Influence of stereochemistry on proton transfer in protonated
tripeptide models

J 2012

Influence of stereochemistry on proton transfer in protonated tripeptide models

SOLIMAN, Namat Ali, Petr KULHÁNEK and Jaroslav KOČA

Basic information

Original name

Influence of stereochemistry on proton transfer in protonated tripeptide models

Authors

SOLIMAN, Namat Ali (434 Libya, belonging to the institution), Petr KULHÁNEK (203 Czech Republic, belonging to the institution) and Jaroslav KOČA (203 Czech Republic, guarantor, belonging to the institution)

Edition

Journal of Molecular Modeling, New York, Springer, 2012, 1610-2940

Other information

Language

English

Type of outcome

Článek v odborném periodiku

Field of Study

10600 1.6 Biological sciences

Country of publisher

United States of America

Confidentiality degree

není předmětem státního či obchodního tajemství

References:

URL

Impact factor

Impact factor: 1.984

RIV identification code

RIV/00216224:14740/12:00060043

Organization unit

Central European Institute of Technology

DOI

http://dx.doi.org/10.1007/s00894-011-1116-2

UT WoS

000303539500005

Keywords in English

Conformational rearrangement; Density functional theory; Protonated peptides; Proton transfer

Abstract

V originále

Vectorial proton transfer among carbonyl oxygen atoms was studied in two models of tripeptide via quantum chemical calculations using the hybrid B3LYP functional and the 6-31++G** basis set. Two principal proton transfer pathways were found: a first path involving isomerization of the proton around the double bond of the carbonyl group, and a second based on the large conformational flexibility of the tripeptide model where all carbonyl oxygen atoms cooperate. The latter pathway has a rate-determining step energy barrier that is only around half of that for the first pathway. As conformational flexibility plays a crucial role in second pathway, the effect of attaching methyl groups to the alpha carbon atoms was studied. The results obtained are presented for all four possible stereochemical configurations.

Links

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

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

Citovat

SOLIMAN, Namat Ali, Petr KULHÁNEK and Jaroslav KOČA. Influence of stereochemistry on proton transfer in protonated tripeptide models. Journal of Molecular Modeling. New York: Springer, 2012, vol. 18, No 3, p. 871-879. ISSN 1610-2940. Available from: https://dx.doi.org/10.1007/s00894-011-1116-2.

@article{983376,
   author = {Soliman, Namat Ali and Kulhánek, Petr and Koča, Jaroslav},
   article_location = {New York},
   article_number = {3},
   doi = {http://dx.doi.org/10.1007/s00894-011-1116-2},
   keywords = {Conformational rearrangement; Density functional theory; Protonated peptides; Proton transfer},
   language = {eng},
   issn = {1610-2940},
   journal = {Journal of Molecular Modeling},
   title = {Influence of stereochemistry on proton transfer in protonated tripeptide models},
   url = {http://link.springer.com/article/10.1007%2Fs00894-011-1116-2},
   volume = {18},
   year = {2012}
}

TY  - JOUR
ID  - 983376
AU  - Soliman, Namat Ali - Kulhánek, Petr - Koča, Jaroslav
PY  - 2012
TI  - Influence of stereochemistry on proton transfer in protonated tripeptide models
JF  - Journal of Molecular Modeling
VL  - 18
IS  - 3
SP  - 871-879
EP  - 871-879
PB  - Springer
SN  - 16102940
KW  - Conformational rearrangement
KW  - Density functional theory
KW  - Protonated peptides
KW  - Proton transfer
UR  - http://link.springer.com/article/10.1007%2Fs00894-011-1116-2
L2  - http://link.springer.com/article/10.1007%2Fs00894-011-1116-2
N2  - Vectorial proton transfer among carbonyl oxygen atoms was studied in two models of tripeptide via quantum chemical calculations using the hybrid B3LYP functional and the 6-31++G** basis set. Two principal proton transfer pathways were found: a first path involving isomerization of the proton around the double bond of the carbonyl group, and a second based on the large conformational flexibility of the tripeptide model where all carbonyl oxygen atoms cooperate. The latter pathway has a rate-determining step energy barrier that is only around half of that for the first pathway. As conformational flexibility plays a crucial role in second pathway, the effect of attaching methyl groups to the alpha carbon atoms was studied. The results obtained are presented for all four possible stereochemical configurations.
ER  -

SOLIMAN, Namat Ali, Petr KULHÁNEK and Jaroslav KOČA. Influence of stereochemistry on proton transfer in protonated tripeptide models. \textit{Journal of Molecular Modeling}. New York: Springer, 2012, vol.~18, No~3, p.~871-879. ISSN~1610-2940. Available from: https://dx.doi.org/10.1007/s00894-011-1116-2.

Detailed Information on Publication Record