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Fluoroprolines as Tools for Protein Design and Engineering.

Christian Renner1, Stefan Alefelder1, Jae H Bae1

  • 1Max-Planck-Institut für Biochemie Am Klopferspitz 18 A, 82152 Martinsried (Germany) Fax: (+49) 89-8578-2847.

Angewandte Chemie (International Ed. in English)
|May 2, 2018
PubMed
Summary

Fluoroproline

Keywords:
NMR spectroscopyfluorineisomerizationprolineproteins

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Area of Science:

  • Biochemistry and structural biology
  • Protein engineering and design

Background:

  • The conformation of peptide bonds influences protein structure and stability.
  • Fluorinated amino acids offer unique properties for protein modification.

Purpose of the Study:

  • To investigate the relationship between fluoroproline conformation and protein thermostability.
  • To assess the impact of specific fluoroproline isomers on protein thermal stability.

Main Methods:

  • Synthesis of model compounds N-acetyl-4-fluoroproline methyl esters.
  • Characterization of cis/trans amide bond preferences.
  • Construction and thermal stability analysis of barstar mutants incorporating fluoroproline.

Main Results:

  • A direct correlation was observed between the cis/trans conformational preference of the fluoroproline amide bond and barstar mutant thermostability.
  • (4S)-L-fluoroproline mutants exhibited enhanced thermal stability compared to wild-type barstar.
  • (4R)-L-fluoroproline mutants displayed reduced thermal stability.

Conclusions:

  • The conformational preference of fluoroproline significantly impacts protein thermostability.
  • Stereochemistry of fluoroproline is a critical determinant for engineering protein stability.
  • Fluoroproline can be utilized as a tool for modulating protein thermal properties.