title: Silver(I)-promoted conversion of thioamides to amidines: divergent synthesis of a key series of vancomycin aglycon residue 4 amidines that clarify binding behavior to model ligands.
abstract: Development of a general Ag(I)-promoted reaction for the conversion of thioamides to amidines is disclosed. This reaction was employed to prepare a key series of vancomycin aglycon residue 4 substituted amidines that were used to clarify their interaction with model ligands of peptidoglycan precursors and explore their resulting impact on antimicrobial properties.
authors.affiliation: Department of Chemistry and Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.
authors.forename: Akinori
authors.initials: A
authors.lastname: Okano
authors.forename: Robert C
authors.initials: RC
authors.lastname: James
authors.forename: Joshua G
authors.initials: JG
authors.lastname: Pierce
authors.forename: Jian
authors.initials: J
authors.lastname: Xie
authors.forename: Dale L
authors.initials: DL
authors.lastname: Boger
mesh_terms: D000578:Amidines / Q000737:chemistry*; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism* / Q000494:pharmacology; D001426:Bacterial Proteins / Q000378:metabolism; D002384:Catalysis; D060326:Chemistry Techniques, Synthetic; D015195:Drug Design; D024881:Drug Resistance, Bacterial / Q000187:drug effects; D013293:Enterococcus faecalis / Q000187:drug effects / Q000378:metabolism; D008024:Ligands; D010457:Peptidoglycan / Q000737:chemistry* / Q000494:pharmacology; D012834:Silver / Q000737:chemistry*; D013854:Thioamides / Q000737:chemistry*; D014640:Vancomycin / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism* / Q000494:pharmacology
chemical_list: D000578:Amidines; D000900:Anti-Bacterial Agents; D001426:Bacterial Proteins; D008024:Ligands; D010457:Peptidoglycan; D013854:Thioamides; D012834:Silver; D014640:Vancomycin