Proton transfer in the catalytic mechanism of carbonic anhydrase.

[1]  J. Evelhoch,et al.  Evidence for direct metal-nitrogen binding in aromatic sulfonamide complexes of cadmium (II)-substituted carbonic anhydrases by cadmium-113 nuclear magnetic resonance. , 1981, Biochemistry.

[2]  K. Fridborg,et al.  Structure and function of carbonic anhydrase: comparative studies of sulphonamide binding to human erythrocyte carbonic anhydrases B and C , 1977 .

[3]  P. Schimmel,et al.  2 Rapid Reactions and Transient States , 1970 .

[4]  S. Lindskog,et al.  Metal binding and catalytic activity in bovine carbonic anhydrase. , 1962, The Journal of biological chemistry.

[5]  A. Scozzafava,et al.  Carbonic anhydrase: An insight into the zinc binding site and into the active cavity through metal substitution , 1982 .

[6]  E. Noltmann,et al.  Basic muscle protein, a third genetic locus isoenzyme of carbonic anhydrase? , 1977, Biochemical and biophysical research communications.

[7]  J. Brackenbury,et al.  Energy consumption and ventilatory mechanisms in the exercising fowl , 1980 .

[8]  B. Jonsson,et al.  The catalytic mechanism of human carbonic anhydrase C: Inhibition of CO2 hydration and ester hydrolysis by HCO− 3 , 1976, FEBS letters.

[9]  J. Coleman Chemical reactions of sulfonamides with carbonic anhydrase. , 1975, Annual review of pharmacology.

[10]  R. Bryant,et al.  Oxygen-17 NMR studies of carbonic anhydrase , 1980 .

[11]  A. Karlin,et al.  Effect of local pH changes caused by substrate hydrolysis on the activity of membrane-bound acetylcholinesterase. , 1967, Proceedings of the National Academy of Sciences of the United States of America.

[12]  W. Cleland What limits the rate of an enzyme-catalyzed reaction , 1975 .

[13]  Y. Pocker,et al.  Comparative studies of bovine carbonic anhydrase in H2O and D2O. Stopped-flow studies of the kinetics of interconversion of CO2 and HCO3. , 1977, Biochemistry.

[14]  G. Karlström,et al.  Ab initio molecular orbital calculations on the water-carbon dioxide system. The reaction hydroxide(1-) ion + carbon dioxide .fwdarw. bicarbonate(1-) ion , 1978 .

[15]  I. Bertini,et al.  Water in the coordination sphere of metallocarbonic anhydrases: A solvent proton longitudinal relaxation study at several frequencies , 1981 .

[16]  Y. Pocker,et al.  Stopped-flow studies of high pH activity and acetazolamide inhibition of bovine carbonic anhydrase. Enzyme-catalyzed hydrolyses of 3-pyridyl and nitro-3-pyridyl acetates. , 1973, Biochemistry.

[17]  P. Nyman,et al.  Inactivation of human erythrocyte carbonic anhydrases by bromopyruvate , 1972, FEBS letters.

[18]  Joseph E. Coleman,et al.  The Catalytic Mechanism of Carbonic Anhydrase , 1973 .

[19]  J. H. Wang,et al.  Infrared studies on the mechanism of action of carbonic anhydrase. , 1968, The Journal of biological chemistry.

[20]  D. Silverman,et al.  Role of hemoglobin in proton transfer to the active site of carbonic anhydrase. , 1979, The Journal of biological chemistry.

[21]  D. Silverman Carbonic anhydrase: oxygen-18 exchange catalyzed by an enzyme with rate-contributing proton-transfer steps. , 1982, Methods in enzymology.

[22]  T. Maren,et al.  Inhibition by anions of human red cell carbonic anhydrase B: physiological and biochemical implications. , 1976, Science.

[23]  Y. Pocker,et al.  Stopped-flow studies of carbon dioxide hydration and bicarbonate dehydration in water and water-d2. Acid-base and metal ion catalysis , 1977 .

[24]  K. Fridborg,et al.  Crystal structure of human erythrocyte carbonic anhydrase B. Three-dimensional structure at a nominal 2.2-A resolution. , 1975, Proceedings of the National Academy of Sciences of the United States of America.

[25]  Y. Pocker,et al.  The catalytic versatility of erythrocyte carbonic anhydrase. 3. Kinetic studies of the enzyme-catalyzed hydrolysis of p-nitrophenyl acetate. , 1967, Biochemistry.

[26]  K. Kannan,et al.  Structure, refinement, and function of human carbonic anhydrase‐B , 1976 .

[27]  N. Limozin,et al.  Structure primaire de l'anhydrase carbonique érythrocytaire bovine CI: II. - Séquence complète , 1976 .

[28]  R. S. Brown,et al.  Carbonic anhydrase models. 4. [Tris[(4,5-dimethyl-2-imidazolyl)methyl]phosphine oxide]cobalt(2+), a small-molecule mimic of the spectroscopic properties of cobalt(II) carbonic anhydrase , 1982 .

[29]  Y. Pocker,et al.  Carbonic anhydrase: structure catalytic versatility, and inhibition. , 1978, Advances in enzymology and related areas of molecular biology.

[30]  P. Boyer,et al.  Uses and limitations of measurements of rates of isotopic exchange and incorporation in catalyzed reactions. , 1959, Archives of biochemistry and biophysics.

[31]  D. Silverman,et al.  Kinetics of the protonation of buffer and hydration of carbon dioxide catalyzed by human carbonic anhydrase II , 1982 .

[32]  R. Prince Some Aspects of the Bioinorganic Chemistry of Zinc , 1979 .

[33]  P. Nyman,et al.  Amino acid sequence of human erythrocyte carbonic anhydrase C. , 1972, Biochemical and biophysical research communications.

[34]  L. Henderson Primary Structure of Carbonic Anhydrases , 1980 .

[35]  J. T. Johansen,et al.  Low and high pH form of cadmium carbonic anhydrase determined by nuclear quadrupole interaction. , 1976, Biochemistry.

[36]  A. Scozzafava,et al.  Characterization of cobalt(II) bovine carbonic anhydrase and of its derivatives , 1978 .

[37]  R. Alberty,et al.  MULTIPLE INTERMEDIATES IN STEADY STATE ENZYME KINETICS. VI. THE MECHANISM INVOLVING A SINGLE SUBSTRATE AND TWO PRODUCTS. , 1959, The Journal of biological chemistry.

[38]  Martin Rb Pyrrole Hydrogen Ionization of Imidazole Derivatives in Metal Ion Complexes and Carbonic Anhydrase , 1974 .

[39]  W. Hartley The Chemical Society , 1876, Nature.

[40]  S. Beychok,et al.  Optical Rotatory Dispersion and Circular Dichroism of Human Carbonic Anhydrases B and C , 1966 .

[41]  T. Maren,et al.  The carbon dioxide hydration activity of skeletal muscle carbonic anhydrase. Inhibition by sulfonamides and anions. , 1982, Molecular pharmacology.

[42]  A S Burgen,et al.  Sulphonamide complexes of human carbonic anhydrases. Ultraviolet difference spectroscopy. , 1970, Biochimica et biophysica acta.

[43]  P. Yeagle,et al.  13-C nuclear magnetic resonance studies on the mechanism of action of carbonic anhydrase. , 1975, Proceedings of the National Academy of Sciences of the United States of America.

[44]  D. Silverman,et al.  Buffer dependence of carbonic anhydrase catalyzed oxygen-18 exchange at equilibrium , 1975 .

[45]  P. Woolley Models for metal ion function in carbonic anhydrase , 1975, Nature.

[46]  P. S. Woolley Metal-ion assisted catalysis of nucleophilic attack. Part 3. Co-operation between metal ion and hydroxide , 1977 .

[47]  D. Silverman,et al.  Rate of exchange of water from the active site of human carbonic anhydrase C , 1979 .

[48]  A. Scozzafava,et al.  A new class of inhibitors capable of binding both the acidic and alkaline forms of carbonic anhydrase. , 1981, Biochimica et biophysica acta.

[49]  S. Jeffery,et al.  A comparison of carbonic anhydrase III isozymes from human, baboon, pig and sheep muscle , 1980 .

[50]  R. Khalifah,et al.  Carbon dioxide hydration activity of carbonic anhydrase: kinetics of alkylated anhydrases B and C from humans (metalloenzymes-isoenzymes-active sites-mechanism). , 1972, Proceedings of the National Academy of Sciences of the United States of America.

[51]  S. H. Koenig,et al.  Kinetic parameters of human carbonic anhydrase B as determined from NMR linewidths of 13 C in CO 2 and HCO 3 - . , 1973, Biochemical and biophysical research communications.

[52]  L. Hager,et al.  STUDIES ON THE MECHANISM OF ACTION OF COLICIN E2 , 1973 .

[53]  S. H. Koenig,et al.  Exchange of labeled nuclei in the CO2--HCO3--solvent system catalyzed by carbonic anhydrase. , 1981, Biophysical journal.

[54]  S. Lindskog Interaction of cobalt(II)--carbonic anhydrase with anions. , 1966, Biochemistry.

[55]  B. Roos,et al.  Ab initio molecular orbital calculations on the water-carbon dioxide system. Reaction pathway for water + carbon dioxide .fwdarw. carbonic acid , 1977 .

[56]  L. Backman Binding of human carbonic anhydrase to human hemoglobin. , 1981, European journal of biochemistry.

[57]  B. Jonsson,et al.  A 13C nuclear-magnetic-resonance study of CO2-HCO3-exchange catalyzed by human carbonic anhydrase C at chemical equilibrium. , 1979, European journal of biochemistry.

[58]  Y. Pocker,et al.  Hydration of propionaldehyde, isobutyraldehyde, and pivalaldehyde. Thermodynamic parameters, buffer catalysis and transition state characterization , 1969 .

[59]  B. Strandberg,et al.  Crystal structure of human erythrocyte carbonic anhydrase C. 3. Molecular structure of the enzyme and of one enzyme-inhibitor complex at 5-5 A resolution. , 1967, Journal of molecular biology.

[60]  J. Edsall,et al.  RATE OF HYDRATION OF CARBON DIOXIDE AND DEHYDRATION OF CARBONIC ACID AT 25 DEGREES. , 1963, The Journal of biological chemistry.

[61]  S. Lindskog,et al.  The interaction of sulfate with carbonic anhydrase. , 1982, European journal of biochemistry.

[62]  K. Fridborg,et al.  Structure and function of carbonic anhydrases , 1977, FEBS letters.

[63]  R. Ferrell,et al.  Amino acid sequence of rabbit carbonic anhydrase II. , 1978, Biochimica et biophysica acta.

[64]  R. Henkens,et al.  Role of zinc (II) in the refolding of guanidine hydrochloride denatured bovine carbonic anhydrase. , 1972, Biochemistry.

[65]  H. F. Deutsch,et al.  Human carbonic anhydrases. XII. The complete primary structure of the C isozyme. , 1974, The Journal of biological chemistry.

[66]  D. Kern The hydration of carbon dioxide , 1960 .

[67]  R. Holmes Mammalian carbonic anhydrase isozymes: evidence for a third locus. , 1976, The Journal of experimental zoology.

[68]  R. Khalifah Kinetics and Mechanistic Implications of CO2 Hydration Activity of Human Erythrocyte Carbonic Anhydrases , 1980 .

[69]  P. Carey,et al.  Resonance Raman studies in some carboni anhydrase-aromatic sulfonamide complexes. , 1976, Biochemistry.

[70]  A. Pullman CARBONIC ANHYDRASE: THEORETICAL STUDIES OF DIFFERENT HYPOTHESES , 1981, Annals of the New York Academy of Sciences.

[71]  J. Coleman Mechanism of action of carbonic anhydrase. Subtrate, sulfonamide, and anion binding. , 1967, The Journal of biological chemistry.

[72]  H. Wennerström,et al.  Diffusion control in reversible enzyme reactions. Applications to carbonic anhydrase. , 1978, Biophysical chemistry.

[73]  T. Nishita,et al.  Isolation of equine muscle carbonic anhydrase in crystalline form. , 1981, Biochemical and biophysical research communications.

[74]  S. H. Koenig,et al.  The pH-Independence of Carbonic Anhydrase Activity: Apparent pKa Due to Inhibition by HSO4− , 1980 .

[75]  R. Schowen,et al.  Protonic reorganization and substrate structure in catalysis by serine proteases , 1980 .

[76]  S. H. Koenig,et al.  H 2 CO 3 as substrate for carbonic anhydrase in the dehydration of HCO 3 . , 1972, Proceedings of the National Academy of Sciences of the United States of America.

[77]  H. F. Deutsch,et al.  Human carbonic anhydrases. XI. The complete primary structure of carbonic anhydrase B. , 1973, The Journal of biological chemistry.

[78]  K. Kannan Crystal Structure of Carbonic Anhydrase , 1980 .

[79]  R. Khalifah Carbon dioxide hydration activity of carbonic anhydrase: paradoxical consequences of the unusually rapid catalysis. , 1973, Proceedings of the National Academy of Sciences of the United States of America.

[80]  H. Urey,et al.  The Kinetics of Isotopic Exchange between Carbon Dioxide, Bicarbonate Ion, Carbonate Ion and Water1 , 1940 .

[81]  A. Burgen,et al.  Kinetic aspects of structure─activity relations: the binding of sulphonamides by carbonic anhydrase , 1976, Proceedings of the Royal Society of London. Series B. Biological Sciences.

[82]  E. Noltmann,et al.  Discovery of carbonic anhydrase in rabbit skeletal muscle and evidence for its identity with "basic muscle protein". , 1978, The Journal of biological chemistry.

[83]  R. Gupta,et al.  NMR Studies of Carbonic Anhydrase , 1980 .

[84]  J. Coleman Human carbonic anhydrase. Protein conformation and metal ion binding. , 1965, Biochemistry.

[85]  S. H. Koenig,et al.  Nuclear magnetic relaxation dispersion in protein solutions. IV. Proton relaxation at the active site of carbonic anhydrase. , 1970, The Journal of biological chemistry.

[86]  R. Tashian,et al.  The amino acid sequence of carbonic anhydrase I from the rhesus macaque. , 1980, Biochemical and biophysical research communications.

[87]  Manfred Eigen,et al.  Proton Transfer, Acid-Base Catalysis, and Enzymatic Hydrolysis. Part I: ELEMENTARY PROCESSES†‡ , 1964 .

[88]  P. Woolley,et al.  On the mechanism of action of carbonic anhydrase , 1973 .

[89]  R. J. Williams,et al.  The catalysis of the reaction between carbon dioxide and water , 1966 .

[90]  D. Eustace,et al.  Participation of Hydroxylic Solvent Molecules , 1975 .

[91]  J. C. Kernohan The activity of bovine carbonic anhydrase in imidazole buffers , 1964 .

[92]  B. Jonsson,et al.  Participation of buffer in the catalytic mechanism of carbonic anhydrase , 1976, FEBS letters.

[93]  S. Lindskog,et al.  The catalytic mechanism of carbonic anhydrase. , 1975, Proceedings of the National Academy of Sciences of the United States of America.

[94]  T. Maren,et al.  A quantitative analysis of CO2 transport at rest and during maximal exercise. , 1978, Respiration physiology.

[95]  F. Schoening,et al.  The crystal structure of zinc acetate dihydrate, Zn(CH3COO)2.2H2O , 1953 .

[96]  K. B. Schowen Solvent Hydrogen Isotope Effects , 1978 .

[97]  B. Gaber,et al.  Laser Raman scattering from an enzyme of well-documented structure, human carbonic anhydrase B. , 1977, Journal of the American Chemical Society.

[98]  I. Bertini,et al.  PH-DEPENDENT PROPERTIES OF A CON4(OH2) CHROMOPHORE: A SPECTROSCOPIC MODEL OF COBALT CARBONIC ANHYDRASE , 1981 .

[99]  Y. Pocker,et al.  The Catalytic Versatility of Erythrocyte Carbonic Anhydrase. II. Kinetic Studies of the Enzyme-Catalyzed Hydration of Pyridine Aldehydes* , 1965 .

[100]  C. Tu,et al.  Kinetics of the exchange of oxygen between carbon dioxide and carbonate in aqueous solution , 1975 .

[101]  A. Burgen,et al.  Kinetics of complex formation between human carbonic anhydrases and aromatic sulfonamides. , 1970, Biochemistry.

[102]  G. Navon,et al.  Nuclear magnetic resonance studies of carbonic anhydrase catalyzed reversible hydration of acetaldehyde by the saturation transfer method. , 1980, Biochemistry.

[103]  P. Argos,et al.  Similarities in active center geometries of zinc-containing enzymes, proteases and dehydrogenases. , 1978, Journal of molecular biology.

[104]  L Järup,et al.  Crystal structure of human carbonic anhydrase C. , 1972, Nature: New biology.

[105]  H. F. Deutsch,et al.  Sequence of the low activity equine erythrocyte carbonic anhydrase and delineation of the amino acid substitutions in various polymorphic forms. , 1980, The Journal of biological chemistry.

[106]  I. Bertini,et al.  Hydrogen-1 NMR spectra of the coordination sphere of cobalt-substituted carbonic anhydrase , 1981 .

[107]  Khalifah Rg Histidine-200 alters inhibitor binding in human carbonic anhydrase B. A carbon-13 nuclear magnetic resonance identification. , 1977 .

[108]  I. Vaara,et al.  STRUCTURAL RELATIONSHIP OF HUMAN ERYTHROCYTE CARBONIC ANHYDRASE ISOZYMES B AND C , 1975 .

[109]  G. B. Kistiakowsky,et al.  The Enzymic Kinetics of Carbonic Anhydrase from Bovine and Human Erythrocytes , 1961 .

[110]  D. Hewett‐Emmett,et al.  Evolution of Structure and Function in the Carbonic Anhydrase Isozymes of Mammals , 1980 .

[111]  M. Rhee,et al.  A rapid and convenient preparation of apocarbonic anhydrase. , 1977, Analytical biochemistry.

[112]  J. Coleman,et al.  Structure of the active site of carbonic anhydrase as determined by electron spin resonance. , 1975, The Journal of biological chemistry.

[113]  W. Siffert,et al.  Carbonic anhydrase C in white-skeletal-muscle tissue. , 1982, The Biochemical journal.

[114]  Alberty Ra The interpretation of steady state kinetic data on enzymatic reactions. , 1962 .

[115]  D. Silverman,et al.  Solvent deuterium isotope effects in the catalysis of oxygen-18 exchange by human carbonic anhydrase II. , 1982, Biochemistry.

[116]  F. Roughton,et al.  Carbonic anhydrase. Its preparation and properties , 1933, The Journal of physiology.

[117]  R. Khalifah,et al.  The carbon dioxide hydration activity of carbonic anhydrase. I. Stop-flow kinetic studies on the native human isoenzymes B and C. , 1971, The Journal of biological chemistry.

[118]  R. Henkens,et al.  Carbon-13 nuclear magnetic relaxation study on cobalt carbonic anhydrase: Evidence on the location of enzyme bound CO2 and HCO3. , 1977, Journal of the American Chemical Society.

[119]  C. Strader,et al.  Interaction of the unique competitive inhibitor imidazole with human carbonic anhydrase B. , 1977, Biochemistry.

[120]  R. Tashian,et al.  Genetic variation in the carbonic anhydrase isozymes of macaque monkeys. 3. Biosynthesis of carbonic anhydrases in bone marrow erythroid cells and peripheral blood reticulocytes of Macaca nemestria. , 1973, Archives of biochemistry and biophysics.

[121]  T. Maren,et al.  The nature of anion inhibition of human red cell carbonic anhydrases. , 1979, Archives of biochemistry and biophysics.

[122]  P. Nyman,et al.  Primary structure of human carbonic anhydrase C. , 1976, The Journal of biological chemistry.

[123]  G. M. Harris,et al.  Kinetics and mechanism of aquation of carbonato complexes of cobalt(III). I. Acid-catalyzed aquation of carbonatopentaamminecobalt(III) ion , 1968 .

[124]  R. Holmes Purification, molecular properties and ontogeny of carbonic anhydrase isozymes. Evidence for A, B and C isozymes in avian and mammalian tissues. , 1977, European journal of biochemistry.

[125]  E. Magid The activity of carbonic anhydrases B and C from human erythrocytes and the inhibition of the enzymes fby copper. , 2009, Scandinavian journal of haematology.

[126]  N. Giraud,et al.  Structure primaire de l'anhydrase carbonique érythrocytaire B humaine: III. Séquence des fragments ICNBr et IIICNBr (résidus 149-260) , 1974 .

[127]  T. Maren,et al.  Carbonic anhydrase: chemistry, physiology, and inhibition. , 1967, Physiological reviews.

[128]  R. Ferrell,et al.  Amino acid sequence of sheep carbonic anhydrase C. , 1974, Biochimica et biophysica acta.

[129]  S. Lindskog,et al.  METAL-BINDING PROPERTIES OF HUMAN ERYTHROCYTE CARBONIC ANHYDRASES. , 1964, Biochimica et biophysica acta.

[130]  W. Jencks Catalysis in chemistry and enzymology , 1969 .

[131]  S. H. Koenig,et al.  The kinetic parameters of carbonic anhydrase by 13C nuclear magnetic resonance , 1974 .

[132]  Venkatasubban Ks,et al.  Carbon dioxide hydration activity of carbonic anhydrase in mixtures of water and deuterium oxide. , 1980 .

[133]  D. Silverman,et al.  Proton transfer between hemoglobin and the carbonic anhydrase active site. , 1978, Journal of Biological Chemistry.

[134]  I. Campbell,et al.  A study of the histidine residues of human carbonic anhydrase C using 270 MHz proton magnetic resonance. , 1975, Journal of molecular biology.

[135]  D. Silverman,et al.  Mechanism of carbonic anhydrase studied by carbon-13 and oxygen-18 labeling of carbon dioxide , 1975 .

[136]  Robert A. Alberty,et al.  Application of the Theory of Diffusion-controlled Reactions to Enzyme Kinetics , 1958 .

[137]  Y. Pocker,et al.  Effects of pH on anionic inhibition of carbonic anhydrase activities , 1982 .

[138]  J. T. Johansen,et al.  Metal coordination geometry and mode of action of carbonic anhydrase. Effect of imidazole on the spectral properties of Co(II) and111Cd(II) human carbonic anhydrase B , 1977 .

[139]  R. F. Chen,et al.  Combination of bovine carbonic anhydrase with a fluorescent sulfonamide. , 1967, The Journal of biological chemistry.

[140]  S. Lindskog,et al.  On the interaction of bovine cobalt carbonic anhydrase with sulfonamides. , 1968, European journal of biochemistry.

[141]  G. Navon,et al.  Temperature and requency dependence of solvent proton relaxation rates in solutions of manganese(II) carbonic anhydrase. , 1975, Biochemistry.

[142]  J. T. Johansen,et al.  Carbon dioxide hydration activity and metal—substrate distances of manganese (II) human carbonic anhydrase B determined by 13C magnetization—transfer NMR , 1982, FEBS letters.

[143]  A. Scozzafava,et al.  Evidence of exchangeable protons in the donor groups of the acidic form of cobalt bovine carbonic anhydrase B. , 1977, Biochemical and biophysical research communications.

[144]  D. Silverman,et al.  Inhibition by cupric ions of 18O exchange catalyzed by human carbonic anhydrase II. Relation to the interaction between carbonic anhydrase and hemoglobin. , 1981, The Journal of biological chemistry.

[145]  Robert P. Davis The Kinetics of the Reaction of Human Erythrocyte Carbonic Anhydrase. II. The Effect of Sulfanilamide, Sodium Sulfide and Various Chelating Agents , 1959 .

[146]  D. Hewett‐Emmett,et al.  Testosterone‐induced, sulfonamide‐resistant carbonic anhydrase isozyme of rat liver is indistinguishable from skeletal muscle carbonic anhydrase III , 1981, FEBS letters.

[147]  M. F. Dunn Mechanisms of zinc ion catalysis in small molecules and enzymes , 1975 .