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

Marcin Czapla , Sylwia Freza


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 (FCh/DTCh/LQCh)
Marcin Czapla,,
- Laboratory of Quantum Chemistry
, Sylwia Freza (FCh/DTCh/LQCh)
Sylwia Freza,,
- Laboratory of Quantum Chemistry
Other language title versions
Journal seriesInternational Journal of Quantum Chemistry, ISSN 0020-7608, (A 20 pkt)
Issue year2017
Publication size in sheets0.50
Article numbere25435
Keywords in Englishab initio calculations, double amino acid, peptide bond formation
ASJC Classification1606 Physical and Theoretical Chemistry; 3104 Condensed Matter Physics; 3107 Atomic and Molecular Physics, and Optics
URL https://doi.org/10.1002/qua.25435
Languageen angielski
Score (nominal)20
Score sourcejournalList
ScoreMinisterial score = 20.0, 05-02-2020, ArticleFromJournal
Publication indicators WoS Citations = 3.000; Scopus SNIP (Source Normalised Impact per Paper): 2017 = 0.959; WoS Impact Factor: 2017 = 2.568 (2) - 2017=1.867 (5)
Citation count*4 (2020-08-08)
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