Highly efficient synthesis of DNA-binding polyamides using a convergent fragment-based approach

Fallows, Andrew J. and Singh, Ishwar and Dondi, Ruggero and Cullis, Paul M. and Burley, Glenn A. (2014) Highly efficient synthesis of DNA-binding polyamides using a convergent fragment-based approach. Organic Letters, 16 (17). pp. 4654-4657. ISSN 1523-7060

[img]
Preview
Text (Fallows-etal-OL-2014-Highly-efficient-synthesis-of-DNA-binding-polyamides-using-a-convergent)
Fallows_etal_OL_2014_Highly_efficient_synthesis_of_DNA_binding_polyamides_using_a_convergent.pdf
Accepted Author Manuscript

Download (894kB)| Preview

    Abstract

    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.