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Flavins and Flavoproteins 1999 FLAVINS AND FLAVOPROTEINS 1999 PROCEEDINGS OF THE THIRTEENTH INTERNATIONAL SYMPOSIUM KONSTANZ, GERMANY, AUGUST 29 - SEPTEMBER 4, 1999 EDITORS S. GHISLA • P. KRONECK P. MACHEROUX • H. SUND RUDOLF WEBER AGENCY FOR SCIENTIFIC PUBLICATIONS BERLIN 1999 XV Contents I. General Aspects: History,Chemistry, Physics and Theory Living through various phases of flavin research 3 Helmut Beinert Synthetic Models of flavoenzyme activity 17 Vincent Rotello NMR-studies of flavocytochrome b2 reconstituted with 15N, I3C labelled flavin Garit Fleischmann, Franz Miiller, Heinz Riiterjans, Florence Lederer One and two electron redox cycles in flavin-dependent dehydrations 31 W. Buckel, I. Cinkaya, S. Dickert, U.Eikmanns, A. Gerhardt, M. Hans, M. Liesert, W. Tammer, A. J. Pierik, E. F. Pai Dipole moments and polarizabilities of flavins explored using Stark-effect spectroscopy ' 41 Robert J. Stanley, Haishan Jang Flavin binding thermodynamics in Enterobacter cloacae nitroreductase 45 Ronald L. Koder, Michael E. Rodgers, Anne-Frances Miller Regulation of flavin functions by hydrogen bondings 49 Yumihiko Yano, Takeshi Kajiki, Hideki Moriya The hydrogen bonding in flavoprotein The effect of hydrogen bonding of flavin (neutral semiquinone state) 53 Yoshitaka Watanabe Substituent effect on redox states, spin densities and hyperfine couplings of free flavins and their 5-deaza analogues 59 Ryszard Zielinski. Henryk Szymusiak Theoretical destabilization of the flavin semiquinone of Enterobacter cloacae nitroreductase by a hydrogen-bonding -bending mechanism 63 Joseph D. Walsh, Anne-Frances Miller XVI Supramolecular models of flavoenzyme redox processes 67 Catherine Mclntosh, Angelika Niemz, Vincent Rotello Electronic effects of 7 and 8 ring substituents as predictors of flavin oxidation-reduction potentials 71 Dale E. Edmondson, Sandro Ghisla Autoxidation of photoreduced 3,4-dihydro-6.7-dimethyl-3-oxo- 4-D-ribityl-2-quinoxalinecarboxamide, an analog of riboflavin, and identification of oxygenated intermediates 77 K. Matsui, Y. Nishina, K. Sato, K. Shiga Intermediate products of 1,5-dihydroflavins autoxidation on the basis of density functional theory studies 81 Henryk Szymusiak, Ryszard Zielinski II. Spectroscopy Advanced EPR spectroscopic studies of mutants of ferredoxin- NADP+ reductase from pea 87 Milagros Medina, Carlos Gomez-Moreno, Richard Cammack, Adrian K. Arakaki, Nestor Carillo, Eduardo A. Ceccarelli Radical intermediates in Escherichia coli DNA photolyase: EPR and ENDOR studies 91 Gerald Richter, Christopher W. M. Kay, K. Struck, Peter Sadewater, Klaus Mobius, Stefan Weber Resonance Raman study on the interaction between Hog kidney D-amino acid oxidase and substrate analogs 95 Ruiwen Shi, Yasuzo Nishina, Kyosuke Sato, Kiyoshi Shiga, Retsu Miura Direct measurements of ultrafast excited state quenching of isoalloxazine by adenine in FAD 99 Robert J. Stanley, Alexander W. MacFarlane IV XVII III. Flavins and Electrons 1. Electron-Transfer in Heme-containing Systems Flavocytochrome c3: The structure and mechanism revealed 105 S.K Chapman, C.A. Morrison, G.A. Reid, S.L. Pealing, P. Taylor, M.D. Walkinshaw Two FCSD flavoproteins involved in sulfur metabolism and a thiosulfate utilization gene cluster from the green phototrophic bacterium, Chlorobium limicola (strain Tassajara) 115 Fabienne Verte, Yves Guisez, Terrance E. Meyer, Michael A.Cusanovich Jozef J. Van Beeumen A flavohemoprotein from the cellulolytic fungus Humicola insolvens contains 6-hydroxy-FAD as the dominant active cofactor 119 Kiyohiko Igarashi, Marc F. J. M. Verhagen, Masahiro Samejima, Martin Schiilein, Karl-Erik L. Erikson, Takeshi Nishino Changing the heme ligands of flavocytochrome b2: site-directed mutagenesis of histidine 66 to cysteine 123 Christopher G. Mowat, Stephen K. Chapman, Caroline S. Miles, Graeme A. Reid, A.W. Munro Cloning and characterization of a membrane-bound flavocytochrome c from the purple phototrophic sulfur bacterium Ectothiorhodospira vacuolata 127 Vesna Kostanjevecki, Yves Guisez, Terrance E. Meyer, Michael A. Cusanovich, Jozef J. Van Beeumen Electron transfer from FAD to heme-Fe in plant NADH: nitrate reductase 131 Jeffrey A. Mertens, Wilbur H. Campbell, Lawrie Skipper, David J. Lowe Expression, purification and mutagenesis of flavocytochrome c-sulfide dehydrogenase from Chromatium rinosum 135 Lina De Smet, Yves Guisez,Terrance E. Meyer, Michael A. Cusanovich, Jozef J. Van Beeumen The active site base of the fumarate reductase from Shewanellaftigidimarina 139 Mary K. Doherty, Stephen K. Chapman Caroline S. Miles, Graeme A. Reid XVIII Molecular recognition in the flavin domain of flavocytochrome b2 143 Ruth K. Moysey, F. Welsh, Stephen K. Chapman, S.L. Rivers, Graeme A. Reid Key substrate binding residues in flavocytochrome P450 BM3 147 T.W.B. Ost, M.A.Noble, S.K.Chapman, Caroline S. Miles, J. Murdoch, G.A. Reid, A.W. Munro The flavoprotein domains of nitric oxide synthase isoforms: site of possible regulatory control of flavin to heme electron transfer 151 R. Timothy Miller, Pavel Martasek, Jonathan S. Nishimura, Satya Panda, Dawn E. Harris, Linda J Roman, Bettie Sue Masters, Jung-Ja P. Kim Analysis of the redox properties of the human diflavin enzyme NADPH- cytochrome P450 reductases and its domains 155 Andrew W. Munro, T. McSorley, Michael A. Noble, Laura Robledo, Stephen K. Chapman Crystallographic insights into the hydride transfer mechanism of NADPH-cytochrome P450 oxidoreductase 159 Paul A. Hubbard, Rosemary Paschke, Jung-Ja P. Kim Anna L. Shen, Charles B. Kasper Flavodoxin as module for transferring electrons to different c-type and P450 cytochromes in artificial redox chains 163 Sheila J. Sadeghi, Yergalem T. Meharenna and Gianfranco Gilardi Mechanic studies on the one-electron reduction of quinones by neuronal nitric-oxide reductase domain 167 Hiroyuki Matsuda, Shigenobu Kimura and Takashi Iyanagi Calmodulin activates intramolecular electron transfer between the two flavins of neuronal nitric-oxide synthase reductase domain 171 Hiroyuki Matsuda, Shigenobu Kimura, Takashi Iyanagi 2. Electron Transfer in Flavodoxins The binding of FMN to Anabaena apoflavodoxin 175 Anabel Lostao, Fatna Daoudi, J. Sancho XIX Egression of recombinantflavodoxin from M^gasp/wera elsdem; effects of mutating the residues (M57, W91) that sandwich the dnnethylisoalloxazine of the bound FMN 179 Mary E. Gallagher, Susan M. Geoghegan, Stephen G. Mayhew Role of conformational dynamics and associated electrostatic and hydrogen bonding interactions in the regulation of redox potentials in the Clostridium beijerinckii flavodoxin 183 Richard P. Swenson, Mumtaz Kasim, Luke H. Bradley, Larry Druhan Effects of pH on the 13C and ISN NMR spectra of the hydroquinone of Desulfovibrio vulgaris flavodoxin and its G61A mutant 187 Garry N. Yalloway, Stephen G. Mayhew, Sjef J. Boeren, Jacques Vervoort Studies on urea-unfolding of flavodoxin and apoflavodoxin from Desulfovibrio vulgaris (Hildenborough) 191 Brian 6 Nuallain, Stephen G. Mayhew 3. Various Aspects Flavin-linked redox components required for AhpC reduction in alkyl hydroperoxide reductase systems . 195 Leslie B. Poole Overexpression of the bifunctional chorismate sythase of Neurospora crassa 203 Karina Kitzing, Nikolaus Amrhein, Peter Macheroux Amino acid substitutions near the FAD in NADH-cytochrome bs reductase: roles of Arg*3 and Thr6* in the electron transfer 207 Shigenobu Kimura, Masanori Kawamura, Takashi Iyanagi Comparison of the spectral properties between pig Megasphaera elsdenii electron-transferring flavoproteins 211 Kyosuke Sato, Yasuzo Nishina, Kiyoshi Shiga Solvent isotope effects on electron transfer in xanthine oxidase 215 Russ Hill, Robert F. Anderson The family of A-type flavoproteins: new members and definition of unique sequence fingerprints 219 Claudio M. Gomes, Miguel Teixeira, Alain Wasserfallen XX Formation of ETF hydroquinone when complexed to trimethylamine dehydrogenase 223 Mei-Huei Jang, Russ Hille, Nigel S. Scrutton Evidence that Megasphaera elsdenii synthesises two different electron-transferring flavoproteins 227 Zuhair Nasrallah, Hugh O'Neill, Stephen G. Mayhew IV. 3D-Structures of Flavoproteins Structural flavinology on the brink 233 P. Andrew Karplus Crystal structures of ,,unactivated" p-hydroxybenzoate hydroxylase 239 Michel H. M. Eppink, Willem J. H. van Berkel, Alex Tepliakov, Herman A. Schreuder NMR-studies on FMN-binding protein from Desulfovibrio vulgaris (Miyazaki F) 243 Masaya Kitamura, Hideo Inoue, Edwards Liepinsh, Gottfried Otting Crystal structure of the respiratory fumarate reductase of reductase of Shewanella putrefaciens MR-1: member of a novel flavocytochrome family 247 David Leys, Terrance E. Meyer , Alexandre I. Tsapin, Michael A. Cusanovich, Jozef J. Van Beeumen The domain structure of flavocytochrome c3 from Shewanella frigidiinarina 251 S.L. Pealing, S.K. Chapman, P. Taylor, G.A. Reid, M.D. Walkinshaw Structural biology of L-aspartate oxidase and polyamine oxidase 255 Claudia Binda, Andrea Mattevi, G. Tedeschi, A. Negri, Rodolfo Federico, Riccardo Angelini A new functional model for the Escherichia coli sulfite reductase: the aipi complex 259 Jaques Coves, Mahel Zeghouf, Marc Fontecave XXI V. Flavins and Pyridine Nucleotides Structural and functional properties of corn root ferredoxin-NADP+-reductase 265 Alessandro Aliverti, Cristian Ferioli, Monica Spinola, Debora Raimondi, GiulianaZanetti, Casey Finnerty, RickFaber, P. Andrew Karplus Role of the C-terminal tyrosine of plant ferredoxin-NADP+-reductase in NADP+ binding affinity and pyridine nucleotide specificity 269 LucianoPiubelli,
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