Fmoc synthesis of peptide thioesters without post-chain-assembly manipulation

J Am Chem Soc. 2011 Jul 27;133(29):11080-3. doi: 10.1021/ja204088a. Epub 2011 Jul 6.

Abstract

An operationally simple method for the synthesis of peptide thioesters is developed using standard Fmoc solid-phase peptide synthesis procedures. The method relies on the use of a premade enamide-containing amino acid which, in the final TFA cleavage step, renders the desired thioester functionality through an irreversible intramolecular N-to-S acyl transfer.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acid Sequence
  • Amino Acids / chemical synthesis
  • Amino Acids / chemistry
  • Carrier Proteins / chemical synthesis
  • Chemistry, Organic / methods*
  • Copper Transport Proteins
  • Esters / chemical synthesis
  • Esters / chemistry
  • Humans
  • Molecular Sequence Data
  • Peptides / chemical synthesis*
  • Peptides / chemistry
  • Sulfhydryl Compounds / chemical synthesis*
  • Sulfhydryl Compounds / chemistry

Substances

  • Amino Acids
  • COX17 protein, human
  • Carrier Proteins
  • Copper Transport Proteins
  • Esters
  • Peptides
  • Sulfhydryl Compounds