title: Investigation into the functional impact of the vancomycin C-ring aryl chloride.
abstract: A vancomycin aglycon analogue that possesses a reduced C-ring and an intact E-ring chloride was prepared and its antimicrobial activity towards Staphylococcus aureus and binding affinity to model cell wall ligands were established. Comparison of the derivative with a series of vancomycin aglycon analogues that possess and lack the chloro substituents on the aryl C- and E-rings defines the impact and further refines the role the C-ring chloride plays in promoting both target binding affinity and binding selectivity for d-Ala-d-Ala and its impact on antimicrobial activity.
authors.affiliation: Department of Chemistry and the Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, United States.
authors.forename: Joseph R
authors.initials: JR
authors.lastname: Pinchman
authors.forename: Dale L
authors.initials: DL
authors.lastname: Boger
mesh_terms: D000900:Anti-Bacterial Agents / Q000737:chemistry* / Q000494:pharmacology*; D002712:Chlorides / Q000737:chemistry* / Q000494:pharmacology*; D004151:Dipeptides / Q000378:metabolism; D006801:Humans; D008826:Microbial Sensitivity Tests; D013203:Staphylococcal Infections / Q000188:drug therapy / Q000382:microbiology; D013211:Staphylococcus aureus / Q000187:drug effects*; D014640:Vancomycin / Q000031:analogs & derivatives* / Q000494:pharmacology*
chemical_list: D000900:Anti-Bacterial Agents; D002712:Chlorides; D004151:Dipeptides; C002956:alanylalanine; D014640:Vancomycin
keywords: Borylation; Vancomycin; Vancomycin analogues