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P. J. Kuhn A. P. J. Trinci M. J. Jung M. W. Goosey L. G. Copping (Eds.) Biochemistry of Cell Walls and Membranes in Fungi With 88 Figures and 46 Tables Springer-Verlag Berlin Heidelberg New York London Paris Tokyo HongKong Dr. PAUL J. KUHN Dr. MICHAEL W. GOOSEY Shell Research Ltd. Shell Research Ltd. Sittingbourne Research Centre Sittingbourne Research Centre Sittingbourne, Kent ME9 8AG Sittingbourne, Kent ME9 8AG United Kingdom United Kingdom Professor ANTHONY P. J. TRINCI Dr. LEONARD G. COPPING Microbiology Group Dow Agricultural Products R&D Department of Cell & Letcombe Laboratory, Letcombe Regis Structural Biology Wantage, Oxfordshire OX12 9JT School of Biological Sciences United Kingdom University of Manchester Manchester M 13 9PL United Kingdom Dr. MICHEL J. JUNG Dow Agricultural Products R&D, Letcombe Laboratory Letcombe Regis, Wantage, Oxfordshire OX12 9JT United Kingdom ISBN-\3: 978-3-642-74217-0 e-ISBN-\3: 978-3-642-74215-6 DOl: 10.1007/978-3-642-74215-6 Library of Congress Cataloging-in-Publication Data Biochemistry of cell walls and membranes in fungi/Po J. Kuhn ... let al.l, eds. p. cm. Includes bibliographical references. ISBN-\3:978-3-642-74217-0 (alk. paper: U.S.) 1. Fungal cell walls. 2. Fungal membranes. 3. Fungi-Cytochemitry. I. Kuhn, P. J. (Paul John), 1954- . QK60l.B54 1989 589.2'04875-dc20 89-21707 This work is subject to copyright. All rights are reserved, whether the whole or part of the materi al is concerned, specifically the rights of translation, reprinting, re-use of illustrations, recitation, broadcasting, reproduction on microfilms or in other ways, and storage in data banks. Duplication of this publication or parts thereof is only permitted under the provisions of the German Copyright Law of September 9, 1965, in its version of June 24, 1985, and a copyright fee must always be paid. Violations fall under the prosecution act of the German Copyright Law. © Springer-Verlag Berlin Heidelberg 1990 Sofleover reprint of the hardcover I st edition 1990 The use of general descriptive names, registered names, trademarks, etc. in this publication does not imply, even in the absence of a specific statement, that such names are exempt from the rele vant protective laws and regulations and therefore free for general use. Product liability: The publisher can give no guarantee for information about drug dosage and ap plication thereof contained in this book. In every individual case the respective user must check its accuracy by consulting other pharmaceutical literature. 1Ypesetting: K+V Fotosatz GmbH, Beerfelden 213113145-543210 - Printed on acid-free paper Preface Despite the many advances made during the last decade in various aspects of fungal biochemistry, there have been very few volumes devoted to the sub ject in recent years. This lack is all the more surprising in view of the increas ing use of fungi in gene manipulation studies and in biotechnological ap plications, and of the current interest in the biorational discovery of novel agents for the control of fungal pathogens of plants and humans. We hope that this book goes some way to rectifying this situation by providing an up to-date account of selected developments in two important areas, namely cell walls and membranes. Topics included in the book concern both yeasts and filamentous fungi. Although the main emphasis is on biogenesis, functional aspects are also discussed, e.g. the role of glycoproteins in recognition of sterols in mem branes and of calcium in regulation. Several contributions describe in terference with the 'normal' biochemistry of cell walls and membranes with a view to increasing fundamental knowledge, but also highly relevant to the design of new fungicides and antimycotics. The steadily increasing impact of molecular biology on the study of fungal biochemistry is highlighted throughout. We would like to thank the following sponsors for their generous sup port: Agricultural Genetics Company Ltd, BASF, Ciba-Geigy AG, Dow Chemical Co Ltd, Glaxo Group Research Ltd, ICI PLC, Monsanto, Pfizer Central Research, Schering AG and Shell Research Ltd. The help of the Bio chemical Society and in particular advice from Dr. Peter Quinn are also gratefully acknowledged. September 1989 P.J. KUHN A. P. J. TRINe I M.J. JUNG M.W. GOOSEY L. G. COPPING Table of Contents Chapter 1 Cell Walls and Membranes in Fungi - An Introdnction P. J. KUHN and A. P. 1. TRINeI .................... . References ................................. . . . . . 4 Chapter 2 Fungal Cell Walls - A Review J. F. PEBERDY ................................... 5 Introduction .................................... 5 2 The Chemistry and Architecture of the Fungal Cell Wall........................................... 6 3 Synthesis of Cell Wall Polymers ................... 9 4 Stability of the Cell Wall ......................... 11 5 Wall Formation During Protoplast Regeneration .... 12 6 Genetics and the Fungal Wall ..................... 13 7 The Cell Wall as a Target ........................ 16 8 The Cell Wall as an Interactive Surface ............ 18 9 The Protective Role of the Cell Wall. . . . . . . . . . . . . . . 21 10 Cell Wall Enzymes, Wall Porosity and Enzyme Secretion ....................................... 22 11 Concluding Statement ........................... 23 References .. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 24 Chapter 3 Chitin Synthesis in Yeast (Saccharomyces cerevisiae) . E. CABlB, S. J. SILVERMAN, A. SBURLATI, and M. L. SLATER ................................... 31 Introduction .................................... 31 2 Zymogen Nature of Chitin Synthetase ............. 31 3 Intracellular Distribution of Chitin Synthetase ...... 32 4 Cloning of a Chitin Synthetase Structural Gene ..... 32 5 A New Chitin Synthetase ........................ 34 6 Cloning of the Chitin Synthetase 2 Structural Gene . . 35 VIII Table of Contents 7 Requirement of Chitin Synthetase 2 for Cell Division 37 8 Chitin Synthetase 1 - A Repair Enzyme? .......... 38 9 The Present Status of Chitin Synthesis in Yeast ..... 39 References .. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 40 Chapter 4 A Novel Computer Model for Generating Cell Shape: Application to Fnngal Morphogenesis S. BARTNICKI-GARCIA, F. HERGERT, and G. GlERZ .... 43 1 Introduction..... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 43 2 Current Concepts of Wall Growth in Fungi ......... 43 3 A Model of Wall Growth Based on Vesicles ........ 44 4 Computer Simulation of Morphogenesis ........... 45 5 Mathematical Model for Hyphal Growth ........... 48 6 Relationship of Spitzenkorper to VSC ............. 51 7 The VSC Concept and Mechanisms for VSC Displacement ................................... 51 8 Simulations of Morphogenetic Processes in Fungi ... 53 9 Limitations.. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 56 10 Discussion and Conclusions ...................... 57 References. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 58 Chapter 5 Inhibition of Chitin Metabolism G. W. GOODAY .................................. 61 Chitin Metabolism as a Target for Antifungal Agents 61 2 Chitin Synthase ................................. 61 3 Glutamine-Fructose-6-P-Aminotransferase .......... 69 4 Chitinase ...................................... 70 5 Conclusions...... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 74 References. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 74 Chapter 6 Wall Structure, Wall Growth, and Fungal Cell Morphogenesis 1. G. H. WESSELS, P. C. MOL, 1. H. SlETSMA, and C. A. VERMEULEN ............................... 81 1 Introduction. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 81 2 Alkali-Insoluble ,B-Glucan in the Mature Wall Forms Part of a Glucosaminoglycan-Glucan Complex ...... 82 3 Secondary Structures in the Glucosaminoglycan- Glucan Wall Complex ........................... 84 Table of Contents IX 4 Apical Biosynthesis and Morphogenesis of the Hyphal Wall . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 86 5 Mycelium.yeast Transitions ....................... 90 6 Diffuse Extension of Hyphal Walls ................ 91 7 Conclusions .................................... 93 References .. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 93 Chapter 7 Cellulose and fi-Glucan Synthesis in Saprolegnia M. FEvRE, V. GIRARD, and P. NODET .............. 97 1 Introduction... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 97 2 Synthesis and Deposition of Cell Wall Glucans in Sapro/egnia hyphae .. . . . . . . . . . . . . . . . . . . . . . . . . . . . . 98 3 Cellulose Synthesis and Hyphal Morphogenesis ..... 99 4 If-Glucan Synthases from Sapro/egnia .............. 100 5 Purification of GIucan Synthases from Sapro/egnia .. 103 6 Conclusions..... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 105 References ..... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 105 Chapter 8 Synthesis and Function of Glycosylated Proteins in Saccharomyces cerevisiae W. TANNER..................................... 109 1 Introduction. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 109 2 Biosynthetic Pathways ........................... 110 3 Functional Aspects .............................. 112 4 Summary ...................................... 115 References ...................................... 116 Chapter 9 Lipids in the Structure and Function of Fungal Membranes D.M. LbsEL .................................... 119 Introduction .................................... 119 2 The Membrane System. . . . . . . . . . . . . . . . . . . . . . . . . . . 119 3 Membrane Structure ............................. 122 4 Membrane Composition ......................... 124 5 Functions of Membrane Lipids ................... 127 6 Influence of Environment, Nutrition, and Development on Membrane Composition and Function ................................... 129 7 Conclusions. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 131 References ...................................... 132 X Table of Contents Chapter 10 Importance and Role of Sterols in Fungal Membranes H. VANDEN BOSSCHE ........................... 135 Introduction ................................... 135 2 Ergosterol: Does It Meet the Requirements of Fungal Membranes? ............................ 141 3 What Are the Consequences for the Cell to Synthesize Alkylated Sterols? .................... 150 4 Why Ergosterol Instead of Cholesterol? ........... 152 References .................................... 153 Chapter 11 HMG-CoA to Isopentenyl Pyrophosphate - Enzymology and Inhibition R.H. ABELES .................................. 159 Hydroxymethylglutaryl-Coenzyme A (HMG-CoA) Reductase ..................................... 159 2 Isopentenyl Pyrophosphate Isomerase (IPPI) ...... 162 3 Inhibition of Mevalonate-5-Pyrophosphate Decarboxylase ................................. 163 References .................................... 166 Chapter 12 Isopentenyl Diphosphate to Squalene - Enzymology and Inhibition C. D. POULTER ................................. 169 1 Introduction. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 169 2 Isopentenyl Diphosphate: Dimethylallyl Diphosphate Isomerase ..................................... 171 3 Farnesyl Diphosphate Synthetase ................. 177 4 Squalene Synthetase ............................ 181 5 Conclusions........ . . . . . . . . . . . . . . . . . . . . . . . . . . . 186 References .................................... 186 Chapter 13 Squalene Epoxidase - Enzymology and . Inhibition N.S. RYDER 189 1 Introduction. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 189 2 Enzymology.......................... . . . . . . . . . 191 3 Squalene Epoxidase Inhibitors ................... 194 4 Squalene Epoxidase Inhibitors as Antifungal Agents .. " ................. " . . . . .. . . . . . . .. . . . 199 References .................................... 200 Table of Contents XI Chapter 14 Inhibition of Sterol Biosynthesis in Higher Plants by Analogues of High Energy Carbocationic Intermediates A. RAHIER, M. TATON, P. BENVENISTE. . . . . . . . . . . . . 205 Introduction ................................... 205 2 Inhibition of Phytosterol Biosynthesis by Carbocationic HEI and Transition State Analogues. 211 3 Conclusions...... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 219 References .................................... 220 Chapter 15 Lanosterol to Ergosterol - Enzymology, Inhibition and Genetics S. L. KELLY, S. KENNA, H. F. J. BLIGH, P. F. WATSON, I. STANSFIELD, S. W. ELLIS, and D. E. KELLY ....... 223 Introduction ................................... 223 2 Antifungal Compounds and Their Activities ....... 225 3 Fungal Cytochrome P-450 ....................... 232 4 Conclusions and Implications for the Discovery of Novel Antifungal Agents ........................ 238 References .................................... 238 Chapter 16 Biosynthesis and Role of Phospholipids in Yeast Membranes l.E. HILL, C. CHUNG, P. MCGRAW, E. SUMMERS, and S. A. HENRY ............................... 245 Regulation of Phospholipid Synthesis in S. cerevisiae - A Review ....................... 245 2 Regulation of Phospholipid Synthesis in S. pombe - Introduction ................................ 252 3 Roles of Phospholipids in S. cerevisiae and S. pombe ..................................... 257 References .................................... 259 Chapter 17 Inhibitors of Phospholipid Biosynthesis G.D. ROBSON, M. WIEBE, P.l. KUHN, and A. P. l. TRINC! ............................. 261 Introduction .. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 261 2 Phospholipid Structure and Biosynthesis .......... 262 3 Inhibitors of Phospholipid Biosynthesis ........... 265 4 Validamycin and Edifenphos as Paramorphogens ... 276 References .................................... 277 XII Table of Contents Chapter 18 Transduction of the Calcium Signal with Special Reference to CaH -Induced Conidiation in Penicillium notatum D. PITT and A. KAILE .......................... 283 1 Introduction. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 283 2 Regulation of Intracellular Calcium .............. 283 3 Calcium as an Intracellular Regulator . . . . . . . . . . . . . 285 4 The Role of Calcium in Fungi ................... 288 5 Ca2+ , Signal Transduction and Morphogenesis in Fungi......................................... 288 6 Ca2+ and Signal Transduction in Penicillium notatum ...................................... 289 7 Concluding Comments . . . . . . . . . . . . . . . . . . . . . . . . . . 295 References .................................... 296 Chapter 19 Structure and Function of Fungal Plasma Membrane ATPases C. L. SLAYMAN, P. KAMINSKI, and D. STETSON 299 1 Introduction. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 299 2 Membrane Appearance of the Plasma Membrane (PM) ATPase .................................. 299 3 Functional Properties of the Proton Pump ........ 301 4 Chemistry of the Enzyme ....................... 304 5 Primary Structure and Predictions . . . . . . . . . . . . . . . . 306 6 Models for Proton Pumping ....... , ... " . . . . .. .. 310 7 Current Directions ............................. 314 References .................................... 315 Subject Index ............................................. 317