Synthesis of (+),(−)-neamine and their positional isomers as potential antibiotics

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Abstract

The syntheses of (+)-neamine 1, (−)-neamine ent-1 and their positional isomers 2, 3, ent-2 and ent-3 are reported as potential new scaffolds for novel aminoglycoside antibiotics. These isomers exhibit similar inhibitory activities, as shown using an in vitro translation assay. A simple model is proposed to explain this lack of stereospecific binding to the ribosomal RNA.

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Acknowledgments

This work was supported by the US Public Health Service NIH Grant EY-12375.

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