Table Of ContentENZYMOLOGY 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
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ENZYMOLOGY AND MOLECULAR BIOLOGY OF CARBONYL METABOLISM 5
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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
