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RNA–Aminoglycoside Interactions: Design, Synthesis, and Binding of “Amino‐aminoglycosides” to RNA
Author(s) -
Wang Hai,
Tor Yitzhak
Publication year - 1998
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/(sici)1521-3773(19980202)37:1/2<109::aid-anie109>3.0.co;2-0
Subject(s) - aminoglycoside , kanamycin , rna , chemistry , antibiotics , binding site , stereochemistry , biophysics , biochemistry , biology , gene
The critical role of electrostatic interactions in the binding of aminoglycoside antibiotics to RNA is demonstrated by replacing the OH group, for example in kanamycin A ( 1 ), by NH 2 . Derivative 2 inhibits a hammerhead ribosyme much more strongly than 1 . It is proposed that the three‐dimensional arrangement of the protonated NH 2 groups determines the binding strength of the aminoglycosides.