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NEWS AND HIGHLIGHTS

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The design, synthesis, and characterization of G-C DNA base hybrids. 

G-C DNA base hybrids are self-complementary molecules which possess the hydrogen bonding codes of both guanine (DDA) and cytosine (AAD).  The information present in the H-bonding faces leads to the unambiguous assembly of a hexameric aggregate, both in the solid state and solution.  This is the first example of a crystallographically characterized hexagonal assembly of its kind.  Recent work has been directed at streamlining the synthesis and the inclusion of a tailgroup with easily derivatizable functionality (primary Br, OH) so that anything which can be chemically linked to the base hybrid molecule will be co-organized in the hexagonal periphery.

 

Lead references:

 

"Programming a Hydrogen-Bonding Code for the Specific Generation of a Super-Macrocycle."  M. Mascal, N. M. Hext, R. Warmuth, M. H. Moore, J. P. Turkenburg, Angew. Chem. Int. Ed. Engl. 1996, 35, 2204.

 

"The G-C DNA Base Hybrid: Synthesis, Self-Organization and Structural Analysis."  M. Mascal, N. M. Hext, R. Warmuth, J. R. Arnall-Culliford, M. H. Moore, J. P. Turkenburg, J. Org. Chem. 1999, 64, 8479.

 

"Synthesis of the G–C DNA Base Hybrid with a Functional Tail."  M. Mascal, S. C. Farmer, J. R. Arnall-Culliford, J. Org. Chem., 2006, 71, 8146.

 

"Putting Anion-π Interactions Into Perspective." A. Frontera, P. Gamez, M. Mascal, T. J. Mooibroek and J. Reedjik, Angew. Chem. Int. Ed., 2011,50, 9564.

 

"Synthesis of N-Substituted Pyrido[4,3-d]pyrimidines for the Large Scale Production of Self-Assembled Rosettes and Nanotubes" A. Durmus, G. Gunbas, S. C. Farmer, M. M. Olmstead, M. Mascal, B. Legesse, J. Cho, R. L. Beingessner, T. Yamazaki, and H. Fenniri, J. Org. Chem. 2013, 50, 11421.