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Homochirality of ?-Peptides: A Significant Biomimetic Property of Unnatural Systems.

ABSTRACT: Homochirality, an interesting phenomenon of life, is mainly an unresolved problem and was thought to be a property of living matter. Herein, we show that artificial ?-peptides have the tendency toward homochiral diastereoselective chain elongation. Chain-length-dependent stereochemical discrimination was investigated in the synthesis of foldamers with various side chains and secondary structures. It was found that there is a strong tendency toward the synthesis of homochiral oligomers. The size of the side chain drastically influenced the selectivity of the stereodiscriminative chain-elongation reaction. It is noteworthy that water as the co-solvent increases the selectivity. Such behavior is a novel fundamental biomimetic property of foldamers with a potential of future industrial application.

SUBMITTER: Mandity IM

PROVIDER: S-EPMC5542748 | biostudies-literature | 2017 Aug

REPOSITORIES: biostudies-literature

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Homochirality of β-Peptides: A Significant Biomimetic Property of Unnatural Systems.

Mándity István M IM Nekkaa Imane I Paragi Gábor G Fülöp Ferenc F

ChemistryOpen 20170720 4

Homochirality, an interesting phenomenon of life, is mainly an unresolved problem and was thought to be a property of living matter. Herein, we show that artificial β-peptides have the tendency toward homochiral diastereoselective chain elongation. Chain-length-dependent stereochemical discrimination was investigated in the synthesis of foldamers with various side chains and secondary structures. It was found that there is a strong tendency toward the synthesis of homochiral oligomers. The size ...[more]

PMID: 28794942

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