Efficient preparation of Fmoc-aminoacyl-N-ethylcysteine unit, a key device for the synthesis of peptide thioesters

Org Biomol Chem. 2011 Oct 7;9(19):6807-13. doi: 10.1039/c1ob05831b. Epub 2011 Aug 15.

Abstract

The synthesis of Fmoc-aminoacyl-N-ethyl-S-triphenylmethylcysteine, an N- to S-acyl migratory device for the preparation of peptide thioesters by Fmoc-SPPS (solid-phase peptide synthesis) is described. Condensation of Fmoc-aminoacyl pentafluorophenyl ester and N-ethyl-S-triphenylmethylcysteine was efficiently performed in the presence of HOOBt (3-hydroxy-3,4-dihydro-4-oxo-1,2,3-benzotriazine) in DMF. A small amount of diastereomer yielded during the reaction was easily separated by HPLC purification and the highly pure devices were obtained for most of the proteinogenic amino acids.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Chemistry Techniques, Synthetic / methods*
  • Cysteine / analogs & derivatives*
  • Cysteine / chemical synthesis
  • Cysteine / chemistry
  • Molecular Structure
  • Peptides / chemical synthesis*
  • Peptides / chemistry
  • Stereoisomerism
  • Sulfhydryl Compounds / chemical synthesis*
  • Sulfhydryl Compounds / chemistry

Substances

  • Peptides
  • Sulfhydryl Compounds
  • Cysteine