Acta Phys. -Chim. Sin. ›› 2013, Vol. 29 ›› Issue (09): 1937-1944.doi: 10.3866/PKU.WHXB201307023

• THEORETICAL AND COMPUTATIONAL CHEMISTRY • Previous Articles     Next Articles

Radicals Created fromthe Reactions of 2’-Deoxyadenosine-5’-monophosphate with Hydroxyl Radical

HOU Ruo-Bing1, TANG Zong-Xiang2, FAN You-Jun1, YI Xiang-Hui3, WANG Bei-Bei1, SUN Yan-Li1   

  1. 1 College of Chemistry and Chemical Engineering, Guangxi Normal University, Guilin 541004, Guangxi Province, P. R. China;
    2 College of Basic Medicine, Nanjing University of Chinese Medicine, Nanjing 210046, P. R. China;
    3 Guilin Normal College, Guilin 541002, Guangxi Province, P. R. China
  • Received:2013-05-08 Revised:2013-07-01 Published:2013-08-28
  • Contact: HOU Ruo-Bing E-mail:rbhou@163.com
  • Supported by:

    The project was supported by the National Natural Science Foundation of China (31271181, 21263002), Natural Science Foundation of Jiangsu Province, China (BK2011811), and Guangxi Natural Science Foundation, China (2013GXNSFAA019024).

Abstract:

The radicals generated fromreactions of 2'-deoxyadenosine-5'-monophosphate (dAMP) with an HO· radical were studied by the reliable B3LYP/DZP++ method. The results show that the initial primary products are the radicals of HO· addition at the C8 and C4 sites of dAMP and those of dehydrogenation from the NH2 moiety of dAMP. Moreover, the initial radicals of the C4 site adducts of HO· tend thermodynamically to take place dehydration reactions that yields strong oxidizing, H-abstraction radicals fromthe NH2 group of dAMP. The electrostatic repeller interaction between the dAMP molecule and HO· results in HO· addition radicals of the C2 atomof dAMP to be a by-product, even if they are relative stable species. These theoretical results agree well with available experimental observations and give proper explanations for some experimental results.

Key words: 2’-Deoxyadenosine-5’-monophosphate, Hydroxyl radical, Addition reaction, Hydrogen abstraction reaction

MSC2000: 

  • O641