Department of Biomolecular Engineering, Graduate School of Engineering, Nagoya University, Furo-cho, Chikusa-ku, Nagoya 464-8603, Japan.
Chem Commun (Camb). 2022 Mar 24;58(25):3993-4004. doi: 10.1039/d1cc05868a.
DNA and RNA have significance as genetic materials, therapeutic potential, and supramolecular properties. Advances in nucleic acid chemistry have enabled large-scale synthesis of DNA and RNA oligonucleotides and oligomers of non-natural nucleic acids, including artificial nucleic acids (xeno nucleic acids; XNAs) with non-ribose scaffolds. In this feature article, we review the chemical structures of XNAs with non-ribose scaffolds, their hybridization abilities, and their unique behaviors with a particular focus on the acyclic XNAs. First, we overview XNAs with non-ribose cyclic scaffolds and then those with acyclic scaffolds by focusing on their hybridization abilities with themselves and with DNA and RNA, and discuss the unexpectedly stable homo-duplex formation of acyclic XNAs. Next, we shed light on our threoninol nucleic acid (TNA) and serinol nucleic acid (SNA) and show their helical preferences based on their chirality, then orthogonal control of hybridization and helical amplification of achiral XNAs are demonstrated. Finally, we show non-enzymatic template-directed synthesis of L-TNA, and the creation of an artificial genetic system with XNAs with non-ribose scaffolds is described as a future prospect.
DNA 和 RNA 作为遗传物质具有重要意义，具有治疗潜力和超分子特性。核酸化学的进步使大规模合成 DNA 和 RNA 寡核苷酸以及非天然核酸的寡聚物成为可能，包括具有非核糖支架的人工核酸（异核酸；XNAs）。在这篇专题文章中，我们综述了具有非核糖支架的 XNAs 的化学结构、杂交能力以及它们与特定的无环 XNAs 的独特行为。首先，我们概述了具有非核糖环支架的 XNAs，然后重点关注它们与自身以及与 DNA 和 RNA 的杂交能力，讨论了无环 XNAs 出人意料的稳定同型双链体形成。接下来，我们介绍了我们的苏氨酸核酸（TNA）和丝氨酸核酸（SNA），并根据它们的手性展示了它们的螺旋偏好性，然后演示了对映体控制杂交和非手性 XNAs 的螺旋放大。最后，我们展示了非酶模板指导的 L-TNA 的合成，并描述了具有非核糖支架的 XNAs 的人工遗传系统的创建，作为未来的展望。
