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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.

SUBMITTER: Makiguchi W 

PROVIDER: S-EPMC4468858 | biostudies-literature | 2015 Jun

REPOSITORIES: biostudies-literature

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

Makiguchi Wataru W   Tanabe Junki J   Yamada Hidekazu H   Iida Hiroki H   Taura Daisuke D   Ousaka Naoki N   Yashima Eiji E  

Nature communications 20150608


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 car  ...[more]

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