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

doi:10.6023/A18070297

Acta Chim. Sinica ›› 2018, Vol. 76 ›› Issue (10): 802-806.DOI: 10.6023/A18070297 Previous Articles Next Articles

Article

常压下水自由基阳离子与双(2-羟乙基)二硫醚作用的质谱研究

高校飞, 何鹏, 陈焕文

东华理工大学江西省质谱科学与仪器重点实验室南昌 330013

投稿日期:2018-07-25 发布日期:2018-08-22
通讯作者: 高校飞, 陈焕文 E-mail:sandy2005327@126.com;chw8868@gmail.com
基金资助:
项目受国家自然科学基金（No.21520102007）、江西省质谱科学与仪器重点实验室开放基金（No.JXMS201701）和东华理工大学博士启动基金（No.DHBK2017114）资助.

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

Gao Xiao-Fei, He Peng, Chen Huanwen

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

Received:2018-07-25 Published:2018-08-22
Contact: 10.6023/A18070297 E-mail:sandy2005327@126.com;chw8868@gmail.com
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21520102007), the Jiangxi Key Laboratory for Mass Spectrometry and Instru-mentation Open Foundation (No. JXMS201701) and the Research Fund of East China University of Technology (No. DHBK2017114).

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.

Key words: water radical cations, disulfide bonds, radical damage, atmospheric pressure chemical ionization

Cite this article

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 Chim. Sinica, 2018, 76(10): 802-806.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Góngora-Benítez, M.; Tulla-Puche, J.; Albericio, F. Chem. Rev. 2014, 114, 901.
[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.
[3] Stoyanovsky, D. A.; Maeda, A.; Atkins, J. L.; Kagan, V. E. Anal. Chem. 2011, 83, 6432.
[4] Cheng, Q.; Evangelista, F. A.; Simmonett, A. C.; Yamaguchi, Y.; Schaefer, H. F. J. Phys. Chem. A 2009, 113, 13779.
[5] Mizuse, K.; Kuo, J.-L.; Fujii, A. Chem. Sci. 2011, 2, 868.
[6] Pan, P.-R.; Lin, Y.-S.; Tsai, M.-K.; Kuo, J.-L.; Chai, J.-D. Phys. Chem. Chem. Phys. 2012, 14, 10705.
[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.
[8] Tyson, E. L.; Ament, M. S.; Yoon, T. P. J. Org. Chem. 2013, 78, 204.
[9] Góngora-Benítez, M.; Tulla-Puche, J.; Albericio, F. Chem. Rev. 2014, 114, 901.
[10] Tang, M.; Hu, C.-E.; Lv, Z.-L.; Chen, X.-R.; Cai, L.-C. J. Phys. Chem. A 2016, 120, 9489.
[11] Ma, J.; Wang, F.; Mostafavi, M. Molecules 2018, 23, 244.
[12] de Visser, S. P.; de Koning, L. J.; Nibbering, N. M. M. J. Phys. Chem. 1995, 99, 15444.
[13] Ouyang, Y.; Hong, F.; Jia, B.; Chen, H. CN203448088U, 2014. (欧阳永中, 洪峰, 贾斌, 陈焕文, CN 203448088U, 2014-02-26.)
[14] Ouyang, Y.; Jia, B.; Chen, L.; Chen, H. The 11th National Biomedical Chromatography and Related Technology Exchange Conference, Chinese Chemical Society, Jinggangshan, 2016, p. 49(in Chinese). (欧阳永中, 贾斌, 陈林飞, 陈焕文, 中国化学会第十一届全国生物医药色谱及相关技术交流会, 中国化学会, 井冈山, 2016, p. 49.)
[15] Zhu, Z.; Han, J.; Zhang, Z.; Zhou, Y.; Xu, N.; Zhang, B.; Gu, H.; Chen, H. Rapid Commun. Mass Spectrom. 2012, 26, 2770.
[16] Yang, S.; Ding, J.; Zheng, J.; Hu, B.; Li, J.; Chen, H.; Zhou, Z.; Qiao, X. Anal. Chem. 2009, 81, 2426.
[17] Chen, H.; Yang, S.; Wortmann, A.; Zenobi, R. Angew. Chem. Int. Ed. 2007, 46, 7591.
[18] Chen, H.; Zenobi, R. Nat. Protoc. 2008, 3, 1467.
[19] Zhang, J.; Wang, H.; Xue, X.; Zhang, Y.; Cheng, X. Acta Chim. Sinica 2012, 70, 2543. (张吉东, 王海锋, 薛新英, 张岩文, 程新路, 化学学报, 2012, 70, 2543).
[20] Chai, Y.; Gan, S.; Pan, Y. Acta Chim. Sinica 2012, 70, 1805(柴云峰, 甘世凤, 潘远江, 化学学报, 2012, 70, 1805).
[21] Zheng, Y.; Zhu, Q.; Li, Z.; Li, X. Acta Chim. Sinica 2013, 71, 81. (郑洋, 朱权, 李泽荣, 李象远, 化学学报, 2013, 71, 81).

常压下水自由基阳离子与双(2-羟乙基)二硫醚作用的质谱研究

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

PDF

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 0

Recommended Articles

Metrics

Comments