Department of Chemistry, Life Sciences and Environmental Sustainability, University of Parma, Parco Area delle Scienze 17/A, Parma, 43123, Italy.
Biosensor Technologies, AIT-Austrian Institute of Technology GmbH, Konrad-Lorenz-Straße 24, 3430, Tulln an der Donau, Austria.
Org Lett. 2021 Feb 5;23(3):902-907. doi: 10.1021/acs.orglett.0c04116. Epub 2021 Jan 8.
A novel synthesis of C(2)-modified peptide nucleic acids (PNAs) is proposed, using a submonomeric strategy with minimally protected building blocks, which allowed a reduction in the required synthetic steps. N(3)-unprotected, d-Lys- and d-Arg-based backbones were used to obtain positively charged PNAs with high optical purity, as inferred from chiral GC measurements. "Chiral-box" PNAs targeting the G12D point mutation of the gene were produced using this method, showing improved sequence selectivity for the mutated- vs wild-type DNA strand with respect to unmodified PNAs.
提出了一种新型的 C(2)-修饰肽核酸（PNA）的合成方法，使用亚单体制备策略和最小保护的构建块，从而减少了所需的合成步骤。使用 N(3)-非保护的、d-Lys-和 d-Arg-为基础的骨架，获得了具有高光学纯度的正电荷 PNA，这可以从手性 GC 测量中推断出来。使用这种方法制备了针对基因 G12D 点突变的“手性盒”PNA，与未修饰的 PNA 相比，对突变型与野生型 DNA 链具有更好的序列选择性。
