Direct synthesis of N-protected β-amino dimethylhydroxamates:: Application to the solid-phase synthesis of a peptide incorporating a new amide bond surrogate Ψ[CH2CH2NH]

A rapid and efficient one-step synthesis of N-protected beta-amino dimethylhydroxamates starting from diazo ketones is reported A Fmoc-protected beta-amino aldehyde obtained by reduction of its corresponding dimethylhydroxamate was incorporated during solid phase assembly of an antigenic peptide. The resulting pseudopeptide containing an ethylene amino bond Psi[CH2CH2NH] was efficiently recovered. (C) 1998 Elsevier Science Ltd. All rights reserved.