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Volumn 52, Issue 2, 2009, Pages 389-396

Crystal structure of the Homo sapiens kynureninase-3-hydroxyhippuric acid inhibitor complex: Insights into the molecular basis of kynureninase substrate specificity

Author keywords

[No Author keywords available]

Indexed keywords

3 HYDROXYHIPPURIC ACID; ALANINE; ASPARAGINE; EXCITOTOXIN; HIPPURIC ACID DERIVATIVE; HISTIDINE; KYNURENINASE; NICOTINAMIDE ADENINE DINUCLEOTIDE; PYRIDOXAL 5 PHOSPHATE; QUINOLINIC ACID; SERINE; TRYPTOPHAN; UNCLASSIFIED DRUG; 3-HYDROXYHIPPURIC ACID; HYDROLASE; PRIMER DNA;

EID: 60549096522     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm8010806     Document Type: Article
Times cited : (37)

References (45)
  • 1
    • 0018657638 scopus 로고
    • Kynureninases: Enzymological properties and regulation mechanism
    • Soda, K.; Tanizawa, K. Kynureninases: enzymological properties and regulation mechanism. Adv Enzymol Relat Area Mol Biol 1979, 49, 1-40.
    • (1979) Adv Enzymol Relat Area Mol Biol , vol.49 , pp. 1-40
    • Soda, K.1    Tanizawa, K.2
  • 2
    • 12444320333 scopus 로고    scopus 로고
    • The pyridine ring of NAD is formed by a nonenzymatic pericyclic reaction
    • Colabroy, K. L.; Begley, T. P. The pyridine ring of NAD is formed by a nonenzymatic pericyclic reaction. J. Am. Chem. Soc. 2005, 127, 840-841.
    • (2005) J. Am. Chem. Soc , vol.127 , pp. 840-841
    • Colabroy, K.L.1    Begley, T.P.2
  • 3
    • 0020702374 scopus 로고
    • Quinolinic acid: An endogenous metabolite that produces axon-sparing lesions in rat brain
    • Schwarcz, R.; Whetsell, W. O., Jr.; Mangano, R. M. Quinolinic acid: an endogenous metabolite that produces axon-sparing lesions in rat brain. Science 1983, 219, 316-318.
    • (1983) Science , vol.219 , pp. 316-318
    • Schwarcz, R.1    Whetsell Jr., W.O.2    Mangano, R.M.3
  • 4
    • 0019440926 scopus 로고
    • Quinolinic acid: A potent endogenous excitant at amino acid receptors in CNS
    • Stone, T. W.; Perkins, M. N. Quinolinic acid: a potent endogenous excitant at amino acid receptors in CNS. Eur. J. Pharmacol. 1981, 72, 411-412.
    • (1981) Eur. J. Pharmacol , vol.72 , pp. 411-412
    • Stone, T.W.1    Perkins, M.N.2
  • 5
    • 0025992743 scopus 로고
    • Cerebrospinal fluid quinolinic acid concentrations are increased in acquired immune deficiency syndrome
    • Heyes, M. P.; Brew, B.; Martin, A.; Markey, S. P.; Price, R. W.; Bhalla, R. B.; Salazar, A. Cerebrospinal fluid quinolinic acid concentrations are increased in acquired immune deficiency syndrome. Adv. Exp. Med. Biol. 1991, 294, 687-690.
    • (1991) Adv. Exp. Med. Biol , vol.294 , pp. 687-690
    • Heyes, M.P.1    Brew, B.2    Martin, A.3    Markey, S.P.4    Price, R.W.5    Bhalla, R.B.6    Salazar, A.7
  • 6
    • 0027225504 scopus 로고
    • Quantitation of human immunodeficiency virus, immune activation factors, and quinolinic acid in AIDS brains
    • Achim, C. L.; Heyes, M. P.; Wiley, C. A. Quantitation of human immunodeficiency virus, immune activation factors, and quinolinic acid in AIDS brains. J. Clin. Invest. 1993, 91, 2769-2775.
    • (1993) J. Clin. Invest , vol.91 , pp. 2769-2775
    • Achim, C.L.1    Heyes, M.P.2    Wiley, C.A.3
  • 7
    • 0026033966 scopus 로고
    • Regional brain and cerebrospinal fluid quinolinic acid concentrations in Huntington's disease
    • Heyes, M. P.; Swartz, K. J.; Markey, S. P.; Beal, M. F. Regional brain and cerebrospinal fluid quinolinic acid concentrations in Huntington's disease. Neurosci. Lett. 1991, 122, 265-269.
    • (1991) Neurosci. Lett , vol.122 , pp. 265-269
    • Heyes, M.P.1    Swartz, K.J.2    Markey, S.P.3    Beal, M.F.4
  • 8
    • 43149110841 scopus 로고    scopus 로고
    • Giorgini, F.; Moller, T.; Kwan, W.; Zwilling, D.; Wacker, J. L.; Hong, S.; Tsai, L. C.; Cheah, C. S.; Schwarcz, R.; Guidetti, P.; Muchowski, P. J. Histone deacetylase inhibition modulates kynurenine pathway activation in yeast, microglia, and mice expressing a mutant huntingtin fragment. J. Biol. Chem. 2008, 283, 7390-7400.
    • Giorgini, F.; Moller, T.; Kwan, W.; Zwilling, D.; Wacker, J. L.; Hong, S.; Tsai, L. C.; Cheah, C. S.; Schwarcz, R.; Guidetti, P.; Muchowski, P. J. Histone deacetylase inhibition modulates kynurenine pathway activation in yeast, microglia, and mice expressing a mutant huntingtin fragment. J. Biol. Chem. 2008, 283, 7390-7400.
  • 9
    • 33744781601 scopus 로고    scopus 로고
    • Implications for the kynurenine pathway and quinolinic acid in amyotrophic lateral sclerosis
    • Guillemin, G. J.; Meininger, V.; Brew, B. J. Implications for the kynurenine pathway and quinolinic acid in amyotrophic lateral sclerosis. Neurodegener. Dis. 2005, 2, 166-176.
    • (2005) Neurodegener. Dis , vol.2 , pp. 166-176
    • Guillemin, G.J.1    Meininger, V.2    Brew, B.J.3
  • 10
    • 34548809845 scopus 로고    scopus 로고
    • Inflammation, depression and dementia: Are they connected
    • Leonard, B. E. Inflammation, depression and dementia: are they connected. Neurochem. Res. 2007, 32, 1749-1756.
    • (2007) Neurochem. Res , vol.32 , pp. 1749-1756
    • Leonard, B.E.1
  • 11
    • 23044462498 scopus 로고    scopus 로고
    • Indoleamine 2,3 dioxygenase and quinolinic acid immunore- activity in Alzheimer's disease hippocampus
    • Guillemin, G. J.; Brew, B. J.; Noonan, C. E.; Takikawa, O.; Cullen, K. M. Indoleamine 2,3 dioxygenase and quinolinic acid immunore- activity in Alzheimer's disease hippocampus. Neuropathol. Appl. Neurobiol. 2005, 31, 395-404.
    • (2005) Neuropathol. Appl. Neurobiol , vol.31 , pp. 395-404
    • Guillemin, G.J.1    Brew, B.J.2    Noonan, C.E.3    Takikawa, O.4    Cullen, K.M.5
  • 13
    • 0036784518 scopus 로고    scopus 로고
    • Manipulation of brain kynurenines: Glial targets, neuronal effects, and clinical opportunities
    • Schwarcz, R.; Pellicciari, R. Manipulation of brain kynurenines: glial targets, neuronal effects, and clinical opportunities. J. Pharmacol. Exp. Ther. 2002, 303, 1-10.
    • (2002) J. Pharmacol. Exp. Ther , vol.303 , pp. 1-10
    • Schwarcz, R.1    Pellicciari, R.2
  • 14
    • 0037025273 scopus 로고    scopus 로고
    • The pharmacological manipulation of glutamate receptors and neuroprotection
    • Stone, T. W.; Addae, J. I. The pharmacological manipulation of glutamate receptors and neuroprotection. Eur. J. Pharmacol. 2002, 447, 285-296.
    • (2002) Eur. J. Pharmacol , vol.447 , pp. 285-296
    • Stone, T.W.1    Addae, J.I.2
  • 16
    • 0016636065 scopus 로고
    • Kynureninase-Type enzymes of Penicillum roqueforti, Aspergillus niger, Rhizopus stolonifer, and Pseudomonas fluorescens: Further evidence for distinct kynureninase and hydroxykynureninase activities
    • Shetty, A. S.; Gaertner, F. H. Kynureninase-Type enzymes of Penicillum roqueforti, Aspergillus niger, Rhizopus stolonifer, and Pseudomonas fluorescens: further evidence for distinct kynureninase and hydroxykynureninase activities. J. Bacteriol. 1975, 122, 235-244.
    • (1975) J. Bacteriol , vol.122 , pp. 235-244
    • Shetty, A.S.1    Gaertner, F.H.2
  • 19
    • 0028174289 scopus 로고
    • Crystal structures of Escherichia coli aspartate aminotransferase in two conformations. Comparison of an unliganded open and two liganded closed forms
    • Jager, J.; Moser, M.; Sauder, U.; Jansonius, J. N. Crystal structures of Escherichia coli aspartate aminotransferase in two conformations. Comparison of an unliganded open and two liganded closed forms. J. Mol. Biol. 1994, 239, 285-305.
    • (1994) J. Mol. Biol , vol.239 , pp. 285-305
    • Jager, J.1    Moser, M.2    Sauder, U.3    Jansonius, J.N.4
  • 20
    • 0029097764 scopus 로고
    • Comparison of the neurochemical and behavioral effects resulting from the inhibition of kynurenine hydroxylase and/or kynureninase
    • Chiarugi, A.; Carpenedo, R.; Molina, M. T.; Mattoli, L.; Pellicciari, R.; Moroni, F. Comparison of the neurochemical and behavioral effects resulting from the inhibition of kynurenine hydroxylase and/or kynureninase. J. Neurochem. 1995, 65, 1176-1183.
    • (1995) J. Neurochem , vol.65 , pp. 1176-1183
    • Chiarugi, A.1    Carpenedo, R.2    Molina, M.T.3    Mattoli, L.4    Pellicciari, R.5    Moroni, F.6
  • 21
    • 0037059896 scopus 로고    scopus 로고
    • 2-Amino- 4-[3'-hydroxyphenyl]-4-hydroxybutanoic acid; a potent inhibitor of rat and recombinant human kynureninase
    • Walsh, H. A.; Leslie, P. L.; O'Shea, K. C.; Botting, N. P. 2-Amino- 4-[3'-hydroxyphenyl]-4-hydroxybutanoic acid; a potent inhibitor of rat and recombinant human kynureninase. Bioorg. Med. Chem. Lett. 2002, 12, 361-363.
    • (2002) Bioorg. Med. Chem. Lett , vol.12 , pp. 361-363
    • Walsh, H.A.1    Leslie, P.L.2    O'Shea, K.C.3    Botting, N.P.4
  • 22
    • 0013902457 scopus 로고
    • Conformation and reaction specificity in pyridoxal phosphate enzymes
    • Dunathan, H. C. Conformation and reaction specificity in pyridoxal phosphate enzymes. Proc. Natl. Acad. Sci. U.S.A. 1966, 55, 712-716.
    • (1966) Proc. Natl. Acad. Sci. U.S.A , vol.55 , pp. 712-716
    • Dunathan, H.C.1
  • 23
    • 0028040757 scopus 로고
    • The function of arginine 363 as the substrate carboxyl-binding site in Escherichia coli serine hydroxymethyltransferase
    • Delle Fratte, S.; Iurescia, S.; Angelaccio, S.; Bossa, F.; Schirch, V. The function of arginine 363 as the substrate carboxyl-binding site in Escherichia coli serine hydroxymethyltransferase. Eur. J. Biochem. 1994, 225, 395-401.
    • (1994) Eur. J. Biochem , vol.225 , pp. 395-401
    • Delle Fratte, S.1    Iurescia, S.2    Angelaccio, S.3    Bossa, F.4    Schirch, V.5
  • 24
    • 0028069453 scopus 로고
    • The structural basis for the altered substrate specificity of the R292D active site mutant of aspartate aminotransferase from E. coli
    • Almo, S. C.; Smith, D. L.; Danishefsky, A. T.; Ringe, D. The structural basis for the altered substrate specificity of the R292D active site mutant of aspartate aminotransferase from E. coli. Protein Eng. 1994, 7, 405-412.
    • (1994) Protein Eng , vol.7 , pp. 405-412
    • Almo, S.C.1    Smith, D.L.2    Danishefsky, A.T.3    Ringe, D.4
  • 25
    • 0000899186 scopus 로고
    • Stereochemistry and mechanism of aldol reactions catalyzed by kynureninase
    • Dua, R.; Phillips, R. S. Stereochemistry and mechanism of aldol reactions catalyzed by kynureninase. J. Am. Chem. Soc. 1991, 113, 7385-7388.
    • (1991) J. Am. Chem. Soc , vol.113 , pp. 7385-7388
    • Dua, R.1    Phillips, R.S.2
  • 26
    • 0032537603 scopus 로고    scopus 로고
    • The Catalytic Mechanism of Kynureninase from Pseudomonas fluorescens: Evidence for Transient Quinonoid and Ketimine Intermediates from Rapid- scanning Stopped-flow Spectrophotometry
    • Phillips, R. S.; Sundararaju, B.; Koushik, S. V. The Catalytic Mechanism of Kynureninase from Pseudomonas fluorescens: Evidence for Transient Quinonoid and Ketimine Intermediates from Rapid- scanning Stopped-flow Spectrophotometry. Biochemistry 1998, 37, 8783-8789.
    • (1998) Biochemistry , vol.37 , pp. 8783-8789
    • Phillips, R.S.1    Sundararaju, B.2    Koushik, S.V.3
  • 27
    • 0029080978 scopus 로고
    • Site-directed Mutagenesis of Tyrosine-71 to Phenylalanine in Citrobacter freundii Tyrosine Phenol-lyase: Evidence for Dual Roles of Tyrosine 71 as a General Acid Catalyst in the Reaction Mechanism and in Cofactor Binding
    • Chen, H. Y.; Demidkina, T. V.; Phillips, R. S. Site-directed Mutagenesis of Tyrosine-71 to Phenylalanine in Citrobacter freundii Tyrosine Phenol-lyase: Evidence for Dual Roles of Tyrosine 71 as a General Acid Catalyst in the Reaction Mechanism and in Cofactor Binding. Biochemistry 1995, 34, 12276-12283.
    • (1995) Biochemistry , vol.34 , pp. 12276-12283
    • Chen, H.Y.1    Demidkina, T.V.2    Phillips, R.S.3
  • 29
    • 0027420131 scopus 로고
    • S-Aryl-L-cysteine S,S- Dioxides: Design and evaluation of a new class of mechanism based inhibitors of kynureninase
    • Dua, R. K.; Taylor, E. W.; Phillips, R. S. S-Aryl-L-cysteine S,S- Dioxides: Design and evaluation of a new class of mechanism based inhibitors of kynureninase J.Am Chem. Soc 1993,115,1264- 1270.
    • (1993) J.Am Chem. Soc , vol.115 , pp. 1264-1270
    • Dua, R.K.1    Taylor, E.W.2    Phillips, R.S.3
  • 30
    • 2942692017 scopus 로고    scopus 로고
    • Comparative inhibition by substrate analogues 3-methoxy- and 03-hydroxydesaminokynurenine and an improved 3 step purification of recombinant human kynureni- nase
    • Walsh, H. A.; O'Shea, K. C.; Botting, N. P. Comparative inhibition by substrate analogues 3-methoxy- and 03-hydroxydesaminokynurenine and an improved 3 step purification of recombinant human kynureni- nase. BMC Biochem. 2003, 4, 13.
    • (2003) BMC Biochem , vol.4 , pp. 13
    • Walsh, H.A.1    O'Shea, K.C.2    Botting, N.P.3
  • 31
    • 0041817911 scopus 로고    scopus 로고
    • Differential effects of bromination on substrates and inhibitors of kynureninase from Pseudomonas fluorescens
    • Heiss, C.; Anderson, J.; Phillips, R. S. Differential effects of bromination on substrates and inhibitors of kynureninase from Pseudomonas fluorescens. Org. mol. Chem. 2003, 1, 288-295.
    • (2003) Org. mol. Chem , vol.1 , pp. 288-295
    • Heiss, C.1    Anderson, J.2    Phillips, R.S.3
  • 32
    • 0035025738 scopus 로고    scopus 로고
    • A comparative study on the inhibition of human and bacterial kynureninase by novel bicyclic kynurenine analogues
    • Fitzgerald, D. H.; Muirhead, K. M.; Botting, N. P. A comparative study on the inhibition of human and bacterial kynureninase by novel bicyclic kynurenine analogues. Bioorg. Med. Chem. 2001, 9, 983-989.
    • (2001) Bioorg. Med. Chem , vol.9 , pp. 983-989
    • Fitzgerald, D.H.1    Muirhead, K.M.2    Botting, N.P.3
  • 33
    • 0028305047 scopus 로고
    • Inhibitors of kynurenine hydroxylase and kynureninase increase cerebral formation of kynurenate and have sedative and anticonvulsant activities
    • Carpenedo, R.; Chiarugi, A.; Russi, P.; Lombardi, G.; Carla, V.; Pellicciari, R.; Mattoli, L.; Moroni, F. Inhibitors of kynurenine hydroxylase and kynureninase increase cerebral formation of kynurenate and have sedative and anticonvulsant activities. Neuroscience 1994, 61, 237-243.
    • (1994) Neuroscience , vol.61 , pp. 237-243
    • Carpenedo, R.1    Chiarugi, A.2    Russi, P.3    Lombardi, G.4    Carla, V.5    Pellicciari, R.6    Mattoli, L.7    Moroni, F.8
  • 34
    • 0031059866 scopus 로고    scopus 로고
    • Otwinowski, Z.; W., M. Processing of X-ray Diffraction Data Collected in Oscillation Mode. Methods Enzymol. 1997, 276, 307-326.
    • Otwinowski, Z.; W., M. Processing of X-ray Diffraction Data Collected in Oscillation Mode. Methods Enzymol. 1997, 276, 307-326.
  • 37
    • 0005797141 scopus 로고    scopus 로고
    • The ARP/WARP suite for automated construction and refinement of protein models
    • Kluwer Academic Publishers: Dordrecht, The Netherlands
    • Lamzin, V. S.; Perrakis, A.; Wilson, K. S. The ARP/WARP suite for automated construction and refinement of protein models. In International Tables for Crystallography, Volume F; Kluwer Academic Publishers: Dordrecht, The Netherlands, 2001.
    • (2001) International Tables for Crystallography , vol.F
    • Lamzin, V.S.1    Perrakis, A.2    Wilson, K.S.3
  • 40
    • 0028103275 scopus 로고    scopus 로고
    • Collaborative Computational Project, N. The CCP4 Suite: Programs for Protein Crystallography Acta Crystallogr., Sect. D: Biol. Crystal- logr. 1994, 50, 760-763.
    • Collaborative Computational Project, N. The CCP4 Suite: Programs for Protein Crystallography Acta Crystallogr., Sect. D: Biol. Crystal- logr. 1994, 50, 760-763.
  • 42
    • 0018735516 scopus 로고
    • Statistical analysis of enzyme kinetic data
    • Cleland, W. W. Statistical analysis of enzyme kinetic data. Methods Enzymol. 1979, 63, 103-138.
    • (1979) Methods Enzymol , vol.63 , pp. 103-138
    • Cleland, W.W.1
  • 43
    • 37049154743 scopus 로고
    • Synthesis of β-(3,4-dihydroxyphenyl)- N-methylserine (adrenalinecarboxylic acid)
    • Dalgliesh, C. E.; Mann, F. G. Synthesis of β-(3,4-dihydroxyphenyl)- N-methylserine (adrenalinecarboxylic acid). J. Chem. Soc. 1947, 658-662.
    • (1947) J. Chem. Soc , pp. 658-662
    • Dalgliesh, C.E.1    Mann, F.G.2
  • 44
    • 0042650033 scopus 로고    scopus 로고
    • Facile Oxidation of Aldehydes to Acids and Esters with Oxone
    • Travis, B. R. S., M.; Hollist, G. O.; Borhan, B. Facile Oxidation of Aldehydes to Acids and Esters with Oxone. Org. Lett. 2003, 5, 1031-1034.
    • (2003) Org. Lett , vol.5 , pp. 1031-1034
    • Travis, B.R.S.M.1    Hollist, G.O.2    Borhan, B.3
  • 45
    • 37049043528 scopus 로고
    • Synthesis of some acylglycines and related oxazolones
    • Acheson, R. M. B. D. A.; Brettle, R.; Harris, A. M. Synthesis of some acylglycines and related oxazolones. J. Chem. Soc. 1960, 3457-3461.
    • (1960) J. Chem. Soc , pp. 3457-3461
    • Acheson, R.M.B.D.A.1    Brettle, R.2    Harris, A.M.3


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