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. 1974 Jul;1(7):855–864. doi: 10.1093/nar/1.7.855

Nucleoside conformations. XVII. A PMR study of 2′-anhydronucleosides and comparison with X-ray data

Wilhelm Guschlbauer 1, Tran-Dinh Son 1, Michel Blandin 1, Joseph C Catlin 1
PMCID: PMC343389  PMID: 10793718

Abstract

A series of 2′-cyclo-nucleosides (2,2′-O-anhydro-uridine, -N3-uridine and cytidine and 8,2′-S-anhydro-guanosine) have been studied by PMR in DMSO and D2O. As expected these compounds are quite rigid, but their solution conformation is considerably different from that observed in single crystal x-ray studies. While the pyrimidine cyclonucleosides in the crystal form show a C4′-endo conformation (pseudorotational phase angle P=212° to 233°), their solution conformation is C1′-exo (P=130° to 138°) and the cyclothioguanosine shows a closely similar one (P=112°). Exocyclic rotamer distribution is different in the various compounds.

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Selected References

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

  1. Altona C., Sundaralingam M. Conformational analysis of the sugar ring in nucleosides and nucleotides. A new description using the concept of pseudorotation. J Am Chem Soc. 1972 Nov 15;94(23):8205–8212. doi: 10.1021/ja00778a043. [DOI] [PubMed] [Google Scholar]
  2. Blandin M., Catlin J. C. Synthèse de la 8,2'-thiocycloguanosine. C R Acad Sci Hebd Seances Acad Sci D. 1972 Oct 9;275(15):1703–1705. [PubMed] [Google Scholar]
  3. Cross B. P., Schleich T. Determination of the molecular conformation of beta-D-O2,2'-cyclouridine in aqueous solution by proton magnetic resonance spectroscopy. Biopolymers. 1973;12(10):2381–2389. doi: 10.1002/bip.1973.360121016. [DOI] [PubMed] [Google Scholar]
  4. Doerr I. L., Fox J. J. Nucleosides. XXXIX. 2'-deoxy-2'-fluorocytidine, 1-beta-D-arabinofuranosyl-2-amino-1,4(2H)-4-iminopyrimidine, and related derivatives. J Org Chem. 1967 May;32(5):1462–1471. doi: 10.1021/jo01280a035. [DOI] [PubMed] [Google Scholar]
  5. Hampton A., Nichol A. W. Nucleotides. V. Purine ribonucleoside 2',3'-cyclic carbonates. Preparation and use for the synthesis of 5'-monosubstituted nucleosides. Biochemistry. 1966 Jun;5(6):2076–2082. doi: 10.1021/bi00870a040. [DOI] [PubMed] [Google Scholar]
  6. Hruska F. E. Molecular conformation of orotidine, a naturally occurring nucleoside, in the syn conformation in aqueous solution. J Am Chem Soc. 1971 Apr 7;93(7):1795–1797. doi: 10.1021/ja00736a046. [DOI] [PubMed] [Google Scholar]
  7. Kikugawa K., Ichino M. Studies on the Vilsmeier-Haack reaction. IV. Convenient synthesis of 2,2'-anhydro-1- -D-arabinofuranosylcytosine (2,2'-cyclocytidine) and its derivatives. J Org Chem. 1972 Jan 28;37(2):284–288. doi: 10.1021/jo00967a021. [DOI] [PubMed] [Google Scholar]
  8. Manor P. C., Saenger W., Davies D. B., Jankowski K., Rabczenko A. Conformation of nucleosides: the comparison of an x-ray diffraction and proton nmr study of 5',2-O-cyclo, 2',3'-O-isopropylidene uridine. Biochim Biophys Acta. 1974 Apr 10;340(4):472–483. doi: 10.1016/0005-2787(74)90068-9. [DOI] [PubMed] [Google Scholar]
  9. Schleich T., Blackburn B. J., Lapper R. D., Smith I. C. A nuclear magnetic resonance study of the influence of aqueous sodium perchlorate and temperature on the solution conformations of uracil nucleosides and nucleotides. Biochemistry. 1972 Jan 18;11(2):137–145. doi: 10.1021/bi00752a001. [DOI] [PubMed] [Google Scholar]
  10. Schweizer M. P., Witkowski J. T., Robins R. K. Nuclear magnetic resonance determination of syn and anti conformations in pyrimidine nucleosides. J Am Chem Soc. 1971 Jan 13;93(1):277–279. doi: 10.1021/ja00730a062. [DOI] [PubMed] [Google Scholar]
  11. Son T. D., Thiéry J., Guschlbauer W., Dunand J. J. Nucleoside conformations. 8. Conformation of guanosine 2'-phosphate in aqueous solution by proton magnetic resonance spectroscopy. Biochim Biophys Acta. 1972 Oct 27;281(3):289–298. [PubMed] [Google Scholar]
  12. Ts'o P. O., Kondo N. S., Schweizer M. P., Hollis D. P. Studies of the conformation and interaction in dinucleoside mono- and diphosphates by proton magnetic resonance. Biochemistry. 1969 Mar;8(3):997–1029. doi: 10.1021/bi00831a033. [DOI] [PubMed] [Google Scholar]
  13. Verheyden J. P., Wagner D., Moffatt J. G. Synthesis of some pyrimidine 2'-amino-2'-deoxynucleosides. J Org Chem. 1971 Jan 29;36(2):250–254. doi: 10.1021/jo00801a002. [DOI] [PubMed] [Google Scholar]

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