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Chemistry

Wayne State University

Wayne State University Theses

Theses/Dissertations

Aminoglycoside

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Synthesis Of 4'-O-Glycopyranosyl Paromomycin Aminoglycoside Antibiotics: Influence Of The Glycoside On Antiribosomal, Antibacterial Activity And Utilization Of Electrospray Ionization Mass Spectrometry To Evaluate Reactivity Of Glycosyl Phosphate, Weiwei Chen Jan 2014

Synthesis Of 4'-O-Glycopyranosyl Paromomycin Aminoglycoside Antibiotics: Influence Of The Glycoside On Antiribosomal, Antibacterial Activity And Utilization Of Electrospray Ionization Mass Spectrometry To Evaluate Reactivity Of Glycosyl Phosphate, Weiwei Chen

Wayne State University Theses

The data in this thesis is trying to address two problems. The first problem is paromomycin associated ototoxicity; the second problem is the lack of precise reactivity data of glycosyl donors in one-pot synthesis.

Paromomycin is out of the market as an antibiotic due to its ototoxicity. Previous work done by Vasella and Böttger's groups identified 4'-O position of paromomycin as a promising site of modification to reduce the side effect. A series of 4'-O-glycopyranosyl paromomycin has been synthesized and tested for their biological activity and selectivity. From the results of anti bacterial ribosomal activity, anti hybrid ribosomal activity and …