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Three-Dimensional Potential Energy Surface of Selected Carbohydrates' CH/p Dispersion Interactions Calculated by High-Level Quantum Mechanical Methods

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KOZMON Stanislav MATUŠKA Radek SPIWOK Vojtech KOČA Jaroslav

Year of publication 2011
Type Article in Periodical
Magazine / Source Chemistry - A European Journal
MU Faculty or unit

Central European Institute of Technology

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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