Citation: LIU Hai-Ying, MENG Fan-Cui, LI Ping, DING Shi-Liang. Effects of CH₃OH and NH₃ on the Hydrolytic Deamination Mechanismof Adenine[J]. Acta Physico-Chimica Sinica, ;2010, 26(11): 3067-3072. doi: 10.3866/PKU.WHXB20101106 shu

Effects of CH₃OH and NH₃ on the Hydrolytic Deamination Mechanismof Adenine

1.
1. School of Science, University of Jinan, Jinan 250022, P. R. China;
2Tianjin Institute of Pharmaceutical Research, Tianjin 300193, P. R. China;
3School of Physics, Shandong University, Jinan 250100, P. R. China

Received Date: 27 April 2010
Available Online: 13 September 2010
Fund Project: 山东省博士基金(2008BS02014) (2008BS02014)济南大学校基金(XKY0809)资助项目 (XKY0809)

The effects of CH₃OH and NH₃ on the hydrolytic deamination mechanism of adenine were studied by density functional theory at the B3LYP/6-311G(d,p) level. The results reveal that a tetrahedral intermediate is formed after a nucleophilic attack by a water molecule. Two intermediates are formed through conformational changes and different pathways are responsible. In pathway a, an assistant molecule takes part in the formation of the transition state and acts as a bridge to transfer a hydrogen atom, while in pathway b the assistant molecule is not involved in the creation of the transition state and acts only as a medium. The adenine takes place an amine-imine tautomerization before the nucleophilic attack under NH₃, which is not the case for the methanol-assisted mechanism. Energy results indicate that the energy barrier of the methanol-assisted adenine deamination is similar to that of the water-assisted reaction while the ammonia-assisted reaction has amuch higher energy barrier compared with the water-assisted reaction.
- Adenine deamination,
- B3LYP,
- G3MP2,
- Ammonia-assistance,
- Methanol-assistance
1. [1]
  
  1. Glaser, R.; Rayat, S.; Lewis, M.; Son, M. S.; Meyer, S. J. Am. Chem. Soc., 1999, 121: 6108
2. [2]
  2. Almatarneh, M. H.; Flinn, C. G.; Poirier, R. A.; Sokalski,W. A. J. Phys. Chem. A, 2006, 110: 8227
3. [3]
  3. Almatarneh, M. H.; Flinn, C. G.; Poirier, R. A. J. Chem. Inf. Model., 2008, 48: 831
4. [4]
  4. Labet, V.; Morell, C.; Grand, A.; Toro-Labbé, A. J. Phys. Chem. A, 2008, 112: 11487
5. [5]
  5. Labet, V.; Morell, C.; Cadet, J.; Eriksson, L. A.; Grand, A. J. Phys. Chem. A, 2009, 113: 2524
6. [6]
  6. Labet, V.; Grand, A.; Cadet, J.; Eriksson, L. A. ChemPhysChem, 2008, 9: 1195
7. [7]
  7. Zhang, A.; Yang, B.; Li, Z. J. Mol. Struct. -Theochem, 2007, 819: 95
8. [8]
  8. Zhu, C.; Meng, F. Struct. Chem., 2009, 20: 685
9. [9]
  9. Zheng, H.; Meng, F. Struct. Chem., 2009, 20: 943
10. [10]
  10. Kim, H. S.; Ahn, D. S.; Chung, S. Y.; Kim, S. K.; Lee, S. J. Phys. Chem. A, 2007, 111: 8007
11. [11]
  11. Gu, J.; Leszczynski, J. J. Phys. Chem. A, 1999, 103: 2744
12. [12]
  12. Matsubara, T.; Ishikura, M.; Aida, M. J. Chem. Inf. Model., 2006, 46: 1276
13. [13]
  13. Danilov, V. I.; van Mourik, T.; Kurita, N.; Wakabayashi, H.; Tsukamoto, T.; Hovorun, D. M. J. Phys. Chem. A, 2009, 113: 2233
14. [14]
  14. Haranczyk, M.; Rak, J.; Gutowski, M.; Radisic, D.; Stokes, S. T.; Bowen, K. H. J. Phys. Chem. B, 2005, 109: 13383
15. [15]
  15. Kabelác, M.; Hobza, P. J. Phys. Chem. B, 2006, 110: 14515
16. [16]
  16. Shukla, M. K.; Dubey, M.; Zakar, E.; Namburu, R.; Leszczynski, J. Chem. Phys. Lett., 2010, 493: 130
17. [17]
  17. Becke, A. D. J. Chem. Phys., 1993, 98: 5648
18. [18]
  18. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B, 1988, 37: 785
19. [19]
  19. Miehlich, B.; Savin, A.; Stoll, H.; Preuss, H. Chem. Phys. Lett., 1989, 157: 200
20. [20]
  20. Baboul, A. G.; Curtiss, L. A.; Redfern, P. C. J. Chem. Phys., 1999, 110: 7650
21. [21]
  21. Curtiss, L. A.; Raghavachari, K. J. Chem. Phys., 1998, 109: 7764
22. [22]
  22. Tang, Y. Z.; Sun, J. Y.; Sun, H.; Pan, Y. R.;Wang, R. S. Theor. Chem. Acc., 2008, 119: 297
23. [23]
  23. Cancès, M. T.; Mennucci, B.; Tomasi, J. J. Chem. Phys., 1997, 107: 3032
24. [24]
  24. Cossi, M.; Barone, V.; Mennucci, B.; Tomasi, J. Chem. Phys. Lett., 1998, 286: 253
25. [25]
  25. Mennucci, B.; Tomasi, J. J. Chem. Phys., 1997, 106: 5151
26. [26]
  26. Rappé, A. K.; Casewit, C. J.; Colwell, K. S.; ddard III, W. A.; Skiff,W. M. J. Am. Chem. Soc., 1992, 114: 10024
27. [27]
  27. Rappé, A. K.; ddard III,W. A. J. Phys. Chem., 1991, 95: 3358
28. [28]
  28. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; et al. Gaussian 03. Revision D.01. Wallingford, CT: Gaussian Inc., 2004
1. [1]
  Liuxie Liu , Jing He , Jiali Du , Shuang Mao , Qianggen Li . Extension of Computational Chemical-Assisted Dipole Moment Measurement Experiment. University Chemistry, 2025, 40(3): 363-370. doi: 10.12461/PKU.DXHX202407108
2. [2]
  Jianjun LI , Mingjie REN , Lili ZHANG , Lingling ZENG , Huiling WANG , Xiangwu MENG . UV-assisted degradation of tetracycline hydrochloride by MnFe₂O₄@activated carbon activated persulfate. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1869-1880. doi: 10.11862/CJIC.20240187
3. [3]
  Mi Wen , Baoshuo Jia , Yongqi Chai , Tong Wang , Jianbo Liu , Hailong Wu . Improvement of Fluorescence Quantitative Analysis Experiment: Simultaneous Determination of Rhodamine 6G and Rhodamine 123 in Food Using Chemometrics-Assisted Three-Dimensional Fluorescence Method. University Chemistry, 2025, 40(4): 390-398. doi: 10.12461/PKU.DXHX202405147
4. [4]
  Meifeng Zhu , Jin Cheng , Kai Huang , Cheng Lian , Shouhong Xu , Honglai Liu . Classical Density Functional Theory for Understanding Electrochemical Interface. University Chemistry, 2025, 40(3): 148-152. doi: 10.12461/PKU.DXHX202405166
5. [5]
  Meijin Li , Xirong Fu , Xue Zheng , Yuhan Liu , Bao Li . The Marvel of NAD⁺: Nicotinamide Adenine Dinucleotide. University Chemistry, 2024, 39(9): 35-39. doi: 10.12461/PKU.DXHX202401027
6. [6]
  Xiaojun Wu , Kai Hu , Faqiong Zhao . Laying the Groundwork for General Chemistry Experiment Teaching: Exploration and Summary of Assisting Experiment Preparatory Work through Online and Offline Integration. University Chemistry, 2024, 39(8): 23-27. doi: 10.3866/PKU.DXHX202312052
7. [7]
  Renqing Lü , Shutao Wang , Fang Wang , Guoping Shen . Computational Chemistry Aided Organic Chemistry Teaching: A Case of Comparison of Basicity and Stability of Diazine Isomers. University Chemistry, 2025, 40(3): 76-82. doi: 10.12461/PKU.DXHX202404119
8. [8]
  Xuejiao Wang , Suiying Dong , Kezhen Qi , Vadim Popkov , Xianglin Xiang . Photocatalytic CO₂ Reduction by Modified g-C₃N₄. Acta Physico-Chimica Sinica, 2024, 40(12): 2408005-. doi: 10.3866/PKU.WHXB202408005
9. [9]
  Liang Ma , Zhou Li , Zhiqiang Jiang , Xiaofeng Wu , Shixin Chang , Sónia A. C. Carabineiro , Kangle Lv . Effect of precursors on the structure and photocatalytic performance of g-C3N4 for NO oxidation and CO2 reduction. Chinese Journal of Structural Chemistry, 2024, 43(11): 100416-100416. doi: 10.1016/j.cjsc.2024.100416
10. [10]
  Hong CAI , Jiewen WU , Jingyun LI , Lixian CHEN , Siqi XIAO , Dan LI . Synthesis of a zinc-cobalt bimetallic adenine metal-organic framework for the recognition of sulfur-containing amino acids. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 114-122. doi: 10.11862/CJIC.20240382
11. [11]
  Zhi Zhu , Xiaohan Xing , Qi Qi , Wenjing Shen , Hongyue Wu , Dongyi Li , Binrong Li , Jialin Liang , Xu Tang , Jun Zhao , Hongping Li , Pengwei Huo . Fabrication of graphene modified CeO2/g-C3N4 heterostructures for photocatalytic degradation of organic pollutants. Chinese Journal of Structural Chemistry, 2023, 42(12): 100194-100194. doi: 10.1016/j.cjsc.2023.100194
12. [12]
  Qingwang LIU . MoS₂/Ag/g-C₃N₄ Z-scheme heterojunction: Preparation and photocatalytic performance. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 821-832. doi: 10.11862/CJIC.20240148
13. [13]
  Zian Lin , Yingxue Jin . Matrix-Assisted Laser Desorption/Ionization Mass Spectrometry (MALDI-MS) for Disease Marker Screening and Identification: A Comprehensive Experiment Teaching Reform in Instrumental Analysis. University Chemistry, 2024, 39(11): 327-334. doi: 10.12461/PKU.DXHX202403066
14. [14]
  Min WANG , Dehua XIN , Yaning SHI , Wenyao ZHU , Yuanqun ZHANG , Wei ZHANG . Construction and full-spectrum catalytic performance of multilevel Ag/Bi/nitrogen vacancy g-C₃N₄/Ti₃C₂T_x Schottky junction. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1123-1134. doi: 10.11862/CJIC.20230477
15. [15]
  Hualin Jiang , Wenxi Ye , Huitao Zhen , Xubiao Luo , Vyacheslav Fominski , Long Ye , Pinghua Chen . Novel 3D-on-2D g-C₃N₄/AgI._x._y heterojunction photocatalyst for simultaneous and stoichiometric production of H₂ and H₂O₂ from water splitting under visible light. Chinese Chemical Letters, 2025, 36(2): 109984-. doi: 10.1016/j.cclet.2024.109984
16. [16]
  Wei Zhong , Dan Zheng , Yuanxin Ou , Aiyun Meng , Yaorong Su . K原子掺杂高度面间结晶的g-C₃N₄光催化剂及其高效H₂O₂光合成. Acta Physico-Chimica Sinica, 2024, 40(11): 2406005-. doi: 10.3866/PKU.WHXB202406005
17. [17]
  Guoqiang Chen , Zixuan Zheng , Wei Zhong , Guohong Wang , Xinhe Wu . 熔融中间体运输导向合成富氨基g-C₃N₄纳米片用于高效光催化产H₂O₂. Acta Physico-Chimica Sinica, 2024, 40(11): 2406021-. doi: 10.3866/PKU.WHXB202406021
18. [18]
  Guangchang Yang , Shenglong Yang , Jinlian Yu , Yishun Xie , Chunlei Tan , Feiyan Lai , Qianqian Jin , Hongqiang Wang , Xiaohui Zhang . Regulating local chemical environment in O3-type layered sodium oxides by dual-site Mg²⁺/B³⁺ substitution achieves durable and high-rate cathode. Chinese Chemical Letters, 2024, 35(9): 109722-. doi: 10.1016/j.cclet.2024.109722
19. [19]
  Xin Jiang , Han Jiang , Yimin Tang , Huizhu Zhang , Libin Yang , Xiuwen Wang , Bing Zhao . g-C₃N₄/TiO_2-X heterojunction with high-efficiency carrier separation and multiple charge transfer paths for ultrasensitive SERS sensing. Chinese Chemical Letters, 2024, 35(10): 109415-. doi: 10.1016/j.cclet.2023.109415
20. [20]
  Jianyu Qin , Yuejiao An , Yanfeng Zhang . In Situ Assembled ZnWO₄/g-C₃N₄ S-Scheme Heterojunction with Nitrogen Defect for CO₂ Photoreduction. Acta Physico-Chimica Sinica, 2024, 40(12): 2408002-. doi: 10.3866/PKU.WHXB202408002

Get Citation

PDF

XML

Metrics

PDF Downloads(1038)
Abstract views(2624)
HTML views(10)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142

Effects of CH3OH and NH3 on the Hydrolytic Deamination Mechanismof Adenine

Metrics

通讯作者: 陈斌, bchen63@163.com

Effects of CH₃OH and NH₃ on the Hydrolytic Deamination Mechanismof Adenine