1428131-68-3Relevant academic research and scientific papers
Synthesis of gem-diamino acid derivatives by a Hofmann rearrangement
Aresu, Emanuele,Fioravanti, Stefania,Gasbarri, Simona,Pellacani, Lucio,Ramadori, Federico
, p. 977 - 982 (2013/07/05)
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.
