Reexamination of neomycin B degradation: efficient preparation of its CD and D rings as protected glycosyl donors.
The degradation of neomycin B was reexamined, and a novel protocol was established to prepare the properly masked neomycin CD ring as a glycol donor in excellent yield. Glycosylation of the CD ring with glycol acceptors provided a facile access to versatile intermediates that could be utilized to synthesize a variety of novel neomycin B mimetics for RNA recognition. [reaction: see text]
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism*; D004355:Drug Stability; D005601:Framycetin / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism*; D006018:Glycols / Q000737:chemistry; D006031:Glycosylation; D015394:Molecular Structure; D012329:RNA, Bacterial / Q000737:chemistry / Q000378:metabolism; D013379:Substrate Specificity
D000900:Anti-Bacterial Agents; D006018:Glycols; D012329:RNA, Bacterial; D005601:Framycetin