Predicting the conformational preferences of N-acetyl-4-hydroxy-L-proline- N′-methylamide from the proline residue

Janice S.W. Lam, Joseph C.P. Koo, Ilona Hudáky, Andras Varro, Julius Gy Papp, Botond Penke, I. G. Csizmadia

Research output: Contribution to journalArticle

9 Citations (Scopus)

Abstract

Ab initio Hartree-Fock (RHF/3-21G* and RHF/6-31G(d)) and density functional (B3LYP/6-31G(d)) molecular computations were performed on N-acetyl-4-hydroxy-L-proline-N′-methylamide with varying torsional angles ω01,ψ,χ1, and χ 5; while the φ torsional angle is restricted in the vicinity of -60° (ω01,ψ,χ1, and χ5 are 'governing coordinates' and other torsional angles χ0,χ234 change with respect to them). The computed results of N-acetyl-4-hydroxy-L-proline- N′-methylamide were then compared to those previously reported for the proline residue at the RHF/6-31+G* level of theory. The calculated torsional angles of the hydroxyproline and proline residues were remarkably similar. When optimized torsional angle values of hydroxyproline were compared to those of proline, a strong correlation was observed (R2=0.9997).

Original languageEnglish
Pages (from-to)285-289
Number of pages5
JournalJournal of Molecular Structure: THEOCHEM
Volume666-667
DOIs
Publication statusPublished - Dec 29 2003

Keywords

  • Ab initio
  • Backbone conformation
  • Cis-trans isomerism
  • Collagen
  • Conformer
  • Density functional geometry optimizations
  • Hartree-Fock
  • Hydroxyproline
  • Proline
  • Ring puckering

ASJC Scopus subject areas

  • Biochemistry
  • Condensed Matter Physics
  • Physical and Theoretical Chemistry

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