Summary
The formation of lactate from glyceraldehyde is catalyzed by the thiol, N-acetylcysteine, at ambient temperature in aqueous sodium phosphate (pH 7.0). The rate of lactate formation is more rapid at higher concentrations of sodium phosphate and is essentially the same in the presence and absence of oxygen. The formation of lactate is efficient, but proceeds slowly with an 8.8% yield of lactate after 16 days from 10 mM glyceraldehyde in the presence of 12.5 mM N-acetylcysteine and 500 mM sodium phosphate (pH 7.0). The formation of glycerate from glyceraldehyde, that occurs in the presence of oxygen and to a small extent when oxygen has been removed, is also catalyzed by the thiol, N-acetylcysteine, under the same conditions. The dramatic increase in the rate of glycerate formation that is brought about by the thiol, N-acetylcysteine, is accompanied by an equally dramatic decrease in the rates of production of glycolate and formate. Presumably, the thiol-dependent formation of lactate and glycerate occurs via their respective thioesters. The significance of these reactions to molecular evolution is discussed.
Article PDF
Similar content being viewed by others
Avoid common mistakes on your manuscript.
Abbreviations
- Ac:
-
Cys
- N:
-
acetylcysteine
- Ac:
-
Cys (Lac)
- N:
-
acetyl
- S:
-
lactoylcysteine
References
Bar-Nun A, Hartman H (1978) Synthesis of organic compounds from carbon monoxide and water by UV photolysis. Orig Life 9:93–101
Beck WS (1957) Carbohydrates: Assay of triose phosphates In: Colowick SP, Kaplan NO (eds) Methods in enzymology, vol III. Academic Press, New York, p 201
Degani CH, Halmann M (1968) Alkaline reactions of glucose 6-phosphate. J Am Chem Soc 90:1313–1317
Decker K, Jungermann K, Thauer RK (1970) Energy production in anaerobic organisms. Angew Chem Internat Edit 9:138–158
Fedoronko M, Kongistein J (1969) Kinetics of mutual isomerization of trioses and their dehydration to methylglyoxal. Collect Czech Chem Commun 34:3881–3894
Gabel NW, Ponnamperuma C (1967) Model for origin of monosaccharides. Nature 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
Grassetti DR, Murray JF (1969) The use of 2,2′-dithiobis-(5-nitropyridine) as a selective reagent for the detection of thiols. J Chromatogr 41:121–123
Green JW (1980) Oxidative reactions and degradations. In: Pigman W, Horton D (eds) The carbohydrates, vol IB. Academic Press, New York, p 1101
Gutsche CD, Redmore D, Buriks RS, Nowotny K, Grassner H, Armbruster CW (1967) Base-catalyzed triose condensations. J Am Chem Soc 89:1235–1245
Hall SS, Doweyko AM, Jordan F (1978) Glyoxalase I enzyme studies. 4. General base catalyzed enediol proton transfer rearrangement of methyl- and phenylglyoxalglutathionylhemithiol acetal to S-lactoyl- and S-mandeloylglutathione followed by hydrolysis. A model for the glyoxalase enzyme system. J Am Chem Soc 100:5934–5939
Hong JH, Becker RS (1979) Hydrogen atom initiated chemistry. J Mol Evol 13:15–26
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, 3rd edn. Physical and chemical data, vol. 1, CRC Press, Cleveland, p 296
Konigstein J, Fedoronko M (1975) Kinetic study of aldolization reactions of trioses. Collect Czech Chem Commun 40:1183–1192
Lederer E, Lederer M (1957) Chromatography. Elsevier, New York, p 184
Miller SL (1957) The formation of organic compounds on the primitive earth. Ann NY Acad Sci 69:260–275
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
Perlin AS (1962) Trioses: D-, L-, and DL-glyceraldehyde, oxidative degradation of ketohexoses. In: Whistler RL, Wolfrom ML (eds) Methods in carbohydrate chemistry, vol. 1. Academic Press, New York, p 61
Putnam EW (1957) Paper chromatography of sugars. In: Colowick SP, Kaplan NO (eds) Methods in enzymology, vol III. Academic Press, New York, p 62
Reid C, Orgel LE (1967) Synthesis of sugars in potentially prebiotic conditions. Nature 216:455
Reynolds SJ, Yates DW, Pogson CI (1971) Dihydroxyacetone phosphate: Its structure and reactivity with α-glycerophosphate dehydrogenase, aldolase and triose phosphate isomerase and some possible metabolic implications. Biochem J 122:285–297
Riddle V, Lorenz FW (1968) Nonenzymic, polyvalent anioncatalyzed formation of methylglyoxal as an explanation of its presence in physiological systems. J Biol Chem 243:2718–2724
Sagan C, Khare BN (1971) Long-wavelength ultraviolet photoproduction of amino acids on the primitive earth. Science 173:417–420
Spoehr HA (1924) The oxidation of carbohydrates with air. J Am Chem Soc 46:1494–1502
Spoehr HA, Milner HW (1934) Studies on atmospheric oxidation. III. The catalytic oxidation of trioses and related compounds. J Am Chem Soc 56:2068–2074
Spoehr HA, Smith JHC (1926) Studies on atmospheric oxidation. I. The oxidation of glucose and related substances in the presence of sodium ferro-pyrophosphate. J Am Chem Soc 48:236–248
Warshowsky B, Sandstrom WM (1952) The action of oxygen on glucose in the presence of potassium hydroxide. Arch Biochem Biophys 37:46–55
Weber AL (1981a) Formation of the thioester, N,S-diacetylcysteine, from acetaldehyde and N,N′-diacetylcystine in aqueous solution with ultraviolet light. J Mol Evol 17:103–107
Weber AL (1981b) Formation of pyrophosphate, tripolyphosphate, and phosphorylimidazole with the thioester, N,S-diacetylcysteamine, as the condensing agent. J Mol Evol 18:24–29
Weber AL (1982a) Formation of the thioester, N-acetyl, S-lactoylcysteine, by reaction of N-acetylcysteine with pyruvaldehyde in aqueous solution. J Mol Evol 18:354–359
Weber AL (1982b) Formation of pyrophosphate on hydroxyapatite with thioesters as condensing agents. BioSystems 15:183–189
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Weber, A.L. Thiol-catalyzed formation of lactate and glycerate from glyceraldehyde. J Mol Evol 19, 237–243 (1983). https://doi.org/10.1007/BF02099971
Received:
Revised:
Issue Date:
DOI: https://doi.org/10.1007/BF02099971