phenylglyoxal

Summary

Summary: A reagent that is highly selective for the modification of arginyl residues. It is used to selectively inhibit various enzymes and acts as an energy transfer inhibitor in photophosphorylation.

Top Publications

  1. Linder M, Morkunaite Haimi S, Kinnunen P, Bernardi P, Eriksson O. Ligand-selective modulation of the permeability transition pore by arginine modification. Opposing effects of p-hydroxyphenylglyoxal and phenylglyoxal. J Biol Chem. 2002;277:937-42 pubmed
    Chemical modification of mitochondria with the arginine-specific reagents phenylglyoxal (PGO) and 2,3-butanedione (BAD) decreases the Ca(2+) sensitivity of the permeability transition pore (PTP) and stabilizes it in the closed ..
  2. Forster I, Kohler K, Stange G, Biber J, Murer H. Modulation of renal type IIa Na+/Pi cotransporter kinetics by the arginine modifier phenylglyoxal. J Membr Biol. 2002;187:85-96 pubmed
    The effects of the arginine-modifying reagent phenylglyoxal on the kinetics of the type IIa Na + /Pi cotransporter expressed in Xenopus, oocytes were studied by means of 32Pi uptake and electrophysiology...
  3. Johans M, Milanesi E, Franck M, Johans C, Liobikas J, Panagiotaki M, et al. Modification of permeability transition pore arginine(s) by phenylglyoxal derivatives in isolated mitochondria and mammalian cells. Structure-function relationship of arginine ligands. J Biol Chem. 2005;280:12130-6 pubmed
    ..In this study, we have investigated how the binding of a panel of synthetic phenylglyoxal derivatives influences the opening and closing of the PTP...
  4. Bicker K, Subramanian V, Chumanevich A, Hofseth L, Thompson P. Seeing citrulline: development of a phenylglyoxal-based probe to visualize protein citrullination. J Am Chem Soc. 2012;134:17015-8 pubmed publisher
    ..For this reason, we developed a citrulline-specific chemical probe, rhodamine-phenylglyoxal (Rh-PG), which we show can be used to investigate protein citrullination...
  5. Calderón Montaño J, Burgos Morón E, Orta M, Pastor N, Pérez Guerrero C, Austin C, et al. Guanidine-reactive agent phenylglyoxal induces DNA damage and cancer cell death. Pharmacol Rep. 2012;64:1515-25 pubmed
    ..b>Phenylglyoxal is a dicarbonyl compound known to react with guanidine groups such as that of the DNA base guanine, therefore ..
  6. Meyer G, Porta C, Garavaglia M, Cremaschi D. Inhibitors of the Cl-/HCO3- exchanger activate an anion channel with similar features in the epithelial cells of rabbit gallbladder: patch-clamp analysis. Pflugers Arch. 2001;441:467-73 pubmed
    ..GCl), non-additively activated by some inhibitors of the Cl-/HCO3- exchanger (hydrochlorothiazide, phlorizin, phenylglyoxal) after the exchanger inhibition in the apical plasma membrane of rabbit gallbladder epithelium, has been ..
  7. Adak S, Bandyopadhyay D, Bandyopadhyay U, Banerjee R. An essential role of active site arginine residue in iodide binding and histidine residue in electron transfer for iodide oxidation by horseradish peroxidase. Mol Cell Biochem. 2001;218:1-11 pubmed
    ..The arginine specific reagent, phenylglyoxal (PGO) irreversibly blocks iodide oxidation following pseudofirst order kinetics with second order rate ..
  8. Adak S, Mazumder A, Banerjee R. Probing the active site residues in aromatic donor oxidation in horseradish peroxidase: involvement of an arginine and a tyrosine residue in aromatic donor binding. Biochem J. 1996;314 ( Pt 3):985-91 pubmed
    ..The arginine-specific reagents phenylglyoxal (PGO), 2,3-butanedione and 1,2-cyclohexanedione all inactivated the enzyme, following pseudo-first-order ..
  9. Campos M, Alarcón M, Gonzalez H, Carvajal N. An arginine residue at the active site of beta-lactamase from Shigella flexneri UCSF-129. Microbios. 1993;73:37-43 pubmed
    ..The enzyme was serine dependent with a molecular weight of 23.6 kD. It was specifically modified with phenylglyoxal (1/830 molar ratio) and incubated for 20 min in the presence of 50 mM sodium phosphate buffer at pH 8.3...
  10. Mousset C, Giraud A, Provot O, Hamze A, Bignon J, Liu J, et al. Synthesis and antitumor activity of benzils related to combretastatin A-4. Bioorg Med Chem Lett. 2008;18:3266-71 pubmed publisher
    ..These results clearly demonstrated that the Z-double bond of CA-4 can be replaced by a 1,2-diketone unit without significant loss of cytotoxicity and inhibition of tubulin assembly potency...

Detail Information

Publications62

  1. Linder M, Morkunaite Haimi S, Kinnunen P, Bernardi P, Eriksson O. Ligand-selective modulation of the permeability transition pore by arginine modification. Opposing effects of p-hydroxyphenylglyoxal and phenylglyoxal. J Biol Chem. 2002;277:937-42 pubmed
    Chemical modification of mitochondria with the arginine-specific reagents phenylglyoxal (PGO) and 2,3-butanedione (BAD) decreases the Ca(2+) sensitivity of the permeability transition pore (PTP) and stabilizes it in the closed ..
  2. Forster I, Kohler K, Stange G, Biber J, Murer H. Modulation of renal type IIa Na+/Pi cotransporter kinetics by the arginine modifier phenylglyoxal. J Membr Biol. 2002;187:85-96 pubmed
    The effects of the arginine-modifying reagent phenylglyoxal on the kinetics of the type IIa Na + /Pi cotransporter expressed in Xenopus, oocytes were studied by means of 32Pi uptake and electrophysiology...
  3. Johans M, Milanesi E, Franck M, Johans C, Liobikas J, Panagiotaki M, et al. Modification of permeability transition pore arginine(s) by phenylglyoxal derivatives in isolated mitochondria and mammalian cells. Structure-function relationship of arginine ligands. J Biol Chem. 2005;280:12130-6 pubmed
    ..In this study, we have investigated how the binding of a panel of synthetic phenylglyoxal derivatives influences the opening and closing of the PTP...
  4. Bicker K, Subramanian V, Chumanevich A, Hofseth L, Thompson P. Seeing citrulline: development of a phenylglyoxal-based probe to visualize protein citrullination. J Am Chem Soc. 2012;134:17015-8 pubmed publisher
    ..For this reason, we developed a citrulline-specific chemical probe, rhodamine-phenylglyoxal (Rh-PG), which we show can be used to investigate protein citrullination...
  5. Calderón Montaño J, Burgos Morón E, Orta M, Pastor N, Pérez Guerrero C, Austin C, et al. Guanidine-reactive agent phenylglyoxal induces DNA damage and cancer cell death. Pharmacol Rep. 2012;64:1515-25 pubmed
    ..b>Phenylglyoxal is a dicarbonyl compound known to react with guanidine groups such as that of the DNA base guanine, therefore ..
  6. Meyer G, Porta C, Garavaglia M, Cremaschi D. Inhibitors of the Cl-/HCO3- exchanger activate an anion channel with similar features in the epithelial cells of rabbit gallbladder: patch-clamp analysis. Pflugers Arch. 2001;441:467-73 pubmed
    ..GCl), non-additively activated by some inhibitors of the Cl-/HCO3- exchanger (hydrochlorothiazide, phlorizin, phenylglyoxal) after the exchanger inhibition in the apical plasma membrane of rabbit gallbladder epithelium, has been ..
  7. Adak S, Bandyopadhyay D, Bandyopadhyay U, Banerjee R. An essential role of active site arginine residue in iodide binding and histidine residue in electron transfer for iodide oxidation by horseradish peroxidase. Mol Cell Biochem. 2001;218:1-11 pubmed
    ..The arginine specific reagent, phenylglyoxal (PGO) irreversibly blocks iodide oxidation following pseudofirst order kinetics with second order rate ..
  8. Adak S, Mazumder A, Banerjee R. Probing the active site residues in aromatic donor oxidation in horseradish peroxidase: involvement of an arginine and a tyrosine residue in aromatic donor binding. Biochem J. 1996;314 ( Pt 3):985-91 pubmed
    ..The arginine-specific reagents phenylglyoxal (PGO), 2,3-butanedione and 1,2-cyclohexanedione all inactivated the enzyme, following pseudo-first-order ..
  9. Campos M, Alarcón M, Gonzalez H, Carvajal N. An arginine residue at the active site of beta-lactamase from Shigella flexneri UCSF-129. Microbios. 1993;73:37-43 pubmed
    ..The enzyme was serine dependent with a molecular weight of 23.6 kD. It was specifically modified with phenylglyoxal (1/830 molar ratio) and incubated for 20 min in the presence of 50 mM sodium phosphate buffer at pH 8.3...
  10. Mousset C, Giraud A, Provot O, Hamze A, Bignon J, Liu J, et al. Synthesis and antitumor activity of benzils related to combretastatin A-4. Bioorg Med Chem Lett. 2008;18:3266-71 pubmed publisher
    ..These results clearly demonstrated that the Z-double bond of CA-4 can be replaced by a 1,2-diketone unit without significant loss of cytotoxicity and inhibition of tubulin assembly potency...
  11. Choudhary M, Hareem S, Siddiqui H, Anjum S, Ali S, Atta Ur Rahman -, et al. A benzil and isoflavone from Iris tenuifolia. Phytochemistry. 2008;69:1880-5 pubmed publisher
    ..Compounds 3, 5 and 7 were also subjected to single-crystal X-ray diffraction analysis and their structures were unambiguously deduced...
  12. Imamura Y, Koga T, Shimada H, Otagiri M. Inactivation of rabbit liver carbonyl reductase by phenylglyoxal and 2,3,4-trinitrobenzenesulfonate sodium. J Enzyme Inhib Med Chem. 2003;18:35-9 pubmed
    The chemical modifications of rabbit liver carbonyl reductase (RLCR) with phenylglyoxal (PGO) and 2,3,4-trinitrobenzenesulfonate sodium (TNBS), which are respective chemical modifiers of arginine and lysine residues, were examined...
  13. Chen H, Xie L, Yu Z, Xu G, Zhang R. Chemical modification studies on alkaline phosphatase from pearl oyster (Pinctada fucata): a substrate reaction course analysis and involvement of essential arginine and lysine residues at the active site. Int J Biochem Cell Biol. 2005;37:1446-57 pubmed
    ..Tsou's plot analysis indicated that the inactivation of PALP by 2,4,6-trinitrobenzenesulfonic acid (TNBS) and phenylglyoxal (PG) is dependent upon modification of one essential lysine and one essential arginine residue, respectively...
  14. Epperly B, Dekker E. Inactivation of Escherichia coli L-threonine dehydrogenase by 2,3-butanedione. Evidence for a catalytically essential arginine residue. J Biol Chem. 1989;264:18296-301 pubmed
    ..preparations of L-threonine dehydrogenase from Escherichia coli with 2,3-butanedione, 2,3-pentanedione, phenylglyoxal, or 1,2-cyclohexanedione causes a time- and concentration-dependent loss of enzymatic activity; plots of log ..
  15. Gould A, Norton R. Chemical modification of cationic groups in the polypeptide cardiac stimulant anthopleurin-A. Toxicon. 1995;33:187-99 pubmed
    ..The positive inotropic activity of the cyclohexanedione adduct on isolated guinea-pig atria was identical to that of unmodified anthopleurin-A, indicating that the side-chain of Arg-14 is not required for cardiotonic activity...
  16. Cottingham I, Austin A, Slabas A. Inhibition and covalent modification of rape seed (Brassica napus) enoyl ACP reductase by phenylglyoxal. Biochim Biophys Acta. 1989;995:273-8 pubmed
    The NADH-dependent enoyl-ACP reductase from oil seed rape (Brassica napus) was inactivated by treatment with phenylglyoxal, a reagent which specifically modifies arginine residues...
  17. Ruiz Gomez A, Morato E, Garcia Calvo M, Valdivieso F, Mayor F. Localization of the strychnine binding site on the 48-kilodalton subunit of the glycine receptor. Biochemistry. 1990;29:7033-40 pubmed
    ..N-Chlorosuccinimide treatment of [3H]strychnine-labeled 48K polypeptide yielded a single labeled peptide of Mr approximately 7300, and cyanogen bromide gave a labeled peptide of Mr 6200.(ABSTRACT TRUNCATED AT 250 WORDS)..
  18. Worayuthakarn R, Boonya udtayan S, Arom oon E, Ploypradith P, Ruchirawat S, Thasana N. Synthesis of unsymmetrical benzil licoagrodione. J Org Chem. 2008;73:7432-5 pubmed publisher
    ..Subsequent removal of protecting groups then furnished the desired product...
  19. Sreelatha T, Hymavathi A, Rama Subba Rao V, Devanand P, Usha Rani P, Madhusudana Rao J, et al. A new benzil derivative from Derris scandens: Structure-insecticidal activity study. Bioorg Med Chem Lett. 2010;20:549-53 pubmed publisher
    ..The new compound, derrisdione A was moderately active with an antifeedant index of 58.6+/-1.7% at 10microg/cm(3) against A. janata...
  20. Mu H, Yu Y, Wasserman B, Carman G. Purification and characterization of the maize amyloplast stromal 112-kDa starch phosphorylase. Arch Biochem Biophys. 2001;388:155-64 pubmed
    ..5 in the phosphorolytic direction. SP activity was inhibited by thioreactive agents, diethyl pyrocarbonate, phenylglyoxal, and ADP-glucose. The activation energies for the synthetic and phosphorolytic reactions were 11.1 and 16...
  21. Tutturen A, Holm A, Jørgensen M, Stadtmüller P, Rise F, Fleckenstein B. A technique for the specific enrichment of citrulline-containing peptides. Anal Biochem. 2010;403:43-51 pubmed publisher
    ..The technique was further applied to enrich citrullinated peptides from a digest of deiminated myelin basic protein...
  22. Wells T, Scully P, Magnenat E. Arginine 304 is an active site residue in phosphomannose isomerase from Candida albicans. Biochemistry. 1994;33:5777-82 pubmed
    ..7. The enzyme can be inhibited in a time-dependent manner using the arginine-specific modification reagent phenylglyoxal. This modification takes place with a rate constant of 0.022 +/- 0...
  23. Maruyama R, Nishizawa M, Itoi Y, Ito S, Inoue M. Isolation and expression of a Bacillus cereus gene encoding benzil reductase. Biotechnol Bioeng. 2001;75:630-3 pubmed
  24. Zhu X, Zheng C, Hu Y, Jiang T, Liu Y, Dong N, et al. Cadmium-induced oxalate secretion from root apex is associated with cadmium exclusion and resistance in Lycopersicon esulentum. Plant Cell Environ. 2011;34:1055-64 pubmed publisher
    ..Cd-induced secretion of oxalate was localized to root apex at which the majority of Cd accumulated. Phenylglyoxal, an anion-channel inhibitor, effectively blocked Cd-induced oxalate secretion and aggravated Cd toxicity while ..
  25. McKee J, Nimmo H. Evidence for an arginine residue at the coenzyme-binding site of Escherichia coli isocitrate dehydrogenase. Biochem J. 1989;261:301-4 pubmed
    The arginine-specific reagent phenylglyoxal inactivated the active, dephosphorylated, form of Escherichia coli isocitrate dehydrogenase rapidly in a pseudo-first-order process...
  26. Li J, Liu X, Sun M. Synthesis of glycoluril catalyzed by potassium hydroxide under ultrasound irradiation. Ultrason Sonochem. 2010;17:55-7 pubmed publisher
    ..Compared to the method using stirring, the main advantage of the present procedure is milder conditions and shorter reaction time...
  27. Winters C, Andreoli T. Chloride channels in basolateral TAL membranes. XVIII. Phenylglyoxal induces functional mcCIC-Ka activity in basolateral MTAL membranes. J Membr Biol. 2003;195:63-71 pubmed
    ..Using basolateral vesicles from MTAL cells fused into bilayers, we evaluated the effects of 1 mM cytosolic phenylglyoxal (PGO), which binds covalently to lysine or arginine, on Cl- channels...
  28. Dutta S. Synthesis and anthelmintic activity of some novel 2-substituted-4,5-diphenyl imidazoles. Acta Pharm. 2010;60:229-35 pubmed publisher
  29. Ibert M, Fuertès P, Merbouh N, Feasson C, Marsais F. Evidence of benzilic rearrangement during the electrochemical oxidation of D-glucose to D-glucaric acid. Carbohydr Res. 2011;346:512-8 pubmed publisher
    ..Its structure was proven by different experiments coupled with several analytical methods, and its appearance during the electrochemical oxidation of D-glucose was rationalized through a thorough study...
  30. Yang J, Zhu X, Peng Y, Zheng C, Ming F, Zheng S. Aluminum regulates oxalate secretion and plasma membrane H+-ATPase activity independently in tomato roots. Planta. 2011;234:281-91 pubmed publisher
    ..An anion channel inhibitor phenylglyoxal inhibited oxalate secretion, but not PM H(+)-ATPase activity...
  31. Hyatt J, Tsurkan L, Wierdl M, Edwards C, Danks M, Potter P. Intracellular inhibition of carboxylesterases by benzil: modulation of CPT-11 cytotoxicity. Mol Cancer Ther. 2006;5:2281-8 pubmed
    ..These results suggest that intracellular modulation of carboxylesterase activity with benzil or its analogues may be applied to minimize the toxicity of normal cells to CPT-11...
  32. Madala N, Steenkamp P, Piater L, Dubery I. Biotransformation of isonitrosoacetophenone (2-keto-2-phenyl-acetaldoxime) in tobacco cell suspensions. Biotechnol Lett. 2012;34:1351-6 pubmed publisher
    ..INAP is thus recognized by the enzymatic machinery of the phenylpropanoid pathway and is converted to a molecule with a substitution pattern similar to ferulic acid...
  33. Pennacchio A, Sannino V, Sorrentino G, Rossi M, Raia C, Esposito L. Biochemical and structural characterization of recombinant short-chain NAD(H)-dependent dehydrogenase/reductase from Sulfolobus acidocaldarius highly enantioselective on diaryl diketone benzil. Appl Microbiol Biotechnol. 2013;97:3949-64 pubmed publisher
    ..The crystal structure of the binary complex SaADH2-NADH, determined at 1.75 Å resolution, reveals details of the active site providing hints on the structural basis of the enzyme enantioselectivity...
  34. Castagna M, Vincenti S, Marciani P, Sacchi V. Inhibition of the lepidopteran amino acid co-transporter KAAT1 by phenylglyoxal: role of arginine 76. Insect Mol Biol. 2002;11:283-9 pubmed
    b>Phenylglyoxal (PGO), an arginine-modifying reagent, is an irreversible inhibitor of KAAT1-mediated leucine transport, expressed in Xenopus oocytes...
  35. Tonooka K, Kabashima T, Yamasuji M, Kai M. Facile determination of DNA-binding nuclear factor-kappaB by chemiluminescence detection. Anal Biochem. 2007;364:30-6 pubmed
    ..Therefore, the current method provides a convenient tool for surveying various DNA-binding proteins...
  36. Lupidi G, Bollettini M, Venardi G, Marmocchi F, Rotilio G. Functional residues on the enzyme active site of glyoxalase I from bovine brain. Prep Biochem Biotechnol. 2001;31:317-29 pubmed
    ..A protective effect of the competitive inhibitor S-hexylglutathione was observed for all reagents used, indicating the presence of modified amino acids in or near the enzyme active site...
  37. McLeish M, Caine J. Chemical modification of PABA synthase. Biochem Int. 1991;24:1033-42 pubmed
    ..Results indicate that cysteine, histidine, arginine and tyrosine residues are important for enzyme activity. Attempts were made to determine the subunits upon which these residues were located...
  38. Guo L, Phillips A, Arteca R. Amino acid N-malonyltransferases from mung beans. Action on 1-aminocyclopropane-1-carboxylic acid and D-phenylalanine. J Biol Chem. 1993;268:25389-94 pubmed
    ..The irreversible inhibitors phenylglyoxal and tetranitromethane reduced malonyltransferase activity towards D-phenylalanine to the same extent as that ..
  39. Redowicz M. Phenylglyoxal reveals phosphorylation-dependent difference in the conformation of Acanthamoeba myosin II active site. Arch Biochem Biophys. 2000;384:413-7 pubmed
    ..In this work, effect of modification of arginine residues with phenylglyoxal on the Ca2+-ATPase activity and susceptibility to endoproteinase ArgC cleavage of monomeric phospho- and ..
  40. Kurosaki F, Togashi K, Arisawa M. Regulation of catalytic activity of a multifunctional polyketide biosynthetic enzyme, 6-hydroxymellein synthase, by interaction between NADPH and phenylglyoxal-sensitive amino acid residue at the reaction center. Biochim Biophys Acta. 2001;1549:51-60 pubmed
    Treatment of 6-hydroxymellein synthase, a multifunctional polyketide biosynthetic enzyme in carrot cells, with phenylglyoxal yielded a chemically modified protein in which approximately two moles of the reagent were covalently attached ..
  41. Lan Y, Peng Y, Thang T, Hwang T, Dai D, Leu Y, et al. New flavan and benzil isolated from Fissistigma latifolium. Chem Pharm Bull (Tokyo). 2012;60:280-2 pubmed
    ..2,5,6,7-Tetramethoxyflavan (1) showed a potent inhibitory effect on superoxide anion production in formyl-L-methionyl-L-leucyl-L-phenylalanine (fMLP)/cytochalasin B (CB)-activated human neutrophils...
  42. Pelletier J, MacKenzie R. Binding of the 2',5'-ADP subsite stimulates cyclohydrolase activity of human NADP(+)-dependent methylenetetrahydrofolate dehydrogenase/cyclohydrolase. Biochemistry. 1994;33:1900-6 pubmed
    ..The interaction of 2',5'-ADP with the cyclohydrolase suggests a potential role for this portion of the molecule in promoting the efficiency of the channeling of endogenously generated methenyltetrahydrofolate...
  43. Ruan L, Shi M, Li N, Ding X, Yang F, Tang J. Practical approach for preparation of unsymmetric benzils from ?-ketoaldehydes. Org Lett. 2014;16:733-5 pubmed publisher
    ..The generation of ?,?-dichloroketones from ?-ketoaldehydes may undergo the following steps: (1) oxidation by sodium hypochlorite, (2) decarboxylation, and (3) chlorination by Cl2 generated from sodium hypochlorite. ..
  44. Dong Q, Liu F, Myers A, Fromm H. Evidence for an arginine residue at the substrate binding site of Escherichia coli adenylosuccinate synthetase as studied by chemical modification and site-directed mutagenesis. J Biol Chem. 1991;266:12228-33 pubmed
    Chemical modification of adenylosuccinate synthetase from Escherichia coli with phenylglyoxal resulted in an inhibition of enzyme activity with a second-order rate constant of 13.6 M-1 min-1...
  45. Mishra P, Dixit A, Ray M, Sabat S. Mechanistic study of CuZn-SOD from Ipomoea carnea mutated at dimer interface: enhancement of peroxidase activity upon monomerization. Biochimie. 2014;97:181-93 pubmed
    ..The inhibitor studies like hydrogen peroxide, diethyldithiocarbamate and phenylglyoxal also indicate higher susceptibility, which might be due to, altered arrangement of active site residues as a ..
  46. Seurynck Servoss S, Brown N, Dohm M, Wu C, Barron A. Lipid composition greatly affects the in vitro surface activity of lung surfactant protein mimics. Colloids Surf B Biointerfaces. 2007;57:37-55 pubmed
  47. Tunnicliff G. Chemical modification of bacterial 4-aminobutyrate aminotransferase by phenylglyoxal. J Enzyme Inhib. 1995;9:309-16 pubmed
    ..6.1.19), obtained from Pseudomonas fluorescens, was irreversibly inhibited by phenylglyoxal, a reagent that specifically modifies arginyl residues...
  48. Sorianello E, Mazzetti M. Function and structure of rat hepatic coproporphyrinogen oxidase. Comp Biochem Physiol B Biochem Mol Biol. 2000;127:155-64 pubmed
  49. Kolev T, Stamboliyska B. Vibrational spectra and structure of benzil and its 18O- and d10-labelled derivatives: a quantum chemical and experimental study. Spectrochim Acta A Mol Biomol Spectrosc. 2002;58:3127-37 pubmed
    ..It turns out that the best structural parameters are predicted by the B3LYP/6-31G* method...
  50. Aifa S, Johansen K, Nilsson U, Liedberg B, Lundstrom I, Svensson S. Interactions between the juxtamembrane domain of the EGFR and calmodulin measured by surface plasmon resonance. Cell Signal. 2002;14:1005-13 pubmed
    ..Chemical modification of EGFR-JM by using arginine-selective phenylglyoxal or deletion of the basic segment Arg(645)-Arg(657) inhibits the interaction...
  51. Hajjou M, Le Gal Y. Catalytic site studies on tuna (Thunnus albacares) pyloric caeca aminopeptidase. Biochim Biophys Acta. 1995;1251:139-44 pubmed
    ..and tyrosine residues at the catalytic site of most metalloproteinases, tAP is reversibly inhibited by phenylglyoxal and inactivated by tetranitromethane in a time-dependent fashion...
  52. Sheldon P, Venis M. Purification and characterization of cytosolic and microsomal cyclophilins from maize (Zea mays). Biochem J. 1996;315 ( Pt 3):965-70 pubmed
    ..The cytosolic enzyme is inactivated by 5 mM N-ethylmaleimide and 2 mM phenylglyoxal. N-terminal sequencing of the microsomal PPI indicates a high level of sequence similarity with the N-terminal ..
  53. Asmussen E, Peutzfeldt A. Influence of composition on rate of polymerization contraction of light-curing resin composites. Acta Odontol Scand. 2002;60:146-50 pubmed
    ..It was concluded that intrinsic slow cure may be obtained with certain compositions of resin composites without impairing the final extent of polymerization...
  54. Suryanti V, Nelson A, Berry A. Cloning, over-expression, purification, and characterisation of N-acetylneuraminate synthase from Streptococcus agalactiae. Protein Expr Purif. 2003;27:346-56 pubmed
    ..The purified enzyme was inhibited by the reagent phenylglyoxal and the substrates N-acetyl mannosamine or phosphoenol pyruvate afforded protection against this inhibition, ..
  55. Li J, Liu X, Wang W. An efficient oxidation of benzoins to benzils by ACC/silica gel under ultrasound irradiation. Ultrason Sonochem. 2009;16:331-3 pubmed publisher
    ..The oxidation of benzoins to the corresponding benzils was carried out in CH2Cl2 by ACC/silica gel in excellent yields within short time under ultrasound irradiation...
  56. Cho D, Kim J, Sessler J. The benzil-cyanide reaction and its application to the development of a selective cyanide anion indicator. J Am Chem Soc. 2008;130:12163-7 pubmed publisher
  57. Marana S, Mendonça L, Andrade E, Terra W, Ferreira C. The role of residues R97 and Y331 in modulating the pH optimum of an insect beta-glycosidase of family 1. Eur J Biochem. 2003;270:4866-75 pubmed
    ..As those residues are conserved among the family 1 beta-glycosidases, it is proposed here that similar interactions modulate the pH optimum of all family 1 beta-glycosidases...
  58. Mahabusarakam W, Deachathai S, Phongpaichit S, Jansakul C, Taylor W. A benzil and isoflavone derivatives from Derris scandens Benth. Phytochemistry. 2004;65:1185-91 pubmed
    ..scandens. Their structures were determined by spectroscopic methods. Radical scavenging, antibacterial and hypertensive activities of some of the compounds were investigated...
  59. Singh S, Pandey V, Naaz H, Dwivedi U. Phylogenetic analysis, molecular modeling, substrate-inhibitor specificity, and active site comparison of bacterial, fungal, and plant heme peroxidases. Biotechnol Appl Biochem. 2012;59:283-94 pubmed publisher
    ..common substrates, namely, H?O?, guaiacol, and ascorbate, and three arginine-specific inhibitors, namely, phenylglyoxal, 1,2-cyclohexanedione, and 2,3-butanedione, revealed that all three inhibitors competed for guaiacol- and ..
  60. Communi D, Lecocq R, Vanweyenberg V, Erneux C. Active site labelling of inositol 1,4,5-trisphosphate 3-kinase A by phenylglyoxal. Biochem J. 1995;310 ( Pt 1):109-15 pubmed
    Chemical modification by phenylglyoxal, an arginine-specific reagent, of both native and recombinant rat brain inositol 1,4,5-trisphosphate [Ins(1,4,5)P3] 3-kinase A was accompanied by irreversible inhibition of enzyme activity...
  61. Ikeda M, Oesterhelt D. A Cl(-)-translocating adenosinetriphosphatase in Acetabularia acetabulum. 2. Reconstitution of the enzyme into liposomes and effect of net charges of liposomes on chloride permeability and reconstitution. Biochemistry. 1990;29:2065-70 pubmed
    ..The preincubation of the enzyme with phenylglyoxal, an arginine-modifying reagent, inactivated ATP-mediated 36Cl- efflux, but the ATPase activity of the ..
  62. Chang L, Lin S, Chang C. Identification of arg-30 as the essential residue for the enzymatic activity of Taiwan cobra phospholipase A2. J Biochem. 1998;124:764-8 pubmed
    Taiwan cobra (Naja naja atra) phospholipase A2 (PLA2) was inactivated by arginine-specific reagents, phenylglyoxal and 1, 2-cyclohexanedione...