Homochiral xanthine quintet networks self-assembled on Au(111) surfaces.
Homochiral xanthine quintet networks self-assembled on Au(111) surfaces.
复制标题
同手性黄嘌呤五重网络在 Au(111) 表面上自组装。
作者：
Yu M
黄嘌呤分子是鸟嘌呤脱胺降解核酸的中间体，也是古代太阳系中存在的一种化合物，在地外陨石中发现了高浓度。因此，黄嘌呤分子在无机表面的自组装对生物化学过程的研究很有兴趣，它也可能与对益生元生物合成的基本理解有关。结合高分辨率扫描隧道显微镜（STM）和密度泛函理论（DFT）计算，在超高真空条件下，在Au（111）上发现了两个新的同手性黄嘌呤结构。黄嘌呤分子被发现自组装成两个扩展的同手性网络，由两种类型的二五聚体单元平铺，并通过分子间双氢键稳定。我们的研究结果表明，鸟嘌呤脱胺成黄嘌呤导致了非常不同的碱基配对电位和碱基的化学性质，这可能与细胞的功能和人类疾病的潜在发展有关。此外，黄嘌呤分子在无机表面的吸附导致同手性组装可能对生命早期出现的手性的基本理解感兴趣。
Xanthine molecule is an intermediate in nucleic acid degradation from the deamination of guanine and is also a compound present in the ancient solar system that is found in high concentrations in extraterrestrial meteorites. The self-assembly of xanthine molecules on inorganic surfaces is therefore of interest for the study of biochemical processes, and it may also be relevant to the fundamental understanding of prebiotic biosynthesis. Using a combination of high-resolution scanning tunneling microscopy (STM) and density functional theory (DFT) calculations, two new homochiral xanthine structures have been found on Au(111) under ultrahigh vacuum conditions. Xanthine molecules are found to be self-assembled into two extended homochiral networks tiled by two types of di-pentamer units and stabilized by intermolecular double hydrogen bonding. Our findings indicate that the deamination of guanine into xanthine leads to a very different base pairing potential and the chemical properties of the base which may be of relevance to the function of the cell and potential development of human diseases. Moreover, the adsorption of xanthine molecules on inorganic surfaces leading to homochiral assemblies may be of interest for the fundamental understanding of the emerged chirality at early stages of life.
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