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]
  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
2. [2]
  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
3. [3]
  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
4. [4]
  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.2023.100416
5. [5]
  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
6. [6]
  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
7. [7]
  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
8. [8]
  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
9. [9]
  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
10. [10]
  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
11. [11]
  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
12. [12]
  Zhen Liu , Zhi-Yuan Ren , Chen Yang , Xiangyi Shao , Li Chen , Xin Li . Asymmetric alkenylation reaction of benzoxazinones with diarylethylenes catalyzed by B(C₆F₅)₃/chiral phosphoric acid. Chinese Chemical Letters, 2024, 35(5): 108939-. doi: 10.1016/j.cclet.2023.108939
13. [13]
  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
14. [14]
  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
15. [15]
  Heng Chen , Longhui Nie , Kai Xu , Yiqiong Yang , Caihong Fang . 两步焙烧法制备大比表面积和结晶性增强超薄g-C₃N₄纳米片及其高效光催化产H₂O₂. Acta Physico-Chimica Sinica, 2024, 40(11): 2406019-. doi: 10.3866/PKU.WHXB202406019
16. [16]
  Kai Han , Guohui Dong , Ishaaq Saeed , Tingting Dong , Chenyang Xiao . Morphology and photocatalytic tetracycline degradation of g-C3N4 optimized by the coal gangue. Chinese Journal of Structural Chemistry, 2024, 43(2): 100208-100208. doi: 10.1016/j.cjsc.2023.100208
17. [17]
  Xiaoming Fu , Haibo Huang , Guogang Tang , Jingmin Zhang , Junyue Sheng , Hua Tang . Recent advances in g-C3N4-based direct Z-scheme photocatalysts for environmental and energy applications. Chinese Journal of Structural Chemistry, 2024, 43(2): 100214-100214. doi: 10.1016/j.cjsc.2024.100214
18. [18]
  Guangming YIN , Huaiyao WANG , Jianhua ZHENG , Xinyue DONG , Jian LI , Yi'nan SUN , Yiming GAO , Bingbing WANG . Preparation and photocatalytic degradation performance of Ag/protonated g-C₃N₄ nanorod materials. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1491-1500. doi: 10.11862/CJIC.20240086
19. [19]
  Juan Guo , Mingyuan Fang , Qingsong Liu , Xiao Ren , Yongqiang Qiao , Mingju Chao , Erjun Liang , Qilong Gao . Zero thermal expansion in Cs₂W₃O₁₀. Chinese Chemical Letters, 2024, 35(7): 108957-. doi: 10.1016/j.cclet.2023.108957
20. [20]
  Haojie Duan , Hejingying Niu , Lina Gan , Xiaodi Duan , Shuo Shi , Li Li . Reinterpret the heterogeneous reaction of α-Fe₂O₃ and NO₂ with 2D-COS: The role of SDS, UV and SO₂. Chinese Chemical Letters, 2024, 35(6): 109038-. doi: 10.1016/j.cclet.2023.109038

Get Citation

PDF

XML

Metrics

PDF Downloads(1038)
Abstract views(2569)
HTML views(6)

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