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Chemical Compound Review

threonine     2-amino-3-hydroxy-butanoic acid

Synonyms: allothreonine, DL-Threonine, H-DL-Thr-OH, threonine(L), THREONINE,(L), ...
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Disease relevance of threonine

  • One hundred and sixteen crossbred male chicks were used in two battery trials to establish the biological efficacy and toxicity of D-allothreonine (D-allo-Thr) relative to L-Thr [1].
  • Protoplasts were prepared from Streptococcus sanguis and some S. mutans serotypes by use of lysozyme (EC under particular conditions: cells had to be grown in DL-threonine (20 mM) and harvested in early exponential phase [2].

High impact information on threonine

  • At pH 7.8 and 25 degrees C, the specificity constants (kcat/Km) were as follows: D-serine (3.4 X 10(5) M-1 s-1), D-threonine (2.9 X 10(4) M-1 s-1), D-allothreonine (7.5 X 10(3) M-1 s-1), and L-serine (38 M-1 s-1) [3].
  • Neither mutation significantly changed the structure of SHMT, the spectral properties of its complexes, or the kinetics of the retroaldol cleavage of allothreonine and 3-phenylserine [4].
  • The pronounced broadening of the DL-threonine carboxyl peak in the presence of the Mn(II)-enzyme complex indicates that an L-threonine binding site is close to the metal binding site of the kinase active site [5].
  • Therefore, studies on protein kinase C and these phospholipids were conducted in hepatocytes of rats maintained on three different diets viz. casein (20% protein) deficient (4% protein, rice flour as source of protein) and supplemented (deficient diet supplemented with L-lysine and DL-threonine) diet for 28 days [6].
  • Lysozyme treatments to weaken the cell wall and possibly mimic the effect of DL-threonine did not yield any transformants [7].

Biological context of threonine

  • A consistent racemization occurred during the acylation of H-His-Pro-Gly-Tyr(Bzl)-OBzl with Z-Val-[GalNAc(Ac)3-alpha]Thr-OH by the BOP-HOBt procedure and the D-allothreonine containing glyco-hexapeptide was isolated in about 20% yield [8].
  • Supplementation of the growth medium with glycine, or particularly DL-threonine, produced cells that could be electrotransformed much more efficiently at frequencies up to 2.5 x 10(3) transformants per microgram plasmid DNA [7].

Analytical, diagnostic and therapeutic context of threonine

  • The resolution of DL-threonine was performed by preferential crystallization experiments in aqueous solution varying several process parameters like supersaturation, seed amount, initial enantiomeric excess, and scale [9].
  • A more complex biochemical explanation of the enhancement of electroporation by growth in DL-threonine is likely, and this is discussed [7].


  1. D-allothreonine has no growth promoting efficacy for chicks. Baker, D.H., Webel, D.M., Fernandez, S.R. Poult. Sci. (1998) [Pubmed]
  2. Protoplast and cytoplasmic membrane preparations from Streptococcus sanguis and Streptococcus mutans. Schöller, M., Klein, J.P., Sommer, P., Frank, R. J. Gen. Microbiol. (1983) [Pubmed]
  3. Characterization of the catalytic pathway for D-serine dehydratase. Evidence for variation of the rate-determining step with substrate structure. Federiuk, C.S., Bayer, R., Shafer, J.A. J. Biol. Chem. (1983) [Pubmed]
  4. Serine hydroxymethyltransferase: role of glu75 and evidence that serine is cleaved by a retroaldol mechanism. Szebenyi, D.M., Musayev, F.N., di Salvo, M.L., Safo, M.K., Schirch, V. Biochemistry (2004) [Pubmed]
  5. Nuclear-magnetic-relaxation studies of the interaction of inhibitor with the threonine-sensitive aspartokinase of Escherichia coli. Tilak, A., Wright, K., Damle, S., Takahashi, M. Eur. J. Biochem. (1976) [Pubmed]
  6. Dietary protein deficiency induced changes in protein kinase C activity and phospholipid metabolism in rat hepatocytes. Kathayat, R., Jaiswal, A.S., Basir, S.F., Bansal, S.K. Indian J. Exp. Biol. (1997) [Pubmed]
  7. Factors affecting the electroporation of Bacillus subtilis. McDonald, I.R., Riley, P.W., Sharp, R.J., McCarthy, A.J. J. Appl. Bacteriol. (1995) [Pubmed]
  8. Solution synthesis of the glyco-hexapeptide sequence of the human oncofetal fibronectin defined by monoclonal antibody FDC-6. Gobbo, M., Biondi, L., Filira, F., Rocchi, R. Int. J. Pept. Protein Res. (1991) [Pubmed]
  9. Online monitoring of preferential crystallization of enantiomers. Alvarez Rodrigo, A., Lorenz, H., Seidel-Morgenstern, A. Chirality. (2004) [Pubmed]
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