Watson-crick base pairs with thiocarbonyl groups: How sulfur changes the hydrogen bonds in DNA

• Authors: Célia Guerra , Evert Baerends , F. Bickelhaupt
• Languages of publication: EN

Abstracts

EN

We have theoretically analyzed mimics of Watson-Crick AT and GC base pairs in which N-H···O hydrogen bonds are replaced by N-H···S, using the generalized gradient approximation (GGA) of density functional theory at BP86/TZ2P level. The general effect of the above substitutions is an elongation and a slight weakening of the hydrogen bonds that hold together the base pairs. However, the precise effects depend on how many, and in particular, on which hydrogen bonds AT and GC are substituted.. Another purpose of this work is to clarify the relative importance of electrostatic attraction versus orbital interaction in the hydrogen bonds involved in the mimics, using a quantitative bond energy decomposition scheme. At variance with widespread believe, the orbital interaction component in these hydrogen bonds is found to contribute more than 40% of the attractive interactions and is thus of the same order of magnitude as the electrostatic component, which provides the remaining attraction. [...]

Keywords

EN

Chitosan Density functional calculations; DNA structures; Sulfur; Hydrogen bonds; Watson-Crick pair mimics

• Publisher: De Gruyter Open
• Journal: Open Chemistry
• Year: 2008
• Volume: 6
• Issue: 1
• Pages: 15-21

Dates

published

1 - 3 - 2008

online

1 - 3 - 2008

Contributors

author

Célia Guerra

• Theoretische Chemie, Scheikundig Laboratorium der Vrije Universiteit, De Boelelaan 1083, NL-1081 HV, Amsterdam, The Netherlands

author

Evert Baerends

• Theoretische Chemie, Scheikundig Laboratorium der Vrije Universiteit, De Boelelaan 1083, NL-1081 HV, Amsterdam, The Netherlands

author

F. Bickelhaupt

• Theoretische Chemie, Scheikundig Laboratorium der Vrije Universiteit, De Boelelaan 1083, NL-1081 HV, Amsterdam, The Netherlands

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Identifiers

DOI

10.2478/s11532-007-0068-y