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Original Articles

The Possible Role of Cyclic Pentacoordinate Phosphorus Intermediates in the Origin and Evolution of Life. are Phosphoric Anhydride and Trimetaphosphates Prebiotic Reagents?

Pages 2173-2186 | Received 29 May 2015, Accepted 07 Aug 2015, Published online: 10 Dec 2015

REFERENCES

  • Pross, A. Origin. Life Evol. Biosph. 2004, 34, 307-321, and ref. cited therein(b)Joyce, G.F. Nature 2002, 418, 214-221.
  • (a) Despois, D.; Cottin, H. Lectures in Astrobiology; Springer: Berlin, 2005, 289-352, and ref. cited therein(b)Ehrenfreund, P.; Charnley, S.B. Annu. Rev. Astron. Astrophys. 2000, 38, 427-483(c)Saladino, R.; Crestini, C.; Ciciriello, F.; Pino, S.; Costanzo, G.; Di Mauro, E. Res. Microbiol. 2009, 160, 441-448.
  • Holmes, R.R. Acc. Chem. Res. 2004, 37, 746-753(b)Holmes, R.R.; Deiters, J.A. Inorg. Chem. 1994, 33, 3235-3238. For reviews on hypervalent phosphorus, see(c)Holmes, R.R. Pentacoordinated Phosphorus Structure and Spectroscopy, ACS Monograph 175; American Chemical Society: Washington, DC, 1980, Vols. 190(d)Holmes, R.R. Acc. Chem. Res. 1998, 31, 535-542(e)Lu, Z.; Dunaway-Mariano, D.; Allen, K.N. PNAS 2008, 105, 5687-5692(f)Lahiri, S.D.; Zhang, G.; Dunaway-Mariano, D.; Allen, K.N. Science 2003, 299, 2067-2071(g)Baxter, N.J.; Bowler, M.W.; Alizadeh, T.; Cliff, M.J.; Hounslow, A.M.; Wu, B.; Waltho, J.P. PNAS 2010, 107, 4555-4560(h)Allen, K.N.; Dunaway-Mariano, D. Science 2003, 301, 1184.
  • Cherkasov, R.A.; Polezhaeva, N.A.; Russ. Chem. Rev. 1989, 56, 163-181(b)Kumara Swamy, K.C.; Sathis Kumar, N. Acc. Chem. Res. 2006, 39, 324-333(c)Baccolini, G.; Micheletti, G.; Boga, C. J. Org. Chem. 2009, 74, 6812-6818(d)Baccolini, G.; Todesco, P.E. J. Org. Chem. 1978, 43, 216(e)Baccolini, G.; Boga, C.; Mazzacurati, M.; Micheletti, G. Chem. Eur. J. 2009, 15, 597-599(f)Baccolini, G.; Todesco, P.E. Tetrahedron Lett. 1978, 19, 2313-2316(g)Kumara Swamy, K.; Day, R.O.; Holmes, J.M.; Holmes, R.R. J. Am. Chem. Soc. 1990, 112, 6095-6103(h)Holmes, R.R.; Swamy, K.K.; Holmes, J.M.; Day, R.O. Inorg. Chem. 1991, 30, 1052-1062.
  • Röschenthaler, G.V. Organophosph. Chem. 2008, 37, 247-261.
  • Gillespie, P.; Ramirez, F.; Ugi, I.; Marquading, D. Angew. Chem. Int. Ed. 1973, 12, 91-119(b)Berry, R.S. J. Chem. Phys. 1960, 32, 933-938.
  • Nakamoto, M.; Kojima, S.; Matsukawa, S.; Yamamoto, Y.; Akiba, K.Y. J. Organomet. Chem. 2002, 643, 441-452.
  • Westheimer, F.H. Acc. Chem. Res. 1968, 1, 70-78.
  • Schray, K.J.; Benkovic, S.J. J. Amer. Chem. Soc. 1971, 93, 2522-2529(b)Baccolini, G.; Boga, C.; Micheletti, G. Phosphorus Sulfur Silicon Relat. Elem. 2010, 185, 2303-2315.
  • Yamagata, Y.; Kojima, H.; Ejiri, K.; Inomata, K. Origins Life 1982, 12, 333-337.
  • Schawalbe, C.H.; Freeman, S. J. Chem. Soc. Chem. Comun. 1990, 3, 251-253.
  • Saladino, R.; Crestini, C.; Pino, S.; Costanzo, G.; Di Mauro, E. Phys Life Rev. 2012, 9, 84-104, and ref. cited therein.
  • Oivanen, M.; Kuusela, S.; Lönnberg, H. Chem. Rev. 1998, 98, 961-990(b)Mikkola, S.;Kaukinen, U.; Lönnberg, H. Cell. Biochem. Biophys. 2001, 34, 95-119.
  • Zhou, D.M.; Taira, K. Chem. Rev. 1998, 98, 991-1026.
  • Zhang, Z.Y. Acc. Chem. Res. 2003, 36, 385-392(b)Kumara Swamy, K.C.; Kumara Swamy, S.; Kommana, P. J. Am. Chem. Soc. 2001, 123, 12642-12649(c)Wang, H.Y.; Ji, Z.L.; Hu, A.F.; Zhao, Y.F. J. Mol. Evol. 2010, 70, 572-582.
  • Baccolini, G.; Micheletti, G. Phosphorus, Sulfur Silicon Relat. Elem. 2014, 189, 1254-1265(b)Baccolini, G.; Boga, C.; Galeotti, M. Angew. Chem. Int. Ed. 2004, 43, 3058-3060.
  • Baccolini, G.; Busetto, L.; Roncarolo, A.; Albano, V.G.; Demartin, F. J. Chem. Soc. Dalton Trans. 1987, 21, 14. In this paper, we obtained crystals of hexacoordinated complex of Re containing only the S form of a racemic phosphine ligand.
  • Yamagata, Y.; Watanabe, H.; Saitoh, M.; Namba, T. Nature 1991, 352, 516-519.
  • (a) Efedrov, D.A.; Zavlin, P.M.; Tebby, J.C., eds. Phosphoric Anhydride: Structure, Chemistry and Applications; John Wiley: Chichester, 1999. (b) Baccolini, G; Boga, C ; Delpivo, C; Micheletti, G. Tetrahedron. Letters 2011,1713-1717 (c) Baccolini, G; Delpivo, C; Micheletti, G. Green Chemistry Letters and Reviews, 2013. 6, 135-139.
  • Fuller, W.D.; Sanchez, R.A.; Orgel, L.E. J. Mol. Biol. 1972, 67, 25-33(b)Schwartz, A.W. Chem. Commun. 1969, 1393(c)Saffhill, R. J. Org. Chem. 1970, 35, 2881-2883(d)Etaix, E.; Orgel, L.E. J. Carb. Nucleos. Nucleot. 1978, 5, 91-110(e)Tsuhako, M.; Fujimoto, M.; Ohashi, S., Nariai, H.; Motooka, I. Bull. Chem. Soc. Jpn. 1984, 57, 3274-3280(f)Yamagata, Y.; Inoue, H.; Inomata, K. Origin. Life Evol. Biosph. 1995, 25, 47-52(g)Cheng, C.; Fan, C.; Wan, R.; Tong, C.; Miao, Z.; Chen, J.; Zhao, Y. Origin. Life Evol. Biosph. 2002, 32, 219-224(h)Ni, F.; Sun, S.; Huang, C.; Zhao, Y. Green Chem. 2009, 11, 569-573.
  • Schramm, G.; Wissmann, H. Chem. Ber. 1958, 91, 1073(b)Schramm, G.; Grôtsch, H.; Pollmann, W. Angew. Chem. 1961, 73, 619 or Angew. Chem. Int. Ed. 1962, 1-7(c)Pollmann, W.; Schramm, G. Biochim. Biophys. Acta, Specialized Section on Nucleic Acids and Related Subjects 1964, 80, 1-7(d) Schramm, G. Synthesis of nucleotides and polynucleotides with metaphosphate esters. In: Sidney W.Fox (Ed.), The Origin of Prebiological Systems and of Their Molecular Matrices; Academic Press, 1965; pp. 299-315.
  • Pino, S.; Ciciriello, F.; Costanzo, G.; Di Mauro, E. J. Biol. Chem. 2008, 283, 36494-36503.
  • Caglioti, L.; Poloni, M.; Rosini, G. J. Org. Chem. 1968, 33, 2979-2981(b)Baccolini, G.; Todesco, P.E. J. Chem. Soc. Chem. Commun. 1981, 563-564(c)Baccolini, G.; Sandali, C. J. Chem. Soc. Chem. Commun. 1987, 788-789(d)Baccolini, G.; Sgarabotto, P. J. Chem. Soc. Chem. Commun. 1991, 34-35.

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