Homochirality of β-peptides: A significant biomimetic property of unnatural systems

István M. Mándity, Imane Nekkaa, Gábor Paragi, Ferenc Fülöp

Research output: Contribution to journalArticle

4 Citations (Scopus)

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 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 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.

Original languageEnglish
Pages (from-to)492-496
Number of pages5
JournalChemistryOpen
Volume6
Issue number4
DOIs
Publication statusPublished - Jan 1 2017

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Keywords

  • Chirality
  • Diastereoselectivity
  • Foldamer
  • Homochiralty
  • β-peptide

ASJC Scopus subject areas

  • Chemistry(all)

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