title: Chirality- and sequence-selective successive self-sorting via specific homo- and complementary-duplex formations.
abstract: Self-recognition and self-discrimination within complex mixtures are of fundamental importance in biological systems, which entirely rely on the preprogrammed monomer sequences and homochirality of biological macromolecules. Here we report artificial chirality- and sequence-selective successive self-sorting of chiral dimeric strands bearing carboxylic acid or amidine groups joined by chiral amide linkers with different sequences through homo- and complementary-duplex formations. A mixture of carboxylic acid dimers linked by racemic-1,2-cyclohexane bis-amides with different amide sequences (NHCO or CONH) self-associate to form homoduplexes in a completely sequence-selective way, the structures of which are different from each other depending on the linker amide sequences. The further addition of an enantiopure amide-linked amidine dimer to a mixture of the racemic carboxylic acid dimers resulted in the formation of a single optically pure complementary duplex with a 100% diastereoselectivity and complete sequence specificity stabilized by the amidinium-carboxylate salt bridges, leading to the perfect chirality- and sequence-selective duplex formation.
authors.affiliation: Department of Molecular Design and Engineering, Graduate School of Engineering, Nagoya University, Chikusa-ku, Nagoya 464-8603, Japan.
authors.forename: Wataru
authors.initials: W
authors.lastname: Makiguchi
authors.affiliation: Department of Molecular Design and Engineering, Graduate School of Engineering, Nagoya University, Chikusa-ku, Nagoya 464-8603, Japan.
authors.forename: Junki
authors.initials: J
authors.lastname: Tanabe
authors.affiliation: Department of Molecular Design and Engineering, Graduate School of Engineering, Nagoya University, Chikusa-ku, Nagoya 464-8603, Japan.
authors.forename: Hidekazu
authors.initials: H
authors.lastname: Yamada
authors.affiliation: Department of Molecular Design and Engineering, Graduate School of Engineering, Nagoya University, Chikusa-ku, Nagoya 464-8603, Japan.
authors.forename: Hiroki
authors.initials: H
authors.lastname: Iida
authors.affiliation: Department of Molecular Design and Engineering, Graduate School of Engineering, Nagoya University, Chikusa-ku, Nagoya 464-8603, Japan.
authors.forename: Daisuke
authors.initials: D
authors.lastname: Taura
authors.affiliation: Department of Molecular Design and Engineering, Graduate School of Engineering, Nagoya University, Chikusa-ku, Nagoya 464-8603, Japan.
authors.forename: Naoki
authors.initials: N
authors.lastname: Ousaka
authors.affiliation: Department of Molecular Design and Engineering, Graduate School of Engineering, Nagoya University, Chikusa-ku, Nagoya 464-8603, Japan.
authors.forename: Eiji
authors.initials: E
authors.lastname: Yashima
mesh_terms: D000578:Amidines / Q000737:chemistry; D002264:Carboxylic Acids / Q000737:chemistry; D018360:Crystallography, X-Ray; D019281:Dimerization; D066244:Proton Magnetic Resonance Spectroscopy; D013237:Stereoisomerism
chemical_list: D000578:Amidines; D002264:Carboxylic Acids