A facile and one-pot synthesis of N-Fmoc/Bsmoc/Boc/Z-protected ureidopeptides and peptidyl ureas employing diphenylphosphoryl azide [DPPA] |
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Authors: | Vommina V Sureshbabu G Chennakrishnareddy N Narendra |
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Institution: | Peptide Research Laboratory, Department of Studies in Chemistry, Central College Campus, Dr. B. R. Ambedkar Veedhi, Bangalore University, Bangalore 560 001, India |
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Abstract: | Diphenylphosphoryl azide (DPPA) mediated one-pot synthesis of Nα-Fmoc/Bsmoc/Boc/Z-protected ureidopeptides and peptidyl ureas as well as phenyl/succinimidyl (Nα-urethane protected) methyl carbamates starting from Nα-protected amino acids is reported. The formation of an azide, its rearrangement and coupling with an amino component is accomplished in a sequence of one-pot operations. The protocol has incorporated urea linkages in a sterically hindered peptide. |
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Keywords: | Diphenylphosphoryl azide Ureidopeptides Peptidyl ureas Curtius rearrangement One-pot synthesis |
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