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Importance of the 6′‐Hydroxy Group and Its Configuration for Apramycin Activity
Author(s) -
Mandhapati Appi Reddy,
Shcherbakov Dimitri,
Duscha Stefan,
Vasella Andrea,
Böttger Erik C.,
Crich David
Publication year - 2014
Publication title -
chemmedchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.817
H-Index - 100
eISSN - 1860-7187
pISSN - 1860-7179
DOI - 10.1002/cmdc.201402146
Subject(s) - antibacterial activity , chemistry , translation (biology) , combinatorial chemistry , antibiotics , stereochemistry , computational biology , biochemistry , biology , bacteria , genetics , messenger rna , gene
A series of apramycin derivatives was prepared and investigated for antibacterial activity and the ability to inhibit protein synthesis in cell‐free translation assays. The effect of various modifications at the 6′‐ and N7′‐positions on antiribosomal activity is discussed in terms of their influence on drug binding to specific residues in the decoding A‐site. These studies contribute to the development of a structure–activity relationship for the antibacterial activity of the apramycin class of aminoglycosides and to the future design and development of more active and less toxic antibiotics.