The semicarbazone peptidomimetic group in imino aza peptides

Article abstract of DOI:10.1016/S0040-4039(00)73078-4

The semicarbazone moiety (C-CH=N-NR-CO-NH-C), either obtained by coupling a peptide aldehyde with a semicarbazide, or by action of an alkylisocyanate on a peptide hydrazone, is a dipeptide isostere. The structure of four amino aza dipeptides, analogues of the Pro-Gly, Pro-Ala and Pro-Phe dipeptides, has been studied in solution by ¹H-NMR and IR spectroscopy, and in the solid state by X-ray diffraction.