Exploratory conformational analysis of N-acetyl-L-tryptophan-N-methylamide. An ab initio study

María L. Ceci, María A. Lopez Verilli, Sandra S. Vallcaneras, José A. Bombasaro, Ana M. Rodríguez, B. Penke, Ricardo D. Enriz

Research output: Contribution to journalArticle

9 Citations (Scopus)

Abstract

The full conformational space of N-acetyl-L-tryptophan-N-methylamide was explored by ab initio MO computations. On the Ramachandran hypersurface of four independent variables E = E(φ, Ψ, χ1, χ2), 36 conformers were located instead of the expected 34 = 81 stable structures. The relative stabilities of the various conformers were analyzed in terms of sidechain-backbone interactions. A comparative study amongst theoretical calculations and experimental (NMR and X-ray) results was carried out.

Original languageEnglish
Pages (from-to)277-290
Number of pages14
JournalJournal of Molecular Structure: THEOCHEM
Volume631
DOIs
Publication statusPublished - Aug 1 2003

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tryptophan
Tryptophan
Theoretical Models
X-Rays
Nuclear magnetic resonance
X rays
nuclear magnetic resonance
x rays
interactions

Keywords

  • Ab initio MO study
  • N-acetyl-L-Tryptophan-N-methylamide
  • Peptide conformation
  • Ramachandran map of tryptophan residue
  • Sidechain orientation

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Computational Theory and Mathematics
  • Atomic and Molecular Physics, and Optics

Cite this

Ceci, M. L., Lopez Verilli, M. A., Vallcaneras, S. S., Bombasaro, J. A., Rodríguez, A. M., Penke, B., & Enriz, R. D. (2003). Exploratory conformational analysis of N-acetyl-L-tryptophan-N-methylamide. An ab initio study. Journal of Molecular Structure: THEOCHEM, 631, 277-290. https://doi.org/10.1016/S0166-1280(03)00261-6

Exploratory conformational analysis of N-acetyl-L-tryptophan-N-methylamide. An ab initio study. / Ceci, María L.; Lopez Verilli, María A.; Vallcaneras, Sandra S.; Bombasaro, José A.; Rodríguez, Ana M.; Penke, B.; Enriz, Ricardo D.

In: Journal of Molecular Structure: THEOCHEM, Vol. 631, 01.08.2003, p. 277-290.

Research output: Contribution to journalArticle

Ceci, María L. ; Lopez Verilli, María A. ; Vallcaneras, Sandra S. ; Bombasaro, José A. ; Rodríguez, Ana M. ; Penke, B. ; Enriz, Ricardo D. / Exploratory conformational analysis of N-acetyl-L-tryptophan-N-methylamide. An ab initio study. In: Journal of Molecular Structure: THEOCHEM. 2003 ; Vol. 631. pp. 277-290.
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