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Sugar in the Primordial Soup
Sugar in the Primordial Soup
Sugar in the Primordial Soup
Sugar in the Primordial Soup
Sugar in the Primordial Soup
Sugar in the Primordial Soup
Sugar in the Primordial Soup
Sugar in the Primordial Soup
Sugar in the Primordial Soup
Sugar in the Primordial Soup
Sugar in the Primordial Soup
Sugar in the Primordial Soup
Sugar in the Primordial Soup
Sugar in the Primordial Soup
Sugar in the Primordial Soup
Sugar in the Primordial Soup
Sugar in the Primordial Soup
Sugar in the Primordial Soup
Sugar in the Primordial Soup
Sugar in the Primordial Soup
Sugar in the Primordial Soup
Sugar in the Primordial Soup
Sugar in the Primordial Soup
Sugar in the Primordial Soup
Sugar in the Primordial Soup
Sugar in the Primordial Soup
Sugar in the Primordial Soup
Sugar in the Primordial Soup
Sugar in the Primordial Soup
Sugar in the Primordial Soup
Sugar in the Primordial Soup
Sugar in the Primordial Soup
Sugar in the Primordial Soup
Sugar in the Primordial Soup
Sugar in the Primordial Soup
Sugar in the Primordial Soup
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Sugar in the Primordial Soup

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The first carbohydrates...

The first carbohydrates...

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  • Title – introduction
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    • 1. Sugar in the primordial soup The formose reaction and the origin of life
    • 2. Content <ul><li>Life from the Soup </li></ul><ul><li>Proteins versus RNA </li></ul><ul><li>Prebiotic syntheses of amino acids & nucleobases </li></ul><ul><li>Prebiotic synthesis of sugars </li></ul><ul><li>Sugar in space </li></ul><ul><li>Conclusion </li></ul>
    • 3. Life on Earth  4.6  10 9 yrs ago – Formation of Earth  3.5  10 9 yrs ago – Prokaryotic organisms Now   1.2  10 9 yrs ago – Eukaryotic organisms  0.7  10 9 yrs ago – Multicellular organisms Prebiotic
    • 4. What started life? What compounds were present in the beginning? What compounds/reactions are required now?
    • 5. The primordial ”soup” CO 2 N 2 CO SO 2 CH 2 O CH 4 Note: no photosynthesis - no O 2 ! NH 3 HCN CH 3 CN CH 2 CHCN HCCCN NCCN H 2 O
    • 6. Natural products Aminoacids Steroids Terpenes Lipids Purines Polyketides Carbohydrates Alkaloids Pyrimidines
    • 7. Some are more important! Aminoacids Steroids Terpenes Lipids Purines Polyketides Carbohydrates Alkaloids Pyrimidines
    • 8. The essentials of (modern) life Proteins composed of amino acids catalyse reactions RNA composed of nucleobases, ribose and phosphate carry genetic information
    • 9. Which was first, RNA or proteins? Proteins – superior catalysts, simple building blocks, stable RNA – can be catalysts, complex building blocks, unstable but can replicate themselves
    • 10. Protein aminoacid
    • 11. Prebiotic amino acid syntheses S.L. Miller Science 117 (1952) 528-529 J. Am. Chem. Soc. 77 (1955) 2351-2361 glycine 2,1% alanine 1,7%
    • 12. RNA ribose nucleobase phosphodiester
    • 13. Prebiotic nucleobase syntheses J. Oró, Nature 191 (1961) 1193-1194
    • 14. Common monosaccharides aldopentoses aldohexoses ketohexose glucose mannose ribose arabinose fructose
    • 15. Prebiotic carbohydrate synthesis: The Formose reaction A. Butlerow, Liebigs Ann. Chem. 53 (1861) 295-298 O. Leow, J. prakt. Chem. 33 (1886) 321-351
    • 16. Some of the reactions involved Cannizzaro de Bruyn-van Ekenstein Aldol condensation Retro-aldol
    • 17. Cannizzaro reaction Cannizzaro, Ann. 88 (1853) 129-
    • 18. de Bruyn-van Ekenstein rearrangement de Bruyn, Rec. Trav. Chim. 14 (1895) 150- Evans, Chem. Rev. 31 (1942) 537-559
    • 19. de Bruyn-van Ekenstein mechanism Glucose Mannose Fructose 1,2-Enediol
    • 20. The first step... formate methanol glycolaldehyde
    • 21. Aldol condensation glyceraldehyde
    • 22. de Bruyn-van Ekenstein glyceraldehyde dihydroxyacetone
    • 23. C 3 +C 1  C 2 +C 2
    • 24. Autocatalytic cycle C 2 C 2 C 3 C 4 C 1 C 1 C 1 C 1 very slow fast
    • 25. The result:
    • 26. Sugars in formose (55% total yield of sugars) Aldopentoses 7% (1.4% ribose) Aldohexoses 18% Ketopentoses 8% Ketohexoses 18%
    • 27. Open chain forms 0.3-0.7% 0.002-0.1% hexoses 8-22% 0.1-0.2% pentoses 100% 11-16% tetroses ketoses aldoses
    • 28. Tautomers of D-ribose Cyclic forms (99,9%) Acyclic forms (0,1%)  -furanose  -furanose  -pyranose  -pyranose hydrate aldehyde
    • 29. Problems Much more hexoses than pentoses Very little ribose Racemic mixture of sugars
    • 30. D-glyceraldehyde dihydroxyacetone D-sorbose 26% D-fructose 34% H.O.L. Fischer & E. Baer, Helv. Chim. Acta 19 (1936) 519-532
    • 31. Glycolaldehyde phosphate 1 Müller et al., Helv. Chim. Acta 73 (1990) 1410
    • 32. Glycolaldehyde phosphate 2
    • 33. Extraterrestial compounds Aminoacids Carbohydrates Pyrimidines Purines 60 ppm 60 0.06 1.2
    • 34. Aminoacids +12 not found in proteins Gly Ala Glu Val Pro Asp Leu
    • 35. Carbohydrates + aldonic acids & alditols Mannose Xylose Glucose Arabinose Dihydroxyacetone
    • 36. Conclusion The basic building blocks of proteins and RNA can be prepared from compounds expected to be present on early Earth. The conditions to make them are incompatible, i.e. they can not be formed under the same reaction conditions and in the same place. The strongest proof that they could have been formed prebiotically is their presence in extraterrestrial matter.

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