Publication details

Systematic Study of Carbohydrate-Aromatic CH-pi Dispersion Interaction by DFT and Highly Correlated Ab Initio Methods


KOZMON Stanislav MATUŠKA Radek SPIWOK Vojtěch KOČA Jaroslav

Year of publication 2011
Type Conference abstract
MU Faculty or unit

Central European Institute of Technology

Description The protein-carbohydrate interactions play essential role in various biologically important issues as pathogene identification, host-guest recognition, intercellular signalling, cell growth and differentiation etc. Non-negligible part of protein-cabohydrate interactions is mediated by CH-pi interactions, which were proved to have strong dispersion character. This study introduces first systematic study of the nature of the CH-pi dispersion interactions between benzene as model for aromatic amino-acids in proteins and three carbohydrates b-D-glucopyranose, b-D-mannopyranose and a-L-fucopyranose. The 3D relaxed scan of interaction energy (E) surface between carbohydrate and benzene was performed at SCC-DFTB-D level, followed by DFT-D BP/def2-TZVPP E evaluation and reoptimization of most stable structures. These structures were used for evaluation of E at MP2/CBS and CCSD(T)/CBS level. Obtained results show that E between apolar faces of carbohydrates and benzene grows up to -5.40 kcal/mol, which corresponds to medium-strong hydrogen bond. Additionally, the aromatic moiety binds most strongly above and under CH-groups of the carbohydrate -the strongest interaction is localized and the aromatic ring is able to recognize specific hydrogens of the saccharide in specific distance. The geometries of most stable benzene-carbohydrate complexes were measured to discover, that most suitable distance between carbohydrate hydrogen and the benzene center is around 2.3 A and the C-H-benzene-center angle slightly varies around 180deg.
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