CH-pi Interaction between Carbohydrates and Aromatic Moieties: Electron Density Issue

KOZMON, Stanislav, Radek MATUŠKA and Jaroslav KOČA. CH-pi Interaction between Carbohydrates and Aromatic Moieties: Electron Density Issue. In XI-Discussions in Structural Molecular Biology, Nové Hrady 2013. 2013.

Basic information

• Original name: CH-pi Interaction between Carbohydrates and Aromatic Moieties: Electron Density Issue
• Authors: KOZMON, Stanislav (203 Czech Republic, belonging to the institution), Radek MATUŠKA (203 Czech Republic, belonging to the institution) and Jaroslav KOČA (203 Czech Republic, guarantor, belonging to the institution).
• Edition: XI-Discussions in Structural Molecular Biology, Nové Hrady 2013, 2013.

Other information

• Original language: English
• Type of outcome: Conference abstract
• Field of Study: 10600 1.6 Biological sciences
• Country of publisher: Czech Republic
• Confidentiality degree: is not subject to a state or trade secret
• RIV identification code: RIV/00216224:14310/13:00066082
• Organization unit: Faculty of Science
• Keywords in English: CH-pi interaction benzene electron density DFT calculations

Abstract

Former studies of the CH-pi interactions between carbohydrates and aromatic moieties were focused on exploration of interaction energies in complexes of selected carbohydrates with benzene and naphthalene as simplest representatives of aromatic amino acids side chains. These studies provided complex insight into the nature and strength of carbohydrate-aromatic CH-pi interaction as well as its additivity with respect to total number of pi-electrons interacting it the aromatic system. The next logical step in complex study of CH-pi interaction is to study the influence of electron density in the aromatic system to the total interaction energy of the carbohydrate-aromatic complex. For this reason, we chose established set of selected carbohydrates mentioned above and constructed aromatic systems derivatives with expected increased and decreased electron density in the cycle – namely symmetrical difluoro-, trifluoro- and tetrafluoro-benzene and symmetrical diazine, triazine and tetrazine. All derivatives underwent electron-density evaluation in ring critical points by AIM analysis (MP2/aug-cc-pVTZ), which clearly shows decreasing electron density with respect to the degree of derivatization of fluorobenzenes and increasing electron density with respect to the degree of derivatization by nitrogens in the aromatic ring. With this set of molecules, we repeat the semiempirical SCC-DFTB-D potential energy scan with DFT-D BP/def2-TZVPP interaction energy refinement to identify stationary structures of potential energy surface. Their interaction energy is calculated after geometry optimization at DFT-D BP/def2 TZVPP level. Such level of theory has been previously proved to be sufficient and giving similar results as CCSD(T)/CBS method.

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

• 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