Mechanism of Proton Transfer in Short Protonated Oligopeptides.
1. N-Methylacetamide and N2-Acetyl-N1-methylglycinamide

J 2003

Mechanism of Proton Transfer in Short Protonated Oligopeptides. 1. N-Methylacetamide and N2-Acetyl-N1-methylglycinamide

KULHÁNEK, Petr, Edward W. SCHLAG and Jaroslav KOČA

Basic information

Original name

Mechanism of Proton Transfer in Short Protonated Oligopeptides. 1. N-Methylacetamide and N2-Acetyl-N1-methylglycinamide

Authors

KULHÁNEK, Petr (203 Czech Republic), Edward W. SCHLAG (276 Germany) and Jaroslav KOČA (203 Czech Republic, guarantor)

Edition

J. Phys. Chem. A, American Chemical Society, 2003, 1089-5639

Other information

Language

English

Type of outcome

Článek v odborném periodiku

Field of Study

10402 Inorganic and nuclear chemistry

Country of publisher

United States of America

Confidentiality degree

není předmětem státního či obchodního tajemství

References:

URL

Impact factor

Impact factor: 2.792

RIV identification code

RIV/00216224:14310/03:00008940

Organization unit

Faculty of Science

Keywords in English

proton transfer; proton exchange; proton interaction; DFT

Abstract

V originále

A study of proton transfer in models of a single peptide unit (N-methylacetamide) and diamide (N2-acetyl-N1-methylglycinamide) as well as the influence of a single water molecule on proton transfer is presented here. Three proton pathways in protonated N-methylacetamide are considered: isomerization, inversion, and 1,3-proton shift. The isomerization step exhibits the lowest energy barrier. When a single water molecule was added, no significant influence on proton isomerization was observed. In the diamide model, the isomerization-jump mechanism of proton transfer along diamide carbonyl oxygens was inspected, and the proton isomerization steps were found to be the most energy-demanding processes (~17 kcal mol-1). The presence of a single water molecule leads to a different, lower-energy-barrier proton-transfer mechanism with proton exchange. The highest energy barrier is only 7.6 kcal mol-1. Possible competing pathways are also discussed.

Links

LN00A016, research and development project

Name: BIOMOLEKULÁRNÍ CENTRUM

Investor: Ministry of Education, Youth and Sports of the CR, Biomolecular Center

Citovat

KULHÁNEK, Petr, Edward W. SCHLAG and Jaroslav KOČA. Mechanism of Proton Transfer in Short Protonated Oligopeptides. 1. N-Methylacetamide and N2-Acetyl-N1-methylglycinamide. J. Phys. Chem. A. American Chemical Society, 2003, vol. 107, No 30, p. 5789-5797, 8 pp. ISSN 1089-5639.

@article{489312,
   author = {Kulhánek, Petr and Schlag, Edward W. and Koča, Jaroslav},
   article_number = {30},
   keywords = {proton transfer; proton exchange; proton interaction; DFT},
   language = {eng},
   issn = {1089-5639},
   journal = {J. Phys. Chem. A},
   title = {Mechanism of Proton Transfer in Short Protonated Oligopeptides. 1. N-Methylacetamide and N2-Acetyl-N1-methylglycinamide},
   url = {http://dx.doi.org/10.1021/jp027689+},
   volume = {107},
   year = {2003}
}

TY  - JOUR
ID  - 489312
AU  - Kulhánek, Petr - Schlag, Edward W. - Koča, Jaroslav
PY  - 2003
TI  - Mechanism of Proton Transfer in Short Protonated Oligopeptides. 1. N-Methylacetamide and N2-Acetyl-N1-methylglycinamide
JF  - J. Phys. Chem. A
VL  - 107
IS  - 30
SP  - 5789-5797
EP  - 5789-5797
PB  - American Chemical Society
SN  - 10895639
KW  - proton transfer
KW  - proton exchange
KW  - proton interaction
KW  - DFT
UR  - http://dx.doi.org/10.1021/jp027689+
N2  - A study of proton transfer in models of a single peptide unit (N-methylacetamide) and diamide (N2-acetyl-N1-methylglycinamide) as well as the influence of a single water molecule on proton transfer is presented here. Three proton pathways in protonated N-methylacetamide are considered: isomerization, inversion, and 1,3-proton shift. The isomerization step exhibits the lowest energy barrier. When a single water molecule was added, no significant influence on proton isomerization was observed. In the diamide model, the isomerization-jump mechanism of proton transfer along diamide carbonyl oxygens was inspected, and the proton isomerization steps were found to be the most energy-demanding processes (~17 kcal mol-1). The presence of a single water molecule leads to a different, lower-energy-barrier proton-transfer mechanism with proton exchange. The highest energy barrier is only 7.6 kcal mol-1. Possible competing pathways are also discussed.
ER  -

KULHÁNEK, Petr, Edward W. SCHLAG and Jaroslav KOČA. Mechanism of Proton Transfer in Short Protonated Oligopeptides. 1. N-Methylacetamide and N2-Acetyl-N1-methylglycinamide. \textit{J. Phys. Chem. A}. American Chemical Society, 2003, vol.~107, No~30, p.~5789-5797, 8 pp. ISSN~1089-5639.

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