Bagwell Claire L, Moloney Mark G, Thompson Amber L
Department of Chemistry, Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford OX1 3TA, UK.
Bioorg Med Chem Lett. 2008 Jul 15;18(14):4081-6. doi: 10.1016/j.bmcl.2008.05.105. Epub 2008 Jun 14.
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 beta-lactones by a range of amines, and their antibacterial activity been shown to vary with the hydrophobic character of the substituents.
