Substrate dehydrogenation by flavoproteins

Accounts of Chemical Research

Volumn 34, Issue 4, 2001, Pages 299-307

  Fitzpatrick, P F ^a  

^a TEXAS A AND M UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; AMINE; AMINO ACID; FLAVINE ADENINE NUCLEOTIDE; FLAVINE MONONUCLEOTIDE; FLAVOPROTEIN; HYDROXYACID; NITROALKANE;

ARTICLE; CATALYSIS; ENZYME SUBSTRATE; HYDROGENATION; OXIDATION;

ALCOHOLS; ALKANES; AMINES; AMINO ACIDS; ENZYMES; FLAVOPROTEINS; HYDROGEN; OXIDATION-REDUCTION; SUBSTRATE SPECIFICITY;

EID: 0034860788     PISSN: 00014842     EISSN: None     Source Type: Journal    
DOI: 10.1021/ar0000511     Document Type: Article

References (88)

1. Free flavins: Syntheses, chemical and physical properties
2. Mechanisms of flavin catalysis
3. Activation of molecular oxygen by flavins and flavoproteins
4. GMC oxidoreductases a newly defined family of homologous proteins with diverse catalytic activities
5. Crystal structure of cholesterol oxidase complexed with a steroid substrate: Implications for flavin adenine dinucleotide dependent alcohol oxidases
6. Glucose oxidase from Penicillium Amagasakiense: Primary structure and comparison with other glucose-methanol-choline (GMC) oxidoreductases
7. Crystal structure of glucose oxidase from Aspergillus Niger refined at 2·3 Å resolution
8. Radical mechanisms for 1,5-dihydroflavin reduction of carbonyl compounds
9. Kinetics and mechanisms of the 1,5-dihydroflavin reduction of carbonyl compounds and the flavin oxidation of alcohols. 4. Interconversion of formaldehyde and methanol
10. Radical mechanisms for 1,5-dihydro-5-methylflavine reduction of carbonyl compounds
11. Mechanism of action of methanol oxidase, reconstitution of methanol oxidase with 5-deazaflavin, and inactivation of methanol oxidase by cyclopropanol
12. 6-flavin adduct is the major product of irreversible inactivation of cholesterol oxidase by 2α,3α-cyclopropano-5α-cholestan-3β-ol
13. The oxidation of 1-deuterated glucose by glucose oxidase
14. 447 in the reaction catalyzed by cholesterol oxidase
15. 361 position in the reaction catalyzed by cholesterol oxidase
16. Substituted alcohols as mechanistic probes of alcohol oxidase
17. pH variation of isotope effects in enzyme-catalyzed reactions. 2. Isotope-dependent step not pH dependent. Kinetic mechanism of alcohol dehydrogenase
18. Rate constants for a mechanism including intermediates in the interconversion of ternary complexes by horse liver alcohol dehydrogenase
19. 1.8 and 1.9 Å resolution structures of the Penicillium Amagasakiense and Aspergillus Niger glucose oxidases as a basis for modeling substrate complexes
20. Studies on the mechanism of action of D-amino acid oxidase evidence for removal of substrate α-hydrogen as a proton
21. Studies on the elimination reaction of D-amino acid oxidase with α-amino-β chlorobutyrate further evidence for abstraction of substrate α-hydrogen as a proton
22. 5-covalent adducts in the flavin oxidation of carbanions
23. Some model reactions and a general mechanism for flavoenzyme-catalyzed dehydrogenations
24. Use of 5-deazaFAD to study hydrogen transfer in the D-amino acid oxidase reaction
25. Enzyme-catalyzed redox reactions with the flavin analogues 5-deazariboflavin, 5-deazariboflavin 5′-phosphate, and 5-deazariboflavin 5′-diphosphate, 5′-5′-adenosine ester
26. Mechanistic features of the D-amino acid oxidase reaction studied by double stopped flow spectrophotometry
27. The kinetic mechanism of D-amino acid oxidase with D-α-aminobutyrate as substrate: Effect of enzyme concentration on the kinetics
28. pH and kinetic isotope effects on the reductive half-reaction of D-amino acid oxidase
29. Intrinsic primary, secondary, and solvent kinetic isotope effects on the reductive half-reaction of D-amino acid oxidase: Evidence against a concerted mechanism
30. Nitrogen isotope effects as probes of the mechanism of d-amino acid oxidase
31. Use of nitrogen-15 and deuterium isotope effects to determine the chemical mechanism of phenylalanine ammonia-lyase
32. 18O equilibrium isotope effects and fractionation factors
33. Proton release during the reductive half-reaction of D-amino acid oxidase
34. The use of pH studies to determine chemical mechanisms of enzyme-catalyzed reactions
35. 2
36. Structural and mechanistic studies on D-amino acid oxidase-substrate complex; implication of the crystal structure of enzyme-substrate analog complex
37. Role of arginine 285 in the active site of Rhodotorula Gracilis D-amino acid oxidase
38. Studies on the kinetic mechanism of pig kidney D-amino acid oxidase by site-directed mutagenesis of tyrosine 224 and tyrosine 228
39. Studies on the reaction mechanism of Rhodotorula Gracilis D-amino-acid oxidase. Role of the highly conserved tyr-223 on substrate binding and catalysis
40. The primary structure of the flavoprotein D-aspartate oxidase from beef kidney
41. Monomeric sarcosine oxidase: Structure of a covalently flavinylated amine oxidizing enzyme
42. Amino acid sequence of long chain α-hydroxy acid. Oxidase from rat kidney, a member of the family of FMN-dependent α-hydroxy acid-oxidizing enzymes
43. Studies on the mechanism of action of the flavoenzyme lactate oxidase: Oxidation and elimination with β-chlorolactate
44. Mechanistic studies on the rat kidney flavoenzyme L-α-hydroxy acid oxidase
45. 2)
46. 2: A mechanistic study of the dehydrohalogenation reaction
47. 2
48. 2
49. Stereochemical analysis of the elimination reaction catalyzed by D-amino-acid oxidase
50. 2: Consequences on catalysis of lactate dehydrogenation
51. The mechanism of flavoprotein-catalyzed α-hydroxy acid dehydrogenation, revisited
52. Mechanism of action of the flavoenzyme lactate oxidase
53. Role of charge-transfer interactions in flavoprotein catalysis
54. Flavoprotein oxidases
55. Mechanism of mycobacterium smegmatis L-lactate oxidase. 5-deazaflavine mononucleotide as a coenzyme analog
56. 2 from baker's yeast
57. Refined structure of spinach glycolate oxidase at 2 Å resolution
58. Three-dimensional structures of glycolate oxidase with bound active-site inhibitors
59. 2 at 2.4 Å resolution
60. 2 by site-directed mutagenesis
61. Lactate monooxygenase III. Additive contributions of active site residues to catalytic efficiency and stabilization of an anionic transition state
62. 2. Primary kinetic isotope effect studies with a phenylalanine mutant
63. Involvement of tyr24 and trp108 in substrate binding and substrate specificity of glycolate oxidase
64. Role of arginine 277 in (S)-mandelate dehydrogenase from Pseudomonas Putida in substrate binding and transition state stabilization
65. Lactate monooxygenase II. Site-directed mutagenesis of the postulated active site base histidine 290
66. 2 (L-lactate dehydrogenase)
67. (S)-mandelate dehydrogenase from Pseudomonas Putida: Mutation of the catalytic base histidine-274 and chemical rescue of activity
68. 2 (L-lactate dehydrogenase): Substitution of asp282 with asparagine
69. Role of tyrosine 129 in the active site of spinach glycolate oxidase
70. Nitroalkanes as reductive substrates for flavoprotein oxidases
71. Mechanism of oxidation of nitro-ethane by glucose oxidase
72. 5-flavin-carbanion adducts as catalytic intermediates in the oxidation of nitroethane by D-amino acid oxidase
73. pH and secondary kinetic isotope effects on the reaction of D-amino acid oxidase with nitroalkane anions: Evidence for direct attack on the flavin by carbanions
74. Purification and properties of nitroalkane-oxidizing enzyme from Hansenula Mrakii
75. Identification of the naturally occurring flavin of nitroalkane oxidase from Fusarium Oxysporum as a 5-nitrobutyl-FAD and conversion of the enzyme to the active FAD-containing form
76. Biochemical and physical characterization of the active FAD-containing form of nitroalkane oxidase from Fusarium Oxysporum
77. Mechanism of nitroalkane oxidase: 2. pH and kinetic isotope effects
78. Use of pH and kinetic isotope effects to dissect the effects of substrate size on binding and catalysis by nitroalkane oxidase
79. Kinetic mechanism and substrate specificity of nitroalkane oxidase
80. The principle of nonperfect synchronization: More than a qualitative concept?
81. Identification of an essential tyrosine residue in nitroalkane oxidase by modification with tetranitromethane
82. Evidence for an essential arginine in the flavoprotein nitroalkane oxidase
83. Monoamine oxidase: Old friends hold many surprises
84. Radical ideas about monoamine oxidase
85. Inactivation of monoamine oxidase by (aminomethyl) cubane. First evidence for an α-amino radical during enzyme catalysis
86. Flavin chemical models for monoamine oxidase inactivation by cyclopropylamines, α-silylamines, and hydrazines
87. Structure-activity relationships in the oxidation of para-substituted benzylamine analogues by recombinant human liver monoamine oxidase A
88. Structure-activity relationships in the oxidation of benzylamine analogues by bovine liver mitochondrial monoamine oxidase B