College of Biological and Environmental Engineering, Zhejiang University of Technology, Hangzhou 310014, China.
Molecules. 2014 Jun 16;19(6):8067-79. doi: 10.3390/molecules19068067.
A newly isolated Galactomyces geotrichum ZJUTZQ200 strain containing an epoxide hydrolase was used to resolve racemic ethyl 3-phenylglycidate (rac-EPG) for producing (2R,3S)-ethyl-3-phenylglycidate ((2R,3S)-EPG). G. geotrichum ZJUTZQ200 was verified to be able to afford high enantioselectivity in whole cell catalyzed synthesis of this chiral phenylglycidate synthon. After the optimization of the enzymatic production and bioresolution conditions, (2R,3S)-EPG was afforded with high enantioselectivity (e.e.S > 99%, E > 49) after a 8 h reaction. The co-solvents, pH buffer solutions and substrate/cell ratio were found to have significant influences on the bioresolution properties of G. geotrichum ZJUTZQ200. Based on the bioresolution product (2R,3S)-EPG, taxol's side chain ethyl (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropionate was successfully synthesized by a chemoenzymatic route with high enantioselectivity (e.e.S > 95%).
一株新分离的含有环氧化物水解酶的酒香酵母（Galactomyces geotrichum）ZJUTZQ200 菌株被用于拆分外消旋的 3-苯基缩水甘油酸乙酯（rac-EPG）以生成（2R，3S）-3-苯基缩水甘油酸乙酯（（2R，3S）-EPG）。证明酒香酵母 ZJUTZQ200 能够在全细胞催化合成这种手性苯甘氨酸合成子中提供高对映选择性。在优化酶法生产和生物拆分条件后，经过 8 小时反应，（2R，3S）-EPG 以高对映选择性（ee.S＞99%，E＞49）获得。共溶剂、pH 缓冲溶液和底物/细胞比被发现对酒香酵母 ZJUTZQ200 的生物拆分性质有显著影响。基于生物拆分产物（2R，3S）-EPG，通过化学酶法以高对映选择性（ee.S＞95%）成功合成了紫杉醇的侧链乙基（2R，3S）-3-苯甲酰氨基-2-羟基-3-苯基丙酸酯。
