Abstract
Starting from commercially available N-protected l-α-amino acids, N,N′-protected gem-diaminic units were obtained by a two-step methodology. A Hofmann reaction performed using a primary alcohol as the solvent to trap the isocyanate intermediate represents the key step of the new synthetic procedure. Then, the methodology was applied to α-carbamoyl α′-carboxyl aziridines, also functionalized with l-α-amino esters and stable gem-diaminic units characterized by an aziridine ring and by a retro-peptide modification were obtained. The use of the latter units in the retro-peptide chemistry allows to obtain modified peptides containing an aziridine ring able to behave as an electrophilic site and as a biomimetic structural analog of proline.
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Università degli Studi di Roma “La Sapienza” is gratefully acknowledged for financial support.
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Aresu, E., Fioravanti, S., Gasbarri, S. et al. Synthesis of gem-diamino acid derivatives by a Hofmann rearrangement. Amino Acids 44, 977–982 (2013). https://doi.org/10.1007/s00726-012-1428-2
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DOI: https://doi.org/10.1007/s00726-012-1428-2