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Chemical Compound Review

threonine     (2S,3R)-2-amino-3-hydroxy- butanoic acid

Synonyms: Threonin, Treonina, Threoninum, thre, L-Threonin, ...
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Disease relevance of threonine


Psychiatry related information on threonine


High impact information on threonine


Chemical compound and disease context of threonine


Biological context of threonine

  • This alkylated protein retains eight binding sites for L-threonine [16].
  • Comparison of kinetics parameters in the presence and absence of a Na+ gradient suggests that both partially and fully loaded forms of the carrier can function to translocate substrate and that Na+ serves to accelerate L-threonine transport by a mechanism that does not involve enhanced substrate binding [17].
  • The single mutation in strain CU18 results in altered regulation of ilv gene expression and in the production of an altered L-threonine deaminase [18].
  • The autoregulatory model specifies that L-threonine deaminase participates in the control of the expression of the ilv ADE gene cluster as well as the ilv B gene and ilv C gene, which constitute three separate units of regulation [18].
  • The influx of L-threonine through system ASC does not influence the membrane potential in cultured human fibroblasts although comparable fluxes of amino acids through another Na(+)-dependent agency, system A, effectively depolarize the cells [19].

Anatomical context of threonine

  • These data indicate that the transport system available for L-threonine in the intestinal brush border membrane (system B) is functionally distinct from other amino acid transport systems [17].
  • L-Threonine dehydrogenase (L-threonine:NAD+ oxidoreductase (EC has been purified to apparent homogeneity from chicken liver mitochondria [20].
  • Biochemical analysis reveals that protein kinase C autophosphorylates on S660, that autophosphorylation on S660 follows T641 autophosphorylation, that autophosphorylation on S660 is accompanied by the release of protein kinase C into the cytosol, and that T500 is not an autophosphorylation site [21].
  • L-threonine transport in pig jejunal brush border membrane vesicles. Functional characterization of the unique system B in the intestinal epithelium [17].
  • Expression of SATT cDNA in HeLa cells induced stereospecific uptake of L-serine, L-alanine, and L-threonine that was not inhibited by excess (3 mM) 2-(methylamino)-isobutyric acid, a specific substrate for the System A amino acid transporter [22].

Associations of threonine with other chemical compounds


Gene context of threonine


Analytical, diagnostic and therapeutic context of threonine


  1. Covalent structure of biodegradative threonine dehydratase of Escherichia coli: homology with other dehydratases. Datta, P., Goss, T.J., Omnaas, J.R., Patil, R.V. Proc. Natl. Acad. Sci. U.S.A. (1987) [Pubmed]
  2. Homoserine dehydrogenase: spontaneous reactivation by dissociation of p-mercuribenzoate from an inactive enzyme--p-mercuribenzoate complex. Epstein, C.C., Datta, P. Proc. Natl. Acad. Sci. U.S.A. (1977) [Pubmed]
  3. Crystal Structures of Salmonella typhimurium Biodegradative Threonine Deaminase and Its Complex with CMP Provide Structural Insights into Ligand-induced Oligomerization and Enzyme Activation. Simanshu, D.K., Savithri, H.S., Murthy, M.R. J. Biol. Chem. (2006) [Pubmed]
  4. A controlled trial of amino acid therapy in amyotrophic lateral sclerosis: I. Clinical, functional, and maximum isometric torque data. Tandan, R., Bromberg, M.B., Forshew, D., Fries, T.J., Badger, G.J., Carpenter, J., Krusinski, P.B., Betts, E.F., Arciero, K., Nau, K. Neurology (1996) [Pubmed]
  5. Bacterial catabolism of threonine. Threonine degradation initiated by L-threonine-NAD+ oxidoreductase. Bell, S.C., Turner, J.M. Biochem. J. (1976) [Pubmed]
  6. Effect of erythromycin on L-threonine transport in rabbit jejunum in vitro. Navarro, H., Arruebo, M.P., Sorribas, V., Alcalde, A.I. J. Vet. Pharmacol. Ther. (1992) [Pubmed]
  7. Structural basis for double-sieve discrimination of L-valine from L-isoleucine and L-threonine by the complex of tRNA(Val) and valyl-tRNA synthetase. Fukai, S., Nureki, O., Sekine, S., Shimada, A., Tao, J., Vassylyev, D.G., Yokoyama, S. Cell (2000) [Pubmed]
  8. A regulatory element in the CHA1 promoter which confers inducibility by serine and threonine on Saccharomyces cerevisiae genes. Bornaes, C., Ignjatovic, M.W., Schjerling, P., Kielland-Brandt, M.C., Holmberg, S. Mol. Cell. Biol. (1993) [Pubmed]
  9. Serine racemase modulates intracellular D-serine levels through an alpha,beta-elimination activity. Foltyn, V.N., Bendikov, I., De Miranda, J., Panizzutti, R., Dumin, E., Shleper, M., Li, P., Toney, M.D., Kartvelishvily, E., Wolosker, H. J. Biol. Chem. (2005) [Pubmed]
  10. Amino acid substitutions in the C-terminal regulatory domain disrupt allosteric effector binding to biosynthetic threonine deaminase from Escherichia coli. Chinchilla, D., Schwarz, F.P., Eisenstein, E. J. Biol. Chem. (1998) [Pubmed]
  11. Expression of the gene for Bacillus subtilis aspartokinase II in Escherichia coli. Bondaryk, R.P., Paulus, H. J. Biol. Chem. (1985) [Pubmed]
  12. L-threonine dehydrogenase. Purification and properties of the homogeneous enzyme from Escherichia coli K-12. Boylan, S.A., Dekker, E.E. J. Biol. Chem. (1981) [Pubmed]
  13. Purification, separation, and characterization of two molecular forms of D-1-amino-2-propanol:NAD+ oxidoreductase activity from extracts of Escherichia coli K-12. Campbell, R.L., Swain, R.R., Dekker, E.E. J. Biol. Chem. (1978) [Pubmed]
  14. Evidence for L-threonine cleavage and allothreonine formation by different enzymes from Clostridium pasteurianum: threonine aldolase and serine hydroxymethyltransferase. Stöcklein, W., Schmidt, H.L. Biochem. J. (1985) [Pubmed]
  15. Bacterial catabolism of threonine. Threonine degradation initiated by L-threonine acetaldehyde-lyase (aldolase) in species of Pseudomonas. Bell, S.C., Turner, J.M. Biochem. J. (1977) [Pubmed]
  16. The threonine-sensitive homoserine dehydrogenase and aspartokinase activities of Escherichia coli K12. Carboxymethylation of the enzyme: threonine binding and inhibition are functionally dissociable. Fontan, E., Truffa-Bachi, P. J. Biol. Chem. (1978) [Pubmed]
  17. L-threonine transport in pig jejunal brush border membrane vesicles. Functional characterization of the unique system B in the intestinal epithelium. Maenz, D.D., Patience, J.F. J. Biol. Chem. (1992) [Pubmed]
  18. Threonine deaminase from Escherichia coli. II. Maturation and physical properties of the enzyme from a mutant altered in its regulation of gene expression. Calhoun, D.H., Kuska, J.S., Hatfield, G.W. J. Biol. Chem. (1975) [Pubmed]
  19. Transport system ASC for neutral amino acids. An electroneutral sodium/amino acid cotransport sensitive to the membrane potential. Bussolati, O., Laris, P.C., Rotoli, B.M., Dall'Asta, V., Gazzola, G.C. J. Biol. Chem. (1992) [Pubmed]
  20. L-Threonine dehydrogenase of chicken liver. Purification, characterization, and physiological significance. Aoyama, Y., Motokawa, Y. J. Biol. Chem. (1981) [Pubmed]
  21. Protein kinase C is regulated in vivo by three functionally distinct phosphorylations. Keranen, L.M., Dutil, E.M., Newton, A.C. Curr. Biol. (1995) [Pubmed]
  22. Cloning and expression of a novel Na(+)-dependent neutral amino acid transporter structurally related to mammalian Na+/glutamate cotransporters. Shafqat, S., Tamarappoo, B.K., Kilberg, M.S., Puranam, R.S., McNamara, J.O., Guadaño-Ferraz, A., Fremeau, R.T. J. Biol. Chem. (1993) [Pubmed]
  23. Purification, properties, and N-terminal amino acid sequence of homogeneous Escherichia coli 2-amino-3-ketobutyrate CoA ligase, a pyridoxal phosphate-dependent enzyme. Mukherjee, J.J., Dekker, E.E. J. Biol. Chem. (1987) [Pubmed]
  24. Novel keto acid formate-lyase and propionate kinase enzymes are components of an anaerobic pathway in Escherichia coli that degrades L-threonine to propionate. Hesslinger, C., Fairhurst, S.A., Sawers, G. Mol. Microbiol. (1998) [Pubmed]
  25. Mechanisms of interaction of Escherichia coli threonine synthase with substrates and inhibitors. Laber, B., Gerbling, K.P., Harde, C., Neff, K.H., Nordhoff, E., Pohlenz, H.D. Biochemistry (1994) [Pubmed]
  26. Threonine is catabolized by L-threonine 3-dehydrogenase and threonine dehydratase in hepatocytes from domestic cats (Felis domestica). Hammer, V.A., Rogers, Q.R., Freedland, R.A. J. Nutr. (1996) [Pubmed]
  27. Identification of glyA (encoding serine hydroxymethyltransferase) and its use together with the exporter ThrE to increase L-threonine accumulation by Corynebacterium glutamicum. Simic, P., Willuhn, J., Sahm, H., Eggeling, L. Appl. Environ. Microbiol. (2002) [Pubmed]
  28. Identification of an evolutionarily conserved extracellular threonine residue critical for surface expression and its potential coupling of adjacent voltage-sensing and gating domains in voltage-gated potassium channels. Mckeown, L., Burnham, M.P., Hodson, C., Jones, O.T. J. Biol. Chem. (2008) [Pubmed]
  29. Activation of tyrosine kinases by mutation of the gatekeeper threonine. Azam, M., Seeliger, M.A., Gray, N.S., Kuriyan, J., Daley, G.Q. Nat. Struct. Mol. Biol. (2008) [Pubmed]
  30. Identification of serine/threonine kinase substrates in the human pathogen group B streptococcus. Silvestroni, A., Jewell, K.A., Lin, W.J., Connelly, J.E., Ivancic, M.M., Tao, W.A., Rajagopal, L. J. Proteome Res. (2009) [Pubmed]
  31. The complete nucleotide sequence of the ilvGMEDA cluster of Escherichia coli K-12. Cox, J.L., Cox, B.J., Fidanza, V., Calhoun, D.H. Gene (1987) [Pubmed]
  32. Glycine metabolism in Candida albicans: characterization of the serine hydroxymethyltransferase (SHM1, SHM2) and threonine aldolase (GLY1) genes. McNeil, J.B., Flynn, J., Tsao, N., Monschau, N., Stahmann, K., Haynes, R.H., McIntosh, E.M., Pearlman, R.E. Yeast (2000) [Pubmed]
  33. Potential genetic markers of sporadic Alzheimer's dementia. Retz, W., Thome, J., Durany, N., Harsányi, A., Retz-Junginger, P., Kornhuber, J., Riederer, P., Rösler, M. Psychiatr. Genet. (2001) [Pubmed]
  34. Crystal structure of the pyridoxal-5'-phosphate-dependent serine dehydratase from human liver. Sun, L., Bartlam, M., Liu, Y., Pang, H., Rao, Z. Protein Sci. (2005) [Pubmed]
  35. A novel membrane-associated threonine permease encoded by the tdcC gene of Escherichia coli. Sumantran, V.N., Schweizer, H.P., Datta, P. J. Bacteriol. (1990) [Pubmed]
  36. Characterization of proteolysis fragments of aspartokinase I: homoserine dehydrogenase I. Fluorescence and circular dichroism studies. McMahon, P.L., Takahashi, M. J. Biol. Chem. (1983) [Pubmed]
  37. A single point mutation increases the affinity of serotonin 5-HT1D alpha, 5-HT1D beta, 5-HT1E and 5-HT1F receptors for beta-adrenergic antagonists. Adham, N., Tamm, J.A., Salon, J.A., Vaysse, P.J., Weinshank, R.L., Branchek, T.A. Neuropharmacology (1994) [Pubmed]
  38. Global analyses of transcriptomes and proteomes of a parent strain and an L-threonine-overproducing mutant strain. Lee, J.H., Lee, D.E., Lee, B.U., Kim, H.S. J. Bacteriol. (2003) [Pubmed]
  39. Evolutionary relationships between yeast and bacterial homoserine dehydrogenases. Thomas, D., Barbey, R., Surdin-Kerjan, Y. FEBS Lett. (1993) [Pubmed]
  40. XbaI polymorphism in DNA at the apolipoprotein B locus is associated with myocardial infarction (MI). Bohn, M., Bakken, A., Erikssen, J., Berg, K. Clin. Genet. (1993) [Pubmed]
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