Uncatalyzed peptide bond formation between two double amino acid molecules in the gas phase

Marcin Czapla , Sylwia Freza

Abstract

The gas phase mechanism for peptide bond formation between two double amino acid (DAA) molecules ((NH2)2C(COOH)2) is investigated in the absence of any catalysts. Two different paths, concerted and stepwise, each leading to both cis and trans DAA-DAA dipeptide products (four mechanisms total) are examined on the basis of theoretical calculations carried out at the CCSD(T)/aug-cc-pVDZ//MP2/aug-cc-pVDZ level. The investigation indicates that the concerted mechanism leading to the trans configuration of the peptide bond in the DAA-DAA dipeptide product is thermodynamically favored by about 5 kcal mol−1 and requires slightly less energy than the remaining pathways considered. Moreover, the peptide bond formation process between two DAA molecules in the gas phase resembles the analogous reactions between two natural amino acids.
Author Marcin Czapla PChK
Marcin Czapla,,
- Laboratory of Quantum Chemistry
, Sylwia Freza PChK
Sylwia Freza,,
- Laboratory of Quantum Chemistry
Other language title versions
Journal seriesInternational Journal of Quantum Chemistry, ISSN 0020-7608
Issue year2017
Vol117
No21
Pages1-6
Publication size in sheets0.5
Keywords in Englishab initio calculations, double amino acid, peptide bond formation
DOIDOI:10.1002/qua.25435
URL https://doi.org/10.1002/qua.25435
Languageen angielski
Score (nominal)20
ScoreMinisterial score = 20.0, 20-12-2017, ArticleFromJournal
Ministerial score (2013-2016) = 20.0, 20-12-2017, ArticleFromJournal
Publication indicators WoS Impact Factor: 2016 = 2.92 (2) - 2016=1.569 (5)
Citation count*2 (2018-07-20)
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* presented citation count is obtained through Internet information analysis and it is close to the number calculated by the Publish or Perish system.
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