Skip to main content
PMC home page
Nucleic Acids Research logoLink to Nucleic Acids Research
. 1976 May;3(5):1295–1306. doi: 10.1093/nar/3.5.1295

Stacking self-association of pyrimidine nucleosides and of cytosines: effects of methylation and thiolation.

E Plesiewicz, E Stepień, K Bolewska, K L Wierzchowski
PMCID: PMC342987  PMID: 940770

Abstract

Stacking self-association equilibria in aqueous solutions of m3uridine, m34,2',3',5'uridine, 2'-deoxyuridine, m13,4,4cytosine, m14,4,4,5cytosine, s2cytidine and s4thymidine were studied at various temperatures by vapour-pressure osmometry. Equilibrium constants Kst's were computed on the assumption of the isodesmic model of self-association. Enthalpies of association were also obtained from the temperature dependence of Kst according to the van't Hoff equation. Analysis of the equilibrium and thermodynamic parameters demonstrated involvement of hydrophobic interactions in the stabilization of complexes of tetramethyluridine. Dipole-induced dipole interactions seem to predominate in the formation of s2C, s4T and of both dimethylaminocytosine complexes.

Full text

PDF
1300

Selected References

These references are in PubMed. This may not be the complete list of references from this article.

  1. Antonovsky V. L., Gukovskaja A. S., Nekrasova G. V., Sukhorukov B. I., Tchervin I. I. Studies of intermolecular interactions of nucleic acid bases in aqueous solutions by the proton magnetic resonance method. Self-association of 6,9-dimethyladenine and its pyrazole analogue and their association with methyl-substituted cytosine and uracil. Biochim Biophys Acta. 1973 Nov 26;331(1):9–20. doi: 10.1016/0005-2787(73)90413-9. [DOI] [PubMed] [Google Scholar]
  2. Bugg C. E., Thomas J. M., Sundaralingam M., Rao S. T. Stereochemistry of nucleic acids and their constituents. X. Solid-state base-stacking patterns in nucleic acid constituents and polynucleotides. Biopolymers. 1971;10(1):175–219. doi: 10.1002/bip.360100113. [DOI] [PubMed] [Google Scholar]
  3. Bähr W., Faerber P., Scheit K. H. The effects of thioketo substitution upon uracil-adenine interactions in polyribonucleotides. Synthesis and properties of poly (2-thiouridylic acid) and poly(2,4-dithiouridylic acid). Eur J Biochem. 1973 Mar 15;33(3):535–544. doi: 10.1111/j.1432-1033.1973.tb02713.x. [DOI] [PubMed] [Google Scholar]
  4. Donohue J. On N-H--S hydrogen bonds. J Mol Biol. 1969 Oct 28;45(2):231–235. doi: 10.1016/0022-2836(69)90102-8. [DOI] [PubMed] [Google Scholar]
  5. Ehrlich M., Ehrlich K., Mayo J. A. Unusual properties of the DNA from Xanthomonas phage XP-12 in which 5-methylcytosine completely replaces cytosine. Biochim Biophys Acta. 1975 Jun 16;395(2):109–119. doi: 10.1016/0005-2787(75)90149-5. [DOI] [PubMed] [Google Scholar]
  6. Faerber P., Scheit K. H., Sommer H. A new polynucleotide complex poly(s 2 C)-poly(I). Eur J Biochem. 1972 May;27(1):109–115. doi: 10.1111/j.1432-1033.1972.tb01816.x. [DOI] [PubMed] [Google Scholar]
  7. Faerber P. The synthesis of the alternating copolymer poly (r(G-s2C) by RNA polymerase of E. coli. A polynucleotide with an extremely high thermal stability. FEBS Lett. 1974 Aug 15;44(1):111–116. doi: 10.1016/0014-5793(74)80317-0. [DOI] [PubMed] [Google Scholar]
  8. Kulakowska I., Geller M., Lesyng B., Bolewska K., Wierzchowski K. L. Barrier to rotation and conformation of the -NR2 group in cytosine and its derivatives. Part II. Experimental and theoretical dipole moments of methylated cytosines. Biochim Biophys Acta. 1975 Nov 4;407(4):420–429. doi: 10.1016/0005-2787(75)90294-4. [DOI] [PubMed] [Google Scholar]
  9. Kulikowski T. D., Shugar D. Cytosine and cytidine analogues: synthesis and properties of 5-ethylcytosine, 5-ethylcytidine and a number of their derivatives. Acta Biochim Pol. 1971;18(2):209–236. [PubMed] [Google Scholar]
  10. Lawaczeck R., Wagner K. G. Stacking specificity and polarization. Comparative synopsis of affinity data. Biopolymers. 1974;13(10):2003–2014. doi: 10.1002/bip.1974.360131006. [DOI] [PubMed] [Google Scholar]
  11. Lumry R., Rajender S. Enthalpy-entropy compensation phenomena in water solutions of proteins and small molecules: a ubiquitous property of water. Biopolymers. 1970;9(10):1125–1227. doi: 10.1002/bip.1970.360091002. [DOI] [PubMed] [Google Scholar]
  12. Scheit K. H., Faerber P. Synthesis and properties of poly(s 2 C), a new poly(C) analog. Eur J Biochem. 1971 Dec;24(2):385–392. doi: 10.1111/j.1432-1033.1971.tb19697.x. [DOI] [PubMed] [Google Scholar]

Articles from Nucleic Acids Research are provided here courtesy of Oxford University Press

RESOURCES