Chiroptical properties of artemisinin and artemether investigated using time-dependent density functional theory  

作　　者：Li Li Bei-Bei Yang Yi-Kang Si 

机构地区：[1]Beijing Key Laboratory of Active Substances Discovery and Druggability Evaluation,Institute of Materia Medica,Chinese Academy of Medical Sciences Peking Union Medical College

出　　处：《Chinese Chemical Letters》2014年第12期1586-1590,共5页中国化学快报（英文版）

基　　金：supported by the Fundamental Research Funds for the Central Institutes of China(No.2012ZD03)

摘　　要：Chiroptical properties including electronic circular dichroism（ECD） and optical rotatory dispersion（ORD） of artemisinin and artemether have been fully studied using quantum-chemical calculation based on time-dependent density functional theory.Both theoretical ECD and ORD of these two compounds were in good match with the experimental data.ECD spectrum of artemether could be totally attributed to the peroxide group,and that of artemisinin was an overlay of contribution from δ-lactone and peroxide moieties,which leading to a positive maximum at 260 nm.Our results showed that peroxide group could produce a broad ECD band in the far-UV region originated from electron transitions of HOMO →LUMO,HOMO-1 →LUMO and HOMO-2 →LUMO in the case of artemether.This work provided a theoretical interpretation of the ECD behavior of peroxide bond.Chiroptical properties including electronic circular dichroism（ECD） and optical rotatory dispersion（ORD） of artemisinin and artemether have been fully studied using quantum-chemical calculation based on time-dependent density functional theory.Both theoretical ECD and ORD of these two compounds were in good match with the experimental data.ECD spectrum of artemether could be totally attributed to the peroxide group,and that of artemisinin was an overlay of contribution from δ-lactone and peroxide moieties,which leading to a positive maximum at 260 nm.Our results showed that peroxide group could produce a broad ECD band in the far-UV region originated from electron transitions of HOMO →LUMO,HOMO-1 →LUMO and HOMO-2 →LUMO in the case of artemether.This work provided a theoretical interpretation of the ECD behavior of peroxide bond.

关 键 词：Chiroptical properties Artemisinin Peroxide group Absolute configuration Time-dependent density functional theory 

分 类 号：TQ460.1[化学工程—制药化工] O621.2[理学—有机化学]