维生素K<sub>3</sub>的激发三重态与色氨酸、酪氨酸电子转移氧化反应的激光闪光光解研究

引用本文: 唐睿智, 李海霞, 刘艳成, 张鹏, 曹西艳, 王文锋. 维生素K₃的激发三重态与色氨酸、酪氨酸电子转移氧化反应的激光闪光光解研究[J]. 物理化学学报, 2012, 28(01): 213-216. doi: 10.3866/PKU.WHXB201228213 shu

Citation: TANG Rui-Zhi, LI Hai-Xia, LIU Yan-Cheng, ZHANG Peng, CAO Xi-Yan, WANG Wen-Feng. Laser Flash Photolysis Study on Electron Transfer Oxidation Reaction of Tryptophan or Tyrosine with Triplet State Vitamin K₃[J]. Acta Physico-Chimica Sinica, 2012, 28(01): 213-216. doi: 10.3866/PKU.WHXB201228213 shu

维生素K₃的激发三重态与色氨酸、酪氨酸电子转移氧化反应的激光闪光光解研究

基金项目:
国家自然科学基金(21173252)资助项目 (21173252)

摘要: 利用时间分辨的激光闪光光解技术研究了乙腈-水混合溶液(1:1, V/V)中2-甲基萘醌(通常称为维生素K₃)的激发三重态对色氨酸、酪氨酸的光敏氧化机理. 通过瞬态吸收光谱的变化可以推断维生素K₃的激发三重态可以与色氨酸、酪氨酸发生电子转移反应, 反应形成的维生素K₃阴离子自由基的吸收峰可以直接从瞬态吸收谱图中观察到. 维生素K₃与色氨酸、酪氨酸的电子转移反应的速率分别为1.1×10⁹和0.6×10⁹ L·mol^-1·s^-1. 吉布斯自由能(ΔG)的计算结果表明维生素K₃的激发三重态与色氨酸、酪氨酸电子转移反应在热力学上是可行的.

关键词:

English

Laser Flash Photolysis Study on Electron Transfer Oxidation Reaction of Tryptophan or Tyrosine with Triplet State Vitamin K₃

1.
1. Shanghai Institute of Applied Physics, Chinese Academy of Sciences, Shanghai 201800, P. R. China;
2. Graduate University of Chinese Academy of Sciences, Beijing 100049, P. R. China;
3. School of Chemistry and Chemical Engineering, Hunan University of Science and Technology, Xiangtan 411201, Hunan Province, P. R. China
Received Date: 07 September 2011
Available Online: 29 December 2011
Fund Project:
国家自然科学基金(21173252)资助项目

Abstract: Laser flash photolysis was used to study the photosensitized oxidation mechanism of vitamin K₃, commonly known as 2-methyl-1,4-naphthoquinone (MQ), with tryptophan (TrpH) or tyrosine (TyrOH) in acetonitrile/water (1:1, V/V) solution. The triplet state of MQ reacted with TrpH or TyrOH by electron transfer with the formation of a MQ anion radical, which was directly observed in the transient absorption spectrum. The rate constants of the electron transfer reactions were determined to be 1.1×10⁹ and 0.6×10⁹ L·mol^-1·s^-1 for TrpH and TyrOH, respectively. The free energy changes (ΔG) of the reactions showed that the proposed electron transfer steps are thermodynamically feasible.

Key words:

1. [1]
  (1) Finkel, T.; Holbrook, N. J. Nature 2000, 408, 239. (1) Finkel, T.; Holbrook, N. J. Nature 2000, 408, 239.
2. [2]
  (2) Harman, D. J. Gerontol. 1957, 2, 298.(2) Harman, D. J. Gerontol. 1957, 2, 298.
3. [3]
  (3) Davies, M. J.; Truscott, R. J.W. J. Photochem. Photobiol. B: Biol. 2001, 63, 114. (3) Davies, M. J.; Truscott, R. J.W. J. Photochem. Photobiol. B: Biol. 2001, 63, 114.
4. [4]
  (4) Silva, E.; Ugarte, R.; Andrade, A.; Edwards, A. M. J. Photochem. Photobiol. B: Biol. 1994, 63, 43.(4) Silva, E.; Ugarte, R.; Andrade, A.; Edwards, A. M. J. Photochem. Photobiol. B: Biol. 1994, 63, 43.
5. [5]
  (5) Jovanovic, S. V.; Harriman, A.; Simic, M. G. J. Phys. Chem. 1986, 90, 1935. (5) Jovanovic, S. V.; Harriman, A.; Simic, M. G. J. Phys. Chem. 1986, 90, 1935.
6. [6]
  (6) Lu, C. Y.; Liu, Y. Y. BBA-Gen. Subj. 2002, 1, 71.(6) Lu, C. Y.; Liu, Y. Y. BBA-Gen. Subj. 2002, 1, 71.
7. [7]
  (7) Zhang, P.; Song, X. Y.; Li, H. X. Yao, S. D.;Wang,W. F. J. Photochem. Photobiol. A: Chem. 2010, 215, 191. (7) Zhang, P.; Song, X. Y.; Li, H. X. Yao, S. D.;Wang,W. F. J. Photochem. Photobiol. A: Chem. 2010, 215, 191.
8. [8]
  (8) Davies, K. J. A. J. Biol. Chem. 1987, 20, 9895.(8) Davies, K. J. A. J. Biol. Chem. 1987, 20, 9895.
9. [9]
  (9) Viteri, G.; Edwards, A. M.; Fuente, J. D. L. Photochem. Photobiol. 2003, 5, 535.(9) Viteri, G.; Edwards, A. M.; Fuente, J. D. L. Photochem. Photobiol. 2003, 5, 535.
10. [10]
  (10) Zhang, Z. X.; Hao, S. M.; Zhu, H. P. ;Wang,W. F. J. Photochem. Photobiol. B: Biol. 2008, 92, 77. (10) Zhang, Z. X.; Hao, S. M.; Zhu, H. P. ;Wang,W. F. J. Photochem. Photobiol. B: Biol. 2008, 92, 77.
11. [11]
  (11) Beal, M. F. Free. Radic. Biol. Med. 2002, 32, 797. (11) Beal, M. F. Free. Radic. Biol. Med. 2002, 32, 797.
12. [12]
  (12) Levine, R. L. Free. Radic. Biol. Med. 2002, 32, 790. (12) Levine, R. L. Free. Radic. Biol. Med. 2002, 32, 790.
13. [13]
  (13) Hakl?, Ö.; Karapire, C.; Posokhov, Y.; Icli, S. J. Photochem. Photobiol. A: Chem. 2004, 162, 283. (13) Hakl?, Ö.; Karapire, C.; Posokhov, Y.; Icli, S. J. Photochem. Photobiol. A: Chem. 2004, 162, 283.
14. [14]
  (14) He, Q. H.;Wang, Z. X.; Cao, X. X. ; Chen, H.W.; Ke, Y. F. Anal. Sci. 2001, 17, 1209. (14) He, Q. H.;Wang, Z. X.; Cao, X. X. ; Chen, H.W.; Ke, Y. F. Anal. Sci. 2001, 17, 1209.
15. [15]
  (15) Vire, J. C.; Patriarche, G. J.; Christian, G. D. Anal. Chem. 1979, 51, 752. (15) Vire, J. C.; Patriarche, G. J.; Christian, G. D. Anal. Chem. 1979, 51, 752.
16. [16]
  (16) Chen, J. F.; Chu, G. S.; Zhang, Z. C.; Yao, S. D.; Lin, N. Y. Radiat. Phys. Chem. 1999, 55, 35. (16) Chen, J. F.; Chu, G. S.; Zhang, Z. C.; Yao, S. D.; Lin, N. Y. Radiat. Phys. Chem. 1999, 55, 35.
17. [17]
  (17) Perez-Ruiz, T.; Martinez-Lozano, C.; Tomas, V.; Martin, J. Talanta 1999, 50, 49. (17) Perez-Ruiz, T.; Martinez-Lozano, C.; Tomas, V.; Martin, J. Talanta 1999, 50, 49.
18. [18]
  (18) BerzasNevado, J. J.; Murillo-Pulgarin, J. A.; Gómez-Laguna, M. A. Talanta 2001, 53, 951. (18) BerzasNevado, J. J.; Murillo-Pulgarin, J. A.; Gómez-Laguna, M. A. Talanta 2001, 53, 951.
19. [19]
  (19) Dozal, A.; Keyzer, H.; Kim, H. K.;Wang,W.W. Int. J. Antimicrob. Agents. 2000, 14, 261. (19) Dozal, A.; Keyzer, H.; Kim, H. K.;Wang,W.W. Int. J. Antimicrob. Agents. 2000, 14, 261.
20. [20]
  (20) Wagner, J. R.; VanLier, J. E.; Johnston, L. J. Photochem. Photobiol. 1990, 52, 333. (20) Wagner, J. R.; VanLier, J. E.; Johnston, L. J. Photochem. Photobiol. 1990, 52, 333.
21. [21]
  (21) Melvin, T.; Bothe, E.; Schulte-Frohlinde, D. Photochem. Photobiol. 1996, 64, 769. (21) Melvin, T.; Bothe, E.; Schulte-Frohlinde, D. Photochem. Photobiol. 1996, 64, 769.
22. [22]
  (22) Ma, J. H.; Lin,W. Z.; Du, F. Q.; Han, Z. H.; Yao, S. D.; Lin, N. Y. Sci. China B Chem. 2005, 48, 292. (22) Ma, J. H.; Lin,W. Z.; Du, F. Q.; Han, Z. H.; Yao, S. D.; Lin, N. Y. Sci. China B Chem. 2005, 48, 292.
23. [23]
  (23) Zhang, H. J.; Li, M. Y.;Wang, P.; Peng, J.;Wang, L.; Ai, X. C.; Zhang, X. K.; Zhang, J. P. Chinese Science Bulletin 2004, 49, 2144.(23) Zhang, H. J.; Li, M. Y.;Wang, P.; Peng, J.;Wang, L.; Ai, X. C.; Zhang, X. K.; Zhang, J. P. Chinese Science Bulletin 2004, 49, 2144.
24. [24]
  (24) Sengupta, T.; Choudhury, S. D.; Basu, S. T. J. Am. Chem. Soc. 2004, 126, 10589. (24) Sengupta, T.; Choudhury, S. D.; Basu, S. T. J. Am. Chem. Soc. 2004, 126, 10589.
25. [25]
  (25) Bose, A.; Basu, S. J. Phys. Chem. A 2008, 112, 12045. (25) Bose, A.; Basu, S. J. Phys. Chem. A 2008, 112, 12045.
26. [26]
  (26) Bose, A.; Dey, D.; Basu, S. J. Phys. Chem. A 2008, 112, 4914. (26) Bose, A.; Dey, D.; Basu, S. J. Phys. Chem. A 2008, 112, 4914.
27. [27]
  (27) Zuo, Z. H.; Yao, S. D.; Luo, J.;Wang,W. F.; Zhang, J. S.; Lin, N. Y. J. Photochem. Photobiol. B: Biol. 1992, 15, 215. (27) Zuo, Z. H.; Yao, S. D.; Luo, J.;Wang,W. F.; Zhang, J. S.; Lin, N. Y. J. Photochem. Photobiol. B: Biol. 1992, 15, 215.
28. [28]
  (28) Bose, A.; Dey, D.; Basu, S. J. Photochem. Photobiol. A: Chem. 2007, 186, 130. (28) Bose, A.; Dey, D.; Basu, S. J. Photochem. Photobiol. A: Chem. 2007, 186, 130.
29. [29]
  (29) Amada, I.; Yamaji, M. Tsunoda, S.; Shizuka, H. J. Photochem. Photobio.. A: Chem. 1996, 95, 27. (29) Amada, I.; Yamaji, M. Tsunoda, S.; Shizuka, H. J. Photochem. Photobio.. A: Chem. 1996, 95, 27.
30. [30]
  (30) Bensasson, R. V.; Land, E. J.; Truscott, T. G. Flash Photolysis and Pulse Radiolysis-Contributions to the Chemistry of Biology and Medicine; Oxford University Press: Oxford; 1983; pp 93-110.(30) Bensasson, R. V.; Land, E. J.; Truscott, T. G. Flash Photolysis and Pulse Radiolysis-Contributions to the Chemistry of Biology and Medicine; Oxford University Press: Oxford; 1983; pp 93-110.
31. [31]
  (31) Solar, S.; Getoff, N.; Surdhar, P. S.; Armstrong, D. A.; Singh, A. J. Phys. Chem. 1991, 95, 3639. (31) Solar, S.; Getoff, N.; Surdhar, P. S.; Armstrong, D. A.; Singh, A. J. Phys. Chem. 1991, 95, 3639.
32. [32]
  (32) Tsentalovich, Y. P.; Snytnikova, O. A.; Sagdeev, R. Z. J. Photochem. Photobiol. A: Chem. 2004, 162, 371(32) Tsentalovich, Y. P.; Snytnikova, O. A.; Sagdeev, R. Z. J. Photochem. Photobiol. A: Chem. 2004, 162, 371
33. [33]
  (33) Chu, G. S.; Zhang, S. J.; Yao, S. D.; Dou, D. Y.; Zhang, Z. C. Acta Phys. Chim. Sin. 2002, 18, 812. [储高升, 张淑娟, 姚思德, 窦大营, 张志成. 物理化学学报, 2002, 18, 812.](33) Chu, G. S.; Zhang, S. J.; Yao, S. D.; Dou, D. Y.; Zhang, Z. C. Acta Phys. Chim. Sin. 2002, 18, 812. [储高升, 张淑娟, 姚思德, 窦大营, 张志成. 物理化学学报, 2002, 18, 812.]
34. [34]
  (34) Rehm, D.;Weller, D. Isr. J. Chem. 1970, 8, 259.(34) Rehm, D.;Weller, D. Isr. J. Chem. 1970, 8, 259.
35. [35]
  (35) Roger, J. E.; Kelly, L. A. J. Am. Chem. Soc. 1999, 121, 3854. (35) Roger, J. E.; Kelly, L. A. J. Am. Chem. Soc. 1999, 121, 3854.
36. [36]
  (36) Defelippis, M. R.; Murthy, C. P.; Faraggi, M.; Klapper, M. H. Biochemistry 1989, 28, 4847. (36) Defelippis, M. R.; Murthy, C. P.; Faraggi, M.; Klapper, M. H. Biochemistry 1989, 28, 4847.

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沈阳化工大学材料科学与工程学院沈阳 110142

维生素K₃的激发三重态与色氨酸、酪氨酸电子转移氧化反应的激光闪光光解研究

English

Laser Flash Photolysis Study on Electron Transfer Oxidation Reaction of Tryptophan or Tyrosine with Triplet State Vitamin K₃

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通讯作者: 陈斌, bchen63@163.com

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