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Chlorophylls and Bacteriochlorophylls: Biochemistry, Biophysics, Functions and Applications / Edition 1

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The first dedicated new work since 1991, this book reviews recent progress and current studies in the chemistry, metabolism and spectroscopy of chlorophylls, bacteriochlorophylls and their protein complexes. Also discussed is progress on the applications of chlorophylls as photosensitizers in photodynamic therapy of cancerous tumours, and as molecular probes in biochemistry, medicine, plant physiology, ecology and geochemistry. Each section offers an introductory overview followed by concise, focused and fully-referenced chapters written by experts.

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Editorial Reviews

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From the reviews:

"This excellent book provides a comprehensive, up to date account of the chemistry and biology of chlorophylls and bacteriochlorophylls, written by world experts. Progress in the past few years in this area of science, especially on how these pigments are synthesised and degraded, and how they function in photosynthesis, has been remarkable. All of these recent advances are beautifully set out in this timely compendium, which is, at the same time, both very readable and very complete. The Editors are to be congratulated. It is interesting to see how fundamental research in this area has led to important, unexpected applications such as the treatment of cancers by photodynamic therapy or remote sensing of photosynthetic capacity from outer space. This will be essential reading for all of my research team and, I expect, for every other research group that works with these fascinating molecules."—- Professor Richard J. Cogdell, University of Glasgow, Scotland, UK

"The importance of the chlorophyll pigments is difficult to overestimate. For the last two to three billion years, chlorophylls have made life possible on earth through the process of photosynthesis. Since the chlorophylls have been around for billions of years, apparently nature achieved perfection eons ago. The attempt to understand the perfection of the chlorophylls is the central theme of this book. In today’s energy hungry world with renewed interest in solar energy, this collection on the chlorophylls is most timely, covering the latest aspects of chlorophyll research through the scholarship of 70 authorities. With the role of chlorophyll and bacteriochlorophyll in photosynthesis as revealed in these pages, the reality of practical applications of solar energy trapping and conversion becomes an intriguing possibility. These applications will go far beyond the biological process of photosynthesis to include such topics as solar energy conversion, environmental science, medical applications, cosmetics, sun screens, etc. Many of these applications are included in this comprehensive volume. Many new applications will arise as a result of this outstanding collection on the functions and applications of chlorophylls and bacteriochlorophylls." —- Professor James R. Norris, University of Chicago, Illinois, USA

"In this electronic age, with most scientific journals going back on line for many years, books sometimes seem to be a threatened species. Every so often a book appears in or close to our special interests that we know will be a valuable occupant of our bookshelves for many years. Chlorophylls and Bacteriochlorophylls: Biochemistry, Biophysics, Functions and Applications is such a volume. It is 16 years since publication of the last comprehensive book on the Chlorophylls and this latest volume is a wonderful synthesis and update of a topic with many ramifications ranging from molecular structure to photodynamic therapy. The chapters range from those suitable for advanced undergraduate students……to the very specialized ….The editors are to be congratulated,….for assembling so many authorities to synthesize the special interests in Chlorophylls ……..its real value is as an onsite comprehensive reference work for any research group with an interest in plant pigments." —-Dr. Roger Hiller, Biology Dept, Macquarie University, Sydney, NSW 2109, Australia

"This book is a part (vol. 25) of the Advances in Photosynthesis and Respiration Series … . Overall this is an interesting, useful and timely book … . I recommend it to graduate students and scientists working on chemistry, biochemistry, molecular biology, biophysics, photo-medicine, remote sensing and molecular evolution of Chl, BChl, carotenoids and photosynthetic processes. … I recommend that major science libraries and research institutions acquire it … . also recommend this book to members of the International Society of Photosynthesis Research … ." (Baishnab C. Tripathy, Current Science, Vol. 92 (12), 2007)

"The volume is subdivided into five sections, which, in general, begins with an overview chapter. …References and content are highly up-to-date. … The volume addresses advanced students as well as unskilled and experienced researchers. In sum, the editors together with the authors of the different chapters have created an outstanding, comprehensive textbook covering all aspects of research related to chlorophylls." (Dieter Dörnemann, Journal of Plant Physiology, Vol. 164 (11), 2007)

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Product Details

  • ISBN-13: 9781402045158
  • Publisher: Springer Netherlands
  • Publication date: 11/28/2006
  • Series: Advances in Photosynthesis and Respiration Series , #25
  • Edition description: 2006
  • Edition number: 1
  • Pages: 603
  • Product dimensions: 82.50 (w) x 10.75 (h) x 1.00 (d)

Table of Contents

Editorial     v
Contents     xi
Preface     xxii
Author Index     xxix
Color Plates     CP1
Structures, Chemistry, Analysis
An Overview of Chlorophylls and Bacteriochlorophylls: Biochemistry, Biophysics, Functions and Applications   Hugo Scheer     1
Summary     1
Introduction     2
Structures     4
Why Chlorophylls?     12
Functions     16
Acknowledgments     19
References     19
Synthesis, Reactivity and Structure of Chlorophylls   Mathias O. Senge   Arno Wiehe   Claudia Ryppa     27
Summary     27
Basic Structure and Reactivity of Chlorophylls     28
Conformational Flexibility of Hydroporphyrins     28
Chemical Synthesis of Chlorophylls and Bacteriochlorophylls     29
Chemical Modifications     30
Acknowledgments     35
References     35
Chlorophyll c Pigments: Current Status   Manuel Zapata   Jose L Garrido   Shirley W. Jeffrey     39
Summary     40
Introduction     40
Chemistry of Chlorophyll c Pigments     41
Biochemistry of Chlorophyll c Pigments     46
Distribution     47
Applications and Future Directions     47
Note Added in Proof     50
Acknowledgments     50
References     50
Unusual Tetrapyrrole Pigments of Photosynthetic Antennae and Reaction Centers: Specially-tailored Chlorophylls   Masami Kobayashi   Machiko Akiyama   Hideo Kise   Tadashi Watanabe     55
Summary     56
Introduction     56
Specially-tailored Chlorophylls in a Limited Number of Organisms     56
Specially-tailored Chlorophylls Associated with Reaction Centers     59
Acknowledgments     63
References     63
[Heavy metal]-Chlorophylls Formed in Vivo During Heavy Metal Stress and Degradation Products Formed During Digestion, Extraction and Storage of Plant Material   Hendrik Kupper   Frithjof C. Kupper   Martin Spiller     67
Summary     67
Introduction     68
Substitution of the Central Mg[superscript 2+] Ion Under Elevated Heavy Metal Concentrations in vivo     68
Occurrence of Partially Degraded and Transmetalated Chlorophyll Derivatives in Marine Invertebrates     72
Chlorophyll Degradation Products Formed During Storage and Extraction of Plant Material     73
Acknowledgments     75
References     75
Spectroscopy and Structure Determination   Masami Kobayashi   Machiko Akiyama   Hiromi Kano   Hideo Kise     79
Summary     79
Introduction     80
Absorption Spectra     80
Fluorescence Spectra     85
Circular Dichroism Spectra     87
Mass Spectra     88
Nuclear Magnetic Resonance Spectra     90
Acknowledgments     93
References     93
Spectrometric Assays for Plant, Algal and Bacterial Chlorophylls   Robert J. Porra     95
Summary     95
Introduction     96
Modern Spectrophotometric Assays of Chlorophylls a and b     96
Choice of Extractant and Determination of Accurate Extinction Coefficients for Chlorophylls a and b in Such Solvents     96
Reliable Simultaneous Equations for the Accurate Assay of Chlorophylls a and b     99
The Unacceptable Errors and Consequences of Using the Arnon Equations     100
Other Spectrophotometric Assays for Chlorophylls a and b in Association with Their Derivatives or Other Pigments     101
Spectrophotometric Assays for Chlorophylls in Chlorophyll c-containing Algae     101
Spectrophotometric Data for the Assay of Bacteriochlorophylls     101
Spectrofluorimetric Assays for Chlorophylls a and b     103
Concluding Remarks     105
Acknowledgments     105
References     105
Chlorophyll Analysis by New High Performance Liquid Chromatography Methods   Jose L. Garrido   Manuel Zapata     109
Summary     109
Introduction     110
New Bonded Phase Columns     110
Mass Spectrometry as High Performance Liquid Chromatography Detection Technique Applied to Chlorophylls     112
Applications     113
Future Directions in the High Performance Liquid Chromatography Analysis of Chlorophylls     115
Acknowledgments     119
References     119
Large Scale Chlorophyll Preparations Using Simple Open-Column Chromatographic Methods   Yuzo Shioi     123
Summary     124
Introduction     124
Extraction of the Pigments     124
Precipitation of Chlorophylls     126
Column Chromatographic Methods     127
Acknowledgments     130
References      131
Chlorophyll Metabolism, an Overview   Wolfhart Rudiger   Bernhard Grimm     133
Summary     133
Introduction     134
The Diversity of Tetrapyrrole Metabolic Pathways     134
Subcellular Location of Enzymes     140
Regulation of Chlorophyll Biosynthesis     140
Incorporation into Proteins     142
Chlorophyll Degradation     143
Concluding Remarks     143
References     143
Biosynthesis of 5-Aminolevulinic Acid   Samuel I. Beale     147
Summary     147
Alternate Pathways for 5-Aminolevulinic Acid Biosynthesis     147
5-Aminolevulinic Acid Biosynthesis from Glycine and Succinyl-Coenzyme A     148
5-Aminolevulinic Acid Biosynthesis from Five-Carbon Precursors     149
Phylogenetic Distribution and Evolutionary Implications of the Two 5-Aminolevulinic Acid Biosynthetic Pathways in Photosynthetic Species     154
Acknowledgments     154
References     154
Transfer RNA-Dependent Aminolevulinic Acid Formation: Structure and Function Of Glutamyl-tRNA Synthetase, Reductase and Glutamate-1-Semialdehyde-2, 1-Aminomutase   Dieter Jahn   Jurgen Moser   Wolf-Dieter Schubert   Dirk W. Heinz      159
Summary     159
Two Pathways for 5-Aminolevulinic Acid Biosynthesis     160
Glutamyl-tRNA Synthetase Forms Glutamyl-tRNA for Protein and Tetrapyrrole Biosynthesis     160
Glutamyl-tRNA     160
Glutamyl-tRNA Synthetase     160
Glutamyl-tRNA Reductase     163
Glutamate-1-Semialdehyde-2, 1-Aminomutase     166
Metabolic Channeling of Glutamate-1-Semialdehyde     167
Concluding Remarks     167
Acknowledgments     168
References     168
The Pathway from 5-Aminolevulinic Acid to Protochlorophyllide and Protoheme   Elena Yaronskaya   Bernhard Grimm     173
Summary     173
Introduction     174
Enzymes of Porphyrin Synthesis     174
The Chlorophyll-synthesizing Branch     178
The Protoheme-synthesizing Branch     182
Concluding Remarks     183
References     183
Biosynthesis of Chlorophylls a and b: The Last Steps   Wolfhart Rudiger     189
Summary     189
Introduction     190
Protochlorophyllide Reduction     190
Metabolism of Chlorophyll b and Chlorophyllide b      193
Esterificatlon     195
Supplement     197
Note Added in Proof     197
Acknowledgments     197
References     197
Bacteriochlorophyll Biosynthesis in Green Bacteria   Niels-Ulrik Frigaard   Aline Gomez Maqueo Chew   Julia A. Maresca   Donald A. Bryant     201
Summary     201
Introduction     202
Approach to Elucidating Bacteriochlorophyll Biosynthesis in Green Bacteria     203
Overview of Proposed Pathways     206
Early Steps in Porphyrin Biosynthesis     209
Bacteriochlorophyll a Biosynthesis     209
Chlorophyll a Biosynthesis     210
Bacteriochlorophyll c Biosynthesis     211
Bacteriochlorophyll d Biosynthesis     215
Bacteriochlorophyll e Biosynthesis     215
Bacteriochlorophyll c Biosynthesis in Green Filamentous Bacteria     216
Future Directions     217
Note added in Proof     217
Acknowledgments     217
References     217
Involvement of Tetrapyrroles in Cellular Regulation   Christoph F. Beck   Bernhard Grimm     223
Summary     223
Introduction      224
Intra-organellar Regulation by Tetrapyrroles     225
Role for Tetrapyrroles in Inter-organellar Signaling     226
Transport of Tetrapyrroles     230
Concluding Remarks     230
References     232
Chlorophyll Catabolites and the Biochemistry of Chlorophyll Breakdown   Bernhard Krautler   Stefan Hortensteiner     237
Summary     237
Introduction     238
Chlorophyll Breakdown and Chlorophyll Catabolites in Higher Plants     239
Chlorophyll Breakdown and Chlorophyll Catabolites in Green Algae     254
Chlorophyll Catabolites from Marine Organisms     255
Conclusions and Outlook     256
Note Added in Proof     256
Acknowledgments     257
References     257
The Evolution of Chlorophylls and Photosynthesis   Anthony W. D. Larkum     261
Summary     261
Introduction     262
The Early Earth and the Origins of Photosynthesis     262
Evolution of the Pathway to the Earliest Photosynthetic Pigments     263
Evolution of Extant Photosynthetic Pigments and Early Photosynthetic Organisms     267
Reaction Centers     272
Evolution of Oxygenic Photosynthesis     275
Light-Harvesting Chlorophyll Proteins     277
Outlook     278
References     278
The Native Environment
The Influence of Protein Interactions on the Properties of the Bacteriochlorophyll Dimer in Reaction Centers   James P. Allen   JoAnn C. Williams     283
Summary     283
Introduction     284
Protein Interactions that Influence the Properties of the Dimer     285
Modeling the Effect of Protein Interactions on the Electronic Structure of the Dimer     288
The Effect of Protein Interactions on Electron Transfer     290
Conclusions     292
Acknowledgments     292
References     293
Magic Angle Spinning Nuclear Magnetic Resonance of the Chlorosomes   Ido de Boer   Huub J. M. de Groot     297
Summary     297
Introduction     297
Aggregated Hydrated Chlorophyll (Chl a/H[subscript 2]O) as a Model for Magic Angle Spinning Nuclear Magnetic Resonance Technology Development     298
Self-organization of Bacteriochlorophyll is the Main Structural Feature of the Chlorosomal Antennae     300
A 3-Dimensional Model for the Structure of the Chlorosomal Antennae     303
Conclusions and Future Prospects      304
Note Added in Proof     305
References     305
Single Molecule Spectroscopy of Pigment Protein Complexes from Purple Bacteria   Jurgen Kohler   Thijs J. Aartsma     309
Summary     309
Introduction     310
Spectroscopy of Individual Light-harvesting Complexes     312
Acknowledgments     319
References     319
Effects of Axial Coordination, Electronic Excitation and Oxidation on Bond Orders in the Bacteriochlorin Macrocycle, and Generation of Radical Cation on Photo-Excitation of in vitro and in vivo Bacteriochlorophyll a Aggregates: Resonance Raman Studies   Yasushi Koyama   Yoshinori Kakitani   Leenawaty Limantara   Ritsuko Fujii     323
Summary     224
The 5- and 6-Coordinated States of Bacteriochlorophyll a in the S[subscript 0], T[subscript 1] and D[subscript 0] Electronic States as Probed by the Ring-Breathing Frequency     324
Changes in Bond Orders as Scaled by Stretching Force Constants in the Conjugated Systems of Bacteriochlorophyll a, Bacteriopheophytin a and Carotenoid: Implication of the Arrangement of Those Pigments in the Reaction Center     329
Generation of the T[subscript 1] State and Subsequent Transformation into the D[subscript 0] State upon Photo-Excitation of in vitro and in vivo Bacteriochlorophyll a Aggregates      331
Acknowledgments     334
References     335
Mapping the Global Ring Currents in Porphyrins and Chlorins   Erich Steiner   Patrick W. Fowler     337
Summary     337
Introduction     337
Electronic Structure and Spectra     337
Ring Currents     339
Orbital Model of Ring Currents     341
The Four-Orbital Model of the Ring Current in Porphyrins     341
Pathways     342
Porphin and Magnesium Porphin     342
Chlorins     346
Appendix     346
Note Added in Proof     346
References     346
Bacteriochlorophyll Protein Maquettes   Dror Noy   Christopher C. Moser   P. Leslie Dutton     349
Summary     349
Protein Maquette Tools for Exploring Natural Design of Chlorophyll- and Bacteriochlorophyll-Proteins     350
Essentials of De Novo Designing Protein Maquettes     352
Adapting Natural LHs to Maquettes     353
Concluding Remarks     360
Acknowledgments     360
References     360
Molecular Assembly of Bacteriochlorophyll Complexes Using Synthetic Light-Harvesting Model Polypeptides   Mamoru Nango     365
Summary     365
Introduction     365
Molecular Assembly of Bacteriochlorophylls with Isolated Light-Harvesting Subunits from Rhodobacter sphaeroides and Synthetic Models     367
Molecular Assembly of Bacteriochlorophyll a Complex and Its Analogues by Synthetic 4[alpha]-Helix Polypeptides     369
Concluding Remarks     371
Acknowledgments     372
References     372
Reconstitution and Pigment Exchange   Harald Paulsen     375
Summary     375
Introduction     376
Reconstitution     376
Pigment Exchange     379
Concluding Remarks     381
Note Added in Proof     381
References     382
Assembly of Model Bacteriochlorophyll Proteins in the Native Lipid Environment   Adela Garcia-Martin   Lee Gyan Kwa   Mathias von Jan   C. Neil Hunter   Paula Braun     387
Summary     387
Introduction     388
Bacteriochlorophyll Proteins with Model Transmembrane Helices     388
Assembly Motifs of (Bacterio)chlorophyll Proteins     391
Acknowledgments     394
References      394
Photosynthetic Functions of Chlorophylls   Alexander N. Melkozernov   Robert E. Blankenship     397
Summary     397
Introduction     398
Structure of Chlorophylls and Their Relevance to Photosynthetic Functions     398
Chlorophyll-Sensitized Electron Transfer     399
Light-harvesting and Energy Transfer     402
Structural Function     408
Photoprotective Function of Chlorophylls     408
Acknowledgments     410
References     410
Excitation Energy Transfer Between (Bacterio)Chlorophylls-the Role of Excitonic Coupling   Dieter Leupold   Heiko Lokstein   Hugo Scheer     413
Summary     413
Introduction     414
Excitation Energy Transfer in Purple Bacteria     415
Excitation Energy Transfer in Light-Harvesting Complex II-type Complexes of Higher Plants     420
Excitation Energy Transfer in Chlorosomes     423
Excitation Energy Transfer in the Fenna-Matthews-Olsen (FMO) Complex     424
Note Added in Proof     425
Acknowledgments     426
References     426
Mechanisms of Carotenoid-to-Bacteriochlorophyll Energy Transfer in the Light Harvesting Antenna Complexes 1 and 2: Dependence on the Conjugation Length of Carotenoids   Yasushi Koyama   Yoshinori Kakitani     431
Summary     431
Introduction     432
Intrinsic Properties of Carotenoids' Excited-States     432
Carotenoid-to-Bacteriochlorophyll Energy Transfer in Light Harvesting Complex 2     434
Carotenoid-to-Bacteriochlorophyll Energy Transfer in Light Harvesting Complex 1     438
Comparison between the Light Harvesting Complexes 1 and 2     439
Acknowledgments     442
References     443
Electron Transfer in Photosynthetic Reaction Centers   Josef Wachtveitl   Wolfgang Zinth     445
Summary     445
Introduction     446
Dynamics and Energetics of the First Electron Transfer Reactions in Bacterial Reaction Centers     446
Optimization of Photosynthesis     454
Concluding Remarks     455
References     455
Chlorophyll Sensitizers in Photodynamic Therapy   Alexander S. Brandis   Yoram Salomon   Avigdor Scherz     461
Summary     462
Introduction     462
Photosensitizers Derived from Chlorophyll a     465
Clinical Trials     476
Acknowledgments     476
References     476
Bacteriochlorophyll Sensitizers in Photodynamic Therapy   Alexander S. Brandis   Yoram Salomon   Avigdor Scherz     485
Summary     486
Introduction     486
Photosensitizers Derived from Bacteriochlorophyll a     487
Clinical trials     491
Conclusions and Perspectives     491
Acknowledgements     491
References     492
Metal-substituted Bacteriochlorophylls: Novel Molecular Tools   Roie Yerushalmi   Idan Ashur   Avigdor Scherz     495
Summary     495
Introduction     496
From Porphyrins to Bacteriochlorophylls: An Experimental Benchmark for Theoretical Approaches     496
Function-Oriented Chemical Modification of Bacteriochlorophylls     497
Applications     499
Concluding Remarks     503
Acknowledgments     503
References     503
Chlorophyll Fluorescence as a Reporter on in vivo Electron Transport and Regulation in Plants   Ladislav Nedbal   Michal Koblizek     507
Summary     507
Introduction      508
Time Scales     508
Analysis of Chlorophyll Fluorescence Transients     511
Beyond the Conventional Analysis     515
Prospects of the Technique and Instrumentation     516
Acknowledgments     516
References     516
Meeting the Challenge of Monitoring Chlorophyll in the Ocean from Outer Space   Andre Morel     521
Summary     521
Introduction     522
Absorbing Substances in the Marine Environment     523
Bio-optical Relationships in Oceanic Waters and Chlorophyll Algorithms     525
Reflectance of Oceanic Waters     528
Phytoplankton Distribution and Primary Production     528
Sun-stimulated Fluorescence     531
Concluding Remarks: The Atmospheric Correction     531
Acknowledgments     532
References     533
Geochemistry of Chlorophylls   Brendan J. Keely     535
Summary     536
Introduction     536
Chlorophyll Transformations     544
Timing and Nature of Transformations     551
Transformation Scheme     553
Applications     554
Concluding Remarks     556
Note Added in Proof     556
Acknowledgments     557
References     557
Index     563
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