Janus-AT bases: synthesis, self-assembly, and solid state structures. Asadi, A., Patrick, B. O, & Perrin, D. M The Journal of organic chemistry, 72(2):466–75, January, 2007.
Paper doi abstract bibtex 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.
@article{Asadi2007,
title = {Janus-{AT} bases: synthesis, self-assembly, and solid state structures.},
volume = {72},
issn = {0022-3263},
url = {http://www.ncbi.nlm.nih.gov/pubmed/17221963},
doi = {10.1021/jo061840k},
abstract = {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.},
number = {2},
journal = {The Journal of organic chemistry},
author = {Asadi, Ali and Patrick, Brian O and Perrin, David M},
month = jan,
year = {2007},
pmid = {17221963},
keywords = {\#nosource, Adenine, Adenine: chemistry, Combinatorial Chemistry Techniques, Combinatorial Chemistry Techniques: methods, Crystallography, Hydrogen Bonding, Models, Molecular, Molecular Structure, Thymine, Thymine: analogs \& derivatives, Thymine: chemical synthesis, Thymine: chemistry, Uracil, Uracil: analogs \& derivatives, Uracil: chemical synthesis, Uracil: chemistry, X-Ray},
pages = {466--75},
}
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