Organic Letters 2011-10-21

Expanding the repertoire of natural product-inspired ring pairs for molecular recognition of DNA.

Katy A Muzikar, Jordan L Meier, Daniel A Gubler, Jevgenij A Raskatov, Peter B Dervan

Index: Org. Lett. 13(20) , 5612-5, (2011)

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Abstract

A furan amino acid, inspired by the recently discovered proximicin natural products, was incorporated into the scaffold of a DNA-binding hairpin polyamide. While unpaired oligomers of 2,4-disubstituted furan amino acids show poor DNA-binding activity, furan (Fn) carboxamides paired with N-methylpyrrole (Py) and N-methylimidazole (Im) rings demonstrate excellent stabilization of duplex DNA as well as discrimination of noncognate sequences, consistent with function as a Py mimic according to the Py/Im polyamide pairing rules.© 2011 American Chemical Society