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Title: An efficient concomitant synthesis of O-succinimidyl-(9H-fluoren-9-yl methoxy carbonylamino)peptidyl carbamates and their application in the synthesis of oligo--peptidyl ureas
Authors: Sureshbabu, Vommina V
Chennakrishnareddy, Gundala
Naik, Shankar A
Keywords: Oligo--ureas;Curtius rearrangement;peptide acid azides;isocyanates;peptidyl carbamates
Issue Date: Jan-2010
Publisher: CSIR
Abstract:  An efficient method for the synthesis of O-succinimidyl (9H-fluorene-9-yl methoxycarbonylamine) peptidyl carbamates from the corresponding N-Fmoc peptidyl isocyanates through the concomitant Curtius rearrangement of N-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--peptidyl ureas are isolated as crystalline solids in 80-85% yield and have been fully characterized by 1H and 13C NMR and mass spectrometry.
Page(s): 69-76
ISSN: 0975-0983(Online); 0376-4699(Print)
Appears in Collections:IJC-B Vol.49B(01) [January 2010]

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