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Chemical Compound Review

Erythrose     (2R,3R)-2,3,4- trihydroxybutanal

Synonyms: Threose, D-Erythrose, AG-E-26244, AG-G-06414, AG-L-65314, ...
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Disease relevance of D-Erythrose

  • For transaldolase, apparent Km values of 0.13 mM (normal liver) and 0.17 mM (hepatoma) were observed for erythrose 4-phosphate and of 0.30 to 0.35 mM for fructose 6-phosphate [1].
  • Erythrose inhibited the growth of a sodA sodB strain of Escherichia coli under aerobiosis; but did not inhibit anaerobic growth of the sodA sodB strain, or the aerobic growth of the superoxide dismutase (SOD)-competent parental strain [2].
  • Treatment of breast cancer cells with the combination of HCT and specific AMF inhibitors, erythrose 4-phosphate or D-mannose 6-phosphate, resulted in an additive inhibitory effect on both the growth rate and invasiveness of cells as compared with treatment with each agent alone [3].
  • Melasma (chloasma) is the most common cause of facial pigmentation, but there are many other forms such as Riehl's melanosis, poikiloderma of Civatte, erythrose peribuccale pigmentaire of Brocq, erythromelanosis follicularis of the face and neck, linea fusca, and cosmetic hyperpigmentations [4].

High impact information on D-Erythrose

  • METHODS: To increase AGE levels, human adult articular cartilage was incubated with threose [5].
  • In the active site of DAH7P synthase the two substrates PEP and erythrose 4-phosphate appear to bind in a configuration similar to that proposed for PEP and A5P in the active site of KDO8P synthase [6].
  • Thus the binding of inorganic phosphate to the Pi site likely is not productive for attacking efficiently the thioacyl intermediate formed with erythrose 4-phosphate, whereas a water molecule is an efficient nucleophile for the hydrolysis of the thioacyl intermediate [7].
  • The chemical mechanism of erythrose 4-phosphate oxidation by GapB-encoded protein is shown to proceed through a two-step mechanism involving covalent intermediates with Cys-149, with rates associated to the acylation and deacylation processes of 280 s-1 and 20 s-1, respectively [7].
  • Since erythrose 4-phosphate can be replaced by any free aldehyde tested thus far, this type of a homogeneous catalysis opens new synthetic routes to alpha-keto-gamma-hydroxy-fatty acids and their derivatives [8].

Chemical compound and disease context of D-Erythrose


Biological context of D-Erythrose


Anatomical context of D-Erythrose


Associations of D-Erythrose with other chemical compounds


Gene context of D-Erythrose

  • Yeast mutants with a deletion of the transketolase gene, TKL1, can grow without aromatic amino acid supplement indicating an additional source of erythrose 4-phosphate in the cells [18].
  • Alkali-washed bovine lens membranes, isolated after glycation with DHA and threose, contained both alpha-crystallin and MP26, as determined by immunoblot and double immunocytochemical labeling studies [14].
  • The PEP synthase effect is not observed without overproduced transketolase, suggesting that erythrose 4-phosphate is the first limiting metabolite [9].
  • These results demonstrate that erythrose is incorporated into the base part of vitamin B12 regiospecifically and that formate is the precursor of the C2 [19].
  • This shows that C1 of erythrose or threose was originally incorporated exclusively into C4 of the 5,6-dimethylbenzimidazole moiety of vitamin B12 [19].

Analytical, diagnostic and therapeutic context of D-Erythrose


  1. Behavior of transaldolase (EC and transketolase (EC Activities in normal, neoplastic, differentiating, and regenerating liver. Heinrich, P.C., Morris, H.P., Weber, G. Cancer Res. (1976) [Pubmed]
  2. Superoxide dependence of the toxicity of short chain sugars. Benov, L., Fridovich, I. J. Biol. Chem. (1998) [Pubmed]
  3. Antihuman epidermal growth factor receptor 2 antibody herceptin inhibits autocrine motility factor (AMF) expression and potentiates antitumor effects of AMF inhibitors. Talukder, A.H., Bagheri-Yarmand, R., Williams, R.R., Ragoussis, J., Kumar, R., Raz, A. Clin. Cancer Res. (2002) [Pubmed]
  4. Management of facial hyperpigmentation. Pérez-Bernal, A., Muñoz-Pérez, M.A., Camacho, F. American journal of clinical dermatology. (2000) [Pubmed]
  5. Crosslinking by advanced glycation end products increases the stiffness of the collagen network in human articular cartilage: a possible mechanism through which age is a risk factor for osteoarthritis. Verzijl, N., DeGroot, J., Ben, Z.C., Brau-Benjamin, O., Maroudas, A., Bank, R.A., Mizrahi, J., Schalkwijk, C.G., Thorpe, S.R., Baynes, J.W., Bijlsma, J.W., Lafeber, F.P., TeKoppele, J.M. Arthritis Rheum. (2002) [Pubmed]
  6. Structure and mechanism of 3-deoxy-D-manno-octulosonate 8-phosphate synthase. Radaev, S., Dastidar, P., Patel, M., Woodard, R.W., Gatti, D.L. J. Biol. Chem. (2000) [Pubmed]
  7. Comparative enzymatic properties of GapB-encoded erythrose-4-phosphate dehydrogenase of Escherichia coli and phosphorylating glyceraldehyde-3-phosphate dehydrogenase. Boschi-Muller, S., Azza, S., Pollastro, D., Corbier, C., Branlant, G. J. Biol. Chem. (1997) [Pubmed]
  8. The synthesis of 3-deoxyheptulosonic acid 7-phosphate. Herrmann, K.M., Poling, M.D. J. Biol. Chem. (1975) [Pubmed]
  9. Engineering of Escherichia coli central metabolism for aromatic metabolite production with near theoretical yield. Patnaik, R., Liao, J.C. Appl. Environ. Microbiol. (1994) [Pubmed]
  10. Biochemical characterization of gapB-encoded erythrose 4-phosphate dehydrogenase of Escherichia coli K-12 and its possible role in pyridoxal 5'-phosphate biosynthesis. Zhao, G., Pease, A.J., Bharani, N., Winkler, M.E. J. Bacteriol. (1995) [Pubmed]
  11. Dimerization of erythrose 4-phosphate. Blackmore, P.F., Williams, J.F., MacLeod, J.K. FEBS Lett. (1976) [Pubmed]
  12. Purification and characterization of a novel erythrose reductase from Candida magnoliae. Lee, J.K., Kim, S.Y., Ryu, Y.W., Seo, J.H., Kim, J.H. Appl. Environ. Microbiol. (2003) [Pubmed]
  13. Hyperproduction of tryptophan by Corynebacterium glutamicum with the modified pentose phosphate pathway. Ikeda, M., Katsumata, R. Appl. Environ. Microbiol. (1999) [Pubmed]
  14. Glycation mediated crosslinking between alpha-crystallin and MP26 in intact lens membranes. Prabhakaram, M., Katz, M.L., Ortwerth, B.J. Mech. Ageing Dev. (1996) [Pubmed]
  15. Increased uptake of alpha-hydroxy aldehyde-modified low density lipoprotein by macrophage scavenger receptors. Kawamura, M., Heinecke, J.W., Chait, A. J. Lipid Res. (2000) [Pubmed]
  16. Fluorogenic stereochemical probes for transaldolases. González-García, E., Helaine, V., Klein, G., Schuermann, M., Sprenger, G.A., Fessner, W.D., Reymond, J.L. Chemistry (Weinheim an der Bergstrasse, Germany) (2003) [Pubmed]
  17. Fumarate-mediated inhibition of erythrose reductase, a key enzyme for erythritol production by Torula corallina. Lee, J.K., Koo, B.S., Kim, S.Y. Appl. Environ. Microbiol. (2002) [Pubmed]
  18. TKL2, a second transketolase gene of Saccharomyces cerevisiae. Cloning, sequence and deletion analysis of the gene. Schaaff-Gerstenschläger, I., Mannhaupt, G., Vetter, I., Zimmermann, F.K., Feldmann, H. Eur. J. Biochem. (1993) [Pubmed]
  19. Biosynthesis of vitamin B12 in anaerobic bacteria. Experiments with Eubacterium limosum on the incorporation of D-[1-13C]erythrose and [13C]formate into the 5,6-dimethylbenzimidazole moiety. Munder, M., Vogt, J.R., Vogler, B., Renz, P. Eur. J. Biochem. (1992) [Pubmed]
  20. Prebiotic synthesis of histidine. Shen, C., Yang, L., Miller, S.L., Oro, J. J. Mol. Evol. (1990) [Pubmed]
  21. 1,8-dihydroxynaphthalene (DHN)-melanin biosynthesis inhibitors increase erythritol production in Torula corallina, and DHN-melanin inhibits erythrose reductase. Lee, J.K., Jung, H.M., Kim, S.Y. Appl. Environ. Microbiol. (2003) [Pubmed]
  22. Chemical properties of lipopolysaccharide-like substance (LLS) extracted from Leptospira interrogans serovar canicola strain Moulton. Shimizu, T., Matsusaka, E., Nagakura, N., Takayanagi, K., Masuzawa, T., Iwamoto, Y., Morita, T., Mifuchi, I., Yanagihara, Y. Microbiol. Immunol. (1987) [Pubmed]
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