Janus-AT bases: synthesis, self-assembly, and solid state structures.
The high yielding synthesis of heterocycles with defined H-bond accepting and donating capabilities provides for the design of self-assembling structures and specific recognition of biological targets. Herein we report the syntheses and solid-state structures of three self-complementary uracil/thymine derivatives where each presents the standard ADA face inherently complementary to adenine and a synthetically appended DAD face complementary to uracil/thymine. These heterocycles, which have never before been reported or characterized, represent diaminopurine-uracil/thymine hybrids that, in two of the three cases, relate to previously reported heterocyclic hybrids of G and C. All three heterocycles crystallized to afford the first X-ray crystal structures of self-complementary heterocycles capable of ADA-DAD pairing. The potential use in DNA and RNA recognition are briefly discussed.
Asadi
Ali
A
Department of Chemistry, University of British Columbia, 2036 Main Mall, Vancouver, British Columbia V6T-1Z1, Canada.
Patrick
Brian O
BO
Perrin
David M
DM
D000225:Adenine / Q000737:chemistry*; D020650:Combinatorial Chemistry Techniques / Q000379:methods*; D018360:Crystallography, X-Ray; D006860:Hydrogen Bonding; D008958:Models, Molecular; D015394:Molecular Structure; D013941:Thymine / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry; D014498:Uracil / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry
D014498:Uracil; D000225:Adenine; D013941:Thymine