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Affinity of guanosine derivatives for polycytidylate revisited

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Abstract

Evidence is presented for complexation of guanosine 5′-monophosphate 2-methylimidazolide (2-MeImpG) with polycytidylate (poly(C)) at pH 8.0 and 23°C in the presence of 1.0 M NaCl and 0.2 M MgCl2 in water. The association of 2-McImpG with poly(C) was investigated using UV-vis spectroscopy as well as by monitoring the kinetics of the nucleophilic substitution reaction of the imidazole moiety by amines. The results of both methods are consistent with moderately strong poly(C) · 2-McImpG complexation and the spectrophotometric measurements allowed the construction of a binding isotherm with a concentration of 2-McImpG equal to 5.55 ± 0.15 mM at half occupancy. UV spectroscopy was employed to establish the binding of other guanosine derivatives on poly(C). These derivatives are guanosine 5′-monophosphate (5′GMP), guanosine 5′monophosphate imidazolide (ImpG), and guanosine 5′monophosphate morpholidate (morpG). Within experimental error these guanosine derivatives exhibit the same affinity for poly(C) as 2-McImpG.

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References

  • Borzo M, Detellier C, Lazlo P, Paris A (1980) 1H, 23Na, and 31P NMR studies of the self-assembly of the 5′-Guanosine monophosphate dianion in neutral aqueous solution in the presence of sodium cations. J Am Chem Soc 102:1124–1134

    Google Scholar 

  • Cantor CR, Schimmel PR (1980) Biophysical chemistry. Freeman, San Francisco, part III, p 864

    Google Scholar 

  • Davies RJH, Davidson N (1971) Base pairing equilibria between polynucleotides and complementary monomers. Biopolymers 10:1455–1479

    Google Scholar 

  • Gukovskaya AS, Gukovsky IYA, Chikh VP, Sukhorukov BI (1980) Study of salt effects on adenosine-polyuridylic acid interaction. Biopolymers 19:453–468

    Google Scholar 

  • Hill AV (1910) The possible effects of the aggregation of the molecules of hemoglobin on its dissociation curves. J Physiol (Lond) 40:iv

    Google Scholar 

  • Hill TL (1960) An introduction to statistical thermodynamics. Addison-Wesley, Reading, MA, p 235

    Google Scholar 

  • Hill TL (1973) Thermodynamics of ligand binding of dilute polymer molecules in solution: complementary monomers and oligomers on polynucleotides. Biopolymers 12:257–285

    Google Scholar 

  • Howard FB, Frazier J, Lipsett MN, Miles HT (1964) Infrared demonstration of two- and three-strand helix formation between poly(C) and guanosine mononucleotides and oligonucleotides. Biochem Biophys Res Commun 17:93–102

    Google Scholar 

  • Howard FB, Frazier J, Singer MF, Miles HT (1966) Helix formation between polyribonucleotides and purines, purine nucleosides and nucleotides. J Mol Biol 16:415–439

    Google Scholar 

  • Howard FB, Roy KB, Frazier J, Miles HT (1981) Does perchlorate ion change A · U combining ratios? Biopolymers 20:1089–1102

    Google Scholar 

  • Huang WK Ts'o POP (1966) Physicochemical basis of the recognition process in nucleic acid interactions. I. Interactions of polyuridylic acid and nucleosides. J Mol Biol 16:523–543

    Google Scholar 

  • Inoue T, Orgel LE (1981) Substiment control of the poly(C)-directed oligomerization of guanosine 5′-phosphoroimidazolide. J Am Chem Soc 103:7666–7667

    Google Scholar 

  • Inoue T, Orgel LE (1982) Oligomerization of (Guanosine 5′-phos-phor)-2-methylimidazolide on poly(C). J Mol Biol 162:201–218

    Google Scholar 

  • Kanavarioti A, Rosenbach MT (1991) Catalysis of hydrolysis and nucleophilic substitution at the P-N bond of phosphoimidazolide activated nucleotides in phosphate buffers. J Org Chem 56:1513–1521

    Google Scholar 

  • Kanavarioti A, Rosenbach MT, Hurley TB (1992) Nucleotides as nucleophiles: reactions of nucleotides with phosphoimidazolide activated guanosine. Orig Life 21:199–217

    Google Scholar 

  • Kanavarioti A, Bernasconi CF, Alberas DJ, Baird EE (1993) Kinetic dissection of individual steps in the poly(C)-directed oligoguanylate synthesis from guanosine 5′-monophosphate 2-methylimidazolide. J Am Chem Soc 115:8537–8546

    Google Scholar 

  • Kanavarioti A (1994) Template-directed chemistry and the origins of the RNA world. Orig Life 24:479–494

    Google Scholar 

  • Kanavarioti A, Baird EE, Smith PJ (1995a) Use of phosphoimidazolide activated guanosine to test the nucleophilicity of spermine and spermidine. J Org Chem (submitted)

  • Kanavarioti A, Stronach MW, Ketner RJ, Hurley TB (1995b) Large steric effect in the substitution reactions of amines with phosphoimidazolide activated nucleosides. J Org Chem 60:632–637

    Google Scholar 

  • Lipsett MN (1964) Complex formation between polycytidylic acid and guanine oligonucleotides. J Biol Chem 239:1256–1260

    Google Scholar 

  • Lohrmann R, Orgel LE (1980) Efficient catalysis of polycytidylic acid-directed oligoguanylate formation by Pb2+. J Mol Biol 142:555–567

    Google Scholar 

  • Mathelier HD, Howard FB, Miles HT (1979) Circular dichroism of helices formed by purine monomers with pyrimidine polynucleotides. Biopolymers 18:709–722

    Google Scholar 

  • Miles HT, Frazier J (1982) Infrared study of G · C complex formation in template-dependent oligo(G) synthesis. J Mol Biol 162:219–230

    Google Scholar 

  • Pinnavaia TJ, Marshall CL, Mettler CM, Fish CL, Miles HT, Becker ED (1978) Alkali metal ion specificity in the solution. Ordering of a nucleotide, 5′-Guanosine monophosphate. J Am Chem Soc 100: 3625–3627

    Google Scholar 

  • Sarocchi M-T, Courtois Y, Guschlbauer W (1970) Protonated polynucleotide structures. Specific complex formation between polycytidylic acid and guanosine or guanylic acids. Eur J Biochem 14:411–421

    Google Scholar 

  • Schleich T, Gould GR (1974) Stability and thermodynamics of polyuridylic acid-deoxyadenosine complexes in aqueous neutral salt solutions. Biopolymers 13:327–337

    Google Scholar 

  • Ts'o POP, Melvin IS, Olson AC (1963) Interaction and association of bases and nucleosides in aqueous solutions. J Am Chem Soc 85: 1289–1296

    Google Scholar 

  • Ts'o POP, Huang WM (1968) Physicochemical basis of the recognition process in nucleic acid interactions. II. Interactions of polyuridylic acid and polycytidylic acid with nucleoside mono- and triphosphates. Biochemistry 7:2954–2962

    Google Scholar 

  • Walmsley JA, Sagan BL (1986) The effect of monovalent cations on the association behavior of guanosine 5′-monophosphate, cytidine 5′-monophosphate, and their equimolar mixture in aqueous solution. Biopolymers 25:2149–2172

    Google Scholar 

  • Wilson GE, Falzone CJ, Dong H (1990) GDP and GTP association equilibria. Use of manganous ion induced paramagnetic relaxation rates to study hydrogen-bonded species. J Am Chem Soc 112: 8269–8273

    Google Scholar 

  • Zimmerman SB (1976) X-ray study by fiber diffraction methods of a self-aggregate of guanosine 5′-phosphate with the same helical parameters as poly(rG). J Mol Biol 106:663–672

    Google Scholar 

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Kanavarioti, A., Hurley, T.B. & Baird, E.E. Affinity of guanosine derivatives for polycytidylate revisited. J Mol Evol 41, 161–168 (1995). https://doi.org/10.1007/BF00170668

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