Summary
The autocondensation of the glyceroyl thioesterS-glyceroyl-ethanethiol yielded oligoglyceric acid. The rates of autocondensation and hydrolysis of the thioester increased from pH 6.5 to pH 7.5 in 2,6-lutidine and imidazole buffers. Autocondensation and hydrolysis were much more rapid in imidazole buffers than in 2,6-lutidine buffers of the same pH. The efficiency of ester bond synthesis was about 20% for 40 mMS-glyceroylethanethiol in 2,6-lutidine and imidazole buffers near neutral pH. The size and yield of the oligoglyceric acid products increased when the concentration of the thioester was increased. The relationship of these results to prebiotic polymer synthesis is discussed.
Article PDF
Similar content being viewed by others
Explore related subjects
Discover the latest articles, news and stories from top researchers in related subjects.Avoid common mistakes on your manuscript.
Abbreviations
- Glc:
-
glyceric acid
- (Glc)n :
-
glyceric acid oligomers, where n=chain length
- Glc-SEt:
-
S-glyceroyl-ethanethiol
- (Glc)2-SEt:
-
S-glyceroylglyceroyl-ethanethiol
- (Glc)3-SEt:
-
S-glyceroylglyceroylglyceroyl-ethanethiol
- Glc-hydrox:
-
glyceric acid hydroxamate
- Glc-Im:
-
N-glyceroyl-imidazole
- Im:
-
imidazole
- DMF:
-
N, N-dimethylformamide
References
Bar-Nun A, Hartman H (1978) Synthesis of organic compounds from carbon monoxide and water by UV photolysis. Origins Life 9:93–101
Braud C, Bunel C, Vert M (1985) Poly(β-malic acid): a new polymeric drug-carrier, evidence for degradation in vitro. Polym Bull 13:293–299
Canuto VM, Levine JS, Augustsson TR, Imhoff CL, Giampapa MS (1983) The young sun and the atmosphere and photochemistry of the early. Earth. Nature (Lond) 305:281–286
Euranto EK (1969) Esterification and ester hydrolysis. In: Patai S (ed) The chemistry of carboxylic acids and esters. Interscience-Publishers, London, p 505
Gabel NW, Ponnamperuma C (1967) Model for origin of monosaccharides. Nature (Lond) 216:453–455
Garrison WM, Morrison DC, Hamilton JG, Benson AA Calvin M (1951) Reduction of carbon dioxide in aqueous solutions by ionizing radiation. Science 114:416–418
Getoff N, Scholes G, Weiss J (1960) Reduction of carbon dioxide in aqueous solutions under the influence of radiation. Tetrahedron Lett 17–23
Hestrin S (1949) The reaction of acetylcholine and other carboxylic acid derivatives with hydroxylamine and its analytical application. J Biol Chem 180:249–261
Hubbard JS, Hardy JP, Horowitz NH (1971) Photocatalytic production of organic compounds from CO and H2O in a simulated Martian atmosphere. Proc Natl Acad Sci USA 68:574–578
Jencks WP (1976) Free energies of hydrolysis and decarboxylation. In: Fasman GD (ed) Handbook of biochemistry and molecular biology, vol I, ed 3. CRC Press, Cleveland, p 296
Jencks WP, Cordes S, Carriuolo J (1960) The free energy of thiol ester hydrolysis. J Biol Chem 235:3608–3614
Kasting JF, Pollack JB (1984) Effects of high CO2 levels on surface temperature and atmospheric oxidation state of the early Earth. J Atmos Chem 1:403–428
Lok CM, Ward JP, Dorp DA (1976) The synthesis of chiral glycerides starting fromD- andl-serine. Chem Phys Lipids 16:115–122
Lynen F (1951) Quantitative Bestimmung von Acyl-mercaptanen mittels der Nitroprussid-Reaktion. Justus Liebigs Ann Chem 574:33–37
Miller SL (1957) The formation of organic compounds on the primitive Earth. Ann NY Acad Sci 69:260–275
Miller SL, Schlesinger G (1984) Carbon and energy yields in prebiotic syntheses using atmospheres containing CH4, CO and CO2. Origins Life 14:83–90
Mizuno T, Weiss AH (1974) Synthesis and utilization of formose sugars. In: Tipson RS, Horton D (eds) Advances in carbohydrate chemistry and biochemistry, vol 29. Academic Press, New York, p 173
Neises B, Steglich W (1978) Simple method for the esterification of carboxylic acids. Angew Chem Int Ed Engl 17:522–524
Pinto JP, Gladstone GR, Yung YL (1980) Photochemical production of formaldehyde in Earth's primitive atmosphere. Science 210:183–185
Profy AT, Usher DA (1984) Stereoselective aminoacylation of a dinucleoside monophosphate by the imidazolides ofDl-alanine and N-(tert-butoxycarbonyl)-Dl-alanine. J Mol Evol 20:147–156
Reid C, Orgel LE (1967) Synthesis of sugars in potentially prebiotic conditions. Nature (Lond) 216:455
Schwartz AW (1971) Phosphate: solubilization and activation on the primitive Earth. In: Buvert R, Ponnamperuma C (eds) Chemical evolution and the origin of life. North-Holland, Amsterdam, p 207
Stadtman ER (1954) On the energy-rich nature of acetyl imidazole, an enzymatically active compound. In: McElroy WD, Glass B (eds) The mechanism of enzyme action. Johns Hopkins Press, Baltimore, p 581
Stadtman ER (1957) Preparation and assay of acyl coenzyme A and other thiol esters: use of hydroxylamine. In: Colowick SP, Kaplan NO (eds) Methods in enzymology, vol III. Academic Press, New York p 931
Thauer RK, Jungermann K, Decker K (1977) Energy conservation in chemotrophic anaerobic bacteria. Bacteriol Rev 41:100–180
Thompson AR (1951) Separation of saturated mono-hydroxamic acids by partition chromatography on paper. Aust J Sci Res, Ser B 4:181–186
Weber AL (1981) Formation of pyrophosphate, tripolyphosphate, and phosphorylimidazole with the thioester, N,S-diacetylcysteamine, as the condensing agent. J Mol Evol 18:24–29
Weber AL (1982) Formation of pyrophosphate on hydroxyapatite with thioesters as condensing agents. BioSystems 15:183–189
Weber AL (1984a) Nonenzymatic formation of “energy-rich” lactoyl and glyceroyl thioesters from glyceraldehyde and a thiol. J Mol Evol 20:157–166
Weber AL (1984b) Prebiotic formation of “energy-rich” thioesters from glyceraldehyde and N-acetylcysteine. Origins Life 15:17–27
Weber AL (1985) Alanine synthesis from glyceraldehyde and ammonium ion in aqueous solution. J Mol Evol 21:351–355
Weber AL (1986) The triose model: glyceraldehyde as a source of energy and monomers for prebiotic condensation reactions. Origins Life (in press)
Weber AL, Fox SW (1973) Aminoacylation and acetylaminoacylation of homopolyribonucleotides. Biochim Biophys Acta 319:174–187
Weber AL, Orgel LE (1978) The formation of peptides from the 2′(3′)-glycyl ester of a nucleotide. J Mol Evol 11:189–198
Weber AL, Orgel LE (1979) The formation of peptides from glycine thioesters. J Mol Evol 13:193–202
Weber AL, Orgel LE (1980) Poly(U)-directed peptide-bond formation from the 2′(3′)-glycyl esters of adenosine derivatives. J Mol Evol 16:1–10
Weber AL, Orgel LE (1981) The effect of poly(C) on the formation of peptide bonds from the 2′(3′)-glycyl ester of a guanosine nucleotide. J Mol Evol 17:190–191
Zahler WL, Cleland WW (1968) A specific and sensitive assay for disulfides. J Biol Chem 243:716–719
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Weber, A.L. Oligoglyceric acid synthesis by autocondensation of glyceroyl thioester. J Mol Evol 25, 191–196 (1987). https://doi.org/10.1007/BF02100011
Received:
Revised:
Issue Date:
DOI: https://doi.org/10.1007/BF02100011