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 (https://doi.org/10.1021/ol9015139)

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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.

  • Item type:Article
    ID code:31838
    Dates:
    Date
    Event
    3 September 2009
    Published
    11 August 2009
    Published Online
    Subjects:Science > Chemistry
    Department:Faculty of Science > Pure and Applied Chemistry
    Depositing user: Pure Administrator
    Date deposited:22 Jun 2011 08:55
    Last modified:11 Nov 2024 09:47
    URI:https://strathprints.strath.ac.uk/id/eprint/31838
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