Pyranmycins, a novel class of aminoglycosides with improved acid stability: the SAR of D-pyranoses on ring III of pyranmycin.
[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.
Chang
Cheng-Wei Tom
CW
Department of Chemistry and Biochemistry, Utah State University, 0300 Old Main Hill, Logan, Utah 84322-0300, USA. chang@cc.usu.edu
Hui
Yu
Y
Elchert
Bryan
B
Wang
Jinhua
J
Li
Jie
J
Rai
Ravi
R
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
D000617:Aminoglycosides; D000900:Anti-Bacterial Agents; C475966:Pyranmycin; D011753:Pyrones; D014312:Trisaccharides; D009355:Neomycin; D006851:Hydrochloric Acid