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.
Bagwell
Claire L
CL
Department of Chemistry, Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford OX1 3TA, UK.
Moloney
Mark G
MG
Thompson
Amber L
AL
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