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Org Lett. 2011 Oct 21;13(20):5612-5. doi: 10.1021/ol202285y. Epub 2011 Sep 29.

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

Author information

1
Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, USA.

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.

PMID:
21957930
PMCID:
PMC3195311
DOI:
10.1021/ol202285y
[Indexed for MEDLINE]
Free PMC Article

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