β-Sheet-induced chirogenesis in polymerization of oligopeptides

Nathaniel Wagner, Boris Rubinov, Gonen Ashkenasy

Research output: Contribution to journalArticlepeer-review

Abstract

The origin of long homochiral biopolymers in living systems has recently been the focus of intense research. In one particular research line, scientists studied, experimentally and theoretically, chiral amplification obtained during peptide formation by polymerization of amino acid building blocks. It was suggested that processes leading to temporal or spatial separation, and thus, to the growth of homochiral polymers at the expense of their heterochiral counterparts, can explain the chirality observed in larger molecules. We introduce a simple model and stochastic simulation for the polymerization of amino acids and β-sheet formation, showing the crucial effects of the β sheets on the distributions of peptide lengths. When chiral affinities are included, racemic β sheets of alternating homochiral strands lead to the formation of chiral peptides, the isotacticity of which increases with length, consistent with previous experimental results in aqueous solutions. The tendency to form isotactic peptides is shown for both initially racemic and initially nonracemic systems, as well as for closed and open systems. We suggest that these or similar mechanisms may explain the origin of chiroselectivity in prebiotic environments. Order emerges: A new model for amino acid polymerization, induced by β-sheet formation, is presented (see picture). Stochastic simulation shows the crucial effects of β sheets on the peptide length distribution and on the tendency to form long isotactic peptides. The authors suggest that this or similar mechanisms may explain the origin of chiroselectivity in prebiotic environments.

Original languageAmerican English
Pages (from-to)2771-2780
Number of pages10
JournalChemPhysChem
Volume12
Issue number15
DOIs
StatePublished - 24 Oct 2011

Keywords

  • chirality
  • origins of life
  • peptides
  • polymers
  • systems chemistry

All Science Journal Classification (ASJC) codes

  • Atomic and Molecular Physics, and Optics
  • Physical and Theoretical Chemistry

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