The cation-π interaction between Lys53 and the flavin of fructosamine oxidase (FAOX-II) is critical for activity

Biochemistry

Volumn 50, Issue 37, 2011, Pages 7977-7986

  Collard, François ^a,c   Fagan, Rebecca L ^b,d   Zhang, Jianye ^a   Nemet, Ina ^a,e   Palfey, Bruce A ^b   Monnier, Vincent M ^a  

^a CASE WESTERN RESERVE UNIVERSITY   (United States)

^b UNIVERSITY OF MICHIGAN MEDICAL SCHOOL   (United States)

^c DE DUVE INSTITUTE   (Belgium)

^d UNIVERSITY OF IOWA   (United States)

^e RUDER BO KOVI INSTITUTE   (Croatia)

Author keywords

[No Author keywords available]

Indexed keywords

AMADORI PRODUCT; AMMONIUM NITROGEN; AROMATIC RINGS; ASPERGILLUS FUMIGATUS; HALF-REACTIONS; LOW MOLECULAR WEIGHT; MUTANT ENZYMES; OXYGEN REACTION; POSITIVE CHARGES; WILD TYPES;

AMINO ACIDS; AMMONIUM COMPOUNDS; CATALYSIS; CATALYSTS; CRYSTAL STRUCTURE; ENZYMES;

MOLECULAR OXYGEN;

CATION; FLAVINE ADENINE NUCLEOTIDE; FLAVOPROTEIN; FRUCTOSAMINE OXIDASE; LYSINE; METHIONINE; MUTANT PROTEIN; OXIDOREDUCTASE; QUERCETIN; UNCLASSIFIED DRUG;

AMINO ACID SUBSTITUTION; ANION EXCHANGE CHROMATOGRAPHY; ARTICLE; ASPERGILLUS FUMIGATUS; CRYSTAL STRUCTURE; DISSOCIATION CONSTANT; ENZYME BINDING; ENZYME KINETICS; ENZYME STRUCTURE; ENZYME SYNTHESIS; MOLECULAR BIOLOGY; MUTAGENESIS; NONHUMAN; OXIDATION; PRIORITY JOURNAL; PROTEIN EXPRESSION; PROTEIN PROTEIN INTERACTION; PROTEIN PURIFICATION;

AMINO ACID OXIDOREDUCTASES; ASPERGILLUS FUMIGATUS; BINDING SITES; CATIONS; ENZYME ACTIVATION; FLAVINS; FRUCTOSAMINE; LYSINE; PROTEIN BINDING; PROTEIN STRUCTURE, SECONDARY;

ASPERGILLUS FUMIGATUS;

EID: 80052698423     PISSN: 00062960     EISSN: 15204995     Source Type: Journal    
DOI: 10.1021/bi1020666     Document Type: Article

References (21)

1. Monnier, V. M., Mustata, G. T., Biemel, K. L., Reihl, O., Lederer, M. O., Zhenyu, D., and Sell, D. R. (2005) Cross-linking of the extracellular matrix by the Maillard reaction in aging and diabetes: an update on "a puzzle nearing resolution Ann. N.Y. Acad. Sci. 1043, 533-544 (Pubitemid 41123943)
2. Gerhardinger, C., Taneda, S., Marion, M. S., and Monnier, V. M. (1994) Isolation, Purification, and Characterization of an Amadori Product Binding Protein from a Pseudomonas sp. Soil Strain J. Biol. Chem. 269, 27297-27302 (Pubitemid 24346550)
3. Collard, F., Zhang, J., Nemet, I., Qanungo, K. R., Monnier, V. M., and Yee, V. C. (2008) Crystal Structure of the Deglycating Enzyme Fructosamine Oxidase (Amadoriase II) J. Biol. Chem. 283, 27007-27016
4. Takahashi, M., Pischetsrieder, M., and Monnier, V. M. (1997) Molecular cloning and expression of amadoriase isozyme (fructosyl amine:oxygen oxidoreductase, EC 1.5.3) from Aspergillus fumigatus J. Biol. Chem. 272, 12505-12507 (Pubitemid 27203341)
5. Grandhee, S. K. and Monnier, V. M. (1991) Mechanism of formation of the Maillard protein cross-link pentosidine. Glucose, fructose, and ascorbate as pentosidine precursors J. Biol. Chem. 266, 11649-11653 (Pubitemid 21906998)
6. Palfey, B. A. (2003) Time Resolved Spectral Analysis in Kinetic Analysis of Macromolecules: A Practical Approach (Johnson, K. A., Ed.) Chapter 9, pp 203-228, Oxford University Press, New York.
7. Williams, C. H., Jr., Arscott, L. D., Matthews, R. G., Thorpe, C., and Wilkinson, K. D. (1979) Methodology employed for anaerobic spectrophotometric titrations and for computer-assisted data analysis Methods Enzymol. 62, 185-198
8. Taira, K. and Benkovic, S. J. (1988) Evaluation of the Importance of Hydrophobic Interactions in Drug Binding to Dihydrofolate Reductase J. Med. Chem. 31, 129-137 (Pubitemid 18027861)
9. Gibson, Q. H., Swoboda, B. E., and Massey, V. (1964) Kinetics and Mechanism of Glucose Oxidase J. Biol. Chem. 239, 3927-3934
10. Fleck, G. M. (1971) Chemical Reaction Mechanisms, pp 66-100, Holt, Rinehart and Winston, New York.
11. Palfey, B. A., Ballou, D. P., and Massey, V. (1995) in Active Oxygen: Reactive Oxygen Species in Biochemistry (Valentine, J. S., Foote, C. S., Greenburg, A., and Lieberman, J. F., Eds.) Chapter 2, pp 37-83, Chapman and Hall, New York.
12. Palfey, B. A. and Massey, V. (1998) in Comprehensive Biological Catalysis (Sinnott, M., Ed.) Vol. III, Chapter 29, pp 83-154, Academic Press, New York.
13. Fagan, R. L. and Palfey, B. A. (2010) Flavin-Dependent Enzymes in Comprehensive Natural Products Chemistry II (Begley, T., Ed.) Vol. 7, Chapter 3, pp 37-114, Elsevier, Oxford, UK.
14. Trickey, P., Wagner, M. A., Jorns, M. S., and Mathews, F. S. (1999) Monomeric sarcosine oxidase: structure of a covalently flavinylated amine-oxidizing enzyme Structure 7, 331-345 (Pubitemid 29159692)
15. Hassan-Abdallah, A., Zhao, G., and Jorns, M. S. (2008) Covalent Flavinylation of Monomeric Sarcosine Oxidase: Identification of a Residue Essential for Holoenzyme Biosynthesis Biochemistry 47, 1136-1143 (Pubitemid 351161870)
16. Hassan-Abdallah, A., Bruckner, R. C., Zhao, G., and Jorns, M. S. (2005) Biosynthesis of Covalently Bound Flavin: Isolation and in vitro Flavinylation of the Monomeric Sarcosine Oxidase Apoprotein Biochemistry 44, 6452-6462 (Pubitemid 40593796)
17. Zhao, G. and Jorns, M. S. (2006) Spectral and Kinetic Characterization of the Michaelis Charge Transfer Complex of Monomeric Sarcosine Oxidase Biochemistry 45, 5985-5992 (Pubitemid 43727090)
18. Wu, X., Palfey, B. A., Mossine, V., and Monnier, V. (2001) Kinetic Studies, Mechanism, and Substrate Specificity of Amadoriase I from Aspergillus sp Biochemistry 40, 12886-12895 (Pubitemid 33026635)
19. Bruice, T. C. (1984) Oxygen-Flavin Chemistry Isr. J. Chem. 24, 54-61
20. Wagner, M. A. and Jorns, M. S. (2000) Monomeric Sarcosine Oxidase: 2. Kinetic Studies with Sarcosine, Alternate Substrates, and a Substrate Analog Biochemistry 39, 8825-8829 (Pubitemid 30602791)
21. Hassan-Abdallah, A., Zhao, G., and Jorns, M. S. (2008) Arginine 49 Is a Bifunctional Residue Important in Catalysis and Biosynthesis of Monomeric Sarcosine Oxidase: A Context-Sensitive Model for the Electrostatic Impact of Arginine to Lysine Mutations Biochemistry 47, 2913-2922 (Pubitemid 351328844)