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

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

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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 beta-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.

Keywords:DNA-binding polyamides, Hairpin pyrrole-imidazole polyamides, Convergent synthetic strategy, C-terminal fragment, N-terminal fragment, Coupling reagents, NotOAChecked
Subjects:F Physical Sciences > F160 Organic Chemistry
F Physical Sciences > F100 Chemistry
Divisions:College of Science > School of Pharmacy
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ID Code:16297
Deposited On:17 Dec 2014 16:10

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