Citation: LIU Xiao-Fang, LI Xue-Qiang, YE Wu-Long, ZHOU Bin-Bin, LIU You-Nian. Synthesis of Ferrocenoyl-Labeled Tripeptide Fc-Gly-Pro-Arg(NO₂)-OMe and Its Interaction with Cu(II)[J]. Acta Physico-Chimica Sinica, ;2010, 26(09): 2381-2386. doi: 10.3866/PKU.WHXB20100827 shu

Synthesis of Ferrocenoyl-Labeled Tripeptide Fc-Gly-Pro-Arg(NO₂)-OMe and Its Interaction with Cu(II)

1.
College of Chemistry and Chemical Engineering, Central South University, Changsha 410083, P. R. China

Received Date: 9 March 2010
Available Online: 25 June 2010
Fund Project: 国家自然科学基金(20876179)资助项目 (20876179)

N-ferrocenoyl-labeled tripeptide Fc-Gly-Pro-Arg(NO₂)-OMe(Fc-GPR) was synthesized from ferrocene-carboxylic acid, glycine (H-Gly-OMe), proline (Boc-Pro-OH) and arginine (H-Arg(NO₂)-OMe) by solution synthesis with a yield of 48.1%. The synthesized Fc-GPR was characterized by infrared spectroscopy (IR), proton nuclear magnetic resonance spectroscopy (¹H-NMR) and electrospray ionization mass spectroscopy (ESI-MS). The electrochemical behavior of Fc-GPR was investigated using electrochemical methods. We observed a pair of well-defined voltammetric peaks with cathodic E_pc and anodic peak potentials E_pa, at 0.552 and 0.624 V (vs Ag/AgCl), respectively. The ratio of oxidative to reductive peak current is 1.13 and the peak currents were found to be proportional to the square root of the scan rates suggesting that Fc-GPRunder es a reversible electron transfer reaction. The molar ratio of Fc-GPR to Cu(II) was found to be 2:1 by the molar ratio method. Furthermore, the electrode reaction of Fc-GPR with Cu(II) is an electrochemical-chemical-electrochemical (ECE) process.
- Ferrocene-peptide,
- Solution synthesis,
- Gly-Pro-Arg,
- Electrochemical-chemical-electrochemical process,
- Cu(II)
1. [1]
  
  1. van Staveren, D. R.; Metzler-Nolte, N. Chem. Rev., 2004, 104: 5931
2. [2]
  2. Duivenvoorden, W. C. M.; Liu, Y. N.; Schatte, G.; Kraatz, H. B. Inorg. Chim. Acta, 2005, 358: 3183
3. [3]
  3. Miklán, Z.; Szabó, R.; Zsoldos-Mády, V.; Reményi, J.; Bánóczi, Z.; Hudecz, F. Biopolymer, 2007, 88: 108
4. [4]
  4. Paitayatat, S.; Tarnchompoo, B.; Thebtaranonth, Y.; Yuthavong, Y. J. Med. Chem., 1997, 40: 633
5. [5]
  5. Chen, C. H.; Li, H.; Zhu, W.; Zhang, Q. X. Acta Phys. -Chin. Sin., 2005, 21: 1067 [陈灿辉,李红,朱伟, 张全新.物理化学学报, 2005, 21: 1067]
6. [6]
  6. swami, T. K.; Roy, M.; Nethaji, M.; Chakravarty, A. R. Organometallics, 2009, 28: 1992
7. [7]
  7. Mahmoud, K. A.; Luong, J. H. T. Anal. Chem., 2008, 80: 7056
8. [8]
  8. Deng, X. H.; Kan, X.W.; Yu, Y.; Zhang, W. Z.; Liu, H. Y.; Fang, B. Acta Phys. -Chim. Sin., 2005, 21: 1399 [邓湘辉,阚显文, 尉艳,张文芝,刘红英,方宾.物理化学学报, 2005, 21: 1399]
9. [9]
  9. Ioudina, M.; Uemura, E. Exp. Neurol., 2003, 184: 923
10. [10]
  10. Furlan, M.; Rupp, C.; Beck, E. A. BBA-Protein. Struct. M., 1983, 742: 25
11. [11]
  11. Furlan, M.; Rupp, C.; Beck, E. A.; Svendsen, L. Thromb. Haemost., 1982, 47: 118
12. [12]
  12. Brewer, G. J. Chem. Res. Toxicol., 2009, 10: 1021
13. [13]
  13. Multhaup, G. Biomed. Pharmacother., 1997, 51: 105
14. [14]
  14. Donnelly, P. S.; Xiao, Z.; Wedd, A. G. Curr. Opin. Chem. Biol., 2007, 11: 128
15. [15]
  15. Meloni, G. J. Biol. Chem., 2007, 282: 16068
16. [16]
  16. Freedman, J. H.; Pickart, L.; Weinstein, B.; Mims, W. B.; Peisach, J. Biochemistry, 1982, 21: 4540
17. [17]
  17. Pickart, L.; Freedman, J. H.; Loker, W. J.; Peisach, J.; Perkins, C. M.; Steinkamp, R. E.; Weinstein, B. Nature, 1980, 288: 715
18. [18]
  18. Freedman, J. H.; Ciriolo, M. R.; Peisach, J. J. Biol. Chem., 1989, 264: 5598
19. [19]
  19. Bari?icc, L.;Cakicc, M.; Mahmoud, K. A.; Liu, Y. N.; Kraatz, H. B.; Pritzkow, H.; Kirin, S. I.; Metzler-Nolte, N.; Rapicc, V. Chem. Eur. J., 2006, 12: 4965
20. [20]
  20. Xiang, J.; Peng, Y.; Schatte, G.; Yang, Q.; Liu, Y. N. Z. Kristallogr., 2009, 224: 551
21. [21]
  21. Wang, F. B.; Peng, Y.; Fan, M. Y.; Liu, Y. N.; Hung, K. L. Acta Phys. -Chim. Sin., 2009, 25: 1125 [王芳斌,彭勇,范美意, 刘又年,黄可龙. 物理化学学报, 2009, 25: 1125]
22. [22]
  22. Momoki, K.; Sekino, J.; Sato, H.; Yamaguchi, N. Anal. Chem., 1969, 41: 1286
23. [23]
  23. Muller, E.; Bernardinelli, G.; Reedijk, J. Inorg. Chem., 1996, 35: 1952
24. [24]
  24. Woltman, S. J.; Alward, M. R.; Weber, S. G. Anal. Chem., 1995, 67: 541
25. [25]
  25. Delavaux-Nicot, B.; Bigeard, A.; Bousseksou, A.; Donnadieu, B.; Commenges, G. Inorg. Chem., 1997, 36: 4789
26. [26]
  26. Taha, A. Spectrochim. Acta A, 2003, 59: 1373
27. [27]
  27. Meng, R.; Weber, S. G. J. Electroanal. Chem., 2007, 600: 325
28. [28]
  28. Feldberg, S. W. J. Phys. Chem., 1971, 75: 2377
29. [29]
  29. Polcyn, D. S.; Shain, I. Anal. Chem., 1966, 38: 370
30. [30]
  30. Bard, A. J.; Faulkner, L. R. Electrochemical methods: fundamentals and applications. 2nd ed. NewYork: Wiley, 2001: 471-528
1. [1]
  Hong LI , Xiaoying DING , Cihang LIU , Jinghan ZHANG , Yanying RAO . Detection of iron and copper ions based on gold nanorod etching colorimetry. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 953-962. doi: 10.11862/CJIC.20230370
2. [2]
  Liangzhen Hu , Li Ni , Ziyi Liu , Xiaohui Zhang , Bo Qin , Yan Xiong . A Green Chemistry Experiment on Electrochemical Synthesis of Benzophenone. University Chemistry, 2024, 39(6): 350-356. doi: 10.3866/PKU.DXHX202312001
3. [3]
  Zhuo Wang , Xue Bai , Kexin Zhang , Hongzhi Wang , Jiabao Dong , Yuan Gao , Bin Zhao . MOF模板法合成氮掺杂碳材料用于增强电化学钠离子储存和去除. Acta Physico-Chimica Sinica, 2025, 41(3): 2405002-. doi: 10.3866/PKU.WHXB202405002
4. [4]
  Caixia Lin , Zhaojiang Shi , Yi Yu , Jianfeng Yan , Keyin Ye , Yaofeng Yuan . Ideological and Political Design for the Electrochemical Synthesis of Benzoxathiazine Dioxide Experiment. University Chemistry, 2024, 39(2): 61-66. doi: 10.3866/PKU.DXHX202309005
5. [5]
  Xiangyu CAO , Jiaying ZHANG , Yun FENG , Linkun SHEN , Xiuling ZHANG , Juanzhi YAN . Synthesis and electrochemical properties of bimetallic-doped porous carbon cathode material. Chinese Journal of Inorganic Chemistry, 2025, 41(3): 509-520. doi: 10.11862/CJIC.20240270
6. [6]
  Jianfeng Yan , Yating Xiao , Xin Zuo , Caixia Lin , Yaofeng Yuan . Comprehensive Chemistry Experimental Design of Ferrocenylphenyl Derivatives. University Chemistry, 2024, 39(4): 329-337. doi: 10.3866/PKU.DXHX202310005
7. [7]
  Qingtang ZHANG , Xiaoyu WU , Zheng WANG , Xiaomei WANG . Performance of nano Li₂FeSiO₄/C cathode material co-doped by potassium and chlorine ions. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1689-1696. doi: 10.11862/CJIC.20240115
8. [8]
  Ping Ye , Lingshuang Qin , Mengyao He , Fangfang Wu , Zengye Chen , Mingxing Liang , Libo Deng . 荷叶衍生多孔碳的零电荷电位调节实现废水中电化学捕集镉离子. Acta Physico-Chimica Sinica, 2025, 41(3): 2311032-. doi: 10.3866/PKU.WHXB202311032
9. [9]
  Li Jiang , Changzheng Chen , Yang Su , Hao Song , Yanmao Dong , Yan Yuan , Li Li . Electrochemical Synthesis of Polyaniline and Its Anticorrosive Application: Improvement and Innovative Design of the “Chemical Synthesis of Polyaniline” Experiment. University Chemistry, 2024, 39(3): 336-344. doi: 10.3866/PKU.DXHX202309002
10. [10]
  Xue Dong , Xiaofu Sun , Shuaiqiang Jia , Shitao Han , Dawei Zhou , Ting Yao , Min Wang , Minghui Fang , Haihong Wu , Buxing Han . 碳修饰的铜催化剂实现安培级电流电化学还原CO₂制C₂₊产物. Acta Physico-Chimica Sinica, 2025, 41(3): 2404012-. doi: 10.3866/PKU.WHXB202404012
11. [11]
  Shengbiao Zheng , Liang Li , Nini Zhang , Ruimin Bao , Ruizhang Hu , Jing Tang . Metal-Organic Framework-Derived Materials Modified Electrode for Electrochemical Sensing of Tert-Butylhydroquinone: A Recommended Comprehensive Chemistry Experiment for Translating Research Results. University Chemistry, 2024, 39(7): 345-353. doi: 10.3866/PKU.DXHX202310096
12. [12]
  Linbao Zhang , Weisi Guo , Shuwen Wang , Ran Song , Ming Li . Electrochemical Oxidation of Sulfides to Sulfoxides. University Chemistry, 2024, 39(11): 204-209. doi: 10.3866/PKU.DXHX202401009
13. [13]
  Shuhui Li , Xucen Wang , Yingming Pan . Exploring the Role of Electrochemical Technologies in Everyday Life. University Chemistry, 2025, 40(3): 302-307. doi: 10.12461/PKU.DXHX202406059
14. [14]
  Zihan Lin , Wanzhen Lin , Fa-Jie Chen . Electrochemical Modifications of Native Peptides. University Chemistry, 2025, 40(3): 318-327. doi: 10.12461/PKU.DXHX202406089
15. [15]
  Yuan ZHU , Xiaoda ZHANG , Shasha WANG , Peng WEI , Tao YI . Conditionally restricted fluorescent probe for Fe³⁺ and Cu²⁺ based on the naphthalimide structure. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 183-192. doi: 10.11862/CJIC.20240232
16. [16]
  Cen Zhou , Biqiong Hong , Yiting Chen . Application of Electrochemical Techniques in Supramolecular Chemistry. University Chemistry, 2025, 40(3): 308-317. doi: 10.12461/PKU.DXHX202406086
17. [17]
  Feiya Cao , Qixin Wang , Pu Li , Zhirong Xing , Ziyu Song , Heng Zhang , Zhibin Zhou , Wenfang Feng . Magnesium-Ion Conducting Electrolyte Based on Grignard Reaction: Synthesis and Properties. University Chemistry, 2024, 39(3): 359-368. doi: 10.3866/PKU.DXHX202308094
18. [18]
  Yongming Zhu , Huili Hu , Yuanchun Yu , Xudong Li , Peng Gao . Construction and Practice on New Form Stereoscopic Textbook of Electrochemistry for Energy Storage Science and Engineering: Taking Basic Course of Electrochemistry as an Example. University Chemistry, 2024, 39(8): 44-47. doi: 10.3866/PKU.DXHX202312086
19. [19]
  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
20. [20]
  Yong Zhou , Jia Guo , Yun Xiong , Luying He , Hui Li . Comprehensive Teaching Experiment on Electrochemical Corrosion in Galvanic Cell for Chemical Safety and Environmental Protection Course. University Chemistry, 2024, 39(7): 330-336. doi: 10.3866/PKU.DXHX202310109

Get Citation

PDF

XML

Metrics

PDF Downloads(1132)
Abstract views(2624)
HTML views(3)

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

Synthesis of Ferrocenoyl-Labeled Tripeptide Fc-Gly-Pro-Arg(NO2)-OMe and Its Interaction with Cu(II)

Metrics

通讯作者: 陈斌, bchen63@163.com

Synthesis of Ferrocenoyl-Labeled Tripeptide Fc-Gly-Pro-Arg(NO₂)-OMe and Its Interaction with Cu(II)