Rajeev Kallanthottathil G, Maier Martin A, Lesnik Elena A, Manoharan Muthiah
Department of Medicinal Chemistry, Isis Pharmaceuticals, Inc., Carlsbad, California 92008, USA.
Org Lett. 2002 Dec 12;4(25):4395-8. doi: 10.1021/ol027026a.
[structure: see text] Peptide nucleic acid (PNA) monomers containing the tricyclic cytosine analogues phenoxazine, 9-(2-aminoethoxy)phenoxazine (G-clamp), and 9-(3-aminopropoxy)phenoxazine (propyl-G-clamp) have been synthesized. The modified nucleobases were incorporated into PNA oligomers using Boc-chemistry for solid-phase synthesis. PNAs containing single G-clamp modifications exhibit significantly enhanced affinity toward RNA and DNA targets relative to unmodified PNA while maintaining mismatch discrimination. These PNA G-clamp modifications exhibit the highest increase in affinity toward nucleic acid targets reported so far for PNA modifications.
[结构：见正文] 已合成了含有三环胞嘧啶类似物吩恶嗪、9-(2-氨基乙氧基)吩恶嗪（G夹）和9-(3-氨基丙氧基)吩恶嗪（丙基-G夹）的肽核酸（PNA）单体。使用Boc化学法进行固相合成，将修饰的核碱基掺入PNA寡聚物中。相对于未修饰的PNA，含有单个G夹修饰的PNA对RNA和DNA靶标的亲和力显著增强，同时保持错配识别能力。这些PNA G夹修饰对核酸靶标的亲和力增加是迄今为止报道的PNA修饰中最高的。
