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Highly Stable Duplex Formation by Artificial Nucleic Acids Acyclic Threoninol Nucleic Acid ( a TNA) and Serinol Nucleic Acid (SNA) with Acyclic Scaffolds

2013; Wiley; Volume: 19; Issue: 42 Linguagem: Inglês

10.1002/chem.201301578

1521-3765

Keiji Murayama, Yoshihiro Tanaka, Takasuke Toda, Hiromu Kashida, Hiroyuki Asanuma,

RNA Interference and Gene Delivery

Abstract The stabilities of duplexes formed by strands of novel artificial nucleic acids composed of acyclic threoninol nucleic acid ( a TNA) and serinol nucleic acid (SNA) building blocks were compared with duplexes formed by the acyclic glycol nucleic acid (GNA), peptide nucleic acid (PNA), and native DNA and RNA. All acyclic nucleic acid homoduplexes examined in this study had significantly higher thermal stability than DNA and RNA duplexes. Melting temperatures of homoduplexes were in the order of a TNA>PNA≈GNA≥SNA≫RNA>DNA. Thermodynamic analyses revealed that high stabilities of duplexes formed by a TNA and SNA were due to large enthalpy changes upon formation of duplexes compared with DNA and RNA duplexes. The higher stability of the a TNA homoduplex than the SNA duplex was attributed to the less flexible backbone due to the methyl group of D ‐threoninol on a TNA, which induced clockwise winding. Unlike a TNA, the more flexible SNA was able to cross‐hybridize with RNA and DNA. Similarly, the SNA/PNA heteroduplex was more stable than the a TNA/PNA duplex. A 15‐mer SNA/RNA was more stable than an RNA/DNA duplex of the same sequence.