Abstract
A peptide nucleic acid (PNA) is a synthetic nucleic acid mimic in which the sugar-phosphate backbone is replaced by a peptide backbone. PNAs hybridize to complementary DNA and RNA with higher affinity and superior sequence selectivity compared to DNA. PNAs are resistant to nucleases and proteases and have a low affinity for proteins. These properties make PNAs an attractive agent for biological and medical applications. To improve the antisense and antigene properties of PNAs, many backbone modifications of PNAs have been explored under the concept of preorganization. This review focuses on chiral PNAs bearing a substituent in the N-(2-aminoethyl)glycine backbone. Syntheses, properties, and applications of chiral PNAs are described.
Highlights
A peptide nucleic acid (PNA) is a synthetic analogue of DNA first reported by Nielsen et al in1991 [1]
We intend to focus on chiral PNAs bearing substituents on the original N-(2-aminoethyl)glycine backbone and present them divided into three groups (α-PNA, β-PNA, and -PNA) based on the position of a substituent in the PNA backbone (Figure 1)
A large number of modified PNAs have been obtained by modifying the PNA backbone, nucleobases, and the linker connecting a nucleobase to the backbone
Summary
A peptide nucleic acid (PNA) is a synthetic analogue of DNA first reported by Nielsen et al in. In PNA, the sugar-phosphate backbone of DNA is replaced by a peptide backbone consisting of N-(2-aminoethyl)glycine units. The relative rigidity of the PNA backbone improves sequence selectivity on hybridization. Some reports suggest that PNAs can target duplex DNA even in living cells by strand invasion [7,8,9,10,11]. To improve the antisense and antigene potency of PNAs, it is reasonable to increase binding affinity for DNA and RNA by suitable preorganization. An approach for improving DNA binding affinity is the design and synthesis of preorganized PNAs preferring a right-handed helical conformation. Reports have appeared demonstrating that preorganization can be achieved by cyclization of the PNA backbone or by adding substituents to the backbone [12,13]. We intend to focus on chiral PNAs bearing substituents on the original N-(2-aminoethyl)glycine backbone and present them divided into three groups (α-PNA, β-PNA, and -PNA) based on the position of a substituent in the PNA backbone (Figure 1)
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