Generation and analysis of the conformational potential energy surfaces of N-acetyl-N-methyl-L-alanine-N′-methylamide. An exploratory ab initio study

István Bágyi, Balázs Balogh, András Czajlik, Olivér Éliás, Zoltán Gáspári, Viktor Gergely, Ilona Hudáky, Péter Hudáky, Adrián Kalászi, László Károlyházy, Katalin Keserû, Róbert Kiss, Gábor Krajsovszky, Barbara Láng, Tamás Nagy, Ákos Rácz, Aletta Szentesi, Tamás Tábi, Pál Tapolcsányi, Judit VaikJoseph C.P. Koo, Gregory A. Chass, Ödön Farkas, András Perczel, Péter Mátyus

Research output: Contribution to journalArticle

12 Citations (Scopus)

Abstract

N-methylation is a naturally occurring modification in small peptides, e.g. antibiotics that can effect the conformational preferences of the molecule as well as the ease of trans to cis isomerization of the involved peptide bond. In the present exploratory study we have calculated the potential energy surface of both N-acetyl-L-alanine-N′-methylamide and N-acetyl-N-methyl-L-alanine-N′-methylamide at the RHF/3-21G level of theory with a cis-trans or with a trans-trans peptide conformation. With respect to the non-methylated model system our results indicate that N-methylation reduces the number of observable backbone conformers in both amide configurations. The effect of methylation on the ease of trans to cis isomerization was assessed by calculating the energetics of the corresponding transition structures. An increase in the activation energies of the trans to cis isomerization of the relevant peptide bond was observed for the N-methylated moiety.

Original languageEnglish
Pages (from-to)121-136
Number of pages16
JournalJournal of Molecular Structure: THEOCHEM
Volume625
Issue number1-3
DOIs
Publication statusPublished - May 5 2003

Keywords

  • Ab initio calculations
  • N-acetyl- N-methyl-L-alanine-N′-methylamide
  • N-acetyl-L-alanine-N′-methylamide
  • Trans to cis Isomerization

ASJC Scopus subject areas

  • Biochemistry
  • Condensed Matter Physics
  • Physical and Theoretical Chemistry

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  • Cite this

    Bágyi, I., Balogh, B., Czajlik, A., Éliás, O., Gáspári, Z., Gergely, V., Hudáky, I., Hudáky, P., Kalászi, A., Károlyházy, L., Keserû, K., Kiss, R., Krajsovszky, G., Láng, B., Nagy, T., Rácz, Á., Szentesi, A., Tábi, T., Tapolcsányi, P., ... Mátyus, P. (2003). Generation and analysis of the conformational potential energy surfaces of N-acetyl-N-methyl-L-alanine-N′-methylamide. An exploratory ab initio study. Journal of Molecular Structure: THEOCHEM, 625(1-3), 121-136. https://doi.org/10.1016/S0166-1280(03)00009-5