Stereoselective Syntheses of Pentose Sugars Under Realistic Prebiotic Conditions

@article{Pizzarello2010StereoselectiveSO,
  title={Stereoselective Syntheses of Pentose Sugars Under Realistic Prebiotic Conditions},
  author={Sandra Pizzarello and Arthur L. Weber},
  journal={Origins of Life and Evolution of Biospheres},
  year={2010},
  volume={40},
  pages={3-10}
}
  • S. PizzarelloA. Weber
  • Published 1 February 2010
  • Biology, Chemistry
  • Origins of Life and Evolution of Biospheres
Glycolaldehyde and dl-glyceraldehyde reacted in a water-buffered solution under mildly acidic conditions and in the presence of chiral dipeptide catalysts produced pentose sugars whose configuration is affected by the chirality of the catalyst. The chiral effect was found to vary between catalysts and to be largest for di-valine. Lyxose, arabinose, ribose and xylose are formed in different amounts, whose relative proportions do not change significantly with the varying of conditions. With LL… 
View on Springer
ncbi.nlm.nih.gov
49 Citations
Highly Influential Citations
2
Background Citations
9
Methods Citations
1

49 Citations

On the prebiotic synthesis of D-sugars catalyzed by L-peptides: assessments from first-principles calculations.

It is confirmed that a prebiotic sugar soup could be fine-tuned in the presence of shorter peptides as catalysts and that D-ribose would have also resulted in an advantageous imbalance for further amplification and chemical evolution.

L-amino acids catalyze the formation of an excess of D-glyceraldehyde, and thus of other D sugars, under credible prebiotic conditions

D-glyceraldehyde, the simplest sugar with a D center, is the basic unit on which other sugars are built and the geometry of sugars referred to D, as in D-ribose or D-glucose, is not an independent mystery.

Prebiotic synthesis of 2-deoxy-d-ribose from interstellar building blocks promoted by amino esters or amino nitriles.

It is demonstrated that three interstellar starting materials, when mixed together with an appropriate promoter, can directly lead to the formation of a mixture of higher carbohydrates, including 2-deoxy-d-ribose.

Hydrothermal formose reaction

The self-condensation of formaldehyde is a one pot reaction resulting in a complex mixture of carbohydrates. Based on a simple chemical, the reaction was previously considered as a prebiotic source…

Formation of L Amino Acids and D Sugars, and Amplification of their Enantioexcesses in Aqueous Solutions, Under Simulated Prebiotic Conditions

It is extended to show how D sugars, such as d-ribose, can have been formed and ampli- fied in solution and the high concentration amplifi- cations of d-nucleosides that can be obtained under credible prebiotic conditions.

Exploratory Experiments on the Chemistry of the “Glyoxylate Scenario”: Formation of Ketosugars from Dihydroxyfumarate

The results suggest that the reaction of DHF with aldehydes could constitute a reasonable pathway for the formation of carbohydrates and allow for alternative potential prebiotic scenarios to the formose reaction to be considered.

Imitating Prebiotic Homochirality on Earth

It is shown that the homochiral compound has two effects on the solubility of the racemate, which explains why the amplification, while large, is not as large as the simple theoretical equation predicts.

Light on Chirality: Absolute Asymmetric Formation of Chiral Molecules Relevant in Prebiotic Evolution.

An overview of the role of chiral molecules in prebiotic evolution with special emphasis on their chiroptical properties and absolute asymmetric photosynthesis is provided.

Nonenzymatic gluconeogenesis-like formation of fructose 1,6-bisphosphate in ice

Evidence that gluconeogenesis, the anabolic counterpart to glycolysis, could have emerged nonenzymatically is provided and the amino acid acceleration of a key cellular anabolic reaction may indicate a link between prebiotic chemistry and the nature of the first metabolic enzymes.

Glycine oligomerization up to triglycine by shock experiments simulating comet impacts

Results indicate that the cryogenic condition at impact shock is a key for the formation of linear peptide, which is more useful than cyclic peptides for further elongation of peptide chain.

References

SHOWING 1-10 OF 10 REFERENCES

The peptide-catalyzed stereospecific synthesis of tetroses: A possible model for prebiotic molecular evolution

It is demonstrated that homochiral l-dipeptide catalysts lead to the stereospecific syntheses of tetroses, and a possible catalytic-reaction intermediate is proposed, consisting of an imidazolidinone ring formed between the two nitrogen atoms of the peptide catalyst and the C1 of one glycolaldehyde molecule.

Transformations of bioactive peptides in the presence of sugars--characterization and stability studies of the adducts generated via the Maillard reaction.

Enantiomeric Excesses in Meteoritic Amino Acids

Gas chromatographic-mass spectral analyses of the four stereoisomers of 2-amino-2,3-dimethylpentanoic acid obtained from the Murchison meteorite show that the L enantiomer occurs in excess, indicative of an asymmetric influence on organic chemical evolution before the origin of life.

Catalysts based on amino acids for asymmetric reactions in water.

An overview of very recent advances in the area of asymmetric catalysis in water with amino acids and their derivatives as effective catalysts or essential components of catalysts is provided.

The Chemistry That Preceded Life's Origin: A Study Guide from Meteorites

Signs that molecular asymmetry in meteorites may not be limited to these compounds, encourage the suggestion of possible involvement of meteoritic material in the induction of selective traits in molecular evolution.

Prebiotic Amino Acids as Asymmetric Catalysts

The exogenous delivery of cometary and asteroidal material is observed today and undoubtedly has showered the Earth through its prior history ([ 1 ][1]). Because carbonaceous meteorites contain amino…

Meteorites and the early solar system II

They range in size from microscopic particles to masses of many tons. The geologic diversity of asteroids and other rocky bodies of the solar system are displayed in the enormous variety of textures…

The Nature and Distribution of the Organic Material in Carbonaceous Chondrites and Interplanetary Dust Particles

1182. Lunar and Planetary Institute, Houston (CD-

Stereoselective alkylation of glycine units in dipeptide derivatives: "Chirality transfer" via a pivalaldehyde N,N-acetal center

Comets and the Formation of Biochemical Compounds on the Primitive Earth