Synthesis of cyclic peptides from unprotected precursors using removable N alpha-(1-(4-methoxyphenyl)-2-mercaptoethyl) auxiliary

J Pept Res. 2003 Mar;61(3):152-7. doi: 10.1034/j.1399-3011.2003.00043.x.

Abstract

A new method to cyclize unprotected peptides is presented. The method involves the use of a 1-phenyl-2-mercaptoethyl derivative on the N-terminal glycine. This template acts as an auxiliary thiol-containing group in order to drive cyclization with a counterpart thioester moiety on the same molecule. Subsequent facile removal of the derivative generates products with only native peptide structure. The successful, high-yield cyclization of the peptide GSPYSSDTTPA is described.

MeSH terms

  • Chromatography, High Pressure Liquid
  • Dimethylformamide / chemistry
  • Esters / chemistry
  • Glycine / chemistry*
  • Hydrogen-Ion Concentration
  • Methylene Chloride / chemistry
  • Models, Chemical
  • Peptide Biosynthesis*
  • Peptides / chemistry*
  • Protein Structure, Tertiary
  • Resins, Synthetic
  • Time Factors
  • Trifluoroacetic Acid / chemistry

Substances

  • Esters
  • Peptides
  • Resins, Synthetic
  • Methylene Chloride
  • Dimethylformamide
  • Trifluoroacetic Acid
  • Glycine