Abstract
The four stereomers of 2-imino-3-methylene-5- l(carboxy- l-valyl)pyrrolidine, a bacterial metabolite that is inhibitory to the fire blight bacterium Erwinia amylovora, were synthesised and compared for antibacterial activity. Several alternative amino acid conjugates with l, l-stereochemistry were also prepared, and the synthesis was extended to 3-methylenepiperidine-6- l-carboxylic acid and a selection of 2-imino-3-methylenepiperidine-6- l-carboxy- l-amino acid conjugates. All synthetic amino acid conjugates ( l, l-stereomers) were inhibitory to the growth of E. amylovora. The likely participation of the conjugated iminomethylene moiety as a Michael acceptor is implicated.
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