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Chemical Compound Review

GLYCERALD     (2R)-2,3-dihydroxypropanal

Synonyms: Triose, D-glycerose, D-aldotriose, PubChem6338, CHEBI:17378, ...
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Disease relevance of glyceraldehyde

  • Carbohydrate fluxes into alginate biosynthesis in Azotobacter vinelandii NCIB 8789: NMR investigations of the triose pools [1].
  • The addition of the triose D-glyceraldehyde (5-20 mM) to HIT-T15 hamster insulinoma cells caused a rapid, marked depolarisation of the plasma membrane accompanied by a pronounced intracellular acidification, an increase in the cytosolic free calcium concentration [Ca2+]i and enhanced secretion of insulin [2].
  • An increase in phosphorylase a and aldolase activity levels suggested the increased formation of triose sugars during phosphamidon toxicity [3].

High impact information on glyceraldehyde

  • Methylglyoxal is a highly reactive dicarbonyl degradation product formed from triose phosphates during glycolysis [4].
  • Comparison of the deduced sequence of pea p36 to that of other known proteins indicates a striking homology to a protein from spinach chloroplasts that was previously suggested to be the triose phosphate-3-phosphoglycerate-phosphate translocator (phosphate translocator) (Flügge, U [5].
  • The triose phosphate-3-phosphoglycerate-phosphate translocator from spinach chloroplasts: nucleotide sequence of a full-length cDNA clone and import of the in vitro synthesized precursor protein into chloroplasts [6].
  • Expression of the coding region of the GPT in transformed yeast cells and subsequent transport experiments with the purified protein demonstrated that the GPT protein mediates a 1:1 exchange of glucose 6-phosphate mainly with inorganic phosphate and triose phosphates [7].
  • Transport was diminished only in triose-depleted cells where metabolite flow through PGK was presumably absent [8].

Biological context of glyceraldehyde

  • We measured gluconeogenesis (GNG) in rats by mass isotopomer distribution analysis, which allows enrichment of the true biosynthetic precursor pool (hepatic cytosolic triose phosphates) to be determined [9].
  • (2)H NMR analysis of purified glycogen revealed that hepatocytes with overexpressed GK synthesized a larger portion of their glycogen from triose phosphates and a smaller portion from tricarboxylic acid cycle intermediates than cells with overexpressed glycogen-targeting subunits [10].
  • The genes cggR, gapA, pgk, tpi, pgm and eno, encoding the enzymes required for the interconversion of triose phosphates, are transcribed as a hexacistronic operon as demonstrated by Northern analysis [11].
  • These results demonstrated that the arabinose carbon skeleton is formed via the nonoxidative pentose shunt and not via hexose decarboxylation or via triose condensations [12].
  • Both fructose and D-glyceraldehyde stimulated the phosphorylation of glucose as estimated by the release of 3H2O from [2-3H]glucose, but the triose was less potent in this respect than fructose and its effect disappeared earlier [13].

Anatomical context of glyceraldehyde

  • Three models of disturbed erythrocyte metabolism, triose-depleted normal, phosphoglycerate kinase (PGK)-deficient, and pyruvate kinase (PK)-deficient cells, have been studied to examine further the role of PGK in erythrocyte cation transport [8].
  • Variations in f show that the 13C labeling of triose phosphates was not equal in all hepatocytes, even when exposed to the same substrate concentrations and enrichments [14].
  • The triose-induced elevation of cytosolic free Ca2+ concentration was not potentiated by the presence of 3 mM glucose, and oxidation of labeled GA by the islet cells was not enhanced by the presence of glucose [15].
  • Thus, the expression of cp-FBPase in tubers allows for a new route of starch biosynthesis from triose-phosphates imported from the cytosol [16].
  • Glycogen synthesis following glucose microinjection in frog oocytes proceeds preferentially by an indirect pathway involving gluconeogenesis from triose compounds [17].

Associations of glyceraldehyde with other chemical compounds


Gene context of glyceraldehyde

  • Combined, these data strongly suggest that glucose flux in the glycolytic and gluconeogenic pathways at the level of triose intermediates could control expression of GR mRNA and participate in controlling its own metabolism [22].
  • Paralogues of dihydroxyacetone kinase also occur in association with transcription regulators and proteins of unknown function pointing to biological roles beyond triose metabolism [23].
  • Although CEL was formed in highest yields during the reaction of methylglyoxal and triose phosphates with lysine and protein, it was also formed in reactions of pentoses, ascorbate and other sugars with lysine and RNase [24].
  • Two bands each of triose phsophate isomerase, fumarase and aldolase are present in brain, but only one band of these enzymes is present in neuroblastoma cells [25].
  • NMR analysis of site-specific mutants of yeast phosphoglycerate kinase. An investigation of the triose-binding site [26].


  1. Carbohydrate fluxes into alginate biosynthesis in Azotobacter vinelandii NCIB 8789: NMR investigations of the triose pools. Beale, J.M., Foster, J.L. Biochemistry (1996) [Pubmed]
  2. Stimulation of HIT-T15 insulinoma cells by glyceraldehyde does not require its metabolism. Elliott, A.C., Trebilcock, R., Yates, A.P., Best, L. Eur. J. Biochem. (1993) [Pubmed]
  3. Modulation of carbohydrate metabolism in the selected tissues of marine prawn, Penaeus indicus (H. Milne Edwards), under phosphamidon-induced stress. Reddy, M.S., Rao, K.V. Ecotoxicol. Environ. Saf. (1988) [Pubmed]
  4. Methylglyoxal modification of mSin3A links glycolysis to angiopoietin-2 transcription. Yao, D., Taguchi, T., Matsumura, T., Pestell, R., Edelstein, D., Giardino, I., Suske, G., Ahmed, N., Thornalley, P.J., Sarthy, V.P., Hammes, H.P., Brownlee, M. Cell (2006) [Pubmed]
  5. The chloroplast import receptor is an integral membrane protein of chloroplast envelope contact sites. Schnell, D.J., Blobel, G., Pain, D. J. Cell Biol. (1990) [Pubmed]
  6. The triose phosphate-3-phosphoglycerate-phosphate translocator from spinach chloroplasts: nucleotide sequence of a full-length cDNA clone and import of the in vitro synthesized precursor protein into chloroplasts. Flügge, U.I., Fischer, K., Gross, A., Sebald, W., Lottspeich, F., Eckerskorn, C. EMBO J. (1989) [Pubmed]
  7. Molecular characterization of a carbon transporter in plastids from heterotrophic tissues: the glucose 6-phosphate/phosphate antiporter. Kammerer, B., Fischer, K., Hilpert, B., Schubert, S., Gutensohn, M., Weber, A., Flügge, U.I. Plant Cell (1998) [Pubmed]
  8. Energy metabolism in human erythrocytes: the role of phosphoglycerate kinase in cation transport. Segel, G.B., Feig, S.A., Glader, B.E., Muller, A., Dutcher, P., Nathan, D.G. Blood (1975) [Pubmed]
  9. Gluconeogenesis and intrahepatic triose phosphate flux in response to fasting or substrate loads. Application of the mass isotopomer distribution analysis technique with testing of assumptions and potential problems. Neese, R.A., Schwarz, J.M., Faix, D., Turner, S., Letscher, A., Vu, D., Hellerstein, M.K. J. Biol. Chem. (1995) [Pubmed]
  10. Glycogen-targeting subunits and glucokinase differentially affect pathways of glycogen metabolism and their regulation in hepatocytes. Yang, R., Cao, L., Gasa, R., Brady, M.J., Sherry, A.D., Newgard, C.B. J. Biol. Chem. (2002) [Pubmed]
  11. Transcription of glycolytic genes and operons in Bacillus subtilis: evidence for the presence of multiple levels of control of the gapA operon. Ludwig, H., Homuth, G., Schmalisch, M., Dyka, F.M., Hecker, M., Stülke, J. Mol. Microbiol. (2001) [Pubmed]
  12. Biosynthetic origin of mycobacterial cell wall arabinosyl residues. Scherman, M., Weston, A., Duncan, K., Whittington, A., Upton, R., Deng, L., Comber, R., Friedrich, J.D., McNeil, M. J. Bacteriol. (1995) [Pubmed]
  13. Fructose 1-phosphate and the regulation of glucokinase activity in isolated hepatocytes. Davies, D.R., Detheux, M., Van Schaftingen, E. Eur. J. Biochem. (1990) [Pubmed]
  14. Limitations of the mass isotopomer distribution analysis of glucose to study gluconeogenesis. Heterogeneity of glucose labeling in incubated hepatocytes. Previs, S.F., Hallowell, P.T., Neimanis, K.D., David, F., Brunengraber, H. J. Biol. Chem. (1998) [Pubmed]
  15. Two signaling pathways, from the upper glycolytic flux and from the mitochondria, converge to potentiate insulin release. Asanuma, N., Aizawa, T., Sato, Y., Schermerhorn, T., Komatsu, M., Sharp, G.W., Hashizume, K. Endocrinology (1997) [Pubmed]
  16. Starch biosynthesis from triose-phosphate in transgenic potato tubers expressing plastidic fructose-1,6-bisphosphatase. Thorbjørnsen, T., Asp, T., Jørgensen, K., Nielsen, T.H. Planta (2002) [Pubmed]
  17. Regulatory role of fructose-2,6-bisP on glucose metabolism in frog oocytes: in vivo inhibition of glycogen synthesis. Guixé, V., Preller, A., Kessi, E., Ureta, T. Arch. Biochem. Biophys. (1997) [Pubmed]
  18. Metformin reduces systemic methylglyoxal levels in type 2 diabetes. Beisswenger, P.J., Howell, S.K., Touchette, A.D., Lal, S., Szwergold, B.S. Diabetes (1999) [Pubmed]
  19. Dihydroxyacetone detoxification in Saccharomyces cerevisiae involves formaldehyde dissimilation. Molin, M., Blomberg, A. Mol. Microbiol. (2006) [Pubmed]
  20. Role of fructose 2,6-bisphosphate in the control by glucagon of gluconeogenesis from various precursors in isolated rat hepatocytes. Hue, L., Bartrons, R. Biochem. J. (1984) [Pubmed]
  21. Triosidines: novel Maillard reaction products and cross-links from the reaction of triose sugars with lysine and arginine residues. Tessier, F.J., Monnier, V.M., Sayre, L.M., Kornfield, J.A. Biochem. J. (2003) [Pubmed]
  22. In vivo and in vitro regulation of hepatic glucagon receptor mRNA concentration by glucose metabolism. Burcelin, R., Mrejen, C., Decaux, J.F., De Mouzon, S.H., Girard, J., Charron, M.J. J. Biol. Chem. (1998) [Pubmed]
  23. Crystal structure of the Citrobacter freundii dihydroxyacetone kinase reveals an eight-stranded alpha-helical barrel ATP-binding domain. Siebold, C., Arnold, I., Garcia-Alles, L.F., Baumann, U., Erni, B. J. Biol. Chem. (2003) [Pubmed]
  24. N-epsilon-(carboxyethyl)lysine, a product of the chemical modification of proteins by methylglyoxal, increases with age in human lens proteins. Ahmed, M.U., Brinkmann Frye, E., Degenhardt, T.P., Thorpe, S.R., Baynes, J.W. Biochem. J. (1997) [Pubmed]
  25. Altered enzyme expression in "differentiated" murine neuroblastoma cells. Prasad, N., Prasad, R. Br. J. Cancer (1976) [Pubmed]
  26. NMR analysis of site-specific mutants of yeast phosphoglycerate kinase. An investigation of the triose-binding site. Fairbrother, W.J., Walker, P.A., Minard, P., Littlechild, J.A., Watson, H.C., Williams, R.J. Eur. J. Biochem. (1989) [Pubmed]
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