Yu, Miao, Wang, Jianguo, Mura, Manuela, Meng, Qiang-qiang, Xu, Wei, Gersen, Henkjan, Lægsgaard, Erik, Stensgaard, Ivan, Kelly, Ross E. A., Kjems, Jørgen, Linderoth, Trolle R., Kantorovich, Lev N. and Besenbacher, Flemming (2011) Homochiral Xanthine Quintet Networks Self-Assembled on Au(111) Surfaces. ACS Nano, 5 (8). pp. 6651-6660. ISSN 1936-0851
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Official URL: http://dx.doi.org/10.1021/nn202157m
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.
|Uncontrolled Keywords (separate with ;):||hydrogen bonding; prebiotic earth; purine; scanning tunneling microscopy; self-assembly|
|Subjects:||Physical sciences > Physics|
|Schools:||College of Science and Technology > School of Physical Sciences and Computing|
|Deposited By:||Malgosia Bagot|
|Deposited On:||28 Jun 2012 09:09|
|Last Modified:||09 Aug 2016 15:16|
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