title: Pyranmycins, a novel class of aminoglycosides with improved acid stability: the SAR of D-pyranoses on ring III of pyranmycin.
abstract: [reaction: see text] The synthesis of a novel class of aminoglycosides, pyranmycins, is reported along with the structure activity relationship (SAR) of their antibacterial activity against Escherichia coli. Two pyranmycins show prominent activity (9 microM). Pyranmycins also manifest superior stability in acidic media. The SAR information will lead to the future designs of pyranmycin against drug resistant bacteria.
authors.affiliation: Department of Chemistry and Biochemistry, Utah State University, 0300 Old Main Hill, Logan, Utah 84322-0300, USA. chang@cc.usu.edu
authors.forename: Cheng-Wei Tom
authors.initials: CW
authors.lastname: Chang
authors.forename: Yu
authors.initials: Y
authors.lastname: Hui
authors.forename: Bryan
authors.initials: B
authors.lastname: Elchert
authors.forename: Jinhua
authors.initials: J
authors.lastname: Wang
authors.forename: Jie
authors.initials: J
authors.lastname: Li
authors.forename: Ravi
authors.initials: R
authors.lastname: Rai
mesh_terms: D000617:Aminoglycosides / Q000138:chemical synthesis / Q000737:chemistry*; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry*; D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D004355:Drug Stability; D006851:Hydrochloric Acid / Q000737:chemistry; D008969:Molecular Sequence Data; D009355:Neomycin / Q000737:chemistry; D011753:Pyrones / Q000737:chemistry; D013329:Structure-Activity Relationship; D014312:Trisaccharides / Q000138:chemical synthesis / Q000737:chemistry
chemical_list: D000617:Aminoglycosides; D000900:Anti-Bacterial Agents; C475966:Pyranmycin; D011753:Pyrones; D014312:Trisaccharides; D009355:Neomycin; D006851:Hydrochloric Acid