Synthesis of 9-Substituted Triptycene Building Blocks for Solid-Phase Diversification and Nucleic Acid Junction Targeting

• DOI: 10.1021/acs.orglett.6b00169
• Publication Date: 2016-02-17T17:52:26Z
• Authors: Ina Yoon; Sung-Eun Suh; Stephanie A. Barros; David M. Chenoweth
• Keywords: Anthracenes; Molecular Structure; Oligodeoxyribonucleotides; Nucleic Acids; 01 natural sciences; Solid-Phase Synthesis Techniques; 0104 chemical sciences

Triptycenes have been shown to bind nucleic acid three-way junctions, but rapid and efficient methods to diversify the triptycene core are lacking. An efficient synthesis of a 9-substituted triptycene scaffold is reported that can be used as a building block for solid-phase peptide synthesis and rapid diversification. The triptycene building block was diversified to produce a new class of tripeptide-triptycenes, and their binding abilities toward d(CAG)·(CTG) repeat junctions were investigated.