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Alpha-Tocopherol and Plastoquinone Synthesis in Chloroplast Membranes

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Alpha-Tocopherol and Plastoquinone Synthesis in Chloroplast Membranes METHODS IN ENZYMOLOGY EDITORS-IN-CHIEF Sidney P. Colo wick Nathan O. Kaplan Methods in Enzymology Volume 148 Plant Cell Membranes EDITED BY Lester Packer Roland Douce DEPARTMENT OF PHYSIOLOGY AND ANATOMY DEPARTEMENT DE RECHERCHE FONDAMENTALE UNIVERSITY OF CALIFORNIA CENTRE D'ETUDES NUCLEA1RES ET UNIVERSITE BERKELEY, CALIFORNIA DE GRENOBLE GRENOBLE, FRANCE ACADEMIC PRESS, INC. Harcourt Brace Jovanovich, Publishers San Diego New York Berkeley Boston London Sydney Tokyo Toronto Table of Contents CONTRIBUTORS ΤΟ VOLUME 148 xi PREFACE xvii VOLUMES IN SERIES xix Section I. Cells, Protoplasts, and Liposomes 1. Techniques of Cell Suspension Culture RICHARD BLIGNY AND JEAN-JACQUES LEGUAY 3 2. Culture and Characteristics of Green Plant Cells COLIN DALTON AND IAN MACKENZIE 16 3. Preparation of Protoplasts from Plant Tissues for MIKIO NISHIMURA, Organelle Isolation Ικυκο HARA-NISHIMURA, AND TAKASHI AKAZAWA 27 4. Interaction of Plant Protoplast and Liposome TOSHIYUKI NAGATA 34 5. Liposomes as Carriers for the Transfer and Ex- MICHEL CABOCHE AND pression of Nucleic Acids into Higher Plant Pro- PAUL F. LURQUIN 39 toplasts 6. Interspecific Transfer of Partial Nuclear Genomic OTTO SCHIEDER 45 Information by Protoplast Fusion Section II. Vacuoles and Tonoplasts 7. Isolation of Mature Vacuoles of Higher Plants: GEORGE J. WAGNER 55 General Principles, Criteria for Purity and In­ tegrity 8. Isolation of Vacuoles and Tonoplast from Proto- ALAIN M. BOUDET AND plasts GILBERT ALIBERT 74 9. Preparation of Tonoplast Vesicles from Isolated ROBERT T. LEONARD 82 Vacuoles 10. Biochemical and Enzymatic Components of a J. D'AUZAC, H. CHRESTIN, Vacuolar Membrane: Tonoplast of Lutoids AND B. MARIN 87 from Hevea Latex ν vi TABLE OF CONTENTS 11. Characterization of Tonoplast Enzyme Activities BENJAMIN JACOBY 105 and Transport 12. Preparation of Tonoplast Vesicles: Applications to EDUARDO BLUMWALD, H+-Coupled Secondary Transport in Plant Vac- PHILIP A. REA, AND uoles RONALD J. POOLE 115 13. Purification and Characterization of the Tonoplast STEPHEN Κ. RANDALL AND H+-Translocating ATPase HEVEN SZE 123 14. High-Performance Liquid Chromatography for Si- Μ. HILL, Α. DUPAIX, multaneous Kinetic Measurements of Adenine P. VOLFIN, A. KURKDJIAN, Nucleotides in Isolated Vacuoles AND B. ARRIO 132 Section III. Plastids 15. Isolation of Intact Chloroplasts: General Princi- DAVID A. WALKER, pies and Criteria of Integrity ZORAN G. CEROVIC, AND SIMON P. ROBINSON 145 16. Isolation of Plastids in Density Gradients of Per- CARL A. PRICE, coll and Other Silica Sols JOHN C. CUSHMAN, LETICIA R. MENDIOLA-MORGENTHALER, AND ELLEN Μ. REARDON 157 17. Purification of Chloroplasts Using Silica Sols K. W. JOY AND W. R. MILLS 179 18. Separation of Chloroplasts and Cytosol from Pro- SIMON P. ROBINSON 188 toplasts 19. Use of Thermolysin to Probe the Cytosolic Sur- JACQUES JOYARD, face of the Outer Envelope Membrane from ALBERT-JEAN DORNE, Plastids AND ROLAND DOUCE 195 20. Characterization of Plastid Polypeptides from the JACQUES JOYARD, Outer and Inner Envelope Membranes MARYSE A. BLOCK, JACQUES COVES, CLAUDE ALBAN, AND ROLAND DOUCE 206 21. Isolation of Amyloplasts from Suspension Cul- TOM AP REES AND tures of Soybean FRÄSER D. MACDONALD 218 22. Isolation of Amyloplasts from Developing Endo- JACK C. SHANNON, sperm of Maize (Zea mays L.) EDGARDO ECHEVERRIA, AND CHARLES BOYER 226 23. Isolation of Plastids from Buds of Cauliflower ETIENNE-PASCAL JOURNET 234 (Brassica οleracea L.) 24. Isolation of Membranous Chromoplasts from Daf- BODO LIEDVOGEL 241 fodil Flowers TABLE OF CONTENTS VÜ 25. Structure and Function of the Inner Membrane SATORU MURAKAMI 246 Systems in Etioplasts 26. Isolation Procedures for Inside-Out Thylakoid HANS-ERIK ÄKERLUND AND Vesicles BERTIL ANDERSSON 252 27. Characterization of Chloroplast Cytochromes DEREK S. BENDALL AND STEPHEN A. ROLFE 259 28. Cell-Free Reconstitution of Protein Transport into MICHAEL L. MISHKIND, Chloroplasts KAREN L. GREER, AND GREGORY W. SCHMIDT 274 29. Polar Lipids of Chloroplast Membranes DAVID J. CHAPMAN AND JAMES BARBER 294 30. Isolation and Reconstitution of Thylakoid Lipids SALLIE G. SPRAGUE AND L. ANDREW STAEHELIN 319 31. Long-Chain Fatty Acid Synthesis and Utilization GRATTAN ROUGHAN 327 by Isolated Chloroplasts 32. Phosphatidylglycerol Synthesis in Chloroplast J. BRIAN MUDD, Membranes JAEN E. ANDREWS, AND S. A. SPARACE 338 33. Galactolipid Biosynthesis in Chloroplast Mem- NORA W. LEM AND branes JOHN P. WILLIAMS 346 34. Chlorophylls and Carotenoids: Pigments of Photo- HARTMUT Κ. LICHTENTHALER 350 synthetic Biomembranes 35. α-Tocopherol and Plastoquinone Synthesis in JÜRGEN SOLL 383 Chloroplast Membranes 36. Solubilization and Reconstitution of Caroteno- P. BEYER 392 genie Enzymes from Daffodil Chromoplast Membranes Using 3-[(3-Cholamidopropyl)di- methylammonioj-1-propane Sulfonate Section IV. Mitochondria 37. Isolation of Plant Mitochondria: General Princi- ROLAND DOUCE, pies and Criteria of Integrity JACQUES BOURGUIGNON, RENAUD BROUQUISSE, AND MICHEL NEUBURGER 403 38. Purification of Plant Mitochondria on Silica Sol ANTHONY L. MOORE AND Gradients MICHAEL O. PROUDLOVE 415 39. Isolation of Mitochondria from Leaves of C3, C4, GERALD E. EDWARDS AND and Crassulacean Acid Metabolism Plants PER GARDESTRÖM 421 viii TABLE OF CONTENTS 40. Separation of Spinach Leaf Mitochondria accord- PER GARDESTRÖM AND ing to Surface Properties: Partition in Aqueous INGEMAR ERICSON 434 Polymer Two-Phase Systems 41. Isolation of Submitochondrial Particles with Dif- IAN M. M0LLER, ferent Polarities ANNIKA C. LID£N, INGEMAR ERICSON, AND PER GARDESTRÖM 442 42. Isolation of the Outer Membrane of Plant Mito- CARMEN A. MANNELLA 453 chondria 43. Characterization of Channels Isolated from Plant MARCO COLOMBINI 465 Mitochondria 44. Phosphoglycerides of Mitochondrial Membranes JOHN L. HARWOOD 475 45. Ubiquinone Biosynthesis in Plant Mitochondria FRIEDHELM LÜTKE-BRINKHAUS AND HANS KLEINIG 486 46. Purification of Complexes II and IV from Plant MASAYOSHI MAESHIMA, Mitochondria TSUKAHO HATTORI, AND TADASHI ASAHI 491 Section V. Peroxisomes and Glyoxysomes 47. Isolation of Glyoxysomes and Purification of Gly- EUGENE L. VIGIL, oxysomal Membranes TUNG K. FANG, AND ROBERT P. DONALDSON 505 48. Peroxisomes and Fatty Acid Degradation BERNT GERHARDT 516 49. Proteins and Phospholipids of Glyoxysomal Mem- HARRY BEEVERS AND branes from Castor Bean ELMA GONZALEZ 526 Section VI. Nuclei, Endoplasmic Reticulum, and Plasma Membrane 50. Isolation of Nuclei from Soybean Suspension PAUL KEIM 535 Cultures 51. Isolation of the Plasma Membrane: Membrane DONALD P. BRISKIN, Markers and General Principles ROBERT T. LEONARD, AND THOMAS K. HODGES 542 52. Preparation of High-Purity Plasma Membranes CHRISTER LARSSON, SUSANNE WIDELL, AND PER KJELLBOM 558 TABLE OF CONTENTS ix 53. Possible Approaches to Surface Labeling of the J. L. HALL 568 Plasma Membrane 54. Isolation of Endoplasmic Reticulum: General J. MICHAEL LORD 576 Principles, Enzymatic Markers, and Endoplas­ mic Reticulum-Bound Polysomes 55. Phosphoglyceride Synthesis in Endoplasmic Re- THOMAS S. MOORE, JR. 585 ticulum Section VII. General Physical and Biochemical Methods 56. Electron Microscopy of Plant Cell Membranes JEAN-PIERRE CARDE 599 57. Two-Dimensional Electrophoresis in the Analysis R. REM Υ AND and Preparation of Cell Organelle Polypeptides F. AMBARD-BRETTEVILLE 623 58. Plant Membrane Sterols: Isolation, Identification, MARIE-ANDR£E HARTMANN and Biosynthesis AND PIERRE BENVENISTE 632 59. Separation of Molecular Species of Plant Glyco- J. KESSELMEIER AND lipids and Phospholipids by High-Performance E. HEINZ 650 Liquid Chromatography 60. Movement of Phospholipids between Membranes: JEAN-CLAUDE KADER, Purification of a Phospholipid Transfer Protein CHANTAL VERGNOLLE, from Spinach Leaf AND PAUL MAZLIAK 661 61. Pesticides and Lipid Synthesis in Plant Mem- C. ANDING 667 branes 62. Rapid Filtration Technique for Metabolite Fluxes YVES DUPONT AND across Cell Organelles MARIE-JOS£ MOUTIN 675 63. Application of Nuclear Magnetic Resonance R. G. RATCLIFFE 683 Methods to Plant Tissues AUTHOR INDEX 701 SUBJECT INDEX 729 [35] PRENYLQUINONE SYNTHESIS IN CHLOROPLASTS 383 [35] α-Tocopherol and Plastoquinone Synthesis in Chloroplast Membranes By JÜRGEN SOLL Plant prenylquinones, a-tocopherol, plastoquinone-9, and phyllo- quinone, function in chloroplasts as membrane constituents, antioxi• dants, or electron carriers. For a long time biosynthetic studies were hampered by the fact that no chemical intermediates of the biosynthetic pathway or biochemically active organelles were available. Earlier stud• ies12 proposed pathways with a multitude of chemically possible interme• diates. The detailed work3 on the chemical synthesis of prenylquinones enabled others4-* to work out the most probable pathway (Fig. 1) in plas• toquinone and tocopherol biosynthesis. Chemical Synthesis of Prenylquinones The small-scale synthesis of IV (Fig. 2) is described here4 and can be applied to the synthesis of other prenylquinones (/, //, ///, V, VI) without problems. In many cases methylquinones are not commercially available and have to be prepared in advance. The corresponding phenol (4 mmol) is dissolved in 10 ml methanol and oxidized by 10 mmol of Fremy's salt7 {[(S03)2NO]K2} in 120 ml water and 4 ml sodium acetate (1 M). The reaction is allowed to continue for 30 min and the quinone is then exten• sively extracted with diethyl ether. The organic solvent is evaporated and the quinone purified by column chromatography (silica gel 60, Merck, FRG) using CHC13 as developing solvent. Quinone
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