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Multiple Reaction Products from the Hydrolysis of Chiral and Prochiral Organophosphate Substrates by the Phosphotriesterase from Sphingobium sp. TCM1
Biochemistry ( IF 2.9 ) Pub Date : 2018-03-07 00:00:00 , DOI: 10.1021/acs.biochem.8b00145 Andrew N. Bigley 1 , Tamari Narindoshvili 1 , Dao Feng Xiang 1 , Frank M. Raushel 1
Biochemistry ( IF 2.9 ) Pub Date : 2018-03-07 00:00:00 , DOI: 10.1021/acs.biochem.8b00145 Andrew N. Bigley 1 , Tamari Narindoshvili 1 , Dao Feng Xiang 1 , Frank M. Raushel 1
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The phosphotriesterase from Sphingobium sp. TCM1 (Sb-PTE) is notable for its ability to hydrolyze organophosphates that are not substrates for other enzymes. In an attempt to determine the catalytic properties of Sb-PTE for hydrolysis of chiral phosphotriesters, we discovered that multiple phosphodiester products are formed from a single substrate. For example, Sb-PTE catalyzes the hydrolysis of the RP-enantiomer of methyl cyclohexyl p-nitrophenyl phosphate with exclusive formation of methyl cyclohexyl phosphate. However, the enzyme catalyzes hydrolysis of the SP-enantiomer of this substrate to an equal mixture of methyl cyclohexyl phosphate and cyclohexyl p-nitrophenyl phosphate products. The ability of this enzyme to catalyze the hydrolysis of a methyl ester at the same rate as the hydrolysis of a p-nitrophenyl ester contained within the same substrate is remarkable. The overall scope of the stereoselective properties of this enzyme is addressed with a library of chiral and prochiral substrates.
中文翻译：
鞘氨醇单胞菌的磷酸三酯酶水解手性和手性有机磷酸酯底物的多种反应产物。中药1
鞘氨醇单胞菌属的磷酸三酯酶。TCM1（Sb -PTE）以其水解不是其他酶底物的有机磷酸酯的能力而著称。为了确定Sb- PTE催化手性磷酸三酯水解的催化性能，我们发现从单个底物形成多个磷酸二酯产物。例如，Sb- PTE催化甲基环己基对硝基苯基磷酸酯的R P-对映异构体的水解，而仅形成甲基环己基磷酸酯。然而，该酶催化S P的水解该底物的β-对映异构体与甲基环己基磷酸酯和环己基对硝基苯基磷酸酯产物的均等混合物。该酶以与包含在同一底物中的对硝基苯基酯的水解相同的速率催化甲酯水解的能力是显着的。该酶的立体选择性性质的整体范围通过手性和前手性底物库解决。
更新日期：2018-03-07
中文翻译：
鞘氨醇单胞菌的磷酸三酯酶水解手性和手性有机磷酸酯底物的多种反应产物。中药1
鞘氨醇单胞菌属的磷酸三酯酶。TCM1（Sb -PTE）以其水解不是其他酶底物的有机磷酸酯的能力而著称。为了确定Sb- PTE催化手性磷酸三酯水解的催化性能，我们发现从单个底物形成多个磷酸二酯产物。例如，Sb- PTE催化甲基环己基对硝基苯基磷酸酯的R P-对映异构体的水解，而仅形成甲基环己基磷酸酯。然而，该酶催化S P的水解该底物的β-对映异构体与甲基环己基磷酸酯和环己基对硝基苯基磷酸酯产物的均等混合物。该酶以与包含在同一底物中的对硝基苯基酯的水解相同的速率催化甲酯水解的能力是显着的。该酶的立体选择性性质的整体范围通过手性和前手性底物库解决。
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