Notes

Intermolecular Ligand Exchange of Penta-oxy Phosphoranes: Potential Chemical Model for RNA Hydrolysis and Fusion

  • Wang Xun ,
  • Chen Su ,
  • Wu Yile ,
  • Wang Xiaoyu ,
  • Tang Guo ,
  • Liu Yan ,
  • Xu Pengxiang ,
  • Gao Xiang ,
  • Zhao Yufen
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  • a Department of Chemistry, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005;
    b School of Pharmaceutical Sciences, Xiamen University, Xiamen 361102;
    c Institute of Drug Discovery Technology, Ningbo University, Ningbo 315211

Received date: 2019-03-20

  Revised date: 2019-04-17

  Online published: 2019-06-03

Supported by

Project supported by the National Natural Science Foundation of China (Nos. 21778042, 41876072, 21772163, 41576081), the Xiamen Southern Oceanographic Center (No. 17GYY002NF02), and the Fundamental Research Funds for the Central Universities (No. 20720170069).

Abstract

Penta-coordinated phosphoranes (ab2) with a five-member cycle and three ligands would simultaneously exchange with themselves under base catalysis to form three different penta-oxy phosphoranes with all the combinatorial ligands referred as a3, b3, and a2b. If we consider a3 and b3 as parents, the products obtained from exchange, namely a2b and ab2, could be regarded as the offspring of the first generation, leading to the diversified chemical structures. Thus, these fascinating reactions could be considered as a promising chemical model for studying the unique chemistry of possible penta-coordinated phosphorus intermediates in the process of RNA self-splicing, hydrolysis and fusion for gene transcription and biological information storage.

Cite this article

Wang Xun , Chen Su , Wu Yile , Wang Xiaoyu , Tang Guo , Liu Yan , Xu Pengxiang , Gao Xiang , Zhao Yufen . Intermolecular Ligand Exchange of Penta-oxy Phosphoranes: Potential Chemical Model for RNA Hydrolysis and Fusion[J]. Chinese Journal of Organic Chemistry, 2019 , 39(8) : 2311 -2316 . DOI: 10.6023/cjoc201905007

References

[1] Lassila, J. K.; Zalatan, J. G.; Herschlag, D. Ann. Rev. Biochem. 2011, 80, 669.
[2] Petrovic, D.; Szeler, K.; Kamerlin, S. C. L. Chem. Commun. 2018, 54, 3077.
[3] Guo, F. M.; Yue, Z. K.; Trajkovski, M.; Zhou, X. P.; Cao, D.; Li, Q.; Wang, B. F.; Wen, X.; Plavec, J.; Peng, Q.; Xi, Z.; Zhou, C. Z. J. Am. Chem. Soc. 2018, 140, 11893.
[4] (a) Messina, K. J.; Bevilacqua, P. C. J. Am. Chem. Soc. 2018, 140, 10578.
(b) Wilson, T. J.; Liu, Y.; Domnick, C.; Kath-Schorr, S.; Lilley, D. M. J. Am. Chem. Soc. 2016, 138, 6151.
[5] Nguyen, T. C.; Cao, X. Y.; Yu, P. F.; Xiao, S.; Lu, J.; Biase, F. H.; Sridhar, B.; Huang, N.; Zhang, K.; Zhong, S. Nat. Commun. 2016, 7, 12023.
[6] (a) Uraguchi, D.; Sasaki, H.; Kimura, Y.; Ito, T.; Ooi, T. J. Am. Chem. Soc. 2018, 140, 2765.
(b) Yliniemela, A.; Uchimaru, T.; Tanabe, K.; Taira, K. J. Am. Chem. Soc. 1993, 115, 3032.
(c) Westheimer, F. H. Acc. Chem. Res. 1968, 1, 70.
[7] Jin, Y.; Richards, N. G.; Waltho, J. P.; Blackburn, G. M. Angew. Chem., Int. Ed. 2017, 56, 4110.
[8] DeYonker, N. J.; Webster, C. E. Biochemistry 2015, 54, 4236.
[9] DeYonker, N. J.; Webster, C. E. J. Am. Chem. Soc. 2013, 135, 13764.
[10] (a) Wittig, G.; Rieber, M. Justus Liebigs Ann. Chem. 1949, 562, 187.
(b) Pajkert, R.; Röeschenthaler, G.-V. Organophosphorus Chem. 2017, 46, 323.
(c) Swamy, K. C. K.; Kumar, N. S. Acc. Chem. Res. 2006, 39, 324.
[11] (a) Hou, J. B.; Tang, G.; Guo, J. N.; Liu, Y.; Zhang, H.; Zhao, Y. F. Tetrahedron:Asymmetry 2009, 20, 1301.
(b) Wang, T.; Zhang, P. B.; Hu, G. B.; Gao, Y. Z.; Wu, Y. L.; Xu, P. X.; Liu, Y.; Zhao, Y. F. ChemistrySelect 2018, 3, 7849.
(c) Fu, H.; Li, Z. L.; Zhao, Y. F.; Tu, G. Z. J. Am. Chem. Soc.1999, 121, 291.
(d) Ying, J. X.; Fu, S. S.; Li, X.; Feng, L. B.; Xu, P. X.; Liu, Y.; Gao, X.; Zhao, Y. F. Chem. Commun. 2018, 54, 8598.
[12] (a) Ramirez, F. Acc. Chem. Res. 1968, 1, 168.
(b) Ramirez, F.; Chaw, Y. F.; Marecek, J. F.; Ugi, I. J. Am. Chem. Soc. 1974, 96, 2429.
[13] (a) Holmes, R. R. Acc. Chem. Res. 2004, 37, 746.
(b) Timosheva, N. V.; Chandrasekaran, A.; Holmes, R. R. Inorg. Chem. 2006, 45, 3113.
[14] (a) Ramirez, F.; Tasaka, K.; Desai, N. B.; Smith, C. P. J. Am. Chem. Soc. 1968, 90, 751.
(b) Ramirez, F.; Loewengart, G. V.; Tsolis, E. A.; Tasaka, K. J. Am. Chem. Soc. 1972, 94, 3531.
[15] Ramirez, F.; Marecek, J. F.; Okazaki, H. V. A. J. Am. Chem. Soc. 1976, 98, 5310.

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