Synthesis of novel aminoglycosides via allylic azide rearrangement for investigating the significance of 2'-amino group

Bioorganic & Medicinal Chemistry
Jianjun ZhangCheng-Wei Tom Chang

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.

References

May 29, 2007·The Journal of Organic Chemistry·Sanjeeva R Guppi, George A O'Doherty
Feb 20, 2008·Tetrahedron·Haibing Guo, George A O'Doherty

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Citations

May 21, 2015·The Journal of Antibiotics·Kazushige SasakiYuzuru Akamatsu
Oct 24, 2012·Organic & Biomolecular Chemistry·Mallikharjuna Rao LSubhash Chandra Taneja
Jan 4, 2018·Chemical Society Reviews·Nishad Thamban Chandrika, Sylvie Garneau-Tsodikova

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