title: Cysteine cyclic pyrrole-imidazole polyamide for sequence-specific recognition in the DNA minor groove.
abstract: Pyrrole-imidazole (PI) polyamides are small DNA-binding molecules that can recognize predetermined DNA sequences with high affinity and specificity. Hairpin PI polyamides have been studied intensively; however, cyclic PI polyamides have received less attention, mainly because of difficulties with their synthesis. Here, we describe a novel cyclization method for producing PI polyamides using cysteine and a chloroacetyl residue. The cyclization reaction is complete within 1 h and has a high conversion efficiency. The method can be used to produce long cyclic PI polyamides that can recognize 7 bp DNA sequences. A cyclic PI polyamide containing two β-alanine molecules had higher affinity and specificity than the corresponding hairpin PI polyamide, demonstrating that the cyclic PI polyamides can be used as a new type of DNA-binding molecule.
authors: Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606-8502, Japan.
authors: Hironobu
authors: H
authors: Morinaga
authors: Toshikazu
authors: T
authors: Bando
authors: Toshiki
authors: T
authors: Takagaki
authors: Makoto
authors: M
authors: Yamamoto
authors: Kaori
authors: K
authors: Hashiya
authors: Hiroshi
authors: H
authors: Sugiyama
mesh_terms: D000085:Acetates / Q000737:chemistry; D001483:Base Sequence; D003500:Cyclization; D003545:Cysteine / Q000737:chemistry*; D004247:DNA / Q000737:chemistry*; D007093:Imidazoles / Q000737:chemistry*; D008958:Models, Molecular; D008969:Molecular Sequence Data; D015394:Molecular Structure; D009757:Nylons / Q000737:chemistry*; D011758:Pyrroles / Q000737:chemistry*
chemical_list: D000085:Acetates; D007093:Imidazoles; D009757:Nylons; D011758:Pyrroles; D004247:DNA; C045557:chloroacetyl chloride; D003545:Cysteine