Synthesis of novel aminoglycosides via allylic azide rearrangement for investigating the significance of 2'-amino group.
Using allylic azide rearrangement, a convenient method has been developed for the synthesis of 2',3'-dideoxyaminoglycosides that are, otherwise, difficult to be prepared. The antibacterial activity of these novel aminoglycosides also confirms the indispensable role of 2'-NH(2) group for both neomycin and kanamycin classes of aminoglycosides. A novel structural motif containing the hexylaminocarbonyl groups at O-5 and/or O-6 of 2',3'-dideoxyneamine could lead to the production of new aminoglycosides against resistant bacteria.
Zhang
Jianjun
J
Department of Chemistry and Biochemistry, Utah State University, Logan, UT 84322-0300, USA.
Litke
Anthony
A
Keller
Katherine
K
Rai
Ravi
R
Chang
Cheng-Wei Tom
CW
D000617:Aminoglycosides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D001386:Azides / Q000737:chemistry*; D002240:Carbohydrate Sequence; D008826:Microbial Sensitivity Tests; D008969:Molecular Sequence Data; D021241:Spectrometry, Mass, Electrospray Ionization
D000617:Aminoglycosides; D000900:Anti-Bacterial Agents; D001386:Azides