Importance of Co-operative Hydrogen Bonding in the Apramycin-Ribosomal Decoding A-Site Interaction
Abstract
An intramolecular hydrogen bond between the protonated equatorial 7’-methylamino group of apramycin and the vicinal axial 6’-hydroxy group acidifies the 6’-hydroxy group leading to a strong hydrogen bond to A1408 in the ribosomal drug binding pocket in the decoding A site of the small ribosomal subunit. In 6’-epiapramycin, the trans-nature of the 6’-hydroxy group and the 7’-methylamino group results in a much weaker intramolecular hydrogen bond, and a consequently weaker cooperative hydrogen bonding network with A1408, resulting overall in reduced inhibition of protein synthesis and antibacterial activity. Show more
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https://doi.org/10.3929/ethz-b-000595220Publication status
publishedExternal links
Journal / series
ChemMedChemVolume
Pages / Article No.
Publisher
Wiley-VCHSubject
hydrogen bonding; aminoglycosides; antibacterial; antiribosomal activity; aminoglycoside modifying enzymesMore
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