Dispersion interactions of carbohydrates with condensate aromatic moieties: Theoretical study on the CH–pi interaction additive properties

KOZMON, Stanislav, Radek MATUŠKA, Vojtech SPIWOK and Jaroslav KOČA. Dispersion interactions of carbohydrates with condensate aromatic moieties: Theoretical study on the CH–pi interaction additive properties. Physical Chemistry Chemical Physics. Great Britain: ROYAL SOC CHEMISTRY, 2011, vol. 13, No 31, p. 14215-14222. ISSN 1463-9076. Available from: https://dx.doi.org/10.1039/c1cp21071h.

Basic information

• Original name: Dispersion interactions of carbohydrates with condensate aromatic moieties: Theoretical study on the CH–pi interaction additive properties
• 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: Physical Chemistry Chemical Physics, Great Britain, ROYAL SOC CHEMISTRY, 2011, 1463-9076.

Other information

• Original language: English
• Type of outcome: Article in a journal
• Field of Study: 10403 Physical chemistry
• Country of publisher: United Kingdom of Great Britain and Northern Ireland
• Confidentiality degree: is not subject to a state or trade secret
• Impact factor: Impact factor: 3.573
• RIV identification code: RIV/00216224:14740/11:00049968
• Organization unit: Central European Institute of Technology
• Doi: http://dx.doi.org/10.1039/c1cp21071h
• UT WoS: 000293172300036
• Keywords in English: SMALL MOLECULAR-INTERACTIONS; DENSITY-FUNCTIONAL THEORY; SEPARATE TOTAL ENERGIES; INTERACTIONS AB-INITIO; MODEL SYSTEM; ANALOG COMPLEXES; EXCHANGE-ENERGY; REDUCED ERRORS; RECOGNITION; APPROXIMATION
• Tags: ok, rivok
• Tags: International impact

Abstract

In this article we present the first systematic study of the additive properties (i.e. degree of additivity) of the carbohydrate-aromatic moiety CH-pi dispersion interaction. The additive properties were studied on the beta-D-glucopyranose, beta-D-mannopyranose and alpha-L-fucopyranose complexes with the naphthalene molecule by comparing the monodentate (single CH-pi) and bidentate (two CH-pi) complexes. All model complexes were optimized using the DFT-D approach, at the BP/def2-TZVPP level of theory. The interaction energies were refined using single point calculations at highly correlated ab initio methods at the CCSD(T)/CBS level, calculated as E(CBS)(MP2) + (E(CCSD(T)) - E(MP2))(Small) (Basis). Bidentate complexes show very strong interactions in the range from -10.79 up to -7.15 and -8.20 up to -6.14 kcal mol(-1) for the DFT-D and CCSD(T)/CBS level, respectively.

Links

• ED1.1.00/02.0068, research and development project: Name: CEITEC - central european institute of technology
• 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

• 2SGA2747, interní kód MU: Name: Saccharide - protein dispersion interactions involved in the bacterial recognition processes (Acronym: SaProDI)

Investor: South-Moravian Region, Incoming grants

• 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