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• W2912805062 endingPage "4372" @default.
• W2912805062 startingPage "4367" @default.
• W2912805062 abstract "Abstract The development of new RNA‐binding ligands is attracting increasing interest in fundamental science and the pharmaceutical industry. The goal of this study was to improve the RNA binding properties of triplex‐forming peptide nucleic acids (PNAs) by further increasing the p K a of 2‐aminopyridine ( M ). Protonation of M was the key for enabling triplex formation at physiological pH in earlier studies. Substitution on M by an electron‐donating 4‐methoxy substituent resulted in slight destabilization of the PNA–dsRNA triplex, contrary to the expected stabilization due to more favorable protonation. To explain this unexpected result, the first NMR structural studies were performed on an M ‐modified PNA–dsRNA triplex which, combined with computational modeling identified unfavorable steric and electrostatic repulsion between the 4‐methoxy group of M and the oxygen of the carbonyl group connecting the adjacent nucleobase to PNA backbone. The structural studies also provided insights into hydrogen‐bonding interactions that might be responsible for the high affinity and unusual RNA‐binding preference of PNAs." @default.
• W2912805062 created "2019-02-21" @default.
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• W2912805062 date "2019-03-04" @default.
• W2912805062 modified "2023-10-12" @default.
• W2912805062 title "Synthetic, Structural, and RNA Binding Studies on 2‐Aminopyridine‐Modified Triplex‐Forming Peptide Nucleic Acids" @default.
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• W2912805062 doi "https://doi.org/10.1002/chem.201806293" @default.
• W2912805062 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/30746843" @default.
• W2912805062 hasPublicationYear "2019" @default.
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