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Janus-AT bases: Synthesis, self-assembly, and solid state structures

TitleJanus-AT bases: Synthesis, self-assembly, and solid state structures
Publication TypeJournal Article
Year of Publication2007
AuthorsAsadi, A, Patrick, BO, Perrin, DM
JournalJournal of Organic Chemistry
Volume72
Pagination466-475
Date PublishedJan
ISBN Number0022-3263
Abstract

[graphics] 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.

URL<Go to ISI>://000243416300019