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Spontaneous Mirror Symmetry Breaking in the Aldol Reaction and its Potential Relevance in Prebiotic Chemistry

  • Michael Mauksch
  • Shengwei Wei
  • Matthias Freund
  • Alexandru Zamfir
  • Svetlana B. Tsogoeva
Chirality

Abstract

The origin of the single chirality of most biomolecules is still a great puzzle. Carbohydrates could form in the formose reaction, which is proposed to be autocatalytic and contains aldol reaction steps. Based on our earlier observation of organoautocatalysis and spontaneous enantioenrichment in absence of deliberate chiral influences in the aldol reaction of acetone and p-nitrobenzaldehyde we suggest that a similar effect might be present also in the aldol reactions involved in gluconeogenesis. Herein we show that reactant precipitation observed in our earlier reported experiments does not affect the asymmetric autocatalysis in the aldol reaction we studied. We explain the phenomenon of spontaneous mirror symmetry breaking in such organocatalytic homogenous systems qualitatively by non-linear reaction network kinetics and classical transition state theory.

Keywords

Aldol reaction Formose reaction Absolute asymmetric synthesis Spontaneous mirror symmetry breaking Homochirality 

Notes

Acknowledgements

Generous support from the Deutsche Forschungsgemeinschaft (DFG) is gratefully acknowledged.

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Copyright information

© Springer Science+Business Media B.V. 2009

Authors and Affiliations

  • Michael Mauksch
    • 1
  • Shengwei Wei
    • 1
  • Matthias Freund
    • 1
  • Alexandru Zamfir
    • 1
  • Svetlana B. Tsogoeva
    • 1
  1. 1.Department of Chemistry and PharmacyUniversity of Erlangen-NurembergErlangenGermany

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