Skip to main content
Nucleic Acids Research logoLink to Nucleic Acids Research
. 1983 Sep 24;11(18):6475–6486. doi: 10.1093/nar/11.18.6475

A novel guanine-guanine base pairing: crystal structure of a complex between 7-methylguanosine and its iodide.

Y Yamagata, S Fukumoto, K Hamada, T Fujiwara, K Tomita
PMCID: PMC326387  PMID: 6622257

Abstract

7-Methylguanosine, one of the biologically important minor nucleosides, could be crystallized as a complex of its zwitterionic form and its iodide, and the crystal structure was determined by the X-ray diffraction method. The crystals belong to the triclinic space group P1 with the unit cell dimensions: a = 7.678(1), b = 18.094(3), and c = 5.711(1) A, alpha = 79.32(1), beta = 80.14(1) and gamma = 76.90(1) degrees. The structure was solved by the heavy atom method and refined by the least-squares method to give a final R index of 0.075. The novel reverse Watson-Crick type base pairing observed between a positively charged molecule and a deprotonated one indicates that the deprotonation at the N(1) position promoted by the alkylation at the N(7) position may interrupt the formation of the normal Watson-Crick type GC base pair. The conformations about the glycosidic bond and the sugar puckering are quite different between the two molecules: the former has anti and C(4')-exo,C(3')-endo and the latter syn and C(1')-exo-C(2')-endo.

Full text

PDF
6485

Selected References

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

  1. Adams J. M., Cory S. Modified nucleosides and bizarre 5'-termini in mouse myeloma mRNA. Nature. 1975 May 1;255(5503):28–33. doi: 10.1038/255028a0. [DOI] [PubMed] [Google Scholar]
  2. Drake J. W., Baltz R. H. The biochemistry of mutagenesis. Annu Rev Biochem. 1976;45:11–37. doi: 10.1146/annurev.bi.45.070176.000303. [DOI] [PubMed] [Google Scholar]
  3. Hakoshima T., Omori H., Tomita K., Miki H., Ikehara M. The crystal and molecular structure of 2'-deoxy-2'-fluoroinosine monohydrate. Nucleic Acids Res. 1981 Feb 11;9(3):711–729. doi: 10.1093/nar/9.3.711. [DOI] [PMC free article] [PubMed] [Google Scholar]
  4. Haschemeyer A. E., Rich A. Nucleoside conformations: an analysis of steric barriers to rotation about the glycosidic bond. J Mol Biol. 1967 Jul 28;27(2):369–384. doi: 10.1016/0022-2836(67)90026-5. [DOI] [PubMed] [Google Scholar]
  5. Jack A., Ladner J. E., Klug A. Crystallographic refinement of yeast phenylalanine transfer RNA at 2-5A resolution. J Mol Biol. 1976 Dec 25;108(4):619–649. doi: 10.1016/s0022-2836(76)80109-x. [DOI] [PubMed] [Google Scholar]
  6. LAWLEY P. D., BROOKES P. FURTHER STUDIES ON THE ALKYLATION OF NUCLEIC ACIDS AND THEIR CONSTITUENT NUCLEOTIDES. Biochem J. 1963 Oct;89:127–138. doi: 10.1042/bj0890127. [DOI] [PMC free article] [PubMed] [Google Scholar]
  7. Quigley G. J., Seeman N. C., Wang A. H., Suddath F. L., Rich A. Yeast phenylalanine transfer RNA: atomic coordinates and torsion angles. Nucleic Acids Res. 1975 Dec;2(12):2329–2341. doi: 10.1093/nar/2.12.2329. [DOI] [PMC free article] [PubMed] [Google Scholar]
  8. Saenger W. A purine nucleoside in syn conformation. Molecular and crystal structures of 5'-methylammonium-5'-deoxyadenosine iodide monohydrate. J Am Chem Soc. 1971 Jun 16;93(12):3035–3041. doi: 10.1021/ja00741a036. [DOI] [PubMed] [Google Scholar]
  9. Sussman J. L., Kim S. H. Idealized atomic coordinates of yeast phenylalanine transfer RNA. Biochem Biophys Res Commun. 1976 Jan 12;68(1):89–96. doi: 10.1016/0006-291x(76)90014-0. [DOI] [PubMed] [Google Scholar]
  10. Thewalt U., Bugg C. E., Marsh R. E. The crystal structure of guanosine dihydrate and inosine dihydrate. Acta Crystallogr B. 1970 Aug 15;26(8):1089–1101. doi: 10.1107/s0567740870003667. [DOI] [PubMed] [Google Scholar]
  11. Watenpaugh K., Dow J., Jensen L. H., Furberg S. Crystal and molecular structure of adenosine 3',5'-cyclic phosphate. Science. 1968 Jan 12;159(3811):206–207. doi: 10.1126/science.159.3811.206. [DOI] [PubMed] [Google Scholar]
  12. Yasuniwa M., Tokuoka R., Ogawa K., Yamagata Y., Fujii S., Tomita K. I., Limn W., Ikehara M. The crystal and molecular structure of 8-methyladenosine 3'-monophosphate dihydrate. Biochim Biophys Acta. 1979 Jan 26;561(1):240–247. doi: 10.1016/0005-2787(79)90507-0. [DOI] [PubMed] [Google Scholar]

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

RESOURCES