Synthesis and Potential Uses of 2-(N-(2-(Fmoc)ethyl)-2-(6-(tert-butoxycarbonylamino)pyridin-3-yl)acetamido) Acetic Acid
Synthesis of peptide nucleic acids with modified nucleobases with high affinity to recognize and complex double-stranded RNA at physiologically relevant conditions
Compared to DNA, molecular recognition of double stranded RNA has received relatively little attention. Since it has been discovered that RNA can catalyze chemical reactions, the important role that non-coding RNAs play has grown. The ability to selectively recognize and control the function of such RNAs is highly useful for both fundamental research and practical applications.
The present invention provides a new monomer for preparation of peptide nucleic acid (PNA) carrying a novel 2-aminopyridine nucleobase. PNAs containing 2-aminopyridine and other modified nucleobases form stable and sequence selective triple helices with double-stranded RNA at physiologically relevant conditions. The modified PNAs display unique RNA selectivity by having two orders of magnitude higher affinity for the double-stranded RNAs than for the same DNA sequences. Results show that nucleobase-modified PNA bind and recognize complex biologically important RNAs, such as double helical precursors of microRNAs.
- Ability to recognize double helical RNA in a sequence selective manner at physiologically relevant conditions.
- Strong and selective triple helical binding of peptide nucleic acids to double-stranded RNA.
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