenylethanol and its ester derivative are important chiral chemicals in diverse industries and the preparation of those optically pure enantiomers is of great importance. One bacterium, Bacillus sp. DL-2, whose extracellular proteases could efficiently asymmetrically hydrolyse (±)-1-phenylethyl acetate, was isolated from the deep sea of the Western Pacific. After the immobilization of extracellular proteases and the optimization of enzymatic reactions, (R)-1-phenylethanol was prepared with the enantiomeric excess (e.e.) being 97% and the yield being 41%, respectively. The optimal resolution reaction condition for the preparation of (R)-1-phenylethanol using immobilized extracellular proteases was found to be 5-mM (±)-1-phenylethyl acetate, 360 mg/mL immobilized extracellular proteases, pH 6.5, and 20 °C for 2 h. (S)-1-phenylethyl acetate was generated through enzymatic kinetic resolution with the e.e. being as high as 99% and the yield being 71%, respectively. The optimal resolution reaction condition for the preparation of (S)-1-phenylethyl acetate was found to be 2.5-mM (±)-1-phenylethyl acetate, 440 mg/mL immobilized extracellular proteases, pH 7.5, and 35 °C for 10 h. Our report is the first report about the kinetic resolution of (±)-1-phenylethyl acetate using proteases and the enantio-preference of the proteases was found to be the same as those of most other esterases/lipases. Also notably, the optical purity of (S)-1-phenylethyl acetate generated through kinetic resolution using the proteases of Bacillus sp. DL-2 was the highest report so far. Proteases from deep-sea Bacillus sp. DL-2 are new contributions to the biocatalyst library for the preparation of valuable chiral alcohols and chiral esters through kinetic resolution.

中文翻译：

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深海细菌芽孢杆菌胞外蛋白酶对 (±)-1-苯基乙酸乙酯的对映选择性拆分。DL-2

摘要 手性1-苯基乙醇及其酯衍生物是各行各业中重要的手性化学品，其光学纯对映体的制备具有重要意义。一种细菌，芽孢杆菌。DL-2 的胞外蛋白酶可以有效地不对称水解 (±)-1-苯乙酸乙酯，是从西太平洋深海中分离出来的。通过胞外蛋白酶的固定化和酶促反应的优化，制备了(R)-1-苯基乙醇，对映体过量(ee)分别为97%和41%。发现使用固定化胞外蛋白酶制备 (R)-1-苯基乙醇的最佳拆分反应条件为 5-mM (±)-1-苯乙酸乙酯、360 mg/mL 固定化胞外蛋白酶、pH 6.5 和 20° C 2 小时。(S)-1-苯乙酸乙酯通过酶动力学拆分产生，ee分别高达99%和71%。发现制备 (S)-1-苯乙酸乙酯的最佳拆分反应条件为 2.5-mM (±)-1-苯乙酸乙酯、440 mg/mL 固定化胞外蛋白酶、pH 7.5 和 35 °C 10 H。我们的报告是关于使用蛋白酶对 (±)-1-苯基乙酸乙酯进行动力学拆分的第一份报告，并且发现蛋白酶的对映体偏好与大多数其他酯酶/脂肪酶的相同。同样值得注意的是，(S)-1-苯基乙酸乙酯的光学纯度通过使用芽孢杆菌蛋白酶的动力学拆分产生。DL-2 是迄今为止最高的报告。来自深海芽孢杆菌的蛋白酶。