Chemoenzymatic synthesis of polypeptides containing the unnatural amino acid 2-aminoisobutyric acid

Chem Commun (Camb). 2017 Jun 29;53(53):7318-7321. doi: 10.1039/c7cc03095a.

Abstract

Polypeptides containing 2-aminoisobutyric acid (Aib) units as an unnatural amino acid residue were synthesized by papain-catalyzed chemoenzymatic polymerization of a tripeptide ethyl ester l-Ala-Aib-l-Ala-OEt in an aqueous medium. The Aib-containing polypeptide adopted an α-helix conformation in both the solid and solution phases, which was induced by the periodic Aib residue.

MeSH terms

  • Aminoisobutyric Acids / chemistry
  • Aminoisobutyric Acids / metabolism*
  • Biocatalysis
  • Molecular Structure
  • Papain / metabolism*
  • Peptides / chemical synthesis*
  • Peptides / chemistry
  • Peptides / metabolism*

Substances

  • Aminoisobutyric Acids
  • Peptides
  • 2-aminoisobutyric acid
  • Papain