Homochiral Xanthine Quintet Networks Self-Assembled on Au(111) Surfaces
| Autor: | Henkjan Gersen, Miao Yu, Wei Xu, Ross E. A. Kelly, Erik Lægsgaard, Jianguo Wang, Flemming Besenbacher, Jørgen Kjems, Trolle R. Linderoth, Ivan Stensgaard, Qiangqiang Meng, Manuela Mura, Lev Kantorovich |
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| Jazyk: | angličtina |
| Rok vydání: | 2011 |
| Předmět: |
Guanine
Hydrogen bond Stereochemistry General Engineering Deamination General Physics and Astronomy 02 engineering and technology 010402 general chemistry 021001 nanoscience & nanotechnology Xanthine 01 natural sciences Combinatorial chemistry 0104 chemical sciences chemistry.chemical_compound chemistry Molecule General Materials Science Density functional theory Self-assembly 0210 nano-technology Chirality (chemistry) |
| Zdroj: | Yu, M, Wang, J, Mura, M, Meng, Q-Q, Xu, W, Gersen, H, Lægsgaard, E, Stensgaard, I, Kelly, R E A, Kjems, J, Linderoth, T R, Kantorovich, L N & Besenbacher, F 2011, ' Homochiral Xanthine Quintet Networks Self-Assembled on Au(111) Surfaces ', ACS Nano, vol. 5, no. 8, pp. 6651-6660 . https://doi.org/10.1021/nn202157m ACS Nano |
| DOI: | 10.1021/nn202157m |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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