The G-C DNA base hybrid: Synthesis, self-organization and structural analysis

Mark Mascal, Nicholas M. Hext, Ralf Warmuth, James R. Arnall-Culliford, Madeleine H. Moore, Johan P. Turkenburg

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Abstract

The guanine-cytosine base hybrid I is synthesized in five steps from the malononitrile dimer. One face of the molecule possesses the cytosine AAD hydrogen bonding code and the other the guanine DDA code. The expression of this information leads to the self-organization of six molecules of I into a hexagonal supermacrocycle in the solid state through the formation of 18 strong hydrogen bonds. This is the first structurally characterized example of a synthetic hexagonal assembly where the molecular program is unambiguous and all of the information required for exclusive rosette formation is contained within hydrogen bonding codes. 1 crystallizes in the very rare, high-symmetry cubic space group Ia3d, with 96 molecules in the unit cell. The crystal is highly solvated and only ca. 35% occupied by molecules of 1, with a criss-crossed network of channel voids generated by the overlapping of 16 hexamers.

Original languageEnglish (US)
Pages (from-to)8479-8484
Number of pages6
JournalJournal of Organic Chemistry
Volume64
Issue number23
DOIs
Publication statusPublished - Nov 12 1999
Externally publishedYes

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All Science Journal Classification (ASJC) codes

  • Organic Chemistry

Cite this

Mascal, M., Hext, N. M., Warmuth, R., Arnall-Culliford, J. R., Moore, M. H., & Turkenburg, J. P. (1999). The G-C DNA base hybrid: Synthesis, self-organization and structural analysis. Journal of Organic Chemistry, 64(23), 8479-8484. https://doi.org/10.1021/jo990719t