Enzymology and Molecular Biology of Carbonyl Metabolism 5 PDF
Preview Enzymology and Molecular Biology of Carbonyl Metabolism 5
ENZYMOLOGY AND MOLECULAR BIOLOGY OF CARBONYL METABOLISM 5 ADVANCES IN EXPERIMENTAL MEDICINE AND BIOLOGY Editorial Board: NATHAN BACK, State University of New York at Buffalo IRUN R. COHEN, The Weizmann Institute of Science DAVID KRITCHEVSKY, Wistar Institute ABEL LAJTHA, N. S. Kline Institute for Psychiatric Research RODOLFO PAOLETTI, University of Milan Recent Volumes in this Series Volume 365 MECHANISMS OF LYMPHOCYTE ACTIVATION AND IMMUNE REGULATION V: Molecular Basis of Signal Transduction Edited by Sudhir Gupta, William E. Paul, Anthony DeFranco, and Roger Perlmutter Volume 366 FREE RADICALS IN DIAGNOSTIC MEDICINE: A Systems Approach to Laboratory Technology, Clinical Correlations, and Antioxidant Therapy Edited by Donald Armstrong Volume 367 CHEMISTRY OF STRUCTURE-FUNCTION RELATIONSHIPS IN CHEESE Edited by Edyth L. Malin and Michael H. Tunick Volume 368 HEPATIC ENCEPHALOPATHY, HYPERAMMONEMIA, AND AMMONIA TOXICITY Edited by Vicente Felipo and Santiago Grisolia Volume 369 NUTRITION AND BIOTECHNOLOGY IN HEART DISEASE AND CANCER Edited by John B. Longenecker, David Kritchevsky, and Marc K. Drezner Volume 370 PURINE AND PYRIMIDINE METABOLISM IN MAN VIII Edited by Amrik Sahota and Milton W. Taylor Volume 371A RECENT ADVANCES IN MUCOSAL IMMUNOLOGY, Part A: Cellular Interactions Edited by Jiri Mestecky, Michael W. Russell, Susan Jackson, Suzanne M. Michalek, Helena Tlaskalova, and laroslav Sterzl Volume 371B RECENT ADVANCES IN MUCOSAL IMMUNOLOGY, Part B: Effector Functions Edited by Jiri Mestecky, Michael W. Russell, Susan Jackson, Suzanne M. Michalek, Helena Tlaskalova, and Jaroslav Sterzl Volume 372 ENZYMOLOGY AND MOLECULAR BIOLOGY OF CARBONYL METABOLISM 5 Edited by Henry Weiner, Roger S. Holmes, and Bendicht Wermuth A Continuation Order Plan is available for this series. A continuation order will bring delivery of each new volume immediately upon publication. Volumes are billed only upon actual shipment. For further information please contact the publisher. ENZYMOLOGY AND MOLECULAR BIOLOGY OF CARBONYL METABOLISM 5 Edited by Henry Weiner Purdue University West Lafayette, Indiana Roger S. Holmes Griffith University Brisbane, Queensland, Australia and Bendicht Wermuth Inselspital Berne, Switzerland SPRINGER SCIENCE+BUSINESS MEDIA, LLC Library of Congress Cataloging-In-Publication Data Enzymology and molecular biology of carbonyl metabolism 5 I edited by Henry Weiner. Roger S. Holmes. and Bendicht Wermuth. p. ; . -- (Advances in experimental medicine and biology; v. 372) Proceedings of the Seventh International Workshop on Enzymology and Molecular Biology of Carbonyl Metabolism. held July 3-7, 1994, in Palmerston North, New Zealand--T.p. verso. Includes bibliographical references and index. ISBN 978-1-4613-5808-4 1. Aldehyde dehydrogenase--Congresses. 2. Aldose reductase -Congresses. 3. Alcohol dehydrogenase--Congresses. 4. Carbonyl compounds--Metabolism--Congresses. I. Weiner, Henry. II. Holmes, Roger S. III. Wermuth, Bendicht. IV. International Workshop on Enzymology and Molecular Biology of Carbonyl Metabolism (7th: 1994 : Palmerston North, N.Z.) V. Series. [DNLM: 1. Aldehyde Dehydrogenase--physiology--congresses. 2. Aldehyde Reductase--physiology--congresses. 3. Alcohol Dehydrogenase--physiology--congresses. W1AD559 v.372 1995 I au 140E61 19951 ap603.A35E574 1995 599'.019258--dc20 DNLM/DLC fer Library of Congress 95-7575 CIP Proceedings of the Seventh International Workshop on Enzymology and Molecular Biology of Carbony 1 Metabolism, held July 3-7,1994, in Palmerston North, New Zealand ISBN 978-1-4613-5808-4 ISBN 978-1-4615-1965-2 (eBook) DOI 10.1007/978-1-4615-1965-2 © 1995 Springer Science+Business Media New York Originally published by Plenum Press, New York in 1995 109 8 7 6 5 4 3 2 1 All rights reserved No part of this book may be reproduced, stored in a retrieval system, or transmitted in any form or by any means, electronic, mechanical, photocopying, microfilming, recording, or otherwise, without written permission from the Publisher PREFACE Since the inception of these meetings in 1982, they have always been a satellite of the International Society for Biomedical Research on Alcoholism meeting. At our 1992 meeting in Dublin we learned that the next ISBRA meeting would be held in Brisbane, Australia. As the scientific organizer of all our previous meetings, I was very concerned about holding a meeting in the Southern Hemisphere for fear that many of our potential participants would not travel that far. I am pleased to say that I was proven to be incorrect. Nearly 90 scientists from a dozen countries participated at our seventh conference. At this meeting, like at all our previous ones, much new information about the three enzyme systems was presented. Of equal importance was, like at all our previous meetings, the extreme openness of the participants to discuss ideas, future directions and unpublished data. On behalf of all the participants I wish to express our sincere thanks to our Massey University colleagues for the excellent organization of this Palmerston North, New Zealand meeting. These included Kathryn Kitson, Michael Hardman, Paul Buckley, Trevor Kitson and Len Blackwell. At this meeting a few new innovations were introduced. Though posters are common at many meetings, bush walks and visits to nature preserves to see kiwi birds are not. Our hosts were able to secure support from the International Union of Biochemistry and Molecular Biology, which allowed us to pay partial travel expenses for a few younger scientists, and from the Alcohol Advisory Council of New Zealand and from Glaxo New Zealand, Ltd., which allowed us to hold down the cost for all participants. I acknowledge their support and thank them, as well as the National Institute on Alcohol Abuse and Alcoholism, for their support. I also thank my two co-editors, Roger Holmes and Benz Wermuth, for their hard work in helping me review all the manuscripts. Most important, I wish to thank all the participants for making this another exciting experience for all of us attending the meeting. Our eighth meeting will be held in South Dakota, June 29-July 4, 1996. I invite scientists from around the world to contact me if they are interesting in attending this meeting. Henry Weiner West Lafayette, Indiana September, 1994 v CONTENTS ALDEHYDE DEHYDROGENASE 1. Site Directed Mutagenesis to Probe for Active Site Components of Liver Mitochondrial Aldehyde Dehydrogenase ............................ . Henry Weiner, Jaume Farres, Ujjwal J. Rout, Xinping Wang and Chao-Feng Zheng 2. Substrate Binding Pocket Structure of Human Aldehyde Dehydrogenases: A Substrate Specificity Approach . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 9 Shih-Jiun Yin, Ming-Fang Wang, Chih-Li Han, and Sung-Ling Wang 3. Human Class 1 Aldehyde Dehydrogenase: Expression and Site-Directed Mutagenesis . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .. 17 Kerrie M. Jones, Trevor M. Kitson, Kathryn E. Kitson, Michael J. Hardman and John W. Tweedie 4. Nitrate Esters as Inhibitors and Substrates of Aldehyde Dehydrogenase. . . . . . . .. 25 Regina Pietruszko, Neeta Mukerjee, Erich E. Blatter, and Teresa Lehmann 5. Use of a Chromophoric Reporter Group to Probe the Active Site of Cytosolic Aldehyde Dehydrogenase ..................... . . . . . . . . . . . . . . . . . . .. 35 Trevor M. Kitson and Kathryn E. Kitson 6. Studies of the Esterase Activity ofCytosolic Aldehyde Dehydrogenase Using Sterically Hindered and Cyclic Substrates . . . . . . . . . . . . . . . . . . . . . . . . . . .. 45 Kathryn E. Kitson, Treena J. Blythe and Trevor M. Kitson 7. The Reduction of Propionic Anhydride by Aldehyde Dehydrogenase-Nadh Mixtures at pH 7 ................................................ 53 Rosemary L. Motion, Jeremy P. Hill, Kimmo Wiltshire, Paul D. Buckley, and Leonard F. Blackwell 8. Cloning and Characterisation of the cDNA for Sheep Liver Cytosolic Aldehyde Dehydrogenase ................................................. 61 Cherie K. Stayner and John W. Tweedie vii viii Contents 9. Crystallization of Sheep Liver Cytosolic Aldehyde Dehydrogenase in a Form Suitable for High Resolution X-Ray Structural Analysis ................ 67 Heather M. Baker, Rosemary 1. Brown, Aaron J. Dobbs, Kathryn E. Kitson, Trevor M. Kitson and Edward N. Baker 10. Progress toward the Tertiary Structure of (Class 3) Aldehyde Dehydrogenase .... 71 Julie Sun, John Hempel, Ronald Lindahl, John Perozich, John Rose and Bi-Cheng Wang 11. UDP-Glucose Dehydrogenase: Structural Characteristics .................... 79 John Perozich, Amy Leksana, and John Hempel 12. Kinetic Studies on Class 3 Aldehyde Dehydrogenase from Bovine Cornea ...... 85 Ian K. Riley, Christopher A. Burrows, Michael J. Hardman and Paul D. Buckley 13. Covalent Modification of Class 2 and Class 3 Aldehyde Dehydrogenase by 4-Hydroxynonenal . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .. 93 Dylan P. Hartley, Ronald Lindahl and Dennis R. Petersen 14. Constitutive and Overexpressed Human Cytosolic Class-3 Aldehyde Dehydrogenases in Normal and Neoplastic Cells/Secretions ............. 103 Norman E. Sladek, Lakshmaiah Sreerama and Ganaganur K. Rekha 15. Metabolism of Cyclophosphamide by Aldehyde Dehydrogenases ............. 115 Dharam P. Agarwal, Ulrich v. Eitzen, Doris Meier-Tackmann and H. Werner Goedde 16. Tissue-Specific Expression and Preliminary Functional Analysis of the 5' Flanking Regions of the Human Mitochondrial Aldehyde Dehydrogenase (ALDH2) Gene .................................................. 123 Katrina M. Dipple, Mark J. Stewart, and David W. Crabb 17. Transgenesis of the Aldehyde Dehydrogenase-2 (ALDH2) Locus in a Mouse Model and in Cultured Human Cells ................................ 131 Cheng Chang, Jerry Mann and Akira Yoshida 18. Class 3 Aldehyde Dehydrogenase: A Northern Perspective in the Land Down Under ......................................................... 137 Josette Feimer, Yiqiang Xie, Koichi Takimoto, David Asman, Henry Pitot and Ronald Lindahl 19. Studies on the Induction of Rat Class 3 Aldehyde Dehydrogenase ............. 143 Perikles Pappas, Vasilis Vasiliou, Maria Karageorgou, Panayiotis Stefanou and Marios Marselos 20. Mouse Class 3 Aldehyde Dehydrogenases ................................ 151 Vasilis Vasiliou, Steven F. Reuter, Christine A. Kozak and Daniel W. Nebert 21. Cloning and Characterization of Genes Encoding Four Additional Human Aldehyde Dehydrogenase Isozymes ........................... '.' .... 159 Lily C. Hsu, Wen-Chung Chang, Sharon W. Lin and Akira Yoshida Contents ix 22. New Human Aldehyde Dehydrogenases .................................. 169 Regina Pietruszko, Pritesh C. Shah, Alexandra Kikonyogo, Ming-Kai Chern and Teresa Lehmann 23. Retinoic Acid Synthesizing Enzymes in the Embryonic and Adult Vertebrate .... 173 Peter McCaffery and Ursula C. Drager 24. Retinoic Acid Synthesis in the Developing Spinal Cord ..................... 185 Ursula C. Drager and Peter McCaffery ALDO-KETO REDUCTASE 25. Structure and Mechanism of Aldehyde Reductase .......................... 193 T. Geoffrey Flynn, Nancy C. Green, Mohit B. Bhatia, and Ossama EI-Kabbani 26. Expression of Human and Rat Carbonyl Reductase in E. coli: Comparison of the Recombinant Enzymes ........................................... 203 Bendicht Wermuth 27. Molecular Cloning and Sequencing of Mouse Hepatic 11 B-Hydroxysteroid Dehydrogenase/Carbonyl Reductase: A Member of the Short Chain Dehydrogenase Superfamily ....................................... 211 Edmund Maser and Udo C.T. Oppermann 28. Molecular Modelling Calculations on the Binding ofD- and L-Xylose to Wild-Type Aldose Reductase and Its H 11 OQ and H 11 OA Mutants ......... 223 Hans L. De Winter and Mark von Itzstein 29. Stopped-Flow Studies of Human Aldose Reductase Reveal which Enzyme Form Predominates during Steady-State Turnover in Either Reaction Direction ... 229 Charles E. Grimshaw and Chung-Jeng Lai 30. Lysine Residues in the Coenzyme-Binding Region of Mouse Lung Carbonyl Reductase ...................................................... 241 Yoshihiro Deyashiki, Masayuki Nakanishi, Masaki Sakai, and Akira Hara 31. Substrate Specificity and Kinetic Mechanism of Tetrahymena 20a-Hydroxysteroid Dehydrogenase ................................ 249 Akira Hara, Ayako Inazu, Yoshihiro Deyashiki, and Yoshinori Nozawa 32. Purification and Characterization of Recombinant Human Placental and Rat Lens Aldose Reductases Expressed in Escherichia coli ...................... 259 Sanai Sato, Susan Old, Deborah Carper, and Peter F. Kador 33. Rat and Human Bile Acid Binders Are Members of the Monomeric Reductase Gene Family ................................................... 269 A. Stolz, L. Hammond and H. Lou x Contents ALDO-KETO REDUCTASE ALDEHYDE DEHYDROGENASE 34. The Alcohol Dehydrogenase System ..................................... 281 Hans Jornvall, Olle Danielsson, Lars Hjelmqvist, Bengt Persson, and Jawed Shafqat 35. Promoters of the Mammalian Class III Alcohol Dehydrogenase Genes ......... 295 Howard J. Edenberg, Wei-Hsien Ho and Man-Wook Hur 36. Class I and Class Iv Alcohol Dehydrogenase (Retinol Dehydrogenase) Gene Expression in Mouse Embryos ..................................... 301 Gregg Duester, Hwee Luan Ang, Louise Deltour, Mario H. Foglio, Terry F. Hayamizu, and Mirna Zgombic-Knight 37. Molecular Evolution of Class I Alcohol Dehydrogenases in Primates: Models for Gene Evolution and Comparison of 3' Untranslated Regions of cDNAS .... 315 Brenda Cheung, Roger S. Holmes and Ifor R. Beacham 38. the Role of Leucine 116 in Determining Substrate Specificity in Human B] Alcohol Dehydrogenase .......................................... 321 Thomas D. Hurley and David L. Vessell 39. Mutations of Human Class III Alcohol Dehydrogenase ...................... 327 Mats Estonius, Jan-Olov Hoog, Olle Danielsson, and Hans Jornvall 40. Human and Rat Class IV Alcohol Dehydrogenases: Correlations of Primary Structures with Enzymatic Properties ................................ 331 Jaume Farres, Alberto Moreno, Bernat Crosas, Ella Cederlund, Abdellah Allali-Hassani, Josep M. Peralba, Lars Hjelmqvist, Hans Jornvall and Xavier Pares 41. Cloning and Expression of a Human Stomach Alcohol Dehydrogenase Isozyme .. 341 Natalia Y. Kedishvili, William F. Bosron, Carol L. Stone, Cara F. Peggs, Holly R. Thomasson, Kirill M. Popov, Lucinda G. Carr, Thomas D. Hurley, Howard J. Edenberg, and Ting-Kai Li 42. Purification and Properties of Murine Corneal Alcohol Dehydrogenase: Evidence for Class IV ADH Properties ...................................... 349 John E. Downes and Roger S. Holmes 43. Mammalian Class VI Alcohol Dehydrogenase: Novel Types of the Rodent Enzymes ....................................................... 355 Jan-Olov Hoog and Margareta Brandt 44. Crystallizations of Novel Forms of Alcohol Dehydrogenase .................. 365 Mustafa EI-Ahmad, Ramaswamy S., Olle Danielsson, Christina Karlsson, Mats Estonius, Jan-Olov Hoog, Hans Eklund and Hans lOrnvall 45. Human Sorbitol Dehydrogenase Gene: cDNA Sequence and Expression ........ 373 Takeshi Iwata and Deborah Carper Contents xi 46. Short-Chain Dehydrogenases/Reductases ................................. 383 Bengt Persson, Maria Krook and Hans Jornvall 47. Zinc Binding of Alcohol and Sorbitol Dehydrogenases ...................... 397 Christina Karlsson, Hans Jornvall, and Jan-Olov Hoog 48. Horse Liver Alcohol Dehydrogenase-Catalyzed Aldehyde Oxidation: The Sequential Oxidation of Alcohols to Carboxylic Acids under NADH Recycling Conditions ............................................ 407 Norman J. Oppenheimer and Gary T. M. Henehan 49. Analytical Approaches to Alcohol Dehydrogenase Structures ................. 417 Madalina T. Gheorghe, Ingemar Lindh, William J. Griffiths, Jan Sjovall and Tomas Bergman 50. Purification and Characterization of S-Formylglutathione Hydrolase from Human, Rat and Fish Tissues ...................................... 427 Martti Koivusalo, Risto Lapatto and Lasse Uotila 51. Useful Mutants of Zymomonas Mobilis Alcohol Dehydrogenase-2 Obtained by the Use of Polymerase Chain Reaction Random Mutagenesis ............ 435 Peter Rellos, Bernadette Schwindt and Robert Scopes Index ................................................................. 441
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