Asadi Ali, Patrick Brian O, Perrin David M
Department of Chemistry, University of British Columbia, 2036 Main Mall, Vancouver, British Columbia V6T-1Z1, Canada.
J Org Chem. 2007 Jan 19;72(2):466-75. doi: 10.1021/jo061840k.
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.
具有明确氢键接受和供体能力的杂环的高产率合成，为自组装结构的设计和生物靶点的特异性识别提供了可能。在此，我们报道了三种自互补尿嘧啶/胸腺嘧啶衍生物的合成及其固态结构，其中每种衍生物都具有与腺嘌呤固有互补的标准ADA面以及与尿嘧啶/胸腺嘧啶互补的合成附加DAD面。这些从未被报道或表征过的杂环代表了二氨基嘌呤 - 尿嘧啶/胸腺嘧啶杂化物，在三种情况中的两种情况下，与先前报道的G和C的杂环杂化物相关。所有三种杂环都结晶，从而得到了能够进行ADA - DAD配对的自互补杂环的首个X射线晶体结构。还简要讨论了它们在DNA和RNA识别中的潜在用途。
