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Chemical Compound Review

Succinyloxide     oxolane-2,5-dione

Synonyms: Rikacid SA, PubChem21337, Succinyl oxide, AGN-PC-00KE3R, HSDB 792, ...
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Disease relevance of HSDB 792


High impact information on HSDB 792

  • Treatments such as protease digestion and chemical modification with acetic anhydride, succinic anhydride, or diazobenzenesulfonic acid destroyed the TF1-binding activity, which was caused by band 6 protein [6].
  • Regioselective alkylation of an unsymmetrical succinic anhydride and a profound effect of pendent coordinating olefins on reaction rate suggest a mechanism involving discrete oxidative addition of the nickel complex into the cyclic anhydride followed by a transmetalation event [7].
  • The L'ELISA used succinic anhydride to derivatize glyphosate, which mimics the epitotic attachment of glyphosate to horseradish peroxidase hapten [8].
  • Three derivatizing agents were examined, the do and d3 forms of N-acetoxysuccinimide, the do and d4 forms of succinic anhydride, and the do and d8 forms of the commercial ICAT reagent Peptide mixtures from control and experimental samples were derivatized individually, mixed, subjected to reversed-phase chromatography, and analyzed by ESI-MS [9].
  • Removal of the Fmoc-group is followed by acylation with a succinic anhydride to introduce the final diversity elements [10].

Biological context of HSDB 792


Anatomical context of HSDB 792


Associations of HSDB 792 with other chemical compounds


Gene context of HSDB 792

  • Yeast hexokinase A (ATP:D-hexose 6-phosphotransferase, EC2.7.1.1) dissociates into its subunits upon reaction with succinic anhydride [26].
  • We succeeded, by using an original approach based upon immunization with ACTH derivatized with succinic anhydride, in raising monoclonal antibodies against this poorly immunogenic peptide [27].
  • Succinylated derivatives of the regulatory subunit of aspartate transcarbamylase of Escherichia coli were prepared by treating the intact enzyme with succinic anhydride followed by dissociation of the modified protein into catalytic and regulatory subunits which were separated by ion exchange chromatography [28].
  • Alanine aminotransferase has been stabilized by using chemical modification with both bis(imidates) (of varying length) and succinic anhydride [29].
  • The optimal conditions for synthesis of Chol HS were explored by checkerboard experiments in which various succinic anhydride/Chol molar ratios ranging from 5:1 to 30:1 were assayed over a wide temperature range (50-85 degrees C) and for various incubation times (3-8 h) [23].

Analytical, diagnostic and therapeutic context of HSDB 792

  • The isolation procedure, which results in a 20,000-fold purification and an overall yield of 15%, employs chromatography on a gel of octyl succinic anhydride coupled to agarose by diaminohexane spacers, isoelectric focusing, Sephadex G-75 chromatography, and DNA agarose affinity chromatography [30].
  • The data reported in the present study show that after treatment by phthalic or succinic anhydride the adjuvant activity of WSA was markedly changed, since high levels of circulating antibodies were produced when these derivatives were administered with an antigen in an aqueous medium [31].
  • Subunits observed to be most accessible or reactive to succinic anhydride were core protein II, the iron-sulfur protein, and polypeptides of SDS-PAGE bands 7,8, and 9 [32].
  • Arrays were blocked with either succinic anhydride (SA), bovine serum albumin (BSA) or left unblocked prior to hybridization with labeled PCR product [33].


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  2. Treatment with succinic anhydride improves the immunogenicity of Shigella flexneri type 2a O-specific polysaccharide-protein conjugates in mice. Pavliakova, D., Chu, C., Bystricky, S., Tolson, N.W., Shiloach, J., Kaufman, J.B., Bryla, D.A., Robbins, J.B., Schneerson, R. Infect. Immun. (1999) [Pubmed]
  3. X-ray crystallographic and mass spectrometric structure determination and functional characterization of succinylated porin from Rhodobacter capsulatus: implications for ion selectivity and single-channel conductance. Przybylski, M., Glocker, M.O., Nestel, U., Schnaible, V., Blüggel, M., Diederichs, K., Weckesser, J., Schad, M., Schmid, A., Welte, W., Benz, R. Protein Sci. (1996) [Pubmed]
  4. Amino groups in Clostridium perfringens epsilon prototoxin and epsilon toxin. Sakurai, J., Nagahama, M. Microb. Pathog. (1986) [Pubmed]
  5. Study of different coupling agents in the conjugation of a V3-based synthetic MAP to carrier proteins. Cruz, L.J., Iglesias, E., Aguilar, J.C., Quintana, D., Garay, H.E., Duarte, C., Reyes, O. J. Pept. Sci. (2001) [Pubmed]
  6. Resolution of the membrane moiety of the H+-ATPase complex into two kinds of subunits. Sone, N., Yoshida, M., Hirata, H., Kagawa, Y. Proc. Natl. Acad. Sci. U.S.A. (1978) [Pubmed]
  7. Highly efficient nickel-catalyzed cross-coupling of succinic and glutaric anhydrides with organozinc reagents. Bercot, E.A., Rovis, T. J. Am. Chem. Soc. (2005) [Pubmed]
  8. Linker-assisted immunoassay and liquid chromatography/mass spectrometry for the analysis of glyphosate. Lee, E.A., Zimmerman, L.R., Bhullar, B.S., Thurman, E.M. Anal. Chem. (2002) [Pubmed]
  9. Fractionation of isotopically labeled peptides in quantitative proteomics. Zhang, R., Sioma, C.S., Wang, S., Regnier, F.E. Anal. Chem. (2001) [Pubmed]
  10. The solid-phase synthesis of novel 14-membered macrocycles for high throughput screening. Lanter, C.L., Guiles, J.W., Rivero, R.A. Mol. Divers. (1998) [Pubmed]
  11. Selective antibodies to methadone enantiomers: synthesis of (R)- and (R,S)-methadone conjugates and determination by an immunoenzymatic method in human serum. Chikhi-Chorfi, N., Galons, H., Pham-Huy, C., Thevenin, M., Warnet, J.M., Claude, J.R. Chirality. (2001) [Pubmed]
  12. Solvent free vapor phase photografting of maleic anhydride onto poly(ethylene terephthalate) and surface coupling of fluorinated probes, PEG, and an RGD-peptide. Wirsén, A., Sun, H., Emilsson, L., Albertsson, A.C. Biomacromolecules (2005) [Pubmed]
  13. Antibody specificity to the chemical structures of organic acid anhydrides studied by in-vitro and in-vivo methods. Zhang, X.D., Lötvall, J., Skerfving, S., Welinder, H. Toxicology (1997) [Pubmed]
  14. Chemical modification of protein surfaces to improve their reversible enzyme immobilization on ionic exchangers. Montes, T., Grazu, V., L??pez-Gallego, F., Hermoso, J.A., Guisan, J.M., Fernandez-Lafuente, R. Biomacromolecules (2006) [Pubmed]
  15. Curing kinetics of o-cresol formaldehyde epoxy resin and succinic anhydride system catalyzed by tertiary amine. Ma, Z., Gao, J. The journal of physical chemistry. B, Condensed matter, materials, surfaces, interfaces & biophysical. (2006) [Pubmed]
  16. Succinylated copper, zinc superoxide dismutase. A novel approach to the problem of active subunits. Marmocchi, F., Mavelli, I., Rigo, A., Stevanato, R., Bossa, F., Rotilio, G. Biochemistry (1982) [Pubmed]
  17. Voltage dependence and ion selectivity of the mitochondrial channel, VDAC, are modified by succinic anhydride. Doring, C., Colombini, M. J. Membr. Biol. (1985) [Pubmed]
  18. The mitochondrial voltage-dependent channel, VDAC, is modified asymmetrically by succinic anhydride. Doring, C., Colombini, M. J. Membr. Biol. (1985) [Pubmed]
  19. Succinylation of proteins associated with the ribosomal attachment site on microsomal membranes. Burden, T.S. Hoppe-Seyler's Z. Physiol. Chem. (1976) [Pubmed]
  20. Shear bond strength to dentin and Ni-Cr-Be alloy with the All-Bond universal adhesive system. Barkmeier, W.W., Suh, B.I., Cooley, R.L. Journal of esthetic dentistry. (1991) [Pubmed]
  21. Role of matrix protein in assembling the membrane of vesicular stomatitis virus: reconstitution of matrix protein with negatively charged phospholipid vesicles. Zakowski, J.J., Petri, W.A., Wagner, R.R. Biochemistry (1981) [Pubmed]
  22. Comparative kinetic study between native and chemically modified Cu,Zn superoxide dismutases. Argese, E., Girotto, R., Orsega, E.F. Biochem. J. (1993) [Pubmed]
  23. An improved method for the microscale preparation and characterization of hapten-protein conjugates: the use of cholesterol as a model for nonchromophore hydroxylated haptens. Naar, J., Branaa, P., Chinain, M., Pauillac, S. Bioconjug. Chem. (1999) [Pubmed]
  24. The influence of a residual group in low-molecular-weight allergoids of Artemisia vulgaris pollen on their allergenicity, IgE- and IgG-binding properties. Cirković, T., Gavrović-Jankulović, M., Prisić, S., Jankov, R.M., Burazer, L., Vucković, O., Sporcić, Z., Paranos, S. Allergy (2002) [Pubmed]
  25. Patch clamping the outer mitochondrial membrane. Tedeschi, H., Mannella, C.A., Bowman, C.L. J. Membr. Biol. (1987) [Pubmed]
  26. Yeast hexokinase A. Succinylation and properties of the active subunit. Rossi, A., Menezes, L.C., Pudles, J. Eur. J. Biochem. (1975) [Pubmed]
  27. Immunoradiometric assay of succinylated corticotropin: an improved method for quantification of ACTH. Kertesz, G., Bourcier, B., Cailla, H., Jean, F. Clin. Chem. (1998) [Pubmed]
  28. Cooperative interactions in hybrids of aspartate transcarbamylase containing succinylated regulatory polypeptide chains. Nagel, G.M., Schachman, H.K. Biochemistry (1975) [Pubmed]
  29. Application of adsorptive voltammetry to assess the stability of modified alanine aminotransferases. Fernández Alvarez, J.M., O'Fagain, C., O'Kennedy, R., Kilty, C.G., Smyth, M.R. Anal. Chem. (1990) [Pubmed]
  30. Human placental apurinic/apyrimidinic endonuclease. Its isolation and characterization. Shaper, N.L., Grafstrom, R.H., Grossman, L. J. Biol. Chem. (1982) [Pubmed]
  31. Activity in saline of phthalylated or succinylated derivatives of mycobacterial water-soluble adjuvant. Audibert, F., Chedid, L. Infect. Immun. (1976) [Pubmed]
  32. Differential labeling of the subunits of respiratory complex III with [3H]succinic anhydride, [14C]succinic anhydride, and p-diazobenzene-[35S]sulfonate. Ho, S.H., Rieske, J.S. J. Bioenerg. Biomembr. (1985) [Pubmed]
  33. Impact of surface chemistry and blocking strategies on DNA microarrays. Taylor, S., Smith, S., Windle, B., Guiseppi-Elie, A. Nucleic Acids Res. (2003) [Pubmed]
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