Revealing the moonlighting role of NADP in the structure of a flavin-containing monooxygenase

Proceedings of the National Academy of Sciences of the United States of America

Volumn 105, Issue 18, 2008, Pages 6572-6577

  Alfieri, Andrea ^a   Malito, Enrico ^a,c   Orru, Roberto ^a   Fraaije, Marco W ^b   Mattevi, Andrea ^a  

^a UNIVERSITY OF PAVIA   (Italy)

^b UNIVERSITY OF GRONINGEN   (Netherlands)

^c UNIVERSITY OF CHICAGO   (United States)

Author keywords

Drug metabolism; Oxygen; Trimethylaminuria

Indexed keywords

CYTOCHROME C PEROXIDASE; DIMETHYLANILINE MONOOXYGENASE; NICOTINAMIDE; NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE; OXIDOREDUCTASE; RIBOSE; DIMETHYLANILINE MONOOXYGENASE (N-OXIDE FORMING); OXYGENASE;

AMINO ACID SEQUENCE; ANIMAL CELL; ARTICLE; BACTERIAL STRAIN; CATALYSIS; CONTROLLED STUDY; CRYSTALLIZATION; GENE MUTATION; METHYLOTROPH; NONHUMAN; OXYGENATION; PRIORITY JOURNAL; PROKARYOTIC CELL; PROTEIN DOMAIN; PROTEIN FUNCTION; PROTEIN LOCALIZATION; PROTEIN STABILITY; PROTEIN STRUCTURE; BINDING SITE; CHEMICAL STRUCTURE; CHEMISTRY; GENETIC POLYMORPHISM; GENETICS; HUMAN; KINETICS; METABOLISM; MOLECULAR GENETICS; MUTATION; PROTEIN SECONDARY STRUCTURE; SPECTROSCOPY; X RAY CRYSTALLOGRAPHY;

MAMMALIA; METHYLOPHAGA; PROKARYOTA;

AMINO ACID SEQUENCE; BINDING SITES; CATALYSIS; CRYSTALLOGRAPHY, X-RAY; HUMANS; KINETICS; MODELS, MOLECULAR; MOLECULAR SEQUENCE DATA; MUTATION; NADP; OXYGENASES; POLYMORPHISM, GENETIC; PROTEIN STRUCTURE, SECONDARY; SPECTRUM ANALYSIS;

EID: 44349089600     PISSN: 00278424     EISSN: 10916490     Source Type: Journal    
DOI: 10.1073/pnas.0800859105     Document Type: Article

References (43)

1. Cashman JR (2005) Some distinctions between flavin-containing and cytochrome P450 monooxygenases. Biochem Biophys Res Commun 338:599-604.
2. van Berkel WJ, Kamerbeek NM, Fraaije MW (2006) Flavoprotein monooxygenases, a diverse class of oxidative biocatalysts. J Biotechnol 124:670-689.
3. Ziegler DM (2002) An overview of the mechanism, substrate specificities, and structure of FMOs. Drug Metab Rev 34:503-511.
4. Poulsen LL, Ziegler DM (1979) The liver microsomal FAD-containing monooxygenase. J Biol Chem 254:6449-6455.
5. Beaty NB, Ballou DP (1981) The reductive half-reaction of liver microsomal FAD-containing monooxygenase. J Biol Chem 256:4611-4618.
6. Beaty NB, Ballou DP (1981) The oxidative half-reaction of liver microsomal FAD-containing monooxygenase. J Biol Chem 256:4619-4625.
7. Beaty NB, Ballou DP (1980) Transient kinetic study of liver microsomal FAD-containing monooxygenase. J Biol Chem 255:3817-3819.
8. Jones KC, Ballou DP (1986) Reactions of the 4a-hydroperoxide of liver microsomal flavin-containing monooxygenase with nucleophlic and electrophilic substrates. J Biol Chem 261:2553-2559.
9. Krueger SK, Williams DE (2005) Mammalian flavin-containing monooxygenases: structure/ function, genetic polymorphisms and role in drug metabolism. Pharmacol Ther 106:357-387.
10. Cashman JR (1995) Structural and catalytic properties of the mammalian flavin-containing monooxygenase. Chem Res Toxicol 8:166-181.
11. Hernandez D, Janmohamed A, Chandan P, Phillips IR, Shephard EA (2004) Organization and evolution of the flavin-containing monooxygenase genes of human and mouse: identification of novel gene and pseudogene clusters. Pharmacogenetics 14:117-130.
12. Cashman JR, Zhang J (2006) Human flavin-containing monooxygenases. Annu Rev Pharmacol Toxicol 46:65-100.
13. Cashman JR (2003) The role of flavin-containing monooxygenases in drug metabolism and development. Curr Opin Drug Discov Devel 6:486-493.
14. Cashman JR (2004) The implications of polymorphisms in mammalian flavin-containing monooxygenases in drug discovery and development. Drug Discov Today 9:574-581.
15. Koukouritaki SB, Hines RN (2005) Flavin-containing monooxygenase genetic polymorphism: impact on chemical metabolism and drug development. Pharmacogenomics 6:807-822.
16. Lattard V, Zhang J, Cashman JR (2004) Alternative processing events in human FMO genes. Mol Pharmacol 65:1517-1525.
17. Zhou J, Shephard EA (2006) Mutation, polymorphism and perspectives for the future of human flavin-containing monooxygenase 3. Mutat Res 612:165-171.
18. Schlaich NL (2007) Flavin-containing monooxygenases in plants: looking beyond detox. Trends Plants Sci 12:412-418.
19. Choi HS, et al. (2003) A novel flavin-containing monooxygenase from Methylophaga sp strain SK1 and its indigo synthesis in Escherichia coli. Biochem Biophys Res Commun 306:930-936.
20. Fraaije MW, Kamerbeek NM, van Berkel WJH, Janssen DB (2002) Identification of a Baeyer-Villiger monooxygenase sequence motif. FEBS Lett 518:43-47.
21. Eswaramoorthy S, Bonanno JB, Burley SK, Swaminathan S (2006) Mechanism of action of a flavin-containing monooxygenase. Proc Natl Acad Sci USA 103:9832-9837.
22. Chenna R, et al. (2003) Multiple sequence alignment with the Clustal series of programs. Nucleic Acids Res 31:3497-3500.
23. Gouet P, Courcelle E, Stuart DI, Metoz F (1999) ESPript: multiple sequence alignments in PostScript. Bioinformatics 15:305-308.
24. Palfey BA, Massey V (1998) in Comprehensive Biological Catalysis (Academic, San Diego, CA), Vol 3, pp 83-154.
25. Kemal C, Bruice TC (1976) Simple synthesis of a 4a-hydroperoxy adduct of a 1,5-dihydroflavine: preliminary studies of a model for bacterial luciferase. Proc Natl Acad Sci USA 73:995-999.
26. Poulsen LL, Ziegler DM (1995) Multisubstrate flavin-containing monooxygenases: applications of mechanism to specificity. Chem Biol Interact 96:57-73.
27. Suh JK, Poulsen LL, Ziegler DM, Robertus JD (1996) Molecular cloning and kinetic characterization of a flavin-containing monooxygenase from Saccharomyces cerevisiae. Arch Biochem Biophys 336:268-274.
28. Derewenda ZS (2004) Rational protein crystallization by mutational surface engineering. Structure 12:529-535.
29. Murshudov GN, Vagin AA, Dodson EJ (1997) Refinement of macromolecular structures by the maximum-likelihood method. Acta Crystallogr D 53:240-255.
30. Laskowski RA, MacArthur MW, Moss DS, Thornton JM (1993) PROCHECK: a program to check the stereochemical quality of protein structures. J Appl Crystallogr 26:283-291.
31. Kleywegt GJ, Jones TA (1994) Detection, delineation, measurement and display of cavities in macromolecular structures. Acta Crystallogr D 50:178-185.
32. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE (2000) The Protein Data Bank. Nucleic Acids Res 28:235-242.
33. Eswaramoorthy S, Bonanno JB, Burley SK, Swaminathan S (2006) Mechanism of action of a flavin-containing monooxygenase. Proc Natl Acad Sci USA 103:9832-9837, and erratum (2007) 104:14543.
34. Sheng D, Ballou DP, Massey V (2001) Mechanistic studies of cyclohexanone monooxygenase: chemical properties of intermediates involved in catalysis. Biochemistry 40:11156-11167.
35. Torres Pazmiño DE, Baas JB, Janssen DB, Fraaije MW (2008) The kinetic mechanism of phenylacetone monooxygenase from Thermobifida fusca. Biochemistry 47:4082-4093.
36. 2+ as a coenzyme substitute in enzymatic oxidations catalyzed by Baeyer-Villiger monooxygenases. Chem Commun 29:3724-3726.
37. Malito E, Alfieri A, Fraaije MW, Mattevi A (2004) Crystal structure of a Baeyer-Villiger monooxygenase. Proc Natl Acad Sci USA 101:13157-13162.
38. Lennon BW, Williams CH, Jr, Ludwig ML (2000) Twists in catalysis: alternating conformations of Escherichia coli thioredoxin reductase. Science 289:1190-1194.
39. CCP4 (Collaborative Computational Project, Number 4) (1994) The CCP4 suite: programs for protein crystallography. Acta Crystallogr D 50:760-763.
40. Schneider TR, Sheldrick GM (2002) Substructure solution with SHELXD. Acta Crystallogr D 58:1772-1779.
41. Bricogne G, Vonrhein C, Flensburg C, Schiltz M, Paciorek W (2003) Generation, representation and flow of phase information in structure determination: recent developments in and around SHARP 2.0. Acta Crystallogr D 59:2023-2030.
42. Perrakis A, Morris R, Lamzin VS (1999) Automated protein model building combined with iterative structure refinement. Nat Struct Biol 6:458-463.
43. Emsley P, Cowtan K (2004) Coot: model-building tools for molecular graphics. Acta Crystallogr D 60:2126-2132.