On the antibiotic activity of oxazolomycin

Structural analysis of oxazolomycin and simpler fragments containing a common 3-hydroxy-2,2-dimethylpropanamide moiety has indicated that a U-shaped conformation is preferred, in some cases stabilised by hydrogen bonding between the N–H and O–H residues, as shown by a combination of molecular modelling, NMR spectroscopic and single crystal X-ray analysis. A direct synthesis of this unit has been established via the opening of β-lactones by a range of amines, and their antibacterial activity been shown to vary with the hydrophobic character of the substituents.