Homochiral xanthine quintet networks self-assembled on Au(111) surfaces

Yu, Miao and Wang, Jianguo and Mura, Manuela and Meng, Qiang-qiang and Gersen, Henkjan and Laegsgard, Erik and Stensgaard, Ivan and Kelly, Ross E. A. and Kjems, Jorgen and Linderoth, Trolle R. and 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

Full content URL: http://dx.doi.org/10.1021/nn202157m

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Item Type:Article
Item Status:Live Archive

Abstract

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. © 2011 American Chemical Society.

Keywords:Acid degradation, Au(1 1 1 ), Au(111) surfaces, Base pairing, Biochemical process, Density functional theory calculations, Double hydrogen bonding, High concentration, High resolution scanning tunneling microscopy, Homochiral, Human disease, Inorganic surfaces, Prebiotics, purine, Self-assembled, Ultrahigh vacuum conditions, Adsorption, Amines, Biochemistry, Chemical properties, Density functional theory, Hydrogen, Hydrogen bonds, Molecules, Nucleic acids, Positive ions, Self assembly, Solar system, Stereochemistry, Scanning tunneling microscopy
Subjects:F Physical Sciences > F390 Physics not elsewhere classified
Divisions:College of Science > School of Mathematics and Physics
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ID Code:16687
Deposited On:18 Feb 2015 16:38

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