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

Authors

Jianjun Zhang, Utah State University
Anthony Litke, Utah State UniversityFollow
Katherine Keller, Utah State University
Ravi Rai, Utah State University
Cheng-Wei Tom Chang, Utah State UniversityFollow

Document Type

Article

Journal/Book Title

Bioorganic & Medicinal Chemistry

Publication Date

2-15-2010

Publisher

Elsevier

Volume

18

Issue

4

First Page

1396

Last Page

1405

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′-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.

Recommended 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.