Jiangxi Key Laboratory of Organic Chemistry, Jiangxi Science and Technology Normal University, 605 Fenglin Avenue, Nanchang, Jiangxi 330013, PR China.
Bioorg Med Chem. 2013 Nov 1;21(21):6778-87. doi: 10.1016/j.bmc.2013.07.052. Epub 2013 Aug 8.
A novel and efficient strategy for the synthesis of phosphoramidon and its β anomer has been developed by manipulating the anomerization of α-l-rhamnose triacetate upon phosphitylation. The experimental results suggest that proton transfer, bond rotation, and N atom are the key factors for the anomerization. The determined Ki and Kd values establish that phosphoramidon prepared by this method possesses excellent biological activity, and indicate that the contacts of rhamnose moiety with the enzyme have limited contribution to the binding.
一种新颖有效的合成磷氨肽酶抑制剂及其β端异构体的方法已被开发出来，该方法通过操纵α-L-鼠李糖三乙酸酯的磷酸化异构化来实现。实验结果表明，质子转移、键旋转和 N 原子是异构化的关键因素。所确定的 Ki 和 Kd 值表明，通过该方法制备的磷氨肽酶抑制剂具有优异的生物活性，表明鼠李糖部分与酶的结合接触对结合的贡献有限。
