Imitating Prebiotic Homochirality on Earth

Abstract

We show how the amino acids needed on prebiotic earth in their homochiral L form can be produced by a reaction of L-alpha-methyl amino acids-that have been identified in the Murchison meteorite-with alpha-keto acids under credible prebiotic conditions. When they are simply heated together they perform a process of decarboxylative transamination but with almost no chiral transfer, and that in the wrong direction, producing D-amino acids from the L-alpha-methyl amino acids. With copper ion a square planar complex with two of the reaction intermediates is formed, and now there is the desired L to L transformation, producing small enantioexcesses of the normal L-amino acids. We also show how these can be amplified, not by making more of the L form but by increasing its concentration in water solution. The process can start with a miniscule excess and in one step generate water solutions with L/D ratios in the over 90% region. Kinetic processes can exceed the results from equilibria. We have also examined such amplifications with ribonucleosides, and have shown that initial modest excesses of the D-nucleosides can be amplified to afford water solutions with D to L ratios in the high 90's. We have shown that the homochiral compound has two effects on the solubility of the racemate. On one hand it decreases the solubility of the racemate by its role in the solubility product, as a theoretical equation predicts. On the other hand, it increases the solubility of the racemate by changing the nature of the solvent, acting as a cosolvent with the water. This explains why the amplification, while large, is not as large as the simple theoretical equation predicts. Thus when credible examples are produced where small enantioexcesses of D-ribose are created under credible prebiotic conditions, the prerequisites for the RNA world will have been exemplified.

Emerging chirality in nanoscience

“…It should be closely related to the beginning of life. 3 Macroscopic bio-structures with consistent chirality can be commonly observed in various organisms, such as seashells, horns, and plant tendrils. It is not clear how the chirality in these cases is controlled by biochemical synthesis and genetic codes.…”

Infrared and reflectron time-of-flight mass spectroscopic study on the synthesis of glycolaldehyde in methanol (CH3OH) and methanol–carbon monoxide (CH3OH–CO) ices exposed to ionization radiation

“…In particular, glycolaldehyde can react via an aldol condensation to ultimately produce ribose. 22 Additionally the polymerization of formaldehyde (the formose reaction 23 ) has been suggested as plausible prebiotic route to glycolaldehyde and ribose (Shapiro, 2000). 24 However, as pointed out by Shapiro (2000), 24 no prebiotic route exists that preferentially leads to the synthesis of ribose specically over a conglomerate of other sugars, despite many efforts.…”

Chiral symmetry breaking in a microscopic model with asymmetric autocatalysis and inhibition

“…4 Thus, the investigation of possible physical mechanisms that can explain the origin of homochirality in a presumably racemic prebiotic environment constitutes an active area of current research. 3,[5][6][7] Both kinetic 8 and equilibrium processes may lead to spontaneous chiral amplification. One possible thermodynamic mechanism entails equilibrium phase behavior in a poor solvent, [9][10][11][12][13][14] and it involves the formation of both racemic and enantiopure crystals in equilibrium with a liquid phase enriched in one of the enantiomers.…”