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Chemical Compound Review

o-Phthalaldehyde     phthalaldehyde

Synonyms: OPTA, phthalaldehyd, PHTHALALDEHYDE, Phtalaldehydes, o-Phthaldehyde, ...
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Disease relevance of o-Phthaldialdehyde


High impact information on o-Phthaldialdehyde


Chemical compound and disease context of o-Phthaldialdehyde


Biological context of o-Phthaldialdehyde

  • Identification of Tyr-93 as the site of alkylation was confirmed by radiosequence analysis utilizing o-phthalaldehyde to establish that the released 3H originated from a peptide containing prolines at residues 2 and 9 [14].
  • Inactivation of the catalytic subunit by o-phthalaldehyde is probably due to the concomitant modification of lysine-72 and cysteine-199 [15].
  • In vivo phosphorylation of FTY720 (1) in rats and humans resulted exclusively in the biologically active (S)-configured enantiomer, which was proven by an ex vivo o-phthaldialdehyde derivatization protocol especially elaborated for phosphates of 1 [16].
  • We have analyzed free chiral amino acids (aspartate and serine) in the human frontal cortex at different ontogenic stages (from 14 weeks of gestation to 101 years of age) by HPLC with fluorometric detection after derivatization with N-tert-butyl-oxycarbonyl-L-cysteine and o-phthaldialdehyde [17].
  • Kinetic analysis of o-phthalaldehyde medicated inactivation showed that the reaction followed pseudo-first-order kinetics and the loss of enzyme activity was due to the formation of a single isoindole derivative per molecule of the enzyme [18].

Anatomical context of o-Phthaldialdehyde


Associations of o-Phthaldialdehyde with other chemical compounds


Gene context of o-Phthaldialdehyde


Analytical, diagnostic and therapeutic context of o-Phthaldialdehyde


  1. Mechanism of inactivation of Escherichia coli 5-enolpyruvoylshikimate-3-phosphate synthase by o-phthalaldehyde. Huynh, Q.K. J. Biol. Chem. (1990) [Pubmed]
  2. Excitatory amino acids in cerebrospinal fluid of patients with acute head injuries. Zhang, H., Zhang, X., Zhang, T., Chen, L. Clin. Chem. (2001) [Pubmed]
  3. Quantitation of free amino acids in biological samples by high-performance liquid chromatography. Application of the method in evaluating amino acid levels in cerebrospinal fluid and plasma of patients with multiple sclerosis. Qureshi, G.A., Baig, M.S. J. Chromatogr. (1988) [Pubmed]
  4. Quantitative analysis of glutathione in human brain tumors. Kudo, H., Mio, T., Kokunai, T., Tamaki, N., Sumino, K., Matsumoto, S. J. Neurosurg. (1990) [Pubmed]
  5. The use of the o-phthalaldehyde reaction as a sensitive assay for protein and to determine protein in bacterial cells and dental plaque. Robrish, S.A., Kemp, C., Bowen, W.H. Anal. Biochem. (1978) [Pubmed]
  6. Forearm 3-methylhistidine efflux in myotonic dystrophy. Rifai, Z., Kingston, W.J., McCraith, B., Moxley, R.T. Ann. Neurol. (1993) [Pubmed]
  7. Separation and identification of major plant sphingolipid classes from leaves. Markham, J.E., Li, J., Cahoon, E.B., Jaworski, J.G. J. Biol. Chem. (2006) [Pubmed]
  8. Inhibition of 1,4-beta-D-xylan xylanohydrolase by the specific aspartic protease inhibitor pepstatin: probing the two-step inhibition mechanism. Vathipadiekal, V., Rao, M. J. Biol. Chem. (2004) [Pubmed]
  9. Ceramide generation by the Reaper protein is not blocked by the caspase inhibitor, p35. Bose, R., Chen, P., Loconti, A., Grüllich, C., Abrams, J.M., Kolesnick, R.N. J. Biol. Chem. (1998) [Pubmed]
  10. Inactivation of chicken mitochondrial phosphoenolpyruvate carboxykinase by o-phthalaldehyde. Chen, C.Y., Emig, F.A., Schramm, V.L., Ash, D.E. J. Biol. Chem. (1991) [Pubmed]
  11. Studies on the inactivation of Leuconostoc mesenteroides NRRL B-512F dextransucrase by o-phthalaldehyde: evidence for the presence of an essential lysine residue at the active site. Goyal, A., Katiyar, S.S. J. Enzym. Inhib. (1998) [Pubmed]
  12. Assessing the residual antibacterial activity of clinical materials disinfected with glutaraldehyde, o-phthalaldehyde, hydrogen peroxide or 2-bromo-2-nitro-1,3-propanediol by means of a bacterial toxicity assay. Lerones, C., Mariscal, A., Carnero, M., García-Rodríguez, A., Fernández-Crehuet, J. Clin. Microbiol. Infect. (2004) [Pubmed]
  13. Plasma level of a 5-fluorouracil metabolite, fluoro-beta-alanine correlates with dihydropyrimidine dehydrogenase activity of peripheral blood mononuclear cells in 5-fluorouracil treated patients. Furuhata, T., Kawakami, M., Okita, K., Kimura, Y., Kihara, C., Tsuruma, T., Ohmura, T., Yamaguchi, K., Hata, F., Katsuramaki, T., Sasaki, K., Hirata, K. J. Exp. Clin. Cancer Res. (2006) [Pubmed]
  14. Structure of the agonist-binding site of the nicotinic acetylcholine receptor. [3H]acetylcholine mustard identifies residues in the cation-binding subsite. Cohen, J.B., Sharp, S.D., Liu, W.S. J. Biol. Chem. (1991) [Pubmed]
  15. Adenosine cyclic 3',5'-monophosphate dependent protein kinase: fluorescent affinity labeling of the catalytic subunit from bovine skeletal muscle with o-phthalaldehyde. Puri, R.N., Bhatnagar, D., Roskoski, R. Biochemistry (1985) [Pubmed]
  16. Novel immunomodulator FTY720 is phosphorylated in rats and humans to form a single stereoisomer. Identification, chemical proof, and biological characterization of the biologically active species and its enantiomer. Albert, R., Hinterding, K., Brinkmann, V., Guerini, D., Müller-Hartwieg, C., Knecht, H., Simeon, C., Streiff, M., Wagner, T., Welzenbach, K., Zécri, F., Zollinger, M., Cooke, N., Francotte, E. J. Med. Chem. (2005) [Pubmed]
  17. Embryonic development and postnatal changes in free D-aspartate and D-serine in the human prefrontal cortex. Hashimoto, A., Kumashiro, S., Nishikawa, T., Oka, T., Takahashi, K., Mito, T., Takashima, S., Doi, N., Mizutani, Y., Yamazaki, T. J. Neurochem. (1993) [Pubmed]
  18. S1 nuclease: immunoaffinity purification and evidence for the proximity of cysteine 25 to the substrate binding site. Gite, S., Shankar, V. J. Mol. Recognit. (1995) [Pubmed]
  19. Labelling the Ca(2+)-ATPase of skeletal-muscle sarcoplasmic reticulum with the cross-linker o-phthalaldehyde. Khan, Y.M., Wictome, M., East, J.M., Lee, A.G. Biochem. J. (1996) [Pubmed]
  20. The mechanism of inhibition of the Ca(2+)-ATPase of skeletal-muscle sarcoplasmic reticulum by the cross-linker o-phthalaldehyde. Khan, Y.M., Starling, A.P., East, J.M., Lee, A.G. Biochem. J. (1996) [Pubmed]
  21. Automated assay of gamma-aminobutyric acid in human cerebrospinal fluid. Böhlen, P., Schechter, P.J., van Damme, W., Coquillat, G., Dosch, J.C., Koch-Weser, J. Clin. Chem. (1978) [Pubmed]
  22. Specific cross-links between fragments of proteolyzed Na,K-ATPase induced by o-phthalaldehyde. Or, E., Goldshleger, R., Shainskaya, A., Karlish, S.J. Biochemistry (1998) [Pubmed]
  23. Performance of throughout in-capillary derivatization capillary electrophoresis employing an on-line sample and run buffer loading device. Oguri, S., Hibino, M., Mizunuma, M. Electrophoresis (2004) [Pubmed]
  24. Succinic semialdehyde dehydrogenase. Reactivity of lysyl residues. Blaner, W.S., Churchich, J. J. Biol. Chem. (1979) [Pubmed]
  25. Asymmetric dimethylarginine plasma concentrations differ in patients with end-stage renal disease: relationship to treatment method and atherosclerotic disease. Kielstein, J.T., Böger, R.H., Bode-Böger, S.M., Schäffer, J., Barbey, M., Koch, K.M., Frölich, J.C. J. Am. Soc. Nephrol. (1999) [Pubmed]
  26. Measurement of urinary histamine: development of methodology and normal values. Myers, G., Donlon, M., Kaliner, M. J. Allergy Clin. Immunol. (1981) [Pubmed]
  27. Measurement of plasma histamine: description of an improved method and normal values. Dyer, J., Warren, K., Merlin, S., Metcalfe, D.D., Kaliner, M. J. Allergy Clin. Immunol. (1982) [Pubmed]
  28. Separation of enantiomers of N-acetylcysteine by capillary electrophoresis after derivatization by o-phthaldialdehyde. Dette, C., Wätzig, H. Electrophoresis (1994) [Pubmed]
  29. Studies on NG-methylarginine derivatives in myelin basic protein from developing and mutant mouse brain. Rawal, N., Lee, Y.J., Paik, W.K., Kim, S. Biochem. J. (1992) [Pubmed]
  30. Inactivation of yeast hexokinase by o-phthalaldehyde: evidence for the presence of a cysteine and a lysine at or near the active site. Puri, R.N., Bhatnagar, D., Roskoski, R. Biochim. Biophys. Acta (1988) [Pubmed]
  31. Accumulation of galactosylsphingosine (psychosine) in the twitcher mouse: determination by HPLC. Shinoda, H., Kobayashi, T., Katayama, M., Goto, I., Nagara, H. J. Neurochem. (1987) [Pubmed]
  32. Sequence analysis of rat hypothalamic corticotropin-releasing factor with the o-phthalaldehyde strategy. Spiess, J., Rivier, J., Vale, W. Biochemistry (1983) [Pubmed]
  33. Kinetic centrifugal analyzer and manual determination of serum urea nitrogen, with use of o-phthaldialdehyde reagent. Levinson, S.S. Clin. Chem. (1978) [Pubmed]
  34. Determination of ammonium ion by fluorometry or spectrophotometry after on-line derivatization with o-phthalaldehyde. Goyal, S.S., Rains, D.W., Huffaker, R.C. Anal. Chem. (1988) [Pubmed]
  35. Precolumn diastereomerization and micellar electrokinetic chromatography on a plastic microchip: rapid chiral analysis of amino acids. Ro, K.W., Hahn, J.H. Electrophoresis (2005) [Pubmed]
  36. Derivatization of ephedrine with o-phthaldialdehyde for liquid chromatography after treatment with sodium hypochlorite. Herráez-Herández, R., Campíns-Falcó, P. Journal of chromatography. A. (2000) [Pubmed]
  37. A comparison of fluorescamine and o-phthaldialdehyde as effective blocking reagents in protein sequence analyses by the Beckman sequencer. Bhown, A.S., Cornelius, T.W., Volanakis, J.E., Bennett, J.C. Anal. Biochem. (1983) [Pubmed]
  38. Separation and o-phthaldehyde fluorometric determination of 5-hydroxy- and 5-methoxyindoleamines by thin-layer chromatography: selected applications. Arqué, J.M., Serrano, J., de Leiva, A., Segura, R. Anal. Biochem. (1988) [Pubmed]
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