Impairment of a model peptide by oxidative stress

Thermodynamic stabilities of asparagine diamide Cα-radical foldamers

Klára Z. Gerlei, Lilla Élo, Béla Fiser, Michael C. Owen, Imre Jákli, Svend J. Knak Jensen, I. Csizmadia, A. Perczel, B. Viskolcz

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

Electron structure calculations on N-acetyl asparagine N-methylamide were performed to identify the global minimum from which radicals were formed after H-abstraction by the OH radical. It was found that the radical generated by breaking the C-H bond of the α-carbon was thermodynamically the most stable one in the gas- and aqueous phases. The extended (βL and βD) backbone conformations are the most stable, but syn-syn or inverse γ-turn (γL) and γ-turn (γ D) have substantial stability too. The highest energy conformers are the degenerate εL and εD foldamers. Clearly, the most stable β foldamer is the most likely intermediate for racemization.

Original languageEnglish
Pages (from-to)104-108
Number of pages5
JournalChemical Physics Letters
Volume593
DOIs
Publication statusPublished - Feb 11 2014

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Diamide
Oxidative stress
Asparagine
impairment
peptides
Conformations
Thermodynamic stability
Carbon
Gases
thermodynamics
Peptides
Electrons
carbon
gases
electrons
energy

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Physics and Astronomy(all)

Cite this

Impairment of a model peptide by oxidative stress : Thermodynamic stabilities of asparagine diamide Cα-radical foldamers. / Gerlei, Klára Z.; Élo, Lilla; Fiser, Béla; Owen, Michael C.; Jákli, Imre; Knak Jensen, Svend J.; Csizmadia, I.; Perczel, A.; Viskolcz, B.

In: Chemical Physics Letters, Vol. 593, 11.02.2014, p. 104-108.

Research output: Contribution to journalArticle

Gerlei, Klára Z. ; Élo, Lilla ; Fiser, Béla ; Owen, Michael C. ; Jákli, Imre ; Knak Jensen, Svend J. ; Csizmadia, I. ; Perczel, A. ; Viskolcz, B. / Impairment of a model peptide by oxidative stress : Thermodynamic stabilities of asparagine diamide Cα-radical foldamers. In: Chemical Physics Letters. 2014 ; Vol. 593. pp. 104-108.
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