title: Biomimetic synthesis, antibacterial activity and structure-activity properties of the pyroglutamate core of oxazolomycin.
abstract: Biomimetic intramolecular aldol reactions on oxazolidine templates derived from serine may be used to generate densely functionalised pyroglutamates, which are simpler mimics of the right hand side of oxazolomycin. Some of the compounds from this sequence exhibit in vivo activity against S. aureus and E. coli, suggesting that pyroglutamate scaffolds may be useful templates for the development of novel antibacterials, and cheminformatic analysis has been used to provide some structure-activity data.
authors.affiliation: Department of Chemistry, Chemistry Research Laboratory, The University of Oxford, 12 Mansfield Road, Oxford, OX1 3TA, UK.
authors.forename: Plamen
authors.initials: P
authors.lastname: Angelov
authors.forename: Yui Kwan Sonia
authors.initials: YK
authors.lastname: Chau
authors.forename: Paul J
authors.initials: PJ
authors.lastname: Fryer
authors.forename: Mark G
authors.initials: MG
authors.lastname: Moloney
authors.forename: Amber L
authors.initials: AL
authors.lastname: Thompson
authors.forename: Paul C
authors.initials: PC
authors.lastname: Trippier
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D032701:Biomimetics / Q000379:methods*; D004926:Escherichia coli / Q000187:drug effects; D008958:Models, Molecular; D008968:Molecular Conformation; D010080:Oxazoles / Q000737:chemistry*; D011760:Pyrrolidinones; D011761:Pyrrolidonecarboxylic Acid / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D013141:Spiro Compounds / Q000737:chemistry*; D013211:Staphylococcus aureus / Q000187:drug effects; D013329:Structure-Activity Relationship
chemical_list: D000900:Anti-Bacterial Agents; D010080:Oxazoles; D011760:Pyrrolidinones; D013141:Spiro Compounds; C077919:diffusomycin; D011761:Pyrrolidonecarboxylic Acid