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 beta-lactones by a range of amines, and their antibacterial activity been shown to vary with the hydrophobic character of the substituents.
Department of Chemistry, Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford OX1 3TA, UK.
Claire L
CL
Bagwell
Mark G
MG
Moloney
Amber L
AL
Thompson
D000588:Amines / Q000737:chemistry; D000900:Anti-Bacterial Agents / Q000494:pharmacology*; D002626:Chemistry, Pharmaceutical / Q000379:methods*; D018360:Crystallography, X-Ray / Q000379:methods; D015195:Drug Design; D006860:Hydrogen Bonding; D057927:Hydrophobic and Hydrophilic Interactions; D007783:Lactones / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D008958:Models, Molecular; D008968:Molecular Conformation; D010080:Oxazoles / Q000494:pharmacology*; D011760:Pyrrolidinones; D013141:Spiro Compounds / Q000494:pharmacology*
D000588:Amines; D000900:Anti-Bacterial Agents; D007783:Lactones; D010080:Oxazoles; D011760:Pyrrolidinones; D013141:Spiro Compounds; C077919:diffusomycin