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Citation: Yan Qianqian, Wu Lidan, Zeng Zhihong, Zeng Nan. Study on Reaction Mechanism of N⁶, N⁶-Dimethyladenine and Hydroxyl Radical[J]. Chemistry, ;2020, 83(3): 265-271. shu

Study on Reaction Mechanism of N⁶, N⁶-Dimethyladenine and Hydroxyl Radical

School of Chemistry and Environmental Science, Shangrao Normal University, Shangrao, 334001

Corresponding author: Wu Lidan, wulidan1987@iccas.ac.cn
Received Date: 18 October 2019
Accepted Date: 20 December 2019

Figures(7)

N⁶, N⁶-Dimethyladenine (DMAP) is component of biomolecules and plays important roles in determining the activity and conformational properties of biomolecules. Hydroxyl radical (·OH) can react with DMAP to change its structure and influence its biological function. It is necessary to understand how DMAP reacts with·OH. In this paper, reaction mechanisms of DMAP and·OH have been investigated using theoretical calculations. Based on the stability of reaction energy barrier and product, the most likely reaction of DMAP and·OH is N(6) methyl H abstraction, N(9)H abstraction and C(8) addition. Methylation on N(6) improves the reactivity of adenine, and affects its reaction mechanism with·OH.
- ·OH,
- N⁶, N⁶-dimethyladenine,
- Reaction mechanism,
- Addition reaction,
- H abstraction reaction
1. [1]
  Brockes J P, Brown P R, Murray K. J. Mol. Biol., 1974, 88(2):437~443.
2. [2]
  Marinus M G, Morris N R. J. Mol. Biol., 1974, 85(2):309~322.
3. [3]
  Saneyoshi M, Harada F, Nishimura S. Biochim. Biophys. Acta, 1969, 190(2):264~273.
4. [4]
  Nishimuka S. Prog. Nucl. Acid Res. Mol. Biol., 1972, 12:49~85.
5. [5]
  Wainfan E, Landsberg B. Biochem. Pharmacol., 1973, 22(4):493~500.
6. [6]
  Grindey G B, Divekar A Y, Hakala M T. Cancer Res., 1973, 33(10):2459~2463.
7. [7]
  Vieira A J S C, Steenken S. J. Phys. Chem., 1987, 91(15):4138~4144.
8. [8]
  Gonzalez C, Schlegel H B. J. Phys. Chem., 1990, 94(14):5523~5527.
9. [9]
  Mennucci B, Tomasi J. J. Chem. Phys., 1997, 106(12):5151~5158.
10. [10]
  Frisch M J, Trucks G W, Schlegel H B, et al. Gaussian 03, revision B.03. Wallingford, CT: Gaussian, Inc., 2004, 3~5.
11. [11]
  Cheng Q Y, Gu J D, Compaan K R, et al. Chem. Eur. J., 2010, 16(39):11848~11858.
12. [12]
  Wu X N, Zhao Y X, Xue W, et al. Phys. Chem. Chem. Phys., 2010, 12(16):3984~3997.
13. [13]
  Zhao Y X, Wu X N, Ma J B, et al. J. Phys. Chem. C, 2010, 114(28):12271~12279.
14. [14]
15. [15]
1. [1]
  Jiajie Li , Xiaocong Ma , Jufang Zheng , Qiang Wan , Xiaoshun Zhou , Yahao Wang . Recent Advances in In-Situ Raman Spectroscopy for Investigating Electrocatalytic Organic Reaction Mechanisms. University Chemistry, 2025, 40(4): 261-276. doi: 10.12461/PKU.DXHX202406117
2. [2]
  Ronghao Zhao , Yifan Liang , Mengyao Shi , Rongxiu Zhu , Dongju Zhang . Investigation into the Mechanism and Migratory Aptitude of Typical Pinacol Rearrangement Reactions: A Research-Oriented Computational Chemistry Experiment. University Chemistry, 2024, 39(4): 305-313. doi: 10.3866/PKU.DXHX202309101
3. [3]
  Wentao Lin , Wenfeng Wang , Yaofeng Yuan , Chunfa Xu . Concerted Nucleophilic Aromatic Substitution Reactions. University Chemistry, 2024, 39(6): 226-230. doi: 10.3866/PKU.DXHX202310095
4. [4]
  Hongting Yan , Aili Feng , Rongxiu Zhu , Lei Liu , Dongju Zhang . Reexamination of the Iodine-Catalyzed Chlorination Reaction of Chlorobenzene Using Computational Chemistry Methods. University Chemistry, 2025, 40(3): 16-22. doi: 10.12461/PKU.DXHX202403010
5. [5]
  Aili Feng , Xin Lu , Peng Liu , Dongju Zhang . Computational Chemistry Study of Acid-Catalyzed Esterification Reactions between Carboxylic Acids and Alcohols. University Chemistry, 2025, 40(3): 92-99. doi: 10.12461/PKU.DXHX202405072
6. [6]
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7. [7]
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8. [8]
  Jiabo Huang , Quanxin Li , Zhongyan Cao , Li Dang , Shaofei Ni . Elucidating the Mechanism of Beckmann Rearrangement Reaction Using Quantum Chemical Calculations. University Chemistry, 2025, 40(3): 153-159. doi: 10.12461/PKU.DXHX202405172
9. [9]
  Yue Zhao , Yanfei Li , Tao Xiong . Copper Hydride-Catalyzed Nucleophilic Additions of Unsaturated Hydrocarbons to Aldehydes and Ketones. University Chemistry, 2024, 39(4): 280-285. doi: 10.3866/PKU.DXHX202309001
10. [10]
  Weina Wang , Lixia Feng , Fengyi Liu , Wenliang Wang . Computational Chemistry Experiments in Facilitating the Study of Organic Reaction Mechanism: A Case Study of Electrophilic Addition of HCl to Asymmetric Alkenes. University Chemistry, 2025, 40(3): 206-214. doi: 10.12461/PKU.DXHX202407022
11. [11]
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12. [12]
  Tongyan Yu , Pan Xu . Visible-Light Photocatalyzed Radical Rearrangement Reaction. University Chemistry, 2025, 40(7): 169-176. doi: 10.12461/PKU.DXHX202409070
13. [13]
  Peng YUE , Liyao SHI , Jinglei CUI , Huirong ZHANG , Yanxia GUO . Effects of Ce and Mn promoters on the selective oxidation of ammonia over V₂O₅/TiO₂ catalyst. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 293-307. doi: 10.11862/CJIC.20240210
14. [14]
  Zhongyan Cao , Shengnan Jin , Yuxia Wang , Yiyi Chen , Xianqiang Kong , Yuanqing Xu . Advances in Highly Selective Reactions Involving Phenol Derivatives as Aryl Radical Precursors. University Chemistry, 2025, 40(4): 245-252. doi: 10.12461/PKU.DXHX202405186
15. [15]
  Qian Huang , Zhaowei Li , Jianing Zhao , Ao Yu . Quantum Chemical Calculations Reveal the Details Below the Experimental Phenomenon. University Chemistry, 2024, 39(3): 395-400. doi: 10.3866/PKU.DXHX202309018
16. [16]
  Yong Wang , Yingying Zhao , Boshun Wan . Analysis of Organic Questions in the 37th Chinese Chemistry Olympiad (Preliminary). University Chemistry, 2024, 39(11): 406-416. doi: 10.12461/PKU.DXHX202403009
17. [17]
  Zihan Lin , Wanzhen Lin , Fa-Jie Chen . Electrochemical Modifications of Native Peptides. University Chemistry, 2025, 40(3): 318-327. doi: 10.12461/PKU.DXHX202406089
18. [18]
  Lancanghong Chen , Xingtai Yu , Tianlei Zhao , Qizhi Yao . Exploration of Abnormal Phenomena in Iodometric Copper Quantitation Experiment. University Chemistry, 2025, 40(7): 315-320. doi: 10.12461/PKU.DXHX202408089
19. [19]
  Mingyang Men , Jinghua Wu , Gaozhan Liu , Jing Zhang , Nini Zhang , Xiayin Yao . Sulfide Solid Electrolyte Synthesized by Liquid Phase Approach and Application in All-Solid-State Lithium Batteries. Acta Physico-Chimica Sinica, 2025, 41(1): 100004-0. doi: 10.3866/PKU.WHXB202309019
20. [20]
  Danqing Wu , Jiajun Liu , Tianyu Li , Dazhen Xu , Zhiwei Miao . Research Progress on the Simultaneous Construction of C—O and C—X Bonds via 1,2-Difunctionalization of Olefins through Radical Pathways. University Chemistry, 2024, 39(11): 146-157. doi: 10.12461/PKU.DXHX202403087