V. Sureshbabu, G. Chennakrishnareddy, Shankar A. Naik
2010
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Indian Journal of Chemistry Section B-organic Chemistry Including Medicinal Chemistry
Abstract
An efficient method for the synthesis of O-succinimidyl (9H-fluorene-9-yl methoxycarbonylamine) peptidyl carbamates from the corresponding N α -Fmoc peptidyl isocyanates through the concomitant Curtius rearrangement of N α Fmoc peptidyl acid azide and coupling with N-hydroxysuccinimide is described. The introduction of urea moiety at various positions in peptidyl backbone of VALVAL hexapeptide sequence has been carried out by the fragment coupling using peptidyl carbamates. All the oligo-α-peptidyl ureas are isolated as crystalline solids in 80-85% yield and have been fully characterized by 1 H and 13 C NMR and mass spectrometry.