Functional analysis of acyl-CoA dehydrogenase catalytic residue mutants using surface plasmon resonance and circular dichroism

Molecular Genetics and Metabolism

Volumn 87, Issue 3 SPEC. ISS., 2006, Pages 233-242

  Goetzman, Eric S ^a   He, Miao ^a   Nguyen, Tien V ^b   Vockley, Jerry ^a  

^a CHILDREN S HOSPITAL OF PITTSBURGH   (United States)

^b Mayo Clinic College of Medicine   (United States)

Author keywords

Circular dichroism; Electron transferring flavoprotein; Isovaleryl CoA dehydrogenase; Short chain acyl CoA dehydrogenase; Surface plasmon resonance

Indexed keywords

ACYL COENZYME A DEHYDROGENASE; ISOVALERYL COENZYME A DEHYDROGENASE; OXIDOREDUCTASE; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; CATALYSIS; CIRCULAR DICHROISM; ENZYME ACTIVITY; ENZYME ANALYSIS; ENZYME SUBSTRATE COMPLEX; MOLECULAR MODEL; PRIORITY JOURNAL; SURFACE PLASMON RESONANCE;

EID: 33644652961     PISSN: 10967192     EISSN: 10967206     Source Type: Journal    
DOI: 10.1016/j.ymgme.2005.09.027     Document Type: Article

References (44)

1. J.-J.P. Kim, M. Wang, R. Paschke, S. Djordjevic, D.W. Bennett, and J. Vockley Three dimensional structures of acyl-CoA dehydrogenases: structural basis of substrate specificity K. Yagi Flavins and Flavoproteins 1993 1994 Walter deGruyter New York 273 282
2. K.P. Battaile, T.V. Nguyen, J. Vockley, and J.J. Kim Structures of isobutyryl-CoA dehydrogenase and enzyme-product complex: comparison with isovaleryl- and short-chain acyl-CoA dehydrogenases J. Biol. Chem. 279 2004 16526 16534
3. Y. Ikeda, C. Dabrowski, and K. Tanaka Separation and properties of five distinct acyl-CoA dehydrogenases from rat liver mitochondria J. Biol. Chem. 258 1983 1066 1076
4. R.J.A. Wanders, P. Vreken, M.E.J. Den Boer, F.A. Wijburg, A.H. Van Gennip, and L. IJlst Disorders of mitochondrial fatty acyl-CoA β-oxidation J. Inher. Metab. Dis. 22 1999 442 487
5. P.M. Coates, and K. Tanaka Molecular basis of mitochondrial fatty acid oxidation defects J. Lipid Res. 33 1992 1099 1110
6. S. Eaton, K. Bartlett, and M. Pourfarzam Mammalian mitochondrial beta-oxidation [Review] Biochem. J. 320 1996 345 357
7. L. Sweetman, and J.D. Williams Branched chain organic acidurias C. Scriver A.L. Beaudet W. Sly D. Valle The Metabolic and Molecular Basis of Inherited Disease eighth edition 2001 McGraw-Hill New York 2125 2164
8. S. Ghisla, C. Thorpe, and V. Massey Mechanistic studies with general acyl-CoA dehydrogenase and butyryl-CoA dehydrogenase: evidence for the transfer of the β-hydrogen to the flavin N(5)-position as a hydride Biochemistry 23 1984 3154 3161
9. C. Thorpe, R.A. Schaller, A.-W. Mohsen, and J. Vockley The Acyl-CoA Dehydrogenases: Some Mechanistic Aspects 1997 University of Calgary Press Calgary, Canada
10. C. Thorpe, and J.J.P. Kim Structure and mechanism of action of the acyl-CoA dehydrogenases FASEB 9 1995 718 725
11. Y. Ikeda, D.G. Hine, K. Okamura-Ikeda, and K. Tanaka Mechanism of action of short-chain, medium-chain, and long-chain acyl-CoA dehydrogenases: Direct evidence for carbanion formation as an intermediate step using enzyme-catalyzed C-2 proton/deuteron exchange in the absence of C-3 exchange J. Biol. Chem. 260 1985 1326 1337
12. R.A. Schaller, and C. Thorpe Oxidative Inactivation of a charge transfer complex in the medium-chain acyl-CoA dehydrogenase Biochemistry 34 1995 16424 16432
13. I. Rudik, S. Ghisla, and C. Thorpe Protonic equilibria in the reductive haft-reaction of the medium-chain acyl-CoA dehydrogenase Biochemistry 37 1998 8437 8445
14. S. Ghisla, and C. Thorpe Acyl-CoA dehydrogenases. A mechanistic overview Eur. J. Biochem. 271 2004 494 508
15. H. Beinert Evidence for an Intermediate in the oxidation-reduction of flavoproteins J. Biol. Chem. 225 1956 465 478
16. K.V. Gopalan Beyond the proton abstracting role of Glu-376 in medium-chain acyl-CoA dehydrogenase: influence of Glue-376/Gln substitution on ligand binding and catalysis Biochemistry 41 2002 4638 4648
17. L.M. Schopfer, V. Massey, S. Ghisla, and C. Thorpe Oxidation-reduction of general acyl-CoA dehydrogenase by the butyryl-CoA/crotonyl-CoA couple. A new investigation of the rapid reaction kinetics Biochemistry 27 1988 6599 6611
18. J.G. Cummings, and C. Thorpe Two new mechanism-based inhibitors of the acyl-CoA dehydrogenases K. Yagi Flavins and Flavoproteins 1994 Walter de Gruyter & Co. Berlin 313 321
19. A.-W.A. Mohsen, and J. Vockley Identification of the active site catalytic residue in human isovaleryl-CoA dehydrogenase Biochemistry 34 1995 10146 10152
20. K.P. Battaile, J.-J. Kim, and J. Vockley Identification of the catalytic residue and characterization of the substrate binding pocket of rat SCAD by in vitro mutagenesis and X-ray crystallography Am. J. Hum. Genet. 57 1995 A175
21. K. Battaile, A.-W. Mohsen, and J. Vockley Functional role of the active site glutamate-368 in rat short chain acyl-CoA dehydrogenase Biochemistry 35 1996 15356 15363
22. P. Bross, S. Engst, A.W. Strauss, D.P. Kelly, I. Rasched, and S. Ghisla Characterization of wild-type and an active site mutant of human medium-chain acyl-CoA dehydrogenase after expression in E. coli J. Biol. Chem. 265 1990 7116 7119
23. S. Djordjevic, Y. Dong, R. Paschke, F.E. Frerman, A.W. Strauss, and J.J.P. Kim Identification of the catalytic base in long chain acyl-CoA dehydrogenase Biochemistry 33 1994 4258 4264
24. H. Katagiri, T. Asano, T. Yamada, T. Aoyama, Y. Fukushima, M. Kikuchi, T. Kodama, and Y. Oka Acyl-coenzyme A dehydrogenases are localized on GLUT4-containing vesicles via association with insulin-regulated aminopeptidase in a manner dependent on its dileucine motif Mol. Endocrinol. 16 2002 1049 1059
25. A.A. Mohsen, and J. Vockley High-level expression of an altered cDNA encoding human isovaleryl-CoA dehydrogenase in Escherichia coli Gene 160 1995 263 267
26. T. Nguyen, C. Riggs, D. Babovic-Vuksanovic, Y.S. Kim, J.F. Carpenter, T.P. Burghardt, N. Gregersen, and J. Vockley Purification and Characterization of two polymorphic variants of short chain acyl-CoA dehydrogenase reveal reduction of catalytic activity and stability of the Gly185Ser enzyme Biochemistry 41 2002 11126 11133
27. G. Williamson, and P.C. Engel A convenient and rapid method for the complete removal of CoA from butyryl-CoA dehydrogenase Biochim. Biophys. Acta 706 1982 245 248
28. G. Williamson, P.C. Engel, J.P. Mizzer, C. Thorpe, and V. Massey Evidence that the greening ligand in native butyryl-CoA dehydrogenase is a CoA persulfide J. Biol. Chem. 257 1982 4314 4320
29. A.W.A. Mohsen, B. Navarette, and J. Vockley Identification of Caenorhabditis elegans isovaleryl-CoA Mol. Genet. Metab. 73 2001 126 137
30. F.E. Frerman, and S.I. Goodman Fluorometric assay of acyl-CoA dehydrogenases in normal and mutant human fibroblasts Biochem. Med. 33 1985 38 44
31. H.M. Hoard-Fruchey, E. Goetzman, L. Benson, S. Naylor, and J. Vockley Mammalian electron transferring flavoprotein.flavoprotein dehydrogenase complexes observed by microelectrospray ionization-mass spectrometry and surface plasmon resonance J. Biol. Chem. 279 2004 13786 13791
32. M. He, T.P. Burghardt, and J. Vockley A novel approach to the characterization of substrate specificity in short/branched chain Acyl-CoA dehydrogenase J. Biol. Chem. 278 2003 37974 37986
33. K.A. Tiffany, D.L. Roberts, M. Wang, R. Paschke, A.W.A. Mohsen, J. Vockley, and J.J.P. Kim Structure of human isovaleryl-CoA dehydrogenase at 2.6 angstrom resolution-basis for substrate specificity Biochemistry 36 1997 8455 8464
34. K. Battaile, J. Molin-Case, R. Paschke, M. Wang, D. Bennett, J. Vockley, and J.-J.P. Kim Crystal structure of rat short shain acyl-CoA dehydrogenase complexed with acetoacetyl-CoA; comparison with other acyl-CoA dehydrogenases J. Biol. Chem. 277 2002 12200 12207
35. H.E. Auer, and F.E. Frerman Circular dichromism studies of acyl-CoA dehydrogenase and electron transfer flavoprotein J. Biol. Chem. 255 1980 8157 8163
36. H.J. Lee, M. Wang, R. Paschke, A. Nandy, S. Ghisla, and J.J.P. Kim Crystal structures of the wild type and the Glu376gly/Thr255glu mutant of human medium-chain acyl-CoA dehydrogenase-influence of the location of the catalytic base on substrate specificity Biochemistry 35 1996 12412 12420
37. J.D. Pellett, D.F. Becker, A.K. Saenger, J.A. Fuchs, and M.T. Stankovich Role of aromatic stacking interactions in the modulation of the two-electron reduction potentials of flavin and substrate/product in Megasphaera elsdenii short-chain acyl-coenzyme A dehydrogenase Biochemistry 40 2001 7720 7728
38. J.J.P. Kim, M. Wang, and R. Paschke Crystal structures of medium-chain acyl-CoA dehydrogenase from pig liver mitochondria with and without substrate Proc. Natl. Acad. Sci. USA 90 1993 7523 7527
39. S. Djordjevic, C.P. Pace, M.T. Stankovich, and J.J.P. Kim Three-dimensional structure of butyryl-CoA dehydrogenase from Megasphaera esdenii Biochemistry 34 1995 2163 2171
40. D.J. Steenkamp, and M. Husain The effect of tetrahydrofolate on the reduction of electron transfer flavoprotein by sarcosine and dimethylglycine dehydrogenases Biochem. J. 203 1982 707 715
41. B.A. Binzak, R.A. Wevers, S.H. Moolenaar, Y.M. Lee, W.L. Hwu, J. Poggi-Bach, U.F. Engelke, H.M. Hoard, J.G. Vockley, and J. Vockley Cloning of dimethylglycine dehydrogenase and a new human inborn error of metabolism, dimethylglycine dehydrogenase deficiency Am. J. Human Genet. 68 2001 839 847
42. G.L. Powell, J.R. Grothusen, J.K. Zimmerman, C.A. Evans, and W.W. Fish A re-examination of some properties of fatty acyl-CoA micelles J. Biol. Chem. 256 1981 12740 12747
43. K.L. Peterson, E.E. Sergienko, Y.H. Wu, N.R. Kumar, A.W. Strauss, A.E. Oleson, W.W. Muhonen, J.B. Shabb, and D.K. Srivastava Recombinant human liver medium-chain acyl-CoA dehydrogenase-purification, characterization, and the mechanism of interactions with functionally diverse C-8-CoA molecules Biochemistry 34 1995 14942 14953
44. H.S. Toogood, A. van Thiel, J. Basran, M.J. Sutcliffe, N.S. Scrutton, and D. Leys Extensive domain motion and electron transfer in the human electron transferring flavoprotein medium chain acyl-CoA dehydrogenase complex J. Biol. Chem. 279 2004 32904 32912