Spontaneous Mirror Symmetry Breaking in the Aldol Reaction and its Potential Relevance in Prebiotic Chemistry
- 390 Downloads
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.
KeywordsAldol reaction Formose reaction Absolute asymmetric synthesis Spontaneous mirror symmetry breaking Homochirality
Generous support from the Deutsche Forschungsgemeinschaft (DFG) is gratefully acknowledged.
- Butlerov AM (1861) Einiges über die chemische Struktur der Körper. Zeitschr Chem 4:549–560Google Scholar
- Calvin M (1969) Chemical evolution. Oxford University Press, LondonGoogle Scholar
- Jackisch MA, Fronczek FR, Butler LG (1989) Structure of 4-nitrobenzaldehyde. Acta Cryst C45:2016–2018Google Scholar
- Pasteur LCR (1848) Recherches sur la Dimorphisme. Ann Chem Phys 23:267–294Google Scholar