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Chemical Compound Review

levulate     4-oxopentanoic acid

Synonyms: levulinate, laevulinate, LEVA, Levulinsaeure, g-Ketovalerate, ...
 
 
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Disease relevance of Acetopropionic acid

  • The crystal structure of the Mg2+-dependent PBGS from the human pathogen Pseudomonas aeruginosa in complex with the competitive inhibitor levulinic acid (LA) solved at 1.67 A resolution shows a homooctameric enzyme that consists of four asymmetric dimers [1].
  • The X-ray structure of the plant like 5-aminolaevulinic acid dehydratase from Chlorobium vibrioforme complexed with the inhibitor laevulinic acid at 2.6 A resolution [2].
  • Previous research showed that the heme-requiring human pathogen Haemophilus influenzae lacks the first six of the seven enzymes required for heme synthesis, starting with the precursor, 5-amino levulinic acid [3].
  • For PDT, delta-amino laevulinic acid at a dose of 60 mg/kg of body weight was intravenously administered 60 min before irradiation at 635 nm [4].
  • The recombinant Propionibacterium produced ALA at a maximum concentration of 8.6 mM in the absence of levulinic acid, an inhibitor of ALA dehydratase, with 1% glucose as a carbon source [5].
 

Psychiatry related information on Acetopropionic acid

  • Studies were carried out on the effects of temperature, acid concentration, liquid:solid ratio and reaction time on levulinic acid production from wheat straw using response surface methodology [6].
 

High impact information on Acetopropionic acid

  • In the presence of levulinic acid, an inhibitor of haem biosynthesis, apocytochrome c550 and aponitrite reductase (cytochrome cd1) accumulated in the periplasm of wild-type cells [7].
  • The active site contains two invariant lysine residues (200 and 253), one of which (Lys253) forms a Schiff base link with the bound substrate analogue, laevulinic acid [2].
  • Inconsistent changes were noted in erythrocyte delta-amino levulinic acid dehydratase, plasma alkaline ribonuclease and the serum alkaline phosphatase isoenzymes [8].
  • Adenosine immunolocalization was performed on frozen sections with an antibody against adenosine conjugated to laevulinic acid using a streptavidin peroxidase technique [9].
  • Finally, we succeeded in obtaining well-ordered crystals of P. aeruginosa PBGS complexed with the substrate analogue levulinic acid [10].
 

Chemical compound and disease context of Acetopropionic acid

 

Biological context of Acetopropionic acid

  • A single molecule of LA binds to a mainly hydrophobic pocket in each monomer where it is covalently attached via a Schiff base to an active site lysine residue [1].
  • When levulinic acid was added to a growing culture of the cyanobacterium (blue-green alga) Agmenellum quadruplicatum PR-6, delta-aminoelevulinic acid accumulated in the medium and chlorophyll a synthesis and cell growth were inhibited, but there was a small amount of c-phycocyanin synthesis [13].
  • Stimulation of Friend erythroleukemic cell cytodifferentiation by 5-amino levulinic acid; porphyrins, cell size, segregation of sialoglycoproteins, and nuclear translocation [14].
  • The equilibrium and kinetics of levulinic acid (LA) adsorption on two basic polymeric adsorbents, 335 (highly porous gel) and D315 (macroreticular), were investigated [15].
  • Growth and PHA accumulation enhancement were observed with concentrations of levulinic acid from 0.07 to 0.52% (w/v), producing dry cell biomass and P(3HB-co-3HV) yields of 9.5 and 4.2 g/L, respectively, at the 0.52% (w/v) concentration of levulinic acid [16].
 

Anatomical context of Acetopropionic acid

  • No differences were found in hepatic delta-amino levulinic acid dehydrase activity, or in the rate of oxygen uptake, ADP:O ratios or respiratory control index between mitochondria from normal and WMD lamb tissue on any of the treatments [17].
  • The photosensitizing agent 5-amino levulinic acid, converted in vivo into the photoactive derivative protoporphyrin IX, sensitizes the mucosa much more than the underlying layers [18].
  • The recombinant P. freudenreichii accumulated 18.8 mmol/g cells ALA in the presence of 1 mM levulinic acid and 30 mM glycine [5].
  • Changes in several biologic indexes (depression of delta-amino levulinic acid dehydratase in kidney and red blood cells, presence of renal intranuclear inclusion bodies, and increased kidney weight) confirmed lead-poisoning in urban rats [19].
  • Radiolabeled phycocyanin and allophycocyanin were isolated from protoplast preparations which had been incubated with L-[U-14]leucine or delta-amino[4-14C] levulinic acid (a precursor of phycocyanobilin) [20].
 

Associations of Acetopropionic acid with other chemical compounds

 

Gene context of Acetopropionic acid

  • In our analyses, 2-methyl-1-pyrroline and laevulinic acid were identified by HPLC and mass spectroscopic analysis, and ammonia was identified by means of glutamate dehydrogenase [26].
  • In this aerobic yeast, cytochrome c+c1 is the most sensitive to levulinic acid, and cytochrome b exhibits intermediate sensitivity [27].
  • Induction of cytochrome P-450 was accompanied by induction of delta-amino levulinic acid synthetase in lung and inhibition of heme oxygenase in both lung and liver [28].
  • It is emphasized that the U.K. favours blood lead estimation, the EEC countries other than Britain use blood lead but are considering more widespread use of delta-amino laevulinic acid dehydratase estimation in blood [29].
  • Levulinic acid (LA; 30 mM) was fed to the fermentation broth at the end of the exponential cell growth phase (about 8 h), and the intracellular activity of ALA dehydratase was efficaciously suppressed [30].
 

Analytical, diagnostic and therapeutic context of Acetopropionic acid

References

  1. High resolution crystal structure of a Mg2+-dependent porphobilinogen synthase. Frankenberg, N., Erskine, P.T., Cooper, J.B., Shoolingin-Jordan, P.M., Jahn, D., Heinz, D.W. J. Mol. Biol. (1999) [Pubmed]
  2. The X-ray structure of the plant like 5-aminolaevulinic acid dehydratase from Chlorobium vibrioforme complexed with the inhibitor laevulinic acid at 2.6 A resolution. Coates, L., Beaven, G., Erskine, P.T., Beale, S.I., Avissar, Y.J., Gill, R., Mohammed, F., Wood, S.P., Shoolingin-Jordan, P., Cooper, J.B. J. Mol. Biol. (2004) [Pubmed]
  3. Ferrochelatase activity and protoporphyrin IX utilization in Haemophilus influenzae. Loeb, M.R. J. Bacteriol. (1995) [Pubmed]
  4. Tumour vessel damage resulting from laser-induced hyperthermia alone and in combination with photodynamic therapy. Liu, D.L., Andersson-Engels, S., Sturesson, C., Svanberg, K., Håkansson, C.H., Svanberg, S. Cancer Lett. (1997) [Pubmed]
  5. Construction of an expression vector for propionibacteria and its use in production of 5-aminolevulinic acid by Propionibacterium freudenreichii. Kiatpapan, P., Murooka, Y. Appl. Microbiol. Biotechnol. (2001) [Pubmed]
  6. Levulinic acid production from wheat straw. Chang, C., Cen, P., Ma, X. Bioresour. Technol. (2007) [Pubmed]
  7. Apo forms of cytochrome c550 and cytochrome cd1 are translocated to the periplasm of Paracoccus denitrificans in the absence of haem incorporation caused either mutation or inhibition of haem synthesis. Page, M.D., Ferguson, S.J. Mol. Microbiol. (1990) [Pubmed]
  8. Nitrogen utilization, enzyme activity, glucose intolerance and leukocyte chemotaxis in human experimental zinc depletion. Baer, M.T., King, J.C., Tamura, T., Margen, S., Bradfield, R.B., Weston, W.L., Daugherty, N.A. Am. J. Clin. Nutr. (1985) [Pubmed]
  9. 5' nucleotidase and adenosine during retinal vasculogenesis and oxygen-induced retinopathy. Lutty, G.A., Merges, C., McLeod, D.S. Invest. Ophthalmol. Vis. Sci. (2000) [Pubmed]
  10. Production, purification, and characterization of a Mg2+-responsive porphobilinogen synthase from Pseudomonas aeruginosa. Frankenberg, N., Heinz, D.W., Jahn, D. Biochemistry (1999) [Pubmed]
  11. On the formation of the mixed pyrrole catalysed by porphobilinogen synthase from Rhodobacter spheroides. Lüönd, R.M., Neier, R. Biochim. Biophys. Acta (1996) [Pubmed]
  12. Polyhydroxyalkanoate copolymers from forest biomass. Keenan, T.M., Nakas, J.P., Tanenbaum, S.W. J. Ind. Microbiol. Biotechnol. (2006) [Pubmed]
  13. Effect of levulinic acid on pigment biosynthesis in Agmenellum quadruplicatum. Kipe-Nolt, J.A., Stevens, S.E. J. Bacteriol. (1979) [Pubmed]
  14. Stimulation of Friend erythroleukemic cell cytodifferentiation by 5-amino levulinic acid; porphyrins, cell size, segregation of sialoglycoproteins, and nuclear translocation. Malik, Z., Lugaci, H., Hanania, J. Exp. Hematol. (1988) [Pubmed]
  15. Parallel pore and surface diffusion of levulinic acid in basic polymeric adsorbents. Liu, B., Yang, Y., Ren, Q. Journal of chromatography. A. (2006) [Pubmed]
  16. Production and characterization of poly-beta-hydroxyalkanoate copolymers from Burkholderia cepacia utilizing xylose and levulinic acid. Keenan, T.M., Tanenbaum, S.W., Stipanovic, A.J., Nakas, J.P. Biotechnol. Prog. (2004) [Pubmed]
  17. Effects of selenium and vitamin E deficiencies in lambs on hepatic microsomal hemoproteins and mitochondrial respiration. Whanger, P.D., Tripp, M.J., Weswig, P.H. J. Nutr. (1977) [Pubmed]
  18. New photosensitizers for photodynamic therapy in gastroenterology. Bown, S.G., Rogowska, A.Z. Can. J. Gastroenterol. (1999) [Pubmed]
  19. Lead. Possible toxicity in urban vs rural rats. Mouw, D., Kalitis, K., Anver, M., Schwartz, J., Constan, A., Hartung, R., Cohen, B., Ringler, D. Arch. Environ. Health (1975) [Pubmed]
  20. Phycobiliprotein synthesis in protoplasts of the unicellular cyanophyte, Anacystis nidulans. Cosner, J.C., Troxler, R.F. Biochim. Biophys. Acta (1978) [Pubmed]
  21. Determinations of tiodazosin and levulinic acid from tablets by high-performance liquid chromatography. Prosser, B.C., Floor, B.J., Klein, A.E., Muhammad, N. Journal of pharmaceutical sciences. (1983) [Pubmed]
  22. Photodynamic therapy in gastroenterology--current status and future prospects. Bown, S.G. Endoscopy. (1993) [Pubmed]
  23. Development of a process for the biotechnological large-scale production of 4-hydroxyvalerate-containing polyesters and characterization of their physical and mechanical properties. Gorenflo, V., Schmack, G., Vogel, R., Steinbüchel, A. Biomacromolecules (2001) [Pubmed]
  24. Labelled acetone and levulinic acid are formed when [14C]acetate is being converted to mycophenolic acid in Penicillium brevicompactum. Nulton, C.P., Campbell, I.M. Can. J. Microbiol. (1978) [Pubmed]
  25. A compartmental model for bilirubin kinetics in isolated perfused rat liver. Anwer, M.S., Gronwall, R. Can. J. Physiol. Pharmacol. (1976) [Pubmed]
  26. Ornithine and glutamate decarboxylases catalyse an oxidative deamination of their alpha-methyl substrates. Bertoldi, M., Carbone, V., Borri Voltattorni, C. Biochem. J. (1999) [Pubmed]
  27. Modulation of cytochrome biosynthesis in yeast by antimetabolite action of levulinic acid. Malamud, D.R., Borralho, L.M., Panek, A.D., Mattoon, J.R. J. Bacteriol. (1979) [Pubmed]
  28. Induction of pulmonary and hepatic cytochrome P-450 species by coal fly ash inhalation in rats. Chauhan, S.S., Singh, S.K., Misra, U.K. Toxicology (1989) [Pubmed]
  29. Tests available for assessing recent exposure to inorganic lead compounds and their use for screening purposes. Roots, L.M. Sci. Total Environ. (1979) [Pubmed]
  30. Effects of medium composition on production of 5-aminolevulinic acid by recombinant Escherichia coli. Qin, G., Lin, J., Liu, X., Cen, P. J. Biosci. Bioeng. (2006) [Pubmed]
  31. Laser Doppler perfusion imaging: new technique for determination of perfusion and reperfusion of splanchnic organs and tumor tissue. Liu, D.L., Svanberg, K., Wang, I., Andersson-Engels, S., Svanberg, S. Lasers in surgery and medicine. (1997) [Pubmed]
  32. Laser-induced fluorescence studies of normal and malignant tumour tissue of rat following intravenous injection of delta-amino levulinic acid. Johansson, J., Berg, R., Svanberg, K., Svanberg, S. Lasers in surgery and medicine. (1997) [Pubmed]
 
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