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Journal of Molecular Modeling

, Volume 15, Issue 6, pp 651–658 | Cite as

Theoretical study of spin-spin coupling across the hydrogen (O-H⋯N) bond in adenosine derivatives

  • Marek Doskocz
  • Agnieszka Strupińska
  • Szczepan Roszak
  • Monika Prokopowicz
  • Leo H. Koole
  • Paweł Kafarski
Original Paper

Abstract

The study of spin-spin coupling constants across hydrogen bond provides useful information about configuration of complexes. The interesting case of such interactions was observed as a coupling across an intramolecular hydrogen bond in 8-bromo-2′,3′-O-isopropylideneadenosine between the -CH2OH (at 5″ proton) group and the nitrogen atom of adenine. In this paper we report theoretical investigations on the 4h J NH coupling across the H″-C-O-H···N hydrogen bond in adenosine derivatives in various solvent models.

Figure

Coupling constants in 8-bromo-2′,3′-O-isopropylideneadenosine

Keywords

Ab initio calculations Adenosine derivatives Coupling across hydrogen bonds Density functional theory 

Notes

Acknowledgments

Authors thank Dr Vladimir Sychrovsky from UCB Prague for discussion and structure of conformers HA, and Professor Roman Gancarz from Wrocław University of Technology for discussion. Calculations were performed at Wroclaw Centre for Networking and Supercomputing (WCSS), Poznań Supercomputing Networking Center (PCSS) and Academic Computer Centre in Gdansk (CI TASK).

Supplementary material

894_2009_473_MOESM1_ESM.doc (761 kb)
ESM 1 (DOC 761 kb)

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Copyright information

© Springer-Verlag 2009

Authors and Affiliations

  • Marek Doskocz
    • 1
  • Agnieszka Strupińska
    • 2
  • Szczepan Roszak
    • 2
  • Monika Prokopowicz
    • 1
  • Leo H. Koole
    • 3
    • 4
  • Paweł Kafarski
    • 1
  1. 1.Department of Bioorganic ChemistryFaculty of Chemistry Wroclaw University of TechnologyWroclawPoland
  2. 2.Institute of Physical and Theoretical ChemistryWroclaw University of TechnologyWroclawPoland
  3. 3.Centre for Biomaterials Research, Faculty of MedicineUniversity of MaastrichtMaastrichtThe Netherlands
  4. 4.Faculty of Biomedical EngineeringEindhoven University of TechnologyEindhovenThe Netherlands

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