(S)-C alpha-ethyl, C alpha-benzylglycine [(S)-(alpha Et)Phe] peptides fold in left-handed helical structures

Pept Res. 1995 Sep-Oct;8(5):294-7.

Abstract

The first x-ray diffraction structure analysis of a C alpha-ethyl, C alpha-benzylglycine [(alpha Et)Phe]-containing peptide, N alpha-benzyloxycarbonyl-alpha-aminoisobutyryl-alpha-amino-isobutyr yl-(S)- C alpha-benzylglycyl-alpha-aminoisobutyric acid (methanol solvate), has been performed. In the crystal state the N alpha-protected tetrapeptide is folded in an incipient, left-handed 3(10)-helical structure. This finding confirms that the relationship between (alpha Et)Phe alpha-carbon chirality and screw sense of the helix that is formed is opposite to that exhibited by protein amino acids, including Phe.

MeSH terms

  • Chemical Phenomena
  • Chemistry, Physical
  • Crystallization
  • Crystallography, X-Ray*
  • Models, Molecular
  • Oligopeptides / chemistry*
  • Protein Folding*
  • Protein Structure, Secondary*

Substances

  • Oligopeptides
  • benzyloxycarbonyl-aminoisobutyryl-aminoisobutyryl-(alpha-ethyl)phenylalanyl-aminoisobutyric acid