Ultrasound accelerated conversion of Nalpha-urethane protected peptide esters to their thiopeptides using P2S5

Ultrason Sonochem. 2008 Sep;15(6):927-9. doi: 10.1016/j.ultsonch.2008.04.009. Epub 2008 Apr 29.

Abstract

A fast and efficient synthesis of N(alpha)-protected thiopeptide esters from the corresponding peptide esters using P(2)S(5) as thionating agent assisted by ultrasonication has been described. The conversion of peptide bond into thioamide was complete in 20-40 min at rt. The reaction was accomplished without using any base. The products isolated were characterized using (1)H NMR, (13)C NMR and mass spectroscopy.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acids / chemistry
  • Indicators and Reagents
  • Magnetic Resonance Spectroscopy
  • Mass Spectrometry
  • Peptides / chemistry*
  • Peptides / radiation effects
  • Phosphorus Compounds / chemistry*
  • Solvents
  • Sulfides / chemistry*
  • Ultrasonics
  • Urethane / chemistry*
  • Urethane / radiation effects

Substances

  • Amino Acids
  • Indicators and Reagents
  • Peptides
  • Phosphorus Compounds
  • Solvents
  • Sulfides
  • phosphorus pentasulfide
  • Urethane