Citation: Qi Qige, Yang Chunfan, Xia Ye, Liu Kunhui, Su Hongmei. Photo-induced Electron Transfer between 4-Thiouracil and Tryptophan[J]. Acta Chimica Sinica, ;2019, 77(6): 515-519. doi: 10.6023/A19040149 shu

Photo-induced Electron Transfer between 4-Thiouracil and Tryptophan

  • Corresponding author: Yang Chunfan, yangchunfan@bnu.edu.cn Su Hongmei, hongmei@bnu.edu.cn
  • Received Date: 29 April 2019
    Available Online: 22 June 2019

    Fund Project: the National Natural Science Foundation of China 21727803the National Natural Science Foundation of China 21425313Project supported by the National Natural Science Foundation of China (Nos. 21425313, 21727803, 21703011)the National Natural Science Foundation of China 21703011

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  • RNA-protein interactions are inevitably existing in many fundamental biological processes of organisms and it is an effective method to investigate the nature of RNA-protein interactions through crosslinking induced by photoactivation. Therefore, it is of great importance to detect the crucial transient intermediates to elucidate the mechanism of photo crosslinking between RNA and proteins, which will shed light on regulating the crosslinking sites as well as the favorable cross-linked amino acids. In this research, we choose the photoactivatable ribonucleotide analog, 4-thiouracil, and the aromatic amino acid, tryptophan, as a model system to study, from which the photo crosslinking is found to be initiated by the electron transfer as the first step. By means of the nanosecond time-resolved laser flash photolysis, the key intermediates of photo-induced electron transfer from tryptophan to the triplet of 4-thiouracil, 4-thiouracil anion radical (4-TU·-)and tryptophan cation radical (TrpH·+) are observed, as well as the deprotonated species of tryptophan neutral radical (Trp·). By monitoring the 4-TU triplet decay kinetics, the pseudo-first order rate constant of photo-induced electron transfer is determined to be 2.88×109 L·mol-1·s-1 and found to be diffusion-controlled. The pH-effect on the electron transfer and proton transfer have been further examined. In addition, the driving force for electron transfer from tryptophan to 4-TU triplet is estimated using the classic Rehm-Weller empirical equation to be -0.15 eV, which means the photo-induced electron transfer process is favorable thermodynamically. These results demonstrate that photo-induced electron transfer between 4-thiouracil triplet and tryptophan is the key step, which can trigger the following proton transfer and radical coupling processes and lead to the covalent photoadducts. These studies provide a basis for mechanistic understandings of photo crosslinking between RNA and proteins in more complex system.
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    1. [1]

      Lin, R. J. RNA-Protein Interaction Protocols, Humana Press, Totowa, USA, 2008, p. 85.

    2. [2]

      Ule, J.; Jensen, K. B.; Ruggiu, M.; Mele, A.; Ule, A.; Darnell, R. B. Science 2003, 302, 1212.  doi: 10.1126/science.1090095

    3. [3]

      Licatalosi, D. D.; Mele, A.; Fak, J. J.; Ule, J.; Kayikci, M.; Chi, S. W.; Clark, T. A.; Schweitzer, A. C.; Blume, J. E.; Wang, X.; Dar-nell, J. C.; Darnell, R. B. Nature 2008, 456, 464.  doi: 10.1038/nature07488

    4. [4]

      Kishore, S.; Jaskiewicz, L.; Burger, L.; Hausser, J.; Khorshid, M.; Zavolan, M. Nat. Methods 2011, 8, 559.  doi: 10.1038/nmeth.1608

    5. [5]

      Hafner, M.; Landthaler, M.; Burger, L.; Khorshid, M.; Hausser, J.; Berninger, P.; Rothballer, A.; Ascano, M. Jr.; Jungkamp, A. C.; Munschauer, M.; Ulrich, A.; Wardle, G. S.; Dewell, S.; Zavolan, M.; Tuschl, T. Cell 2010, 141, 129.  doi: 10.1016/j.cell.2010.03.009

    6. [6]

      Ascano, M.; Hafner, M.; Cekan, P.; Gerstberger, S.; Tuschl, T. WIRES RNA 2012, 3, 159.  doi: 10.1002/wrna.v3.2

    7. [7]

      Kstharina, K.; Timo, S.; Benedikt, M. B.; Saadia, Q.; Kum, L. B.; Matthias, W. H.; Oliver, K.; Urlaub, H. Nat. Methods 2014, 11, 1064.  doi: 10.1038/nmeth.3092

    8. [8]

      Zhou, D. J.; Ye, K. Q. Chin. Bull. Life Sci. 2014, 26, 207(in Chinese).

    9. [9]

      Favre, A.; Saintome, C.; Fourrey, J. L.; Clivio, P.; Laugaa, P. J. Photochem. Photobiol. B-Biol. 1998, 42, 109.  doi: 10.1016/S1011-1344(97)00116-4

    10. [10]

      Shalitin, N.; Feitelson, J. Biochemistry 1976, 15, 2092.  doi: 10.1021/bi00655a010

    11. [11]

      Zou, X. R.; Dai, X. J.; Liu, K. H.; Zhao, H. M.; Song, D.; Su, H. M. J. Phys. Chem. B 2014, 118, 5864.  doi: 10.1021/jp501658a

    12. [12]

      Milder, S. J.; Kliger, D. S. J. Am. Chem. Soc. 1985, 107, 7365.  doi: 10.1021/ja00311a025

    13. [13]

      Khvorostov, A.; Lapinski, L.; Rostkowska, H.; Nowak, M. J. Photochem. Photobiol. 2005, 81, 1205.  doi: 10.1562/2005-05-19-RA-534

    14. [14]

      Gagliardi, C. J.; Binstead, R. A.; Thorp, H. H.; Meyer, T. J. J. Am. Chem. Soc. 2011, 133, 19594.  doi: 10.1021/ja207379n

    15. [15]

      Zhang, M. T.; Hammarström, L. J. Am. Chem. Soc. 2011, 133, 8806.  doi: 10.1021/ja201536b

    16. [16]

      Miller, J. E.; Gradinaru, C.; Crane, B. R.; Di Bilio, A. J.; Wehbi, W. A.; Un, S.; Winkler, J. R.; Gray, H. B. J. Am. Chem. Soc. 2003, 125, 14220.  doi: 10.1021/ja037203i

    17. [17]

      Lassmann, G.; Lendzian, F.; MacMillian, F.; Bittl, R.; Potsch, S.; Sahlin, M.; Sjoberg, B. M.; Graslund, A.; Lubitz, W. FASEB J. 1997, 11, A882.

    18. [18]

      Solar, S.; Getoff, N.; Surdhar, P. S.; Armstrong, D. A.; Singh, A. J. Phys. Chem. 1991, 95, 3639.  doi: 10.1021/j100162a038

    19. [19]

      Katharina, K.; Petra, H.; He, H. H.; Xiao, L.; Markus, W.; Urlaub, H. Int. J. Mass Spectrom. 2011, 304, 184.  doi: 10.1016/j.ijms.2010.10.009

    20. [20]

      Rehm, D.; Weller, A. Isr. J. Chem. 1970, 8, 259.  doi: 10.1002/ijch.v8.2

    21. [21]

      Holzer, K. P.; Wrona, Z. Bioelectrochem. Bioenerg. 1983, 11, 3.  doi: 10.1016/0302-4598(83)85096-X

    22. [22]

      Wrona, Z.; Czochralska, B.; Shugar, D. J. Electroanal. Chem. 1976, 68, 355.  doi: 10.1016/S0022-0728(76)80275-6

    23. [23]

      Sjödin, M.; Styring, S.; Åkermark, B.; Sun, L. C.; Hammarström, L. J. Am. Chem. Soc. 2000, 122, 3932.  doi: 10.1021/ja993044k

    24. [24]

      Tsentalovich, Y. P.; Lopez, J. J.; Hore, P. J.; Sagdeev, R. Z. Spectrochim. Acta, Part A 2002, 58, 2043.  doi: 10.1016/S1386-1425(01)00652-7

    25. [25]

      Psoda, A.; Kazimierczuk, Z.; Shugar, D. J. Am. Chem. Soc. 1974, 96, 6832.  doi: 10.1021/ja00829a003

    26. [26]

      Cardoso, D. R.; Franco, D. W.; Olsen, K.; Andersen, M. L.; Skibsted, L. H. J. Agric. Food Chem. 2004, 52, 6602.  doi: 10.1021/jf0401165

    27. [27]

      Heelis, P. F.; Parsons, B. J.; Phillips, G. O. Biochim. Biophys. Acta 1979, 587, 455.  doi: 10.1016/0304-4165(79)90449-5

    28. [28]

      Sjödin, M.; Styring, S.; Wolpher, H.; Xu, Y.; Sun, L.; Ham-marström, L. J. Am. Chem. Soc. 2005, 127, 3855.  doi: 10.1021/ja044395o

    29. [29]

      Wu, L. D.; Jie, J. L.; Liu, K. H.; Su, H. M. Acta Chim. Sinica 2014, 72, 1182(in Chinese).
       

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