Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 134, Issue 11, Pages 5165-5172Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja2105027
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Funding
- Research Corporation (Cottrell College) [7742]
- Jeffress Memorial Trust [J-903]
- NSF [CHE-1056430]
- NSF RUI [CHE-0809462]
- Department of Energy [CHE-0239664]
- Henry Dreyfus Teacher Scholar Award
- Floyd D. and Elisabeth S. Gottwald Endowment
- American Chemical Society
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [1056430, 1229354] Funding Source: National Science Foundation
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [0809462, 0958696] Funding Source: National Science Foundation
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Halogen bonding (R-X center dot center dot center dot Y) is a qualitative analogue of hydrogen bonding that may prove useful in the rational design of artificial proteins and nucleotides. We explore halogen-bonded DNA base pairs containing modified guanine, cytosine, adenine and thymine nudeosides. The structures and stabilities of the halogenated systems are compared to the normal hydrogen bonded base pairs. In most cases, energetically stable, coplanar structures are identified. In the most favorable cases, halogenated base pair stabilities are within 2 kcal mol(-1) of the hydrogen bonded analogues. Among the halogens X = Cl, Br, and I, bromine is best suited for inclusion in these biological systems because it possesses the best combination of polarizability and steric suitability. We find that the most stable structures result from a single substitution of a hydrogen bond for a halogen bond in dA:dT and dG:dC base pairs, which allows 1 or 2 hydrogen bonds, respectively, to complement the halogen bond.
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