Synthesis of Novel Aminoglycosides via Allylic Azide Rearrangement for Investigating the Significance of 2'-Amino Group
Bioorganic & Medicinal Chemistry
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′-NH2 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, J.; Litke, A.; Keller, K.; Rai, R.; Chang, C.-W. T. “Synthesis of Novel Aminoglycosides via Allylic Azide Rearrangement for Investigating the Significance of 2'-Amino Group.” Bioorg. Med. Chem. 2010, 18, 1396-1405.