a 2012

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

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

Language

English

Type of outcome

Konferenční abstrakt

Field of Study

10403 Physical chemistry

Country of publisher

Spain

Confidentiality degree

není předmětem státního či obchodního tajemství

RIV identification code

RIV/00216224:14740/12:00058653

Organization unit

Central European Institute of Technology

Keywords in English

dispersion interaction carbohydrates ch/pi
Změněno: 5/4/2013 15:11, Olga Křížová

Abstract

V originále

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