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Dimers, trimers, and tetramers of cytosine with guanine

Publication ,  Journal Article
Williams, NG; Williams, LD; Shaw, BR
Published in: Journal of the American Chemical Society
January 1, 1989

Cytosine and guanine have been shown previously to form Watson-Crick type base pairs in nonaqueous solvents, suggesting that the monomers can be used to understand and possibly to predict structures of the polymeric nucleic acids. Yet, the poor solubility properties of cytosine and guanine (and their corresponding nucleosides) have limited the utility of the monomeric model of polymeric nucleic acids. The 2'-deoxynucleosides, which are substituted at both ribose hydroxyls with triisopropylsilyl groups, have high solubilities (greater than 200 mM) in nonpolar solvents such as chloroform-d. These substituted nucleosides are appropriate for detailed 1H NMR study of hydrogen bonding between cytosine and guanine over a wide temperature range. In this DNA model system, cytosine and guanine form the stable Watson-Crick type dimer, as would be expected from previous studies of bases in higher dielectric solvents or at lower concentrations. We report here that the bases form such dimers and additional, more intricate hydrogen-bonded complexes. Cytosine and guanine monomers form both trimers (cytosine:guanine2) and tetramers [(cytosine:guanine)2] in low-dielectric solution. Thus, the interactions of monomers are consistent with formation of two-, three-, and four-stranded nucleic acid polymers. © 1989, American Chemical Society. All rights reserved.

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Published In

Journal of the American Chemical Society

DOI

EISSN

1520-5126

ISSN

0002-7863

Publication Date

January 1, 1989

Volume

111

Issue

18

Start / End Page

7205 / 7209

Related Subject Headings

  • General Chemistry
  • 40 Engineering
  • 34 Chemical sciences
  • 03 Chemical Sciences
 

Citation

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Williams, N. G., Williams, L. D., & Shaw, B. R. (1989). Dimers, trimers, and tetramers of cytosine with guanine. Journal of the American Chemical Society, 111(18), 7205–7209. https://doi.org/10.1021/ja00200a046
Williams, N. G., L. D. Williams, and B. R. Shaw. “Dimers, trimers, and tetramers of cytosine with guanine.” Journal of the American Chemical Society 111, no. 18 (January 1, 1989): 7205–9. https://doi.org/10.1021/ja00200a046.
Williams NG, Williams LD, Shaw BR. Dimers, trimers, and tetramers of cytosine with guanine. Journal of the American Chemical Society. 1989 Jan 1;111(18):7205–9.
Williams, N. G., et al. “Dimers, trimers, and tetramers of cytosine with guanine.” Journal of the American Chemical Society, vol. 111, no. 18, Jan. 1989, pp. 7205–09. Scopus, doi:10.1021/ja00200a046.
Williams NG, Williams LD, Shaw BR. Dimers, trimers, and tetramers of cytosine with guanine. Journal of the American Chemical Society. 1989 Jan 1;111(18):7205–7209.
Journal cover image

Published In

Journal of the American Chemical Society

DOI

EISSN

1520-5126

ISSN

0002-7863

Publication Date

January 1, 1989

Volume

111

Issue

18

Start / End Page

7205 / 7209

Related Subject Headings

  • General Chemistry
  • 40 Engineering
  • 34 Chemical sciences
  • 03 Chemical Sciences