Citation: Gao Xiao-Fei, He Peng, Chen Huanwen. Study on the Interaction Between Water Radical Cations and Bis(2-hydroxyethyl) Disulfide at Ambient Temperature and Pressure Using Mass Spectrometry[J]. Acta Chimica Sinica, ;2018, 76(10): 802-806. doi: 10.6023/A18070297 shu

Study on the Interaction Between Water Radical Cations and Bis(2-hydroxyethyl) Disulfide at Ambient Temperature and Pressure Using Mass Spectrometry

Jiangxi Key Laboratory for Mass Spectrometry and Instrumentation, East China University of Technology, Nanchang 330013

Corresponding author: Gao Xiao-Fei, sandy2005327@126.com Chen Huanwen, chw8868@gmail.com
Received Date: 25 July 2018
Available Online: 22 October 2018
Fund Project: Project supported by the National Natural Science Foundation of China (No. 21520102007), the Jiangxi Key Laboratory for Mass Spectrometry and Instrumentation Open Foundation (No. JXMS201701) and the Research Fund of East China University of Technology (No. DHBK2017114)the National Natural Science Foundation of China 21520102007the Jiangxi Key Laboratory for Mass Spectrometry and Instrumentation Open Foundation JXMS201701the Research Fund of East China University of Technology DHBK2017114

Figures(7)

In vivo, free radical damage of disulfide bonds in proteins affects the structure and function of proteins, and has an important relationship with cell aging. Therefore, studying the mechanism of the interaction between free radicals and disulfide bonds, and understanding the interaction process between free radicals and disulfide bonds, is important for the cleavage or proteciton of disulfide bond. In this paper, liquid-assisted surface desorption atmospheric pressure chemical ionization technology is adopted (LA-DAPCI), to construct a two-channel ion source device, obtaining high abundance water radical cations (H₂O)_n^+· (n=2~4). Using linear ion trap mass spectrometer, combining with Density Functional Theory, the interaction process between (H₂O)_n^+· and bis(2-hydroxyethyl) disulfide (HEDS) in mass spectrometer and thermodynamic process of the interaction were studied. The results indicated that (H₂O)_n^+· interacted with HEDS, forming a radical complex (M+H₂O)^+· (m/z 172) without covalent bond, and H₂O in complex (M+H₂O)^+· (m/z 172) is derived from (H₂O)_n^+·, not from the H₂O of sample solution. Furthermore, thermodynamic theoretical calculation results demonstrated that H on the β-hydroxyl group of HEDS structure forms a weak hydrogen bond with S in the form of an intramolecular five-membered ring. During the interaction process, (H₂O)_n^+· preferentially binds to the hydroxyl group of HEDS, forming a radical complex (M+H₂O)^+·, whose disulfide bond will be difficult to be cleaved. In conclusion, the β-hydroxyl group has a protective effect on the disulfide bond of HEDS during the interaction with water radical cations.
- water radical cations,
- disulfide bonds,
- radical damage,
- atmospheric pressure chemical ionization
1. [1]
  Góngora-Benítez, M.; Tulla-Puche, J.; Albericio, F. Chem. Rev. 2014, 114, 901. doi: 10.1021/cr400031z
2. [2]
  Nicastri, M. C.; Xega, K.; Li, L. Y.; Xie, J.; Wang, C. Y.; Linhardt, R. J.; Reitter, J. N.; Mills, K. V. Biochemistry 2013, 52, 5920. doi: 10.1021/bi400736c
3. [3]
  Stoyanovsky, D. A.; Maeda, A.; Atkins, J. L.; Kagan, V. E. Anal. Chem. 2011, 83, 6432. doi: 10.1021/ac200418s
4. [4]
  Cheng, Q.; Evangelista, F. A.; Simmonett, A. C.; Yamaguchi, Y.; Schaefer, H. F. J. Phys. Chem. A 2009, 113, 13779. doi: 10.1021/jp907715a
5. [5]
  Mizuse, K.; Kuo, J.-L.; Fujii, A. Chem. Sci. 2011, 2, 868. doi: 10.1039/C0SC00604A
6. [6]
  Pan, P.-R.; Lin, Y.-S.; Tsai, M.-K.; Kuo, J.-L.; Chai, J.-D. Phys. Chem. Chem. Phys. 2012, 14, 10705. doi: 10.1039/c2cp41116d
7. [7]
  Nicastri, M. C.; Xega, K.; Li, L. Y.; Xie, J.; Wang, C. Y.; Linhardt, R. J.; Reitter, J. N.; Mills, K. V. Biochemistry 2013, 52, 5920. doi: 10.1021/bi400736c
8. [8]
  Tyson, E. L.; Ament, M. S.; Yoon, T. P. J. Org. Chem. 2013, 78, 204. doi: 10.1021/jo302230m
9. [9]
  Góngora-Benítez, M.; Tulla-Puche, J.; Albericio, F. Chem. Rev. 2014, 114, 901. doi: 10.1021/cr400031z
10. [10]
  Tang, M.; Hu, C.-E.; Lv, Z.-L.; Chen, X.-R.; Cai, L.-C. J. Phys. Chem. A 2016, 120, 9489. doi: 10.1021/acs.jpca.6b09866
11. [11]
  Ma, J.; Wang, F.; Mostafavi, M. Molecules 2018, 23, 244. doi: 10.3390/molecules23020244
12. [12]
  de Visser, S. P.; de Koning, L. J.; Nibbering, N. M. M. J. Phys. Chem. 1995, 99, 15444. doi: 10.1021/j100042a017
13. [13]
  Ouyang, Y. ; Hong, F. ; Jia, B. ; Chen, H. CN203448088U, 2014.
14. [14]
  Ouyang, Y. ; Jia, B. ; Chen, L. ; Chen, H. The 11^th National Biomedical Chromatography and Related Technology Exchange Conference, Chinese Chemical Society, Jinggangshan, 2016, p. 49(in Chinese).
15. [15]
  Zhu, Z.; Han, J.; Zhang, Z.; Zhou, Y.; Xu, N.; Zhang, B.; Gu, H.; Chen, H. Rapid Commun. Mass Spectrom. 2012, 26, 2770. doi: 10.1002/rcm.6387
16. [16]
  Yang, S.; Ding, J.; Zheng, J.; Hu, B.; Li, J.; Chen, H.; Zhou, Z.; Qiao, X. Anal. Chem. 2009, 81, 2426. doi: 10.1021/ac900063u
17. [17]
  Chen, H.; Yang, S.; Wortmann, A.; Zenobi, R. Angew. Chem. Int. Ed. 2007, 46, 7591. doi: 10.1002/(ISSN)1521-3773
18. [18]
  Chen, H.; Zenobi, R. Nat. Protoc. 2008, 3, 1467. doi: 10.1038/nprot.2008.109
19. [19]
  Zhang, J.; Wang, H.; Xue, X.; Zhang, Y.; Cheng, X. Acta Chim. Sinica 2012, 70, 2543. doi: 10.3866/PKU.WHXB201208135
20. [20]
  Chai, Y.; Gan, S.; Pan, Y. Acta Chim. Sinica 2012, 70, 1805
21. [21]
  Zheng, Y.; Zhu, Q.; Li, Z.; Li, X. Acta Chim. Sinica 2013, 71, 81. doi: 10.3969/j.issn.1001-4861.2013.00.035
1. [1]
  Zijian Zhao , Yanxin Shi , Shicheng Li , Wenhong Ruan , Fang Zhu , Jijun Jiang . A New Exploration of the Preparation of Polyacrylic Acid by Free Radical Polymerization Based on the Concept of Green Chemistry. University Chemistry, 2024, 39(5): 315-324. doi: 10.3866/PKU.DXHX202311094
2. [2]
  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
3. [3]
  Lei Shi . Nucleophilicity and Electrophilicity of Radicals. University Chemistry, 2024, 39(11): 131-135. doi: 10.3866/PKU.DXHX202402018
4. [4]
  Jiajia Li , Xiangyu Zhang , Zhihan Yuan , Zhengyang Qian , Jian Zhu . 3D Printing Based on Photo-Induced Reversible Addition-Fragmentation Chain Transfer Polymerization. University Chemistry, 2024, 39(5): 11-19. doi: 10.3866/PKU.DXHX202309073
5. [5]
  Jinyao Du , Xingchao Zang , Ningning Xu , Yongjun Liu , Weisi Guo . Electrochemical Thiocyanation of 4-Bromoethylbenzene. University Chemistry, 2024, 39(6): 312-317. doi: 10.3866/PKU.DXHX202310039
6. [6]
  Guang Huang , Lei Li , Dingyi Zhang , Xingze Wang , Yugai Huang , Wenhui Liang , Zhifen Guo , Wenmei Jiao . Cobalt’s Valor, Nickel’s Foe: A Comprehensive Chemical Experiment Utilizing a Cobalt-based Imidazolate Framework for Nickel Ion Removal. University Chemistry, 2024, 39(8): 174-183. doi: 10.3866/PKU.DXHX202311051
7. [7]
  Yinuo Wang , Siran Wang , Yilong Zhao , Dazhen Xu . Selective Synthesis of Diarylmethyl Anilines and Triarylmethanes via Multicomponent Reactions: Introduce a Comprehensive Experiment of Organic Chemistry. University Chemistry, 2024, 39(8): 324-330. doi: 10.3866/PKU.DXHX202401063
8. [8]
  Tengjiao Wang , Tian Cheng , Rongjun Liu , Zeyi Wang , Yuxuan Qiao , An Wang , Peng Li . Conductive Hydrogel-based Flexible Electronic System: Innovative Experimental Design in Flexible Electronics. University Chemistry, 2024, 39(4): 286-295. doi: 10.3866/PKU.DXHX202309094
9. [9]
  Doudou Qin , Junyang Ding , Chu Liang , Qian Liu , Ligang Feng , Yang Luo , Guangzhi Hu , Jun Luo , Xijun Liu . Addressing Challenges and Enhancing Performance of Manganese-based Cathode Materials in Aqueous Zinc-Ion Batteries. Acta Physico-Chimica Sinica, 2024, 40(10): 2310034-. doi: 10.3866/PKU.WHXB202310034
10. [10]
  Zhiquan Zhang , Baker Rhimi , Zheyang Liu , Min Zhou , Guowei Deng , Wei Wei , Liang Mao , Huaming Li , Zhifeng Jiang . Insights into the Development of Copper-based Photocatalysts for CO₂ Conversion. Acta Physico-Chimica Sinica, 2024, 40(12): 2406029-. doi: 10.3866/PKU.WHXB202406029
11. [11]
  Chengqian Mao , Yanghan Chen , Haotong Bai , Junru Huang , Junpeng Zhuang . Photodimerization of Styrylpyridinium Salt and Its Application in Silk Screen Printing. University Chemistry, 2024, 39(5): 354-362. doi: 10.3866/PKU.DXHX202312014
12. [12]
  Lu XU , Chengyu ZHANG , Wenjuan JI , Haiying YANG , Yunlong FU . Zinc metal-organic framework with high-density free carboxyl oxygen functionalized pore walls for targeted electrochemical sensing of paracetamol. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 907-918. doi: 10.11862/CJIC.20230431
13. [13]
  Honglian Liang , Xiaozhe Kuang , Fuping Wang , Yu Chen . Exploration and Practice of Integrating Ideological and Political Education into Physical Chemistry: a Case on Surface Tension and Gibbs Free Energy. University Chemistry, 2024, 39(10): 433-440. doi: 10.12461/PKU.DXHX202405073
14. [14]
  Shasha Liu , Yongmei Liu , Youqin Li , Juan Wang , Lisen Sun , Jinfen Zhang , Xiang Gao , Xingwen Sun . “Cognitive Experience-Strengthening Foundation-Frontier Innovation”: Construction and Practice of the Chemistry Experimental Curriculum System for Fudan University. University Chemistry, 2024, 39(7): 180-187. doi: 10.12461/PKU.DXHX202405095
15. [15]
  Rui Li , Jiayu Zhang , Anyang Li . Two Levels of Understanding of Chemical Bonds: a Case of the Bonding Model of Hypervalent Molecules. University Chemistry, 2024, 39(2): 392-398. doi: 10.3866/PKU.DXHX202308051
16. [16]
  Yanan Liu , Yufei He , Dianqing Li . Preparation of Highly Dispersed LDHs-based Catalysts and Testing of Nitro Compound Reduction Performance: A Comprehensive Chemical Experiment for Research Transformation. University Chemistry, 2024, 39(8): 306-313. doi: 10.3866/PKU.DXHX202401081
17. [17]
  Yinuo Wu , Jiantao Ye , Xie Zhou , Yu Qian , Lei Guo . Teaching Design of Basic Chemistry Based on PBL Methodology for Medical Undergraduates: A Case Study on “Osmotic Pressure of Solution”. University Chemistry, 2024, 39(3): 149-157. doi: 10.3866/PKU.DXHX202309077
18. [18]
  Yuhao SUN , Qingzhe DONG , Lei ZHAO , Xiaodan JIANG , Hailing GUO , Xianglong MENG , Yongmei GUO . Synthesis and antibacterial properties of silver-loaded sod-based zeolite. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 761-770. doi: 10.11862/CJIC.20230169
19. [19]
  Yuanyin Cui , Jinfeng Zhang , Hailiang Chu , Lixian Sun , Kai Dai . Rational Design of Bismuth Based Photocatalysts for Solar Energy Conversion. Acta Physico-Chimica Sinica, 2024, 40(12): 2405016-. doi: 10.3866/PKU.WHXB202405016
20. [20]
  Dan Li , Hui Xin , Xiaofeng Yi . Comprehensive Experimental Design on Ni-based Catalyst for Biofuel Production. University Chemistry, 2024, 39(8): 204-211. doi: 10.3866/PKU.DXHX202312046

Get Citation

PDF

XML

Metrics

PDF Downloads(10)
Abstract views(1175)
HTML views(186)

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