title: Expanding the repertoire of natural product-inspired ring pairs for molecular recognition of DNA.
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.
authors.affiliation: Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, USA.
authors.forename: Katy A
authors.initials: KA
authors.lastname: Muzikar
authors.forename: Jordan L
authors.initials: JL
authors.lastname: Meier
authors.forename: Daniel A
authors.initials: DA
authors.lastname: Gubler
authors.forename: Jevgenij A
authors.initials: JA
authors.lastname: Raskatov
authors.forename: Peter B
authors.initials: PB
authors.lastname: Dervan
mesh_terms: D001483:Base Sequence; D001688:Biological Products / Q000737:chemistry; D004247:DNA / Q000737:chemistry* / Q000378:metabolism; D005663:Furans / Q000737:chemistry; D015394:Molecular Structure; D009429:Netropsin / Q000031:analogs & derivatives* / Q000737:chemistry; D009757:Nylons / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D001688:Biological Products; D005663:Furans; D009757:Nylons; C529559:proximicin A; D009429:Netropsin; D004247:DNA