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

J 2011

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 a Jaroslav KOČA

Základní údaje

Originální název

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

Autoři

KOZMON, Stanislav (703 Slovensko, domácí), Radek MATUŠKA (203 Česká republika, domácí), Vojtech SPIWOK (203 Česká republika) a Jaroslav KOČA (203 Česká republika, garant, domácí)

Vydání

Chemistry - A European Journal, Weinheim, WILEY-VCH Verlag, 2011, 0947-6539

Další údaje

Jazyk

angličtina

Typ výsledku

Článek v odborném periodiku

Obor

10403 Physical chemistry

Stát vydavatele

Spojené státy

Utajení

není předmětem státního či obchodního tajemství

Impakt faktor

Impact factor: 5.925

Kód RIV

RIV/00216224:14740/11:00049962

Organizační jednotka

Středoevropský technologický institut

DOI

http://dx.doi.org/10.1002/chem.201002876

UT WoS

000290216000024

Klíčová slova anglicky

carbohydrates; CH/pi interactions; DFT calculations; dispersion interactions; molecular recognition

Štítky

ok, rivok

Změněno: 27. 1. 2017 21:01, prof. RNDr. Jaroslav Koča, DrSc.

Anotace

V originále

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.

Návaznosti

GD301/09/H004, projekt VaV

Název: Molekulární a strukturní biologie vybraných cytostatik. Od mechanistických studií k chemoterapii rakoviny

Investor: Grantová agentura ČR, Molekulární a strukturní biologie vybraných cytostatik. Od mechanických studií k chemoterapii rakoviny

LC06030, projekt VaV

Název: Biomolekulární centrum

Investor: Ministerstvo školství, mládeže a tělovýchovy ČR, Biomolekulární centrum

MSM0021622413, záměr

Název: Proteiny v metabolismu a při interakci organismů s prostředím

Investor: Ministerstvo školství, mládeže a tělovýchovy ČR, Proteiny v metabolismu a při interakci organismů s prostředím

205872, interní kód MU

Název: Program developing interdisciplinary research POtential for the STudies of BIOMolecular INteractions (Akronym: POSTBIOMIN)

Investor: Evropská unie, Program developing interdisciplinary research POtential for the STudies of BIOMolecular INteractions, Kapacity

Citovat

KOZMON, Stanislav, Radek MATUŠKA, Vojtech SPIWOK a 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, roč. 17, č. 20, s. 5680-5690. ISSN 0947-6539. Dostupné z: https://dx.doi.org/10.1002/chem.201002876.

@article{949890,
   author = {Kozmon, Stanislav and Matuška, Radek and Spiwok, Vojtech and Koča, Jaroslav},
   article_location = {Weinheim},
   article_number = {20},
   doi = {http://dx.doi.org/10.1002/chem.201002876},
   keywords = {carbohydrates; CH/pi interactions; DFT calculations; dispersion interactions; molecular recognition},
   language = {eng},
   issn = {0947-6539},
   journal = {Chemistry - A European Journal},
   title = {Three-Dimensional Potential Energy Surface of Selected Carbohydrates' CH/p Dispersion Interactions Calculated by High-Level Quantum Mechanical Methods},
   volume = {17},
   year = {2011}
}

TY  - JOUR
ID  - 949890
AU  - Kozmon, Stanislav - Matuška, Radek - Spiwok, Vojtech - Koča, Jaroslav
PY  - 2011
TI  - Three-Dimensional Potential Energy Surface of Selected Carbohydrates' CH/p Dispersion Interactions Calculated by High-Level Quantum Mechanical Methods
JF  - Chemistry - A European Journal
VL  - 17
IS  - 20
SP  - 5680-5690
EP  - 5680-5690
PB  - WILEY-VCH Verlag
SN  - 09476539
KW  - carbohydrates
KW  - CH/pi interactions
KW  - DFT calculations
KW  - dispersion interactions
KW  - molecular recognition
N2  - 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.
ER  -

KOZMON, Stanislav, Radek MATUŠKA, Vojtech SPIWOK a Jaroslav KOČA. Three-Dimensional Potential Energy Surface of Selected Carbohydrates' CH/p Dispersion Interactions Calculated by High-Level Quantum Mechanical Methods. \textit{Chemistry - A European Journal}. Weinheim: WILEY-VCH Verlag, 2011, roč.~17, č.~20, s.~5680-5690. ISSN~0947-6539. Dostupné z: https://dx.doi.org/10.1002/chem.201002876.

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