Koszelewski Dominik, Zysk Małgorzata, Brodzka Anna, Żądło Anna, Paprocki Daniel, Ostaszewski Ryszard
Institute of Organic Chemistry PAS Kasprzaka 44/52, 01-224 Warsaw, Poland.
Org Biomol Chem. 2015 Dec 7;13(45):11014-20. doi: 10.1039/c5ob01380a. Epub 2015 Sep 18.
The application of tandem metal-enzyme dynamic kinetic resolution (DKR) is a powerful tool for the manufacture of high-value chemical commodities. A new protocol of kinetic resolution based on irreversible enzymatic esterification of carboxylic acids with orthoesters was introduced to obtain optically active β-hydroxy esters. This procedure was combined with metal catalyzed racemization of the target substrate providing both (R) and (S) enantiomers of ethyl 3-hydroxy-3-(4-nitrophenyl)propanoate with a high yield of 89% at 40 °C. A substantial influence of the enzyme type, organic co-solvent, and metal catalyst on the conversion and enantioselectivity of the enzymatic dynamic kinetic resolution was noted.
串联金属酶动态动力学拆分（DKR）的应用是生产高价值化学产品的有力工具。引入了一种基于羧酸与原酸酯的不可逆酶促酯化反应的动力学拆分新方案，以获得光学活性的β-羟基酯。该过程与金属催化的目标底物外消旋化相结合，在40℃下以89%的高产率提供了3-羟基-3-(4-硝基苯基)丙酸乙酯的(R)和(S)对映体。研究发现酶的类型、有机共溶剂和金属催化剂对酶促动态动力学拆分的转化率和对映选择性有重大影响。
