Abstract
The 5′-phosphorimidazolide of uridine reacts on Na+-montmorillonite 22A in aqueous solution to give oligomers as long as 7 mers. The maximum chain length increases to 9 mers and the overall oligomer yield increases when 9:1 ImpU, A5′ ppA mixtures react under the same conditions. The oligomer yield and maximum chain length decreases with the structure of the added pyrophosphate in the order A5′ ppA>A5′ ppU>U5′ ppU. Structure analysis of individual oligomer fractions was performed by selective enzymatic hydrolyses followed by HPLC analysis of the products. The regioselectivity for 3′,5′-bond formation is 80–90% in the 9:1 ImpU, A5′ ppA reaction, a percentage comparable to that observed in the 9:1 ImpA, A5′ ppA reaction. Oligomerization of ImpU is inhibited by addition of dA5′ ppdA, and MeppA. No oligomers containing A5′ ppU were products of the 9:1 ImpU, A5′ ppA reaction, a finding consistent with the simple addition of the ImpU to the A5′ ppA and not the rearrangement of an ImpU-A5′ ppA adduct. Concentrations of lysine or arginine which were close to that of the ImpU did not inhibit oligomer formation. Treatment of Na+-montmorillonite with 1 M arginine yielded arginine-montmorillonite, an amino acid-mineral adduct which did not catalyze ImpU oligomerization. Neither the 4–9 mers formed in the 9:1 ImpU, A5′ ppA reaction nor the 4–9 mers formed by the base hydrolysis of poly(U) served as templates for the formation of oligo(A)s.
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Brindley, G. W. and Ertem, G.: 1971,Clays Clay Minerals 19 399–404.
Cech, T. R.: 1986,Proc. Natl. Acad. Sci., U.S.A. 83 4360–4363.
Cech, T. R., Zaug, A. J. and Grabowski, P. J.: 1981,Cell 27 487–496.
Darzynkiewicz, E., Ekiel, I., Tahara, S. M., Seliger, L. S. and Shatkin, A. J.: 1985,Biochemistry 24 1701–1707.
Dawson, R. M. C., Elliot, D. C., Elliot, W. H. and Jones, K. M.: 1969,Data for Biochemical Research, Oxford University Press.
Ferris, J. P. and Ertem, G.: 1992,Science 257 1387–1389.
Ferris, J. P. and Ertem, G.: 1992A,Origins Life Evol. Biosphere 22 369–381.
Ferris, J. P. and Ertem, G.: 1993,J. Am. Chem. Soc. 115 12270–12275.
Furuta, H., Ogawa, Y. and Yanagawa, H.: 1988,Nucleic Acids Symp. Ser. 20 87–88.
Gilbert, W.: 1986,Nature 319 618.
Glonek, T. and van Wazer, J. R.: 1976,J. Phys. Chem. 80 639–643.
Guerrier-Takada, C., Gardiner, K., Marsh, T., Pace, N. and Altman, S.: 1983,Cell 35 849–857.
Hohn, T. H. and Schaller, H.: 1967,Biochim. Biophys. Acta 138 466–473.
Inoue, T. and Orgel, L. E.: 1981,J. Am. Chem. Soc. 103 7666–7667.
Izatt, R. M., Hansen, L. D., Rytting, J. H. and Christensen, J. J.: 1965,J. Am. Chem. Soc. 87 2760–2761.
Joyce, G. F., Inoue, T. and Orgel, L. E.: 1984,J. Mol. Biol. 176 279–306.
Kanavarioti, A., Lu, J., Rosenback, M. T. and Hurley, T. B.: 1991,Tett. Letts. 32 6065–6068.
Kawamura, K. and Ferris, J. P.: 1994,J. Am. Chem. Soc. 116 7564–7572.
Li, T. and Nicolaou, K. C.: 1994,Nature 369 218–221.
Lohrmann, R. and Orge, L. E.: 1978,34, 853–855.
Lohrmann, R. and Orgel, L. E.: 1979,J. Mol. Evol. 12 237–257.
Prabahar, K. J., Cole, T. D. and Ferris, J. P.: 1994,J. Am. Chem. Soc. 116 10914–10920.
Rosen, H.: 1957,Arch. Biochem. Biophys. 67 10–15.
Sadtler: 1981,Sadtler Standard Spectra, Sadtler, Philadelphia.
Saffhill, R.: 1970,J. Org. Chem. 35 2881–2883.
Sawai, H.: 1976,J. Am. Chem. Soc. 98 7037–7039.
Sievers, D. and von Kiedrowski, G.: 1994,Nature 369 221–224.
Sleeper, H. L., Lohrmann, R. and Orgel, L. E.: 1979,J. Mol. Evol. 12 203–214.
Theng, B. K. G.: 1974,The Chemistry of Clay-Organic Reactions. Halsted Press, New York.
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Ding, P.Z., Kawamura, K. & Ferris, J.P. Oligomerization of uridine phosphorimidazolides on montmorillonite: A model for the prebiotic synthesis of rna on minerals. Origins Life Evol Biosphere 26, 151–171 (1996). https://doi.org/10.1007/BF01809853
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DOI: https://doi.org/10.1007/BF01809853