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Related Experiment Videos

Factors affecting conformation in proline-containing peptides.

Carol M Taylor1, Renaud Hardré, Patrick J B Edwards

  • 1Institute of Fundamental Sciences, Massey University, Private Bag 11-222, Palmerston North, New Zealand. c.m.taylor@massey.ac.nz

Organic Letters
|November 7, 2003
PubMed
Summary

Nuclear magnetic resonance (NMR) studied cis-trans isomerization in prolyl amide bonds. Esters showed stronger backbone effects than amides, and N-terminal bulk favored trans, while Phenylalanine favored cis conformations.

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Area of Science:

  • Chemical Thermodynamics
  • Structural Biology
  • Organic Chemistry

Background:

  • Prolyl amide bonds are crucial in peptide and protein structure.
  • Understanding cis-trans isomerization is key to protein folding and function.
  • Stereoelectronic effects and N-terminal residue influence peptide bond conformation.

Purpose of the Study:

  • To investigate the thermodynamics of cis --> trans isomerization for prolyl amide bonds.
  • To elucidate the impact of C-terminal modifications (esters vs. amides) on isomerization.
  • To determine how N-terminal residue steric bulk and aromatic interactions affect prolyl conformation.

Main Methods:

  • Nuclear magnetic resonance (NMR) spectroscopy was employed to study isomerization.
  • Thermodynamic analysis of cis/trans equilibrium was performed.

Related Experiment Videos

  • Various N-terminal residues and C-terminal modifications were synthesized and analyzed.

    • Main Results:

    • The equilibrium constant for cis/trans isomerization (K(t/c)) was significantly greater for C-terminal esters compared to amides.
    • Increased steric bulk of the N-terminal residue (acetylglycine vs. acetyl) favored the trans conformation.
    • Incorporation of a Phenylalanine residue N-terminal to proline shifted the equilibrium towards the cis conformation.

    Conclusions:

    • Esters exhibit stronger backbone stereoelectronic effects influencing prolyl amide bond isomerization than amides.
    • N-terminal residue properties, including steric bulk and aromatic interactions, play a critical role in dictating prolyl cis/trans isomerism.
    • A stabilizing aromatic-proline interaction was identified as a key factor favoring the cis conformation when Phenylalanine is present.