title: Synthesis of pyrrole-imidazole polyamide oligomers based on a copper-catalyzed cross-coupling strategy.
abstract: Pyrrole-imidazole (Py-Im) polyamides are useful tools for chemical biology and medicinal chemistry studies due to their unique binding properties to the minor groove of DNA. We developed a novel method of synthesizing Py-Im polyamide oligomers based on a Cu-catalyzed cross-coupling strategy. All four patterns of dimer fragments could be synthesized using a Cu-catalyzed Ullmann-type cross-coupling with easily prepared monomer units. Moreover, we demonstrated that pyrrole dimer, trimer, and tetramer building blocks for Py-Im polyamide synthesis were accessible by combining site selective iodination of the pyrrole/pyrrole coupling adduct.
authors.affiliation: Graduate School of Pharmaceutical Sciences, Chiba University, 1-8-1, Inohana, Chuo-ku, Chiba 260-8675, Japan.
authors.forename: Naoki
authors.initials: N
authors.lastname: Shiga
authors.affiliation: Graduate School of Pharmaceutical Sciences, Chiba University, 1-8-1, Inohana, Chuo-ku, Chiba 260-8675, Japan.
authors.forename: Shihori
authors.initials: S
authors.lastname: Takayanagi
authors.affiliation: Graduate School of Pharmaceutical Sciences, Chiba University, 1-8-1, Inohana, Chuo-ku, Chiba 260-8675, Japan.
authors.forename: Risa
authors.initials: R
authors.lastname: Muramoto
authors.affiliation: Graduate School of Pharmaceutical Sciences, Chiba University, 1-8-1, Inohana, Chuo-ku, Chiba 260-8675, Japan.
authors.forename: Tasuku
authors.initials: T
authors.lastname: Murakami
authors.affiliation: Graduate School of Pharmaceutical Sciences, Chiba University, 1-8-1, Inohana, Chuo-ku, Chiba 260-8675, Japan.
authors.forename: Rui
authors.initials: R
authors.lastname: Qin
authors.affiliation: Graduate School of Pharmaceutical Sciences, Chiba University, 1-8-1, Inohana, Chuo-ku, Chiba 260-8675, Japan.
authors.forename: Yuta
authors.initials: Y
authors.lastname: Suzuki
authors.affiliation: Graduate School of Medicine, Chiba University, 1-8-1, Inohana, Chuo-ku, Chiba 260-8670, Japan.
authors.forename: Ken-Ichi
authors.initials: KI
authors.lastname: Shinohara
authors.affiliation: Graduate School of Medicine, Chiba University, 1-8-1, Inohana, Chuo-ku, Chiba 260-8670, Japan.
authors.forename: Atsushi
authors.initials: A
authors.lastname: Kaneda
authors.affiliation: Graduate School of Pharmaceutical Sciences, Chiba University, 1-8-1, Inohana, Chuo-ku, Chiba 260-8675, Japan; Molecular Chirality Research Center, Chiba University, 1-33, Yayoi-cho, Inage-ku, Chiba 263-8522, Japan. Electronic address: tnemoto@faculty.chiba-u.jp.
authors.forename: Tetsuhiro
authors.initials: T
authors.lastname: Nemoto
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry; D001665:Binding Sites; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D004247:DNA / Q000737:chemistry / Q000378:metabolism; D007093:Imidazoles / Q000737:chemistry*; D009757:Nylons / Q000737:chemistry*; D011758:Pyrroles / Q000737:chemistry*
chemical_list: D000970:Antineoplastic Agents; D007093:Imidazoles; D009757:Nylons; D011758:Pyrroles; D003300:Copper; D004247:DNA
keywords: Copper; Cross-coupling; Polyamides; Synthetic methods