Publication. SBC

Title:

Synthesis of Novel Aminoglycosides via Allylic Azide Rearrangement for Investigating the Significance of 2'-Amino Group

Author:

Zhang, J.; Litke, A.; Keller, K.; Rai, R.; Chang, C.-W. T.

Journal:

Bioorg. Med. Chem.

Abstract:

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.

Citation:

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.

Hyperlink:

http://www.ncbi.nlm.nih.gov/pubmed/20133139