title: Investigation of the regioselectivity for the staudinger reaction and its application for the synthesis of aminoglycosides with N-1 modification.
abstract: The criteria for controlling the regioselectivity of Staudinger reduction of azides have been investigated. These findings enable a convenient direct N-1 modification of the perazidoneamine and perazidoribostamycin resulting in the synthesis of aminoglycoside antibiotics with activity against drug-resistant bacteria.
authors.affiliation: Department of Chemistry and Biochemistry, Utah State University, 0300 Old Main Hill, Logan, Utah 84322-0300, USA.
authors.forename: Jie
authors.initials: J
authors.lastname: Li
authors.forename: Fang-I
authors.initials: FI
authors.lastname: Chiang
authors.forename: Hsiao-Nung
authors.initials: HN
authors.lastname: Chen
authors.forename: Cheng-Wei Tom
authors.initials: CW
authors.lastname: Chang
mesh_terms: D000617:Aminoglycosides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D001386:Azides / Q000737:chemistry*; D001419:Bacteria / Q000187:drug effects*; D001424:Bacterial Infections / Q000188:drug therapy / Q000382:microbiology; D002240:Carbohydrate Sequence; D004352:Drug Resistance, Microbial; D008969:Molecular Sequence Data
chemical_list: D000617:Aminoglycosides; D000900:Anti-Bacterial Agents; D001386:Azides