Toward an artificial oxidative DNA photolyase.
Toward an artificial oxidative DNA photolyase.
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人工氧化 DNA 光裂合酶。
DOI：
10.1021/jo0354600
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发表时间：
2004
期刊：
影响因子：
--
通讯作者：
Wiest,Olaf
中科院分区：
文献类型：
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作者：
Pauvert,Mickael;Laine,Patrick;Jonas,Marco;Wiest,Olaf
报道了用于顺式、顺式环丁烷嘧啶二聚体选择性分子识别的两种光学受体的设计、合成、结构和结合亲和力。该设计基于两个2，6-二(乙酰氨基)吡啶识别单元，它们通过三键共价连接到一个蒽醌功能间隔基上。收敛合成使用了涉及锌易位的改进的Sonogashira反应作为关键步骤。其中一个受体的晶体结构显示了一种超分子一维聚合物，通过形状自互补、π堆积和相邻分子之间的氢键介导了强烈的相互作用。相邻链之间的氢键强制平行取向，这导致高极性化合物的非中心对称晶体结构。该受体与顺式、顺式嘧啶二聚体的结合常数为Ka=1.0×103m-1，而与反式、顺式异构体的结合约弱1个数量级。
The design, synthesis, structure, and binding affinity of two dioptic receptors for the selective molecular recognition of the cis,syn cyclobutane pyrimidine dimer are reported. The design is based on two 2,6-di(acetamino)pyridine recognition units that are covalently linked via triple bonds to an anthraquinone functional spacer unit. The convergent synthesis uses a modified Sonogashira reaction involving a zinc transmetalation as the key step. The crystal structure of one of the receptors reveals a supramolecular 1D polymer with strong interactions mediated by shape self-complementarity, π-stacking, and hydrogen bonding between adjacent molecules. Hydrogen bonding between adjacent strands enforces a parallel orientation, which leads to a noncentrosymmetric crystal structure of the highly polar compound. The receptor has an association constant ofKa= 1.0 × 103M-1with the cis,syn pyrimidine dimer, whereas binding of the trans,syn isomer is approximately 1 order of magnitude weaker.