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ID: ALA1147432

Journal: Bioorg Med Chem Lett

Title: Rational design of azepane-glycoside antibiotics targeting the bacterial ribosome.

Authors: Barluenga S, Simonsen KB, Littlefield ES, Ayida BK, Vourloumis D, Winters GC, Takahashi M, Shandrick S, Zhao Q, Han Q, Hermann T.

Abstract: RNA recognition by natural aminoglycoside antibiotics depends on the 2-deoxystreptamine (2-DOS) scaffold which participates in specific hydrogen bonds with the ribosomal decoding-site target. Three-dimensional structure information has been used for the design of azepane-monoglycosides, building blocks for novel antibiotics in which 2-DOS is replaced by a heterocyclic scaffold. Azepane-glycosides showed target binding and translation inhibition in the low micromolar range and inhibited growth of Staphylococcus aureus, including aminoglycoside-resistant strains.

CiteXplore: 14741274

DOI: 10.1016/j.bmcl.2003.11.028