title: Synthesis of gem-diamino acid derivatives by a Hofmann rearrangement.
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.
authors.affiliation: Dipartimento di Chimica, Università degli Studi di Roma La Sapienza, P.le Aldo Moro 5, 00185 Rome, Italy.
authors.forename: Emanuele
authors.initials: E
authors.lastname: Aresu
authors.forename: Stefania
authors.initials: S
authors.lastname: Fioravanti
authors.forename: Simona
authors.initials: S
authors.lastname: Gasbarri
authors.forename: Lucio
authors.initials: L
authors.lastname: Pellacani
authors.forename: Federico
authors.initials: F
authors.lastname: Ramadori
mesh_terms: D000599:Amino Acids, Diamino / Q000138:chemical synthesis* / Q000737:chemistry; D060326:Chemistry Techniques, Synthetic; D015394:Molecular Structure; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000599:Amino Acids, Diamino; D010455:Peptides