The pH dependence of kinetic isotope effects in monoamine oxidase A indicates stabilization of the neutral amine in the enzyme-substrate complex

FEBS Journal

Volumn 275, Issue 15, 2008, Pages 3850-3858

  Dunn, Rachel V ^a   Marshall, Ker R ^b   Munro, Andrew W ^a   Scrutton, Nigel S ^a  

^a UNIVERSITY OF MANCHESTER   (United Kingdom)

^b UNIVERSITY OF LEICESTER   (United Kingdom)

Author keywords

Kinetic isotope effect; Mechanism; Monoamine oxidase; pH dependence

Indexed keywords

AMINE; AMINE OXIDASE (FLAVIN CONTAINING) ISOENZYME A; QUERCETIN;

ARTICLE; BINDING KINETICS; CATALYSIS; ENZYME ACTIVE SITE; ENZYME KINETICS; ENZYME STABILITY; ENZYME SUBSTRATE; ENZYME SUBSTRATE COMPLEX; IONIZATION; PH; PHYSIOLOGY; PRIORITY JOURNAL; PROTON TRANSPORT; REACTION OPTIMIZATION; STEADY STATE;

AMINES; BASE SEQUENCE; CATALYSIS; DNA PRIMERS; HUMANS; HYDROGEN-ION CONCENTRATION; ISOTOPES; KINETICS; LIVER; MONOAMINE OXIDASE; SUBSTRATE SPECIFICITY;

EID: 47249152398     PISSN: 1742464X     EISSN: 17424658     Source Type: Journal    
DOI: 10.1111/j.1742-4658.2008.06532.x     Document Type: Article

References (30)

1. Binda C, Newton-Vinson P, Hubalek F, Edmondson DE Mattevi A (2002) Structure of human monoamine oxidase B, a drug target for the treatment of neurological disorders. Nat Struct Biol 9, 22 26.
2. Cesura AM Pletscher A (1992) The new generation of monoamine oxidase inhibitors. Prog Drug Res 38, 171 297.
3. Scrutton NS (2004) Chemical aspects of amine oxidation by flavoprotein enzymes. Nat Prod Rep 21, 722 730.
4. Silverman RB (1995) Radical ideas about monoamine-oxidase. Acc Chem Res 28, 335 342.
5. Edmondson DE, Binda C Mattevi A (2007) Structural insights into the mechanism of amine oxidation by monoamine oxidases A and B. Arch Biochem Biophys 464, 269 276.
6. Li M, Binda C, Mattevi A Edmondson DE (2006) Functional role of the 'aromatic cage' in human monoamine oxidase B: structures and catalytic properties of Tyr435 mutant proteins. Biochemistry 45, 4775 4784.
7. Erdem SS, Karahan O, Yildiz I Yelekci K (2006) A computational study on the amine-oxidation mechanism of monoamine oxidase: insight into the polar nucleophilic mechanism. Org Biomol Chem 4, 646 658.
8. Akyuz MA, Erdem SS Edmondson DE (2007) The aromatic cage in the active site of monoamine oxidase B: effect on the structural and electronic properties of bound benzylamine and p-nitrobenzylamine. J Neural Transm 114, 693 698.
9. Ralph EC, Hirschi JS, Anderson MA, Cleland WW, Singleton DA Fitzpatrick PF (2007) Insights into the mechanism of flavoprotein-catalyzed amine oxidation from nitrogen isotope effects on the reaction of N-methyltryptophan oxidase. Biochemistry 46, 7655 7664.
10. Rigby SEJ, Hynson RMG, Ramsay RR, Munro AW Scrutton NS (2005) A stable tyrosyl radical in monoamine oxidase A. J Biol Chem 280, 4627 4631.
11. Kay CW, El Mkami H, Molla G, Pollegioni L Ramsay RR (2007) Characterization of the covalently bound anionic flavin radical in monoamine oxidase a by electron paramagnetic resonance. J Am Chem Soc 129, 16091 16097.
12. Miller JR Edmondson DE (1999) Structure-activity relationships in the oxidation of para-substituted benzylamine analogues by recombinant human liver monoamine oxidase A. Biochemistry 38, 13670 13683.
13. McEwen CM, Sasaki G Lenz WR (1968) Human liver mitochondrial monoamine oxidase. I. Kinetic studies of model interactions. J Biol Chem 243, 5217 5225.
14. Edmondson DE, Bhattacharrya AK Xu J (2000) Evidence for alternative binding modes in the interaction of benzylamine analogues with bovine liver monoamine oxidase B. Biochim Biophys Acta 1479, 52 58.
15. Jones TZE, Balsa D, Unzeta M Ramsay RR (2007) Variations in activity and inhibition with pH: the protonated amine is the substrate for monoamine oxidase, but uncharged inhibitors bind better. J Neural Transm 114, 707 712.
16. Ramsay RR (1991) Kinetic mechanism of monoamine oxidase A. Biochemistry 30, 4624 4629.
17. Nandigama RK Edmondson DE (2000) Structure-activity relations in the oxidation of phenethylamine analogues by recombinant human liver monoamine oxidase A. Biochemistry 39, 15258 15265.
18. Basran J, Sutcliffe MJ Scrutton NS (2001) Optimizing the Michaelis complex of trimethylamine dehydrogenase - identification of interactions that perturb the ionization of substrate and facilitate catalysis with trimethylamine base. J Biol Chem 276, 42887 42892.
19. Perrin CL, Ohta BK, Kuperman J, Liberman J Erdelyi M (2005) Stereochemistry of beta-deuterium isotope effects on amine basicity. J Am Chem Soc 127, 9641 9647.
20. Bary Y, Gilboa H Halevi EA (1979) Secondary hydrogen isotope effects.5. Acid and base strengths - corrigendum and addendum. J Chem Soc Perkin Trans 2, 938 942.
21. Basran J, Sutcliffe MJ Scrutton NS (2001) Deuterium isotope effects during carbon-hydrogen bond cleavage by trimethylamine dehydrogenase - implications for mechanism and vibrationally assisted hydrogen tunneling in wild-type and mutant enzymes. J Biol Chem 276, 24581 24587.
22. Tipton KF Dixon HB (1979) Effects of pH on enzymes. Methods Enzymol 63, 183 234.
23. Royo M Fitzpatrick PF (2005) Mechanistic studies of mouse polyamine oxidase with N1,N12-bisethylspermine as a substrate. Biochemistry 44, 7079 7084.
24. Zhao G Jorns MS (2005) Ionization of zwitterionic amine substrates bound to monomeric sarcosine oxidase. Biochemistry 44, 16866 16874.
25. Son S-Y, Ma J, Kondou Y, Yoshimura M, Yamashita E Tsukihara T (2008) Structure of human monoamine oxidase A at 2.2-Å resolution: the control of opening the entry for substrates/inhibitors. Proc Natl Acad Sci USA 105, 5739 5744.
26. Invitrogen Corporation (1998) EasySelect Pichia Expression Kit: A Manual of Methods For Expression of Recombinant Proteins Using pPICZ and pPICZα in Pichia pastoris. Invitrogen Corporation, San Diego, CA.
27. Li M, Hubalek F, Newton-Vinson P Edmondson DE (2002) High-level expression of human liver monoamine oxidase a in Pichia pastoris: comparison with the enzyme expressed in Saccharomyces cerevisiae. Protein Expr Purif 24, 152 162.
28. Weyler W Salach JI (1985) Purification and properties of mitochondrial monoamine-oxidase type-A from human-placenta. J Biol Chem 260, 13199 13207.
29. Walker MC Edmondson DE (1994) Structure-activity-relationships in the oxidation of benzylamine analogs by bovine liver mitochondrial monoamine-oxidase-B. Biochemistry 33, 7088 7098.
30. Strickland S, Palmer G Massey V (1975) Determination of dissociation-constants and specific rate of constants of enzyme-substrate (or protein-ligand) interactions from rapid reaction kinetic data. J Biol Chem 250, 4048 4052.