Title

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

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

DOI

10.1016/j.bmc.2010.01.027

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.

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