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.

Creators(s): Su, Wu, Gray, Stephen J, Dondi, Ruggero and Burley, Glenn;
Item type:Article
ID code:31838
Keywords:solid phase synthesis , hairpin DNA-binding polyamides , polyamide sequences , Chemistry, Biochemistry, Organic Chemistry, Physical and Theoretical Chemistry
Subjects:Science > Chemistry
Department:Faculty of Science > Pure and Applied Chemistry
Depositing user: Pure Administrator
Date deposited:22 Jun 2011 08:55
Last modified:20 Jan 2021 19:26
URI:https://strathprints.strath.ac.uk/id/eprint/31838
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