title: Site-selective bromination of vancomycin.
abstract: We report the site-selective bromination of vancomycin to produce, with substantial efficiency, previously unknown monobromovancomycins, a dibromovancomycin, and a tribromovancomycin. We document the inherent reactivity of native vancomycin toward N-bromophthalimide. We then demonstrate significant rate acceleration and perturbation of the inherent product distribution in the presence of a rationally designed peptide-based promoter. Alternative site selectivity is observed as a function of solvent and replacement of the peptide with guanidine.
authors.affiliation: Department of Chemistry, Yale University, 225 Prospect Street, New Haven, Connecticut 06520-8107, USA.
authors.forename: Tejas P
authors.initials: TP
authors.lastname: Pathak
authors.forename: Scott J
authors.initials: SJ
authors.lastname: Miller
mesh_terms: D000900:Anti-Bacterial Agents / Q000737:chemistry*; D001665:Binding Sites; D001703:Biophysics / Q000379:methods*; D001966:Bromine / Q000737:chemistry*; D002384:Catalysis; D002851:Chromatography, High Pressure Liquid / Q000379:methods; D019791:Guanidine / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy / Q000379:methods; D008956:Models, Chemical; D010455:Peptides / Q000737:chemistry; D010797:Phthalimides / Q000737:chemistry; D011401:Promoter Regions, Genetic; D012997:Solvents / Q000737:chemistry; D014640:Vancomycin / Q000737:chemistry*
chemical_list: D000900:Anti-Bacterial Agents; D010455:Peptides; D010797:Phthalimides; D012997:Solvents; C056577:N-bromophthalimide; D014640:Vancomycin; D019791:Guanidine; D001966:Bromine