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Chemical Compound Review

itaconate     2-methylidenebutanedioic acid

Synonyms: Itaconic acid, CHEMBL359159, NSC-3357, ACMC-1CFCS, I29204_ALDRICH, ...
 
 
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Disease relevance of NSC3357

 

Psychiatry related information on NSC3357

  • The infrared spectra displayed a clear isolated absorption band at a wavenumber of 6186 cm(-1) (wavelength 1.617 microm) resulting from the =C-H bonds of itaconic acid, which was found to decrease in intensity with increasing reaction time [3].
 

High impact information on NSC3357

 

Biological context of NSC3357

 

Associations of NSC3357 with other chemical compounds

  • We report on a new class of P-O monophosphite ligands (designated 3a-k) with a double six-membered-ring backbone onto which are attached additional groups and on applications of their Rh complexes in the hydrogenation of enamides, alpha-dehydroamino acid esters, dimethyl itaconate, and beta-(acylamino)acrylates [12].
  • Rhodium complexes with chiral bisphospholanes are highly enantioselective catalysts for the asymmetric hydrogenation of various kinds of functionalized olefins such as dehydroamino acid derivatives, itaconic acid derivatives, and enamides [13].
  • The new ligands exhibit excellent enantioselectivities (over 99% ee) in the Rh-catalyzed asymmetric hydrogenation of enamides, dimethyl itaconate, and methyl (Z)-acetamidocinnamate even with high catalyst turnovers (S/C=10,000) [14].
  • The production of itaconic acid from glucose-based media by Aspergillus terreus NRRL 1960 was found to be controlled by stirring rate and pH [15].
  • Thermoprecipitation of lysozyme from egg white was demonstrated using copolymers of N-isopropylacrylamide with acrylic acid, methacrylic acid, 2-acryloylamido-2-methylpropane-sulfonic acid and itaconic acid, respectively [16].
 

Gene context of NSC3357

  • The effects of the isocitrate lyase-directed growth inhibitor itaconate on the growth of certain methylotrophic organisms was investigated [17].
  • It was shown that in cell extracts of R. rubrum itaconate inhibited propionyl-CoA carboxylase (PCC) activity [18].
  • We hypothesized that itaconate is incorporated into liver cells and suppresses fat synthesis by inhibiting liver glycolysis at the step of phosphofructokinase, which is activated by F26BP [1].
 

Analytical, diagnostic and therapeutic context of NSC3357

References

  1. Itaconate reduces visceral fat by inhibiting fructose 2,6-bisphosphate synthesis in rat liver. Sakai, A., Kusumoto, A., Kiso, Y., Furuya, E. Nutrition (Burbank, Los Angeles County, Calif.) (2004) [Pubmed]
  2. Efficient conversion of itaconic acid to (S)-(+)-citramalic acid by Alcaligenes xylosoxydans IL142. He, B.F., Ozawa, T., Nakajima-Kambe, T., Nakahara, T. J. Biosci. Bioeng. (2000) [Pubmed]
  3. Monitoring of itaconic acid hydrogenation in a trickle bed reactor using fiber-optic coupled near-infrared spectroscopy. Wood, J., Turner, P.H. Applied spectroscopy. (2003) [Pubmed]
  4. Identification of the gene and characterization of the activity of the trans-aconitate methyltransferase from Saccharomyces cerevisiae. Cai, H., Dumlao, D., Katz, J.E., Clarke, S. Biochemistry (2001) [Pubmed]
  5. Design and synthesis of new transition-state analogue inhibitors of aspartate transcarbamylase. Farrington, G.K., Kumar, A., Wedler, F.C. J. Med. Chem. (1985) [Pubmed]
  6. Synthesis and application of phosphinoferrocenylaminophosphine ligands for asymmetric catalysis. Boaz, N.W., Mackenzie, E.B., Debenham, S.D., Large, S.E., Ponasik, J.A. J. Org. Chem. (2005) [Pubmed]
  7. Itaconate biosynthesis in Aspergillus terreus. Bonnarme, P., Gillet, B., Sepulchre, A.M., Role, C., Beloeil, J.C., Ducrocq, C. J. Bacteriol. (1995) [Pubmed]
  8. Asymmetric hydrogenation of itaconic acid and enol acetate derivatives with the Rh-TangPhos catalyst. Tang, W., Liu, D., Zhang, X. Org. Lett. (2003) [Pubmed]
  9. In vitro swelling studies and preliminary biocompatibility evaluation of acrylamide-based hydrogels. Karadağ, E., Saraydin, D., Cetinkaya, S., Güven, O. Biomaterials (1996) [Pubmed]
  10. Factors affecting broadband acoustic emission measurements of a heterogeneous reaction. Nordon, A., Carella, Y., Gachagan, A., Littlejohn, D., Hayward, G. The Analyst. (2006) [Pubmed]
  11. Novel method for cell immobilization and its application for production of organic acid. Iqbal, M., Saeed, A. Lett. Appl. Microbiol. (2005) [Pubmed]
  12. A novel class of P-O monophosphite ligands derived from D-mannitol: broad applications in highly enantioselective Rh-catalyzed hydrogenations. Huang, H., Zheng, Z., Luo, H., Bai, C., Hu, X., Chen, H. J. Org. Chem. (2004) [Pubmed]
  13. Synthesis of chiral hydroxyl phospholanes from D-mannitol and their use in asymmetric catalytic reactions. Li, W., Zhang, Z., Xiao, D., Zhang, X. J. Org. Chem. (2000) [Pubmed]
  14. Unsymmetrical hybrid ferrocene-based phosphine-phosphoramidites: a new class of practical ligands for Rh-catalyzed asymmetric hydrogenation. Hu, X.P., Zheng, Z. Org. Lett. (2004) [Pubmed]
  15. Effect of pH and stirring rate on itaconate production by Aspergillus terreus. Riscaldati, E., Moresi, M., Federici, F., Petruccioli, M. J. Biotechnol. (2000) [Pubmed]
  16. Thermoprecipitation of lysozyme from egg white using copolymers of N-isopropylacrylamide and acidic monomers. Vaidya, A.A., Lele, B.S., Kulkarni, M.G., Mashelkar, R.A. J. Biotechnol. (2001) [Pubmed]
  17. Inhibition by itaconate of growth of methylotrophic bacteria. Bellion, E., Kelley, R.L. J. Bacteriol. (1979) [Pubmed]
  18. Inhibition of acetate and propionate assimilation by itaconate via propionyl-CoA carboxylase in isocitrate lyase-negative purple bacterium Rhodospirillum rubrum. Berg, I.A., Filatova, L.V., Ivanovsky, R.N. FEMS Microbiol. Lett. (2002) [Pubmed]
  19. Itaconic acid carrier ampholytes for isoelectric focusing. Brenna, O. J. Chromatogr. (1977) [Pubmed]
  20. Monitoring of a heterogeneous reaction by acoustic emission. Nordon, A., Waddell, R.J., Bellamy, L.J., Gachagan, A., McNab, D., Littlejohn, D., Hayward, G. The Analyst. (2004) [Pubmed]
  21. Identification of a novel series of alkylitaconic acids in wood cultures of Ceriporiopsis subvermispora by gas chromatography/mass spectrometry. del Río, J.C., Gutiérrez, A., Martínez, M.J., Martínez AT, A.T. Rapid Commun. Mass Spectrom. (2002) [Pubmed]
  22. A new NMR airlift bioreactor used in 31P-NMR studies of itaconic acid producing Aspergillus terreus. Lyngstad, M., Grasdalen, H. J. Biochem. Biophys. Methods (1993) [Pubmed]
 
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