title: A preorganized β-amino acid bearing a guanidinium side chain and its use in cell-penetrating peptides.
abstract: A cyclic β-amino acid (APC(Gu)) bearing a side-chain guanidinium group has been developed. The APC(Gu) residue was incorporated into an α/β-peptide based on the Tat(47-57) fragment, leading to an oligomer with substantial helicity in methanol that enters HeLa cells much more readily than does the corresponding Tat α-peptide.
authors.affiliation: Department of Chemistry, University of Wisconsin, 1101 University Avenue, Madison, WI 53707, USA. demizu@nihs.go.jp.
authors.forename: Yosuke
authors.initials: Y
authors.lastname: Demizu
authors.forename: Makoto
authors.initials: M
authors.lastname: Oba
authors.forename: Koyo
authors.initials: K
authors.lastname: Okitsu
authors.forename: Hiroko
authors.initials: H
authors.lastname: Yamashita
authors.forename: Takashi
authors.initials: T
authors.lastname: Misawa
authors.forename: Masakazu
authors.initials: M
authors.lastname: Tanaka
authors.forename: Masaaki
authors.initials: M
authors.lastname: Kurihara
authors.forename: Samuel H
authors.initials: SH
authors.lastname: Gellman
mesh_terms: D000595:Amino Acid Sequence; D000596:Amino Acids / Q000737:chemistry*; D057846:Cell-Penetrating Peptides / Q000737:chemistry* / Q000378:metabolism*; D015696:Gene Products, tat / Q000737:chemistry* / Q000378:metabolism*; D019791:Guanidine / Q000737:chemistry*; D006367:HeLa Cells; D006801:Humans; D008969:Molecular Sequence Data; D017433:Protein Structure, Secondary; D017386:Sequence Homology, Amino Acid
chemical_list: D000596:Amino Acids; D057846:Cell-Penetrating Peptides; D015696:Gene Products, tat; D019791:Guanidine