Chirality- and sequence-selective successive self-sorting via specific homo- and complementary-duplex formations

Wataru Makiguchi, Junki Tanabe, Hidekazu Yamada, Hiroki Iida, Daisuke Taura, Naoki Ousaka and Eiji Yashima ()
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Wataru Makiguchi: Graduate School of Engineering, Nagoya University
Junki Tanabe: Graduate School of Engineering, Nagoya University
Hidekazu Yamada: Graduate School of Engineering, Nagoya University
Hiroki Iida: Graduate School of Engineering, Nagoya University
Daisuke Taura: Graduate School of Engineering, Nagoya University
Naoki Ousaka: Graduate School of Engineering, Nagoya University
Eiji Yashima: Graduate School of Engineering, Nagoya University

Nature Communications, 2015, vol. 6, issue 1, 1-12

Abstract: 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.

Date: 2015
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DOI: 10.1038/ncomms8236

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