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Issue 13, 2017
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Competition between stacked and hydrogen bonded structures of cytosine aggregates

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Abstract

The four bases of DNA constitute what is known as the “alphabet of life”. Their combination of proton-donor and acceptor groups and aromatic rings allows them to form stacking structures and at the same time establish hydrogen bonds with their counterparts, resulting in the formation of the well-known double-helix structure of DNA. Here we explore the aggregation preferences of cytosine in supersonic expansions, using a combination of laser spectroscopic techniques and computations. The data obtained from the experiments carried out in the cold and isolated environment of the expansion allowed us to establish which are the leading interactions behind aggregation of cytosine molecules. The results obtained demonstrated that ribbon-like structures held together by hydrogen bonds are the preferred conformations in the small clusters, but once the tetramer was reached, the stacking structures became enthalpically more stable. Stacking is further favoured when cytosine is replaced by its 1′-methylated version, as demonstrated by quantum-mechanical calculations performed using the same level that reproduced the experimental results obtained for cytosine aggregates. A discussion on the biological implications that such observations may have is also offered.

Graphical abstract: Competition between stacked and hydrogen bonded structures of cytosine aggregates

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Publication details

The article was received on 12 Dec 2016, accepted on 01 Mar 2017, published on 02 Mar 2017 and first published online on 02 Mar 2017


Article type: Paper
DOI: 10.1039/C6CP08476A
Citation: Phys. Chem. Chem. Phys., 2017,19, 8826-8834
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    Competition between stacked and hydrogen bonded structures of cytosine aggregates

    J. González, I. Usabiaga, P. F. Arnaiz, I. León, R. Martínez, J. Millán and J. A. Fernández, Phys. Chem. Chem. Phys., 2017, 19, 8826
    DOI: 10.1039/C6CP08476A

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