Spontaneous mirror symmetry breaking in the aldol reaction and its potential relevance in prebiotic chemistry.
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.
Mauksch
Michael
M
Department of Chemistry and Pharmacy, University of Erlangen-Nuremberg, Erlangen, Germany.
Wei
Shengwei
S
Freund
Matthias
M
Zamfir
Alexandru
A
Tsogoeva
Svetlana B
SB
D000096:Acetone / Q000737:chemistry; D000447:Aldehydes / Q000737:chemistry*; D002241:Carbohydrates / Q000737:chemistry; D002384:Catalysis; D019418:Evolution, Chemical; D005943:Gluconeogenesis; D015394:Molecular Structure; D000069497:Origin of Life; D013237:Stereoisomerism
D000447:Aldehydes; D002241:Carbohydrates; D000096:Acetone; C010963:formose sugars; C116609:3-hydroxybutanal