☆ 4.8 Article

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

ORGANIC LETTERS (2016)

Journal

ORGANIC LETTERS

Volume 18, Issue 5, Pages 1096-1099

Publisher

AMER CHEMICAL SOC

DOI: 10.1021/acs.orglett.6b00169

Keywords

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Categories

Chemistry, Organic

Funding

University of Pennsylvania
National Science Foundation
National Institutes of Health [NIH RR-023/11, CHE-0840438]
Kwanjeong Educational Foundation

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Abstract

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)center dot(CTG) repeat junctions were investigated.

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