Synthesis of epoxy and aziridino malonyl peptidomimetics

Fioravanti, Stefania; Gasbarri, Simona; Pellacani, Lucio; Ramadori, Federico; Tardella, Paolo A.

doi:10.1016/j.tet.2010.09.097

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Cited by 5 publications

References 22 publications

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Synthesis of gem-diamino acid derivatives by a Hofmann rearrangement

et al. 2012

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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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Synthesis of gem-diamino acid derivatives by a Hofmann rearrangement

et al. 2012

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Trifluoromethyl-modified dipeptides by ZrCl4-promoted aza-Henry reactions

et al. 2014

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Chiral (R)-1-phenylethylamine was successfully employed in a tandem aza-Henry addition-reduction reaction to give chiral β-nitro α-trifluoromethyl amines. A subsequent coupling reaction with N-Boc-protected amino acids leads to obtain optically pure CF3-modified dipeptides carrying two different N-protecting groups. These peptidomimetic units are characterized by the presence of the [CH(CF3)NH] group as mimetic of the natural [CONH] peptidic bond and can be used for the synthesis of more complex CF3-modified peptides after selective deprotection of one of the two amine functions. 2D NMR spectral analyses were employed to determine the absolute configurations of all newly synthesized chiral compounds.

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Three-Membered Ring Systems

Bergmeier

Lapinsky

2011

Progress in Heterocyclic Chemistry

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Synthesis of epoxy and aziridino malonyl peptidomimetics

Cited by 5 publications

References 22 publications

Synthesis of gem-diamino acid derivatives by a Hofmann rearrangement

Synthesis of gem-diamino acid derivatives by a Hofmann rearrangement

Trifluoromethyl-modified dipeptides by ZrCl4-promoted aza-Henry reactions

Three-Membered Ring Systems

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