STUDY OF THE ADDITIVE PROPERTIES OF THE CARBOHYDRATE AROMATIC CH-Pi INTERACTION BY THE DFT AND AB INITIO CALCULATIONS

KOZMON, Stanislav, Radek MATUŠKA, Vojtěch SPIWOK and Jaroslav KOČA. STUDY OF THE ADDITIVE PROPERTIES OF THE CARBOHYDRATE AROMATIC CH-Pi INTERACTION BY THE DFT AND AB INITIO CALCULATIONS. In 26th International Carbohydrates Symposium. 2012.

Basic information

• Original name: STUDY OF THE ADDITIVE PROPERTIES OF THE CARBOHYDRATE AROMATIC CH-Pi INTERACTION BY THE DFT AND AB INITIO CALCULATIONS
• Authors: KOZMON, Stanislav (703 Slovakia, belonging to the institution), Radek MATUŠKA (203 Czech Republic, belonging to the institution), Vojtěch SPIWOK (203 Czech Republic) and Jaroslav KOČA (203 Czech Republic, guarantor, belonging to the institution).
• Edition: 26th International Carbohydrates Symposium, 2012.

Other information

• Original language: English
• Type of outcome: Conference abstract
• Field of Study: 10403 Physical chemistry
• Country of publisher: Spain
• Confidentiality degree: is not subject to a state or trade secret
• RIV identification code: RIV/00216224:14740/12:00058653
• Organization unit: Central European Institute of Technology
• Keywords in English: dispersion interaction carbohydrates ch/pi

Abstract

The CH/pi interactions that occur between carbohydrates and aromatic amino-acids are strongly involved in carbohydrate-recognition process. However, their influence to the recognition process has been underestimated for a long time. It has been recently shown that the strength of the CH/pi interactions is comparable to classical hydrogen bond. Presented computational study aims to describe the degree of additivity of the CH/pi interaction analyzing the interaction energy of carbohydrate-benzene complexes with monodentate (one CH/pi contact) and bidentate (two CH/pi contacts) carbohydrate-naphtalene complexes. All model complexes were optimized at DFT-D BP/def2 TZVPP level of theory, followed by refinement of interaction energies at highly-correlated and accurate CCSD(T)/CBS level. Also Boltzmann weighted populations of naphtalene/carbohydrate complexes were calculated for each carbohydrate apolar face.Deeper analysis discovers certain measurable degree of additivity. More precisely, the interaction energy of bidentate complex is 2/3 of the sum of interaction energies of appropriate monodentate complexes. Similarly, the interaction energy value for bidentante carbohydrate-naphtalene complexes is comparable to 4/5 of the sum of interaction energies of corresponding carbohydrate-benzene complexes. The study also shows that DFT-D methods describe CH/pi interactions in qualitatively similar manner as more computationally demanding CCSD(T)/CBS method. Based on our observations, we can conclude that DFTD approach may be utilized for computational treatment of larger complexes of biological interest, where CH/pi dispersion interactions play non-negligible role.

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

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

Investor: South-Moravian Region, Incoming grants

• 286154, interní kód MU: Name: SYLICA - Synergies of Life and Material Sciences to Create a New Future (Acronym: SYLICA)

Investor: European Union, Capacities