Highly efficient synthesis of DNA-binding hairpin polyamides via the use of a new triphosgene coupling strategy

Su, Wu and Gray, Stephen J and Dondi, Ruggero and Burley, Glenn (2009) Highly efficient synthesis of DNA-binding hairpin polyamides via the use of a new triphosgene coupling strategy. Organic Letters, 11 (17). pp. 3910-3913. ISSN 1523-7060

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Abstract

A facile and highly efficient solid phase synthesis method is reported for the preparation of hairpin DNA-binding polyamides using the cost-effective triphosgene (BTC) activating agent. Difficult polyamide sequences were prepared from N-methylimidazole (Im) and N-methylpyrrole (Py) building blocks with high stepwise yields (>98%) using Boc chemistry. The versatility of the triphosgene coupling approach was also demonstrated for the first time on aryl hydrazine resins to afford biomedically relevant tail-truncated polyamides in excellent isolated yields.