Three-Dimensional Potential Energy Surface of Selected Carbohydrates' CH/p Dispersion Interactions Calculated by High-Level Quantum Mechanical Methods
| Authors | |
|---|---|
| Year of publication | 2011 |
| Type | Article in Periodical |
| Magazine / Source | Chemistry - A European Journal |
| MU Faculty or unit | |
| Citation | |
| Doi | http://dx.doi.org/10.1002/chem.201002876 |
| Field | Physical chemistry and theoretical chemistry |
| Keywords | carbohydrates; CH/pi interactions; DFT calculations; dispersion interactions; molecular recognition |
| Description | In this study we present the first systematic computational three-dimensional scan of carbohydrate hydrophobic patches for the ability to interact through CH/pi dispersion interactions. The carbohydrates beta-D-glucopyranose, beta-D-mannopyranose and alpha-l-fucopyranose were studied in a complex with a benzene molecule, which served as a model of the CH/pi interaction in carbohydrate/protein complexes. The 3D relaxed scans were performed at the SCC-DFTB-D level with 3 757 grid points for both carbohydrate hydrophobic sides. The interaction energy of all grid points was recalculated at the DFT-D BP/def2-TZVPP level. The results obtained clearly show highly delimited and separated areas around each CH group, with an interaction energy up to -5.40 kcal mol(-1). The results also show that with increasing H center dot center dot center dot pi distance these delimited areas merge and form one larger region, which covers all hydrogen atoms on that specific carbohydrate side. |
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