Table Of Content

ALS Advances in Life Sciences Biochem.istryof Vitam.in B6 and PQQ Edited by G. Marino G.Sannia F. Bossa Birkha,user Verlag Basel· Boston· Berlin Editors G. Marino and G. Sannia F.Bossa Dipartimento di Chimica Organic a e Biologica Dipartimento di Scienze Biochimiche Universita di Napoli "Federico II" Universita di Roma "La Sapienza" Via Mezzocannone 16 P.le Aldo Moro 5 1-80134 Napoli 1-00185 Roma Italy Italy A CIP catalogue record for this book is available from the Library of Congress, Washington D.C., USA Deutsche Bibliothek Cataloging-in- Publication Data Biochemistry of vitamin B8 and PQQ / ed. by G. Marino ... - Basel; Boston; Berlin: Birkhauser, 1994 (Advances in life sciences) ISBN 978-3-0348-7395-6 ISBN 978-3-0348-7393-2 (eBook) DOI 10.1007/978-3-0348-7393-2 NE: MarinO, Gennaro [Hrsg.] The publisher and editor can give no guarantee for the information on drug dosage and administration contained in this publication. The respective user must check its accuracy by consulting other sources of reference in each individual case. The use of registered names, trademarks etc. in this publication, even if not identified as such, does not imply that they are exempt from the relevant protective laws and regulations or free for general use. This work is subject to copyright. All rights are reserved, whether the whole or part of the material is concerned, specifically the rights of translation, reprinting, re-use of1llustrations, reCitation, broadcasting, reproduction on microfilms or in other ways, and storage in data banks. For any kind of use permission of the copyright owner must be obtained. © 1994 Birkhauser Verlag, PO Box 133, CH-40l0 Basel, Switzerland Softcover reprint of the hardcover 15t edition 1994 Camera-readY copy prepared by the authors Printed on acid-free paper produced from chlorine-free pulp ISBN 978-3-0348-7395-6 987654321 In memory of Vincenzo Scardi 1924-1992 CONTENTS Preface ................................................ XIII Acknowledgement ......................................... XIV Contributors . . . . . . . xv History of Vitamin B6 E.E. Snell ...... . I Molecular evolution Molecular evolution of pyridoxal-5' -phosphate-dependent enzymes P. Christen, P.K. Mehta and E. Sandmeier . . . . . . . . . . . . . . . . . . . . . . . . . . 9 Stereospecificity of aminotransferases for C-4' hydrogen transfer and enzyme evolution K. Soda, T. Yoshimura and N. Esaki . . . . . . . . . . . . . . . . . . . . . . . . . . . . .. 15 Detection of weak structural similarities among PLP dependent enzymes S. Pascarella and F. Bossa ................................. 21 Aminotransferases Crystallographic studies on the Vitamin B -assisted enzymic transamination 6 reaction J.N. Jansonius, J.-c. Genovesio-Taverne, M. Hennig, E. Hohenester, M. Jenny, Y.N. Malashkevich, M. Moser, R. Muller, B. W. Shen, W. Stark, A. von Stosch and M.D. Toney .......................................... 29 Redesign of aspartate aminotransferase specificity to that of tyrosine aminotrans ferase J. F. Kirsch and J.J. Onuffer . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .. 37 Enzyme-substrate interactions modulating protonation and tautomerization states of the aldimines of pyridoxal enzymes H. Kagamiyama, H. Hayashi, T. Yano, H. Mizuguchi and S. Ishii . . . . . . . . . .. 43 Functional role of the mobile stretch Gly36-Va137-Gly38 of porcine cytosolic aspartate aminotransferase Y. Morino, S. Tanase, Q.-w. Pan, N. Hamasaki, M. Mayumi, S. Rhee, P.H. Rogers and A. Arnone ........................................... 49 Using lH- and 15N-NMR spectroscopy to observe active sites of porcine cytosolic and Escherichia coli aspartate aminotransferases D.E. Metzler, C.M. Metzler, E. T. Mollova, R.D. Scott, A. Kintanar, S. Tanase, K. Kogo, T. Higaki, Y. Morino, H. Kagamiyama, T. Yano, S. Kuramitsu, H. Hayashi, K. Hirotsu and I. Miyahara . . . . . . . . . . . . . . . . . . . . . . . . . .. 55 VIII Aspartate aminotransferases like it hot G. Marino, L. Birolo and G. Sannia ... 61 Studies on the mechanism of action of D-amino acid transaminase J.M. Manning . ................................ . 67 Cytosolic factors and the twisting path from birth to berth in aspartate aminotrans ferases A. Iriarte, A Artigues, B. Lain, J.R. Mattingly, Jr. and M. Martinez-Carrion ... 75 Mitochondrial protein import: Role of certain domains of mitochondrial aspartate aminotransferase S. Giannattasio, A Azzariti, R.A. Vacca, P. Lattanzio, R.S. Mera/ina and E. Marra ............................................ 81 Cytosolic aspartate aminotransferase: Tissue-specific hormonal regulation of a housekeeping gene promoter e. R. Barouki, M. Garlatti, S. Feilleux-Duche, Toussaint, M. Aggerbeck and J. Hanoune . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .. 87 Regulation by glucagon of serine: pyruvate/alanine:glyoxylate aminotransferase gene expression in cultured hepatocytes e. Uchida, T. Funai, K. Ohbayashi, T. Oda and A Ichiyama . . . . . . . . . . . . .. 93 Glutamate I-semialdehyde aminotransferase, a unique enzyme in chlorophyll biosynthesis B. Grimm .............................................. 99 Mechanism of glutamate semialdehyde aminotransferase probed with substrate analogues R. Tyacke, B. Grimm, J.L. Harwood and R.A John. . . . . . . . . . . . . . . . . .. 105 Tryptophan-synthase and decarboxylases Crystallographic and kinetic studies of the tryptophan synthase a2~2 complex with a mutation in ~ subunit lysine-87 that binds pyridoxal phosphate e.e. E. W. Miles, U. Banik, Z. Lu, AA Ahmed, K.D. Parris, Hyde and D.R. Davies ...... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 113 The roles of chemical transformation, loop closure, tunnel function and metal ion activation in the tryptophan synthase mechanism M. F. Dunn, P. S. Brzovic, e.A. Leja, P. Pan and E. U. Woehl . . . . . . . . . . . . .. 119 Effects of monovalent cations on functional properties of the tryptophan synthase a2~2 complex in solution and in the crystal A. Peracchi, A. Mozzarelli and G.L. Rossi ......................... 125 The long-range effect on the mutual activation of the a and ~ subunits in the a2~2 complex of tryptophan synthase K. Hiraga and K. Yutani ..................................... 131 IX X-ray structure, sequence and solution properties of ornithine decarboxylase from Lactobacillus 30a M.L. Hackert, D. Carroll, R. Ghosh, A. Kern, C. Momany, M. Oliveira and L. Zhang . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .. 135 Dialkylglycine decarboxylase structure: Alkali metal binding sites and bifunctional active site M.D. Toney, E. Hohenester, J.w. KellerandJ.N. Jansonius. . . . . . . . ... . . . .. 141 The location and role of active-site bases in PLP-dependent decarboxylase enzymes as deduced from stereochemical and kinetic studies D. Gani, M. Akhtar, J.E. Rose and K. Tilley ........................ 147 GuCl-induced unfolding of pig kidney dopa decarbocylase: Evidence for a multi state process P. Dominici, P.S. Moore and C. Borri Voltattorni ..................... 153 Phosphorylases The transition state complex in the phosphorylase catalyzed reaction D. Palm, S. Becker and R. Schinzel ..................... . 161 Binding mode of glucans to a-glucan phosphorylase isozymes and their chimeric enzymes T. Fukui, H. Mori and K. Tanizawa . . . . . . . . . . . . . . . . . . . . . . . . . . . . .. 167 Slow conformational transitions of muscle glycogen phosphorylase b B.1. Kurganov and E.1. Schors ......................... . 173 Other pyridoxal-dependent enzymes X-ray study of tryptophanase at 2.1 A resolution M. Isupov, 1. Dementieva, L. Zakomirdina, K.S. Wilson, Z. Dauter, A.A. Antson, G. G. Dodson and E. G. Harutyunyan ............................ 183 Crystallographic studies of tyrosine phenol-lyase A.A. Antson, G. G. Dodson, K.S. Wilson, S. V. Pletnev, E. G. Harutyunyan and T. V. Demidkina . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 187 Studies of the mechanism of tyrosine phenol-lyase: Kinetics and site-directed mutagenesis R. S. Phillips, H. Chen and P. Gollnick . . . . . . . . . . . . . . . . . . . . . . . . . . .. 193 The role of pyridoxal phosphate in the refolding of serine hydroxymethyltransferase K. Cai and V. Schirch ..................................... 199 The mechanism of O-acetylserine sulfhydrylase from Salmonella typhimurium K.D. Schnackerz and P.F. Cook .............................. 205 Involvement of PLP in biological formation iron-sulfur clusters L. Zheng and D.R. Dean ....................... . 2lJ x Iron-sulfur clusters as alternatives to pyridoxal-5'-phosphate in bacterial L-serine dehydratases: Cloning of the gene encoding the f)-subunit of the enzyme from Peptostreptococcus asaccharolyticus A.E.M. Hofmeister, R. Grabowski and W. Buckel. . . . . . . . . . . . . . . . . . . .. 217 Phosphorescence of pyridoxal kinase at room temperature: The effects of ligands bound to the nucleotide site M. Blazquez, T. Pineda, F. Kwok and J.E. Churchich .................. 223 The Schiff base of pyridoxal-5'-phosphate with ethylenediamine and ethylamine: Species in solution J.M. Sevilla, C. Hidalgo, T. Pineda, F. Garcia-Blanco and M. Blazquez . . . . . .. 229 Amine oxidases Biological role and reactivity of TPQ containing amine oxidases B. Mondovi ............................................. 235 Two distinct quinoprotein amine oxidases are functioning in Aspergillus niger I. Frebort, H. Toyama, K. Matsushita, H. Kumagai, P. Pee, L. Luhova and o. Adachi. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 241 The catalytic competence of cobalt-time oxidase E. Agostinelli, L. Morpurgo, C. Wang, B. Mondovi and A. Giartosio 247 Mechanistic studies of copper/topa amine oxidases D.M. Dooley, D.E. Brown, M.A. McGuirl and L.J. Sears 253 Design, synthesis and evaluation of mechanism-based inhibitors of copper amine oxidases L.M. Sayre, F. Wang, Y. Lee, H. Huang, F.T. Greenaway, Z. He, A. Lightning and H. M. Kagan . . . . . . . . . .. '. . . . . . . . . . . . . . . . . . . . . . . . . . . . . .. 259 Copper ion-dependent biogenesis of topa quinone cofactor covalently bound to bacterial monoamine oxidase K. Tanizawa, R. Matsuzaki and T. Fukui . . . . . . . . . . . . . . . . . . . . . . . . . .. 263 Modulation of lysyl oxidase activity toward peptidyl lysine by vicinal dicarboxylic amino acid residues N. Nagan and H. M. Kagan ................................... 269 Quinoprotein dehydrogenases The structure and function of quinoprotein dehydrogenases C. Anthony ............................................. 277 Quinoprotein oxidoreductases for the oxidation of alcohols, sugars and amines J.A. Duine, J.A. Jongejan and S. de Vries . . . . . . . . . . . . . . . . . . . . . . . . .. 283 XI The ternary complex between methylamine dehydrogenase, amicyanin and cyto chrome C SS1i F.S. Mathews, L. Chen, R.C.E. Durley, v.L. Davidson ................. 291 Model studies directed toward the action of quinoprotein methanol dehydrogenase S.1toh . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .. 297 Molecular physiology Nutritional aspects of vitamin B6: Requirements, recommendations and intake D.A. Bender. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 305 Vitamin B6 transport and metabolism: Clues for delivery of bioactive compounds D.B. McCormick. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .. 311 Vitamin B6 modulation of steroid receptor-mediated gene expression D.B. Tully, A.B. Scoltock and l.A. Cidlowski .............. . 319 Molecular pathology Pyridoxine (vitamin B6), neurotransmitters and hypertension K. Dakshinamurti, K.J. Lal and S. K. Sharma ......... . 331 A liver enzyme, serine:pyruvate/alanine:glyoxylate aminotransferase and its mutant in a primary hyperoxaluria type I case K. Ishikawa, T. Suzuki, T. Funai, K. Nishiyama, C. Uchida and A. 1chiyama 337 Pyridoxal phosphate, GAB A and seizure susceptibility D.L. Martin . .......................... . 343 Monoclonal antibodies to bovine brain GABA transaminase S. Y. Choi, S.H. lang, B.R. Lee, Y.K. Kim, S.-W Cho and E. Y. Choi 349 Effects of pyrroloquinoline quinone (PQQ) on the SLE-like (Systemic Lupus Ery thematosus) disease in MRL-lpr/lpr mice B.J. Weimann . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .. 353 Conclusions F. Bossa . .. 359 Subject index 361