Two advances in the synthesis of hairpin pyrrole-imidazole polyamides (PAs) are described. First, the application of a convergent synthetic strategy is shown, involving the Boc-based solid phase synthesis of a C-terminal fragment and the solution phase synthesis of the N-terminal fragment. Second a new hybrid resin is developed that allows for the preparation of hairpin PAs lacking a C-terminal β-alanine tail. Both methods are compatible with a range of coupling reagents and provide a facile, modular route to prepare PA libraries in high yield and crude purity.
- hairpin pyrrole-imidazole polyamides
- convergent synthetic strategy
- DNA binding polymides
Fallows, A. J., Singh, I., Dondi, R., Cullis, P. M., & Burley, G. A. (2014). Highly efficient synthesis of DNA-binding polyamides using a convergent fragment-based approach. Organic Letters, 16(17), 4654-4657. https://doi.org/10.1021/ol502203y