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Control of Self‐Assembled 2D Nanostructures by Methylation of Guanine
Author(s) -
Bald Ilko,
Wang Yaoguang,
Dong Mingdong,
Rosen Christian B.,
Ravnsbæk Jens B.,
Zhuang Guilin,
Gothelf Kurt V.,
Wang Jianguo,
Besenbacher Flemming
Publication year - 2011
Publication title -
small
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 3.785
H-Index - 236
eISSN - 1613-6829
pISSN - 1613-6810
DOI - 10.1002/smll.201002033
Subject(s) - guanine , nucleobase , hydrogen bond , intermolecular force , methylation , stacking , density functional theory , chemistry , dna methylation , crystallography , dna , molecule , materials science , computational chemistry , biochemistry , gene , gene expression , nucleotide , organic chemistry
Methylation of DNA nucleobases is an important control mechanism in biology applied, for example, in the regulation of gene expression. The effect of methylation on the intermolecular interactions between guanine molecules is studied through an interplay between scanning tunneling microscopy (STM) and density functional theory with empirical dispersion correction (DFT‐D). The present STM and DFT‐D results show that methylation of guanine can have subtle effects on the hydrogen‐bond strength with a strong dependence on the position of methylation. It is demonstrated that the methylation of DNA nucleobases is a precise means to tune intermolecular interactions and consequently enables very specific recognition of DNA methylation by enzymes. This scheme is used to generate four different types of artificial 2D nanostructures from methylated guanine. For instance, a 2D guanine windmill motif that is stabilized by cooperative hydrogen bonding is revealed. It forms by self‐assembly on a graphite surface under ambient conditions at the liquid–solid interface when the hydrogen‐bonding donor at the N1 site of guanine is blocked by a methyl group.