Abstract
Peptide nucleic acids (PNAs) are structural mimics of nucleic acids that form stable hybrids with DNA and RNA. In addition, PNAs can invade double-stranded DNA. Due to these characteristics, PNAs are widely used as biochemical tools, for example, in antisense/antigene therapy. Interstrand crosslink formation in nucleic acids is one of the strategies for preparing a stable duplex by covalent bond formation. In this study, we have synthesized PNAs incorporating 4-amino-6-oxo-2-vinylpyrimidine (AOVP) as a crosslinking agent and evaluated their reactivities for targeting DNA and RNA.
Highlights
Peptide nucleic acids (PNAs) are synthetic nucleic acid analogs, in which the sugar phosphate backbone is replaced with N-(2-aminoethyl)glycine [1] (Figure 1)
We describe the synthesis of PNAs containing AOVP and the evaluation of their crosslinking reactivities
The synthesis of the PNA monomer (8) as a stable precursor of AOVP is summarized in Scheme 1
Summary
Peptide nucleic acids (PNAs) are synthetic nucleic acid analogs, in which the sugar phosphate backbone is replaced with N-(2-aminoethyl)glycine [1] (Figure 1). PNAs are chemically stable in comparison to DNA over a wide range of temperatures and pH values and are resistant to nucleases and proteases [2]. This invasion ability of the PNAs raises the possibility their use to control gene expression at the DNA level with high efficiency. One strategy for increasing the stability of the PNA-DNA complex is by forming a covalent bond between the PNA and the target DNA. The bis-PNA conjugated with nitrogen mustard is reported to suppress transcription in a model system by forming a strand invasion complex and covalent bond with the target duplex DNA [21]. A PNA bearing an alkylating group provides an efficient strategy for gene targeting via the inhibition of transcription with high sequence selectivity. We describe the synthesis of PNAs containing AOVP and the evaluation of their crosslinking reactivities
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