3-Azidoazetidines as the first scaffolds for β-amino azetidine carboxylic acid peptidomimetics: azetidine iminosugars containing an acetamido group do not inhibit β-N-acetylhexosaminidases

Stable amides and oligopeptides derived from methyl trans,trans-3-azido-4-hydroxymethyl-L-azetidine carboxylate, prepared in 19% yield from diacetone allose, is the first example of a β-amino-azetidine carboxylic acid incorporated into peptidomimetics and provides a scaffold for investigating secondary structure induced by a novel β-amino acid. A number of azetidine iminosugars containing a NHAc substituent were prepared but none of them were β-N-acetylhexosaminidase inhibitors.