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

KOZMON, Stanislav, Radek MATUŠKA, Vojtech SPIWOK and Jaroslav KOČA. Three-Dimensional Potential Energy Surface of Selected Carbohydrates' CH/p Dispersion Interactions Calculated by High-Level Quantum Mechanical Methods. Chemistry - A European Journal. Weinheim: WILEY-VCH Verlag, 2011, vol. 17, No 20, p. 5680-5690. ISSN 0947-6539. Available from: https://dx.doi.org/10.1002/chem.201002876.

Basic information

• Original name: Three-Dimensional Potential Energy Surface of Selected Carbohydrates' CH/p Dispersion Interactions Calculated by High-Level Quantum Mechanical Methods
• Authors: KOZMON, Stanislav (703 Slovakia, belonging to the institution), Radek MATUŠKA (203 Czech Republic, belonging to the institution), Vojtech SPIWOK (203 Czech Republic) and Jaroslav KOČA (203 Czech Republic, guarantor, belonging to the institution).
• Edition: Chemistry - A European Journal, Weinheim, WILEY-VCH Verlag, 2011, 0947-6539.

Other information

• Original language: English
• Type of outcome: Article in a journal
• Field of Study: 10403 Physical chemistry
• Country of publisher: United States of America
• Confidentiality degree: is not subject to a state or trade secret
• Impact factor: Impact factor: 5.925
• RIV identification code: RIV/00216224:14740/11:00049962
• Organization unit: Central European Institute of Technology
• Doi: http://dx.doi.org/10.1002/chem.201002876
• UT WoS: 000290216000024
• Keywords in English: carbohydrates; CH/pi interactions; DFT calculations; dispersion interactions; molecular recognition
• Tags: ok, rivok

Abstract

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.

Links

• GD301/09/H004, research and development project: Name: Molekulární a strukturní biologie vybraných cytostatik. Od mechanistických studií k chemoterapii rakoviny

Investor: Czech Science Foundation

• LC06030, research and development project: Name: Biomolekulární centrum

Investor: Ministry of Education, Youth and Sports of the CR, Biomolecular centre

• MSM0021622413, plan (intention): Name: Proteiny v metabolismu a při interakci organismů s prostředím

Investor: Ministry of Education, Youth and Sports of the CR, Proteins in metabolism and interaction of organisms with the environment

• 205872, interní kód MU: Name: Program developing interdisciplinary research POtential for the STudies of BIOMolecular INteractions (Acronym: POSTBIOMIN)

Investor: European Union, Program developing interdisciplinary research POtential for the STudies of BIOMolecular INteractions, Capacities