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Kinetics Study on Reaction between Dihydroartemisinic Acid and Singlet Oxygen: An Essential Step to Photochemical Synthesis of Artemisinin
Xian-wang Zhang1,2,3, Xuan Zhao2, Kun-hui Liu*2, Hong-mei Su*2
1.Beijing National Laboratory for Molecular Science, Institute of Chemistry, Chinese Academy of Science, Beijing 100190, China;2.College of Chemistry, Beijing Normal University, Beijing 100875, China;3.University of Chinese Academy of Sciences, Beijing 100049, China
Abstract:
Artemisinin is an excellent antimalarial drug widely used in clinical medicine. However, due to the limitation of natural source of artemisinin, the chemical synthesis of artemisinin has achieved substantial attention. Dihydroartemisinic acid is a key precursor for the synthesis of artemisinin. The reaction of dihydroartemisinic acid with singlet oxygen to form peroxide is a pivotal step in the photochemical preparation of artemisinin. Nevertheless, the reaction kinetics of dihydroartemisinic acid with singlet oxygen has not been investigated previously. Herein, we report the rate constants of the reaction between dihydroartemisinic acid and singlet oxygen. By directly detecting the luminescence decay kinetics of singlet oxygen at 1270 nm at room temperature, the reaction rate constants of singlet oxygen and dihydroartemisinic acid in different solvents are obtained to be 1.81×105 (mol/L)-1·s-1 in CCl4, 5.69×105 (mol/L)-1· s-1 in CH3CN, and 3.27×106 (mol/L)-1· s-1 in DMSO, respec-tively. It is found that the reaction rate constants of dihydroartemisinic acid with singlet oxygen increase as polarity of the solvent increases among the three solvents. These results provide fundamental knowledge to optimize experiment conditions of photochemical synthesis of artemisinin for improving the yields of artemisinin.
Key words:  Dihydroartemisinic acid, Artemisinin, Singlet oxygen, Rate constant, Transient absorption spectroscopy
FundProject:
附件
青蒿素光化学合成中二氢青蒿酸与单线态氧反应的动力学研究
张献旺1,2,3, 赵 璇2, 刘坤辉*2, 苏红梅*2
1.中国科学院化学研究所分子反应动力学国家重点实验室,北京 100190;2.北京师范大学化学学院,北京 100875;3.中国科学院大学,北京 100049
摘要:
青蒿素是一种优异的抗疟药,广泛用于临床医学. 但由于青蒿素天然来源的限制,青蒿素的化学合成一直受到高度关注. 二氢青蒿酸是合成青蒿素的关键前体. 二氢青蒿酸与单线态氧反应形成过氧化物是青蒿素光化学制备中的关键步骤,制约着青蒿素化学合成的产率. 然而关于二氢青蒿酸与单线态氧反应的重要动力学信息并未有报道. 本文通过光敏化法产生单线态氧,研究二氢青蒿酸与单线态氧之间的反应速率常数. 通过直接检测单线态氧在1270 nm处的发光衰减动力学,得出单线态氧与二氢青蒿酸在不同溶剂中的反应速率常数分别为:在CCl4中为1.81×105 (mol/L)-1·s-1,在CH3CN中为5.69×105 (mol/L)-1·s-1,DMSO中为3.27×106 (mol/L)-1·s-1. 发现在三种溶剂中二氢青蒿酸与单线态氧的反应速率常数随着溶剂极性的增加而增加. 这些结果为优化青蒿素光化学合成的实验条件提供了基础知识,有助于提高青蒿素的合成效率.
关键词:  二氢青蒿酸,青蒿素,单线态氧,反应速率常数,瞬态紫外-可见吸收光谱
DOI:10.1063/1674-0068/cjcp2002021
分类号: