Ultrasound accelerated conversion of Nalpha-urethane protected peptide esters to their thiopeptides using P2S5.
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.
Sureshbabu
Vommina V
VV
Peptide Research Laboratory, Department of Studies in Chemistry, Central College Campus, Bangalore University, Dr. B. R. Ambedkar Veedhi, Bangalore 560 001, India. hariccb@rediffmail.com
Nagendra
G
G
Venkataramanarao
R
R
D000596:Amino Acids / Q000737:chemistry; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D010455:Peptides / Q000737:chemistry* / Q000528:radiation effects; D017553:Phosphorus Compounds / Q000737:chemistry*; D012997:Solvents; D013440:Sulfides / Q000737:chemistry*; D014465:Ultrasonics; D014520:Urethane / Q000737:chemistry* / Q000528:radiation effects
D000596:Amino Acids; D007202:Indicators and Reagents; D010455:Peptides; D017553:Phosphorus Compounds; D012997:Solvents; D013440:Sulfides; C500376:phosphorus pentasulfide; D014520:Urethane