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Carbonyldiimidazole (CDI) Mediated Synthesis of Nα-Protected Amino Acid Azides: Application to the One-pot Preparation of Ureidopeptides

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Synthesis of Nα-protected amino acyl azides starting from corresponding acids via the carbonyldiimidazole (CDI) activation is described. The protocol is extended for a one-pot preparation of ureido peptides that circumvents the isolation of acyl azide and isocyanate intermediates. The reaction was accomplished without using any additives and base. The protocol is simple, clean, high yielding and free from racemization.

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Keywords: Acyl azide; Buchi model; CDI; EDC; HBTU; HIV-1 protease inhibitors; HR-MS; Leuch's anhydride; MAPI; cycloaddition reactions; diphenylphosphoryl azide (DPPA); isocyanates; one-pot reaction; ureidopeptides

Document Type: Research Article

Publication date: November 1, 2011

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  • Protein & Peptide Letters publishes short papers in all important aspects of protein and peptide research, including structural studies, recombinant expression, function, synthesis, enzymology, immunology, molecular modeling, drug design etc. Manuscripts must have a significant element of novelty, timeliness and urgency that merit rapid publication. Reports of crystallisation, and preliminary structure determinations of biologically important proteins are acceptable. Purely theoretical papers are also acceptable provided they provide new insight into the principles of protein/peptide structure and function.
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