The Porphyrin Handbook. The Iron and Cobalt Pigments: Biosynthesis, Structure and Degradation PDF
Preview The Porphyrin Handbook. The Iron and Cobalt Pigments: Biosynthesis, Structure and Degradation
Volumes in This Set Volume 11 / Bioinorganic and Bioorganic Chemistry Volume 12 / The Iron and Cobalt Pigments: Biosynthesis, Structure, and Degradation Volume 13/Chlorophylls and Bilins:Biosynthesis, Synthesis, and Degradation Volume 14/Medical Aspects of Porphyrins Volume 15/Phthalocyanines: Synthesis Volume 16/Phthalocyanines: Spectroscopic and Electrochemical Characterization Volume 17/ Phthalocyanines: Properties and Materials Volume 18/Multiporphyrins, Multiphthalocyanines, and Arrays Volume 19/Applications of Phthalocyanines Volume 20/Phthalocyanines: Structural Characterization The Porphyrin Handbook Volume 12 / The Iron and Cobalt Pigments: Biosynthesis, Structure, and Degradation Editors Karl M. Kadish Department of Chemistry University of Houston Houston, Texas Kevin M. Smith Department of Chemistry Louisiana State University Baton Rouge, Louisiana Roger Guilard Faculte des Sciences Gabriel Universite de Bourgogne Dijon, France @ ACADEMIC PRESS An imprintofElsevier Science Amsterdam· Boston· London· New York· Oxford· Paris San Diego· San Francisco· Singapore· Sydney· Tokyo AcademicPress An imprint ofElsevier Science 525BStreet, Suite 1900 San Diego, California92101-4495 USA © 2003 Elsevier Science (USA) All rights reserved. This workisprotectedundercopyrightbyElsevierScience, andthe followingtermsandconditionsapplytoitsuse: Photocopying Single photocopiesofsingle chaptersmay be madefor personal use as allowed by nationalcopyrightlaws. Permissionofthe Publisherand paymentofa feeisrequired for all otherphotocopying, includingmultipleor systematiccopying,copyingfor advertisingor promotionalpurposes, resale, and all forms ofdocument delivery. 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TransferredtoDigital Printing 2011 Preface Volumes 1-10 of The Porphyrin Handbook were first solidations were taking place in the publishing sector, published in late 1999 and met with resounding and the new set of volumes would be published by international acclaim. After only two months on the Elsevier. shelves,ourpublisher, AcademicPress, was awardedthe Oursequel, in ten more volumes (11-20), builds upon 1999Chemistryawardbythe Professionaland Scholarly the first published set of works by extending its Publishing Division of the American Association of authoritative treatise of the tetrapyrroles. We have Publishers, Inc.; this honor recognized The Porphyrin moved on from synthesis, chemistry, spectroscopy and Handbook as the "best chemistry book ofthe year." At applications of porphyrins to address, in depth, many that time we,the three editors, began receiving calls and of the sub-fields not covered in the first treatise requests from our colleagues and our Academic Press (Volumes 1-10). To be sure, there were still some publisherto "expandthe work andfillin the gaps" so as loose ends, but we believe that our plan was fairly to assemble the best ever up-to-date compendium of comprehensive. New topics this time include biology every possible aspect of the field of porphyrins, other and medical implications of porphyrin systems, the tetrapyrroles, and related macrocycles. biosynthesis of porphyrins, chlorophylls and vitamin Shortly after publication of the first ten volumes of B12. Other areas covered include clinical and biochem The Porphyrin Handbook, the First International ical aspects of genetically transmitted or drug induced Conference on Porphyrins and Phthalocyanines diseases associated with errors in heme metabolism, as (ICPP-1) took place in Dijon, France (June 2000), well as the transformation of hemes into bile pigments, hosted by one ofthe three editors of the Handbook. At the organic synthesis of bilins, recent work on phyto thatmajorinternationalevent, the Society ofPorphyrins chrome and the pathways ofdegradation ofchlorophyll and Phthalocyanines (SPP) was created, and in early in senescent plants. In addition, Volumes 11-20 address 2002 our fledgling SPP took over publication of the every aspect of the synthesis, chemistry, structure and Journal ofPorphyrins and Phthalocyanines (JPP) from spectroscopy of phthalocyanines. John Wiley & Sons, with one of the three Handbook Our 61 chapters (coincidentally the same number of editors serving as Editor-in-Chief. At ICPP-2 in Kyoto, chapters as in the 1-10 set of volumes) are once again Japan (July 2002), it became abundantly clear that The written by internationally recognized experts and we Porphyrin Handbook, Volumes 1-10, was serving well were particularly gratified by two organizational our community of research scientists. This applied aspects; firstly, we received almost no rejections of our equally to our society (SPP) and journal (JPP), which requests for chapters, and secondly, almost all of our are incrementally enhancing the international visibility contractedauthorsprovideduswith chaptersin a timely of our field. Our new series of Handbook volumes (11 manner which, we believe, are as good in quality, or 20) and the continuation of our popular international even better, than those in the first ten volumes. Indeed, conference series (ICPP-3, to be held in New Orleans, once again we believe that our contributors have USA, in 2004) each in their own way will contribute produced research articles.that will be dominant in further to the scientificenrichment of the porphyrin and their specific areas for another fifteen years. phthalocyanine research areas. We sincerelyhopethatourreaderswillappreciatethis However, even before publication ofVolumes 1-10, new treatise as much as they liked our first venture. The we were becoming aware of the great interest and tetrapyrrolefieldcontinuesto expandintonewareasand excitement about the treatise from our real audience, togathernewrecruitsandconverts.Wethinkthathaving the scientists, clinicians, and engineers working in our the research field available at ones' fingertips (even if it field - "you won't be covering biology or biosynthesis, comprisestwentyvolumes)isawonderfulthing, and this let's have Volume 11soon" - "what about phthalocya can only serve to facilitate future expansion while at the nines? They're (tetraazatetrabenzo)porphyrins too!" same time recording our field's rich history. So, in very short order the three ofus met, put together a plan for continuation, and obtained the publisher's Karl M. Kadish, Houston approval and blessings for ten more volumes; this Kevin M. Smith, Baton Rouge last action was no mean accomplishment since con- Roger Guilard, Dijon ix Contributors to Volumes 1-20 Takuzo Aida Karine Auclair Departmentof Chemistry and Biotechnology Department of Chemistry Graduate School of Engineering McGill University The University of Tokyo 801 Sherbrooke StreetWest Hongo, Bunkyo-ku, Tokyo 113-8656,Japan Montreal, Quebec, Canada H3A 2K6 [email protected] [email protected] Chapters 23, 42 Chapter75 Muhammad Akhtar Nick Bampos School of Biological Sciences University Chemical Laboratory University of Southampton Cambridge University BassettCrescent East Cambridge, CB2 1EW, UK Southampton S016 7PX,UK Chapter 15 [email protected] Lucia Banci Chapter71 CERMand Department of Chemistry Karl E. Anderson University of Florence 50019 SestoFiorentino (Florence), Italy Departments of Preventive Medicine and [email protected] Community Health Internal Medicine, Chapter39 and Pharmacology and Toxicology The University of TexasMedical Branch at Galveston Jean-Michel Barbe Texas77555-1109, USA Laboratoire d'Ingenierie Mcleculaire [email protected] pour la Separation et lesApplications desGaz Chapter 94 LIMSAG (UMR 5633) Universite de Bourgogne JohnArnold Faculte desSciences "Gabrielli Department of Chemistry 6, BdGabriel 21000 Dijon, France University of California, Berkeley [email protected] Berkeley, California 94720-1460, USA Chapters 19 116 [email protected] 1 Chapter 17 Pierrette Battioni Universite ReneDescartes Laboratoire de Chimie et Biochimie Pharmacologiques et Toxicologiques UMR 8061 75270 Paris,France xi xii Contributors to Volumes 1-20 [email protected] Sylvia S.Bottomley Chapter 26 Department of Medicine University of Oklahoma College of Medicine and Carl E.Bauer Department of VeteransAffairs Medical Center Departmentof Biology Hematology-Oncology Section (111J) Indiana University 921 N.E. 13th Street Bloomington, Indiana 47405, USA Oklahoma City [email protected] Oklahoma 73104-5007, USA Chapter 80 [email protected] Marc Benard Chapter 85 Laboratoire de Chimie Quantique UMR 7551 Roman Boulatov Universite Louis Pasteur Department of Chemistry 67000 Strasbourg,France Stanford University [email protected] Stanford, California 94305-5080, USA Chapter 48 [email protected] EhudBen-Hur Chapter 62 Consultant in Photomedicine Marcel Bouvet 160 West EndAvenue # 24P, New York, NY 10023, USA Laboratoire de Chimie Inorganique et Materiaux Moleculaires [email protected] CNRS- UMR7071 Chapter 117 Universite PierreetMarie Curie JeanBernadou 4, place lussieu, CaseCourrier 42 Laboratoire de Chimie de Coordination du CNRS 75252 Pariscedex 05, France 31077 Toulouse, France [email protected] [email protected] Chapter 118 Chapter 31 JohannW. Buchler Ivano Bertini Institut fur Anorganische Chemie CERMand Departmentof Chemistry Darmstadt University of Technology University of Florence 0-64287 Darmstadt, Germany 50019 SestoFiorentino (Florence), Italy [email protected] [email protected] [email protected] Chapter 39 Chapter 20 David W. Bollivar Henry J.Callot Department of Biology Faculte de Chimie Illinois Wesleyan University Universite Louis Pasteur P.O. Box 2900, Bloomington, Illinois 61702-2900, USA F-67000 Strasbourg,France [email protected] [email protected] Chapter 78 Chapter 7 Arnaud Bondon Isabelle Chambrier UMR 6509, Organornetallique etCatalyse, Wolfson Materials & CatalysisCentre Chimie et Electrochirnie Moleculaires School of Chemical Sciencesand Pharmacy Universite de RennesI University of East Anglia 35042 Rennes,France Norwich NR4 7TJ, UK [email protected] [email protected] Chapter 38 Chapter 108 Contributors to Volumes 1-20 xiii Jean-ClaudeChambron Anne Corrigall Laboratoire de Chimie Organo-Minerale Lennox EalesPorphyria Laboratories Universite Louis Pasteur Departmentof Medicine Institut LeBel University of CapeTown Medical School 67070 Strasbourg,France Observatory, SouthAfrica 7925 [email protected] [email protected] Chapter 40 Chapter 89 Wai-Shun Chan Timothy M. Cox Progenitor Cell Therapy, L.L.C. Departmentof Medicine Park80 West, PlazaII, Suite200 University of Cambridge, Box 157 SaddleBrook, NewJersey 07663, USA Addenbrooke's Hospital, Cambridge CB2 2QQ, UK [email protected] [email protected] Chapter 117 Chapter 90 JenniferCheek Claudia Crestini School of Medicine Dipartimento di Scienze eTecnologie Chimiche University of SouthCarolina Tor Vergata University Columbia, SouthCarolina 29208, USA Via Della Ricerca scientifica Chapter 53 00133, Rome, Italy LinCheng [email protected] Department of Chemistry and Biochemistry Chapter 66 University of Oklahoma Roman S.Czernuszewicz Norman, Oklahoma 73019, USA Department of Chemistry Chapter 33 University of Houston Jun-Hong Chou Houston, Texas77204-5003, USA School of Chemical Sciences [email protected] University of Illinois at Urbana-Champaign Chapter 52 Urbana, Illinois 61801, USA Harry A. Dailey Chapter 41 Biomedical and Health SciencesInstitute Zoe Clyde-Watson Departmentof Microbiology, and University Chemical Laboratory Departmentof Biochemistry &Molecular Biology Cambridge University A220 Life SciencesBuilding Cambridge, CB2 1EW, UK University of Georgia Chapter 15 Athens, Georgia 30602-7229, USA James P.Collman [email protected] Departmentof Chemistry Chapter 72 Stanford University Tamara A. Dailey Stanford, California 94305-5080, USA Biomedical and Health SciencesInstitute [email protected] Department of Microbiology, and Chapter 62 Departmentof Biochemistry & Molecular Biology Michael J.Cook A220 Life SciencesBuilding Wolfson Materials & CatalysisCentre University of Georgia School of Chemical Sciencesand Pharmacy Athens, Georgia 30602-7229, USA University of EastAnglia [email protected] Norwich NR4 7T),UK Chapter 72 [email protected] Chapter 108 xiv Contributors to Volumes 1-20 ScottL. Darling Jean-Charles Deybach University Chemical Laboratory Centre FrancaisdesPorphyries, INSERMU409 Cambridge University 178 rue des Renouillers Cambridge, CB2 1EW, UK 92701 Colombes Cedex, France; Chapter 15 andFaculte de Medecine Xavier Bichat Universite ParisVII John Dawson 16 rue Henri Huchard Department of Chemistry and Biochemistry BP416, 75870 ParisCedex 18, France University of South Carolina [email protected] Columbia, South Carolina 29208, USA Chapter 86 [email protected] Chapter 53 Danilo Dini Institutfur Organische Chemie Gema de la Torre UniversitatTubingen Departamento de Qufmica Organics 72076 Tubingen, Germany Universidad Autonorna de Madrid [email protected] 28049 Cantoblanco, Madrid, Spain Chapters 107, 114 [email protected] Chapter 99 Maria Pia Donzello Dipartimento di Chimica FelixW. M. de Rooij Universita degli Studi di Roma "La Sapienza" Department of Internal Medicine, ErasmusMC P.IeAldo Moro 5, 1-00185 Roma, Italy University Medical Center Rotterdam [email protected] P.B.2040, 3000 CA Rotterdam Chapter 112 The Netherlands [email protected] Annie Edixhoven Chapters93, 95 Departmentof Internal Medicine, ErasmusMC University Medical Center Rotterdam JefferyS.de Ropp P.B.2040, 3000 CA Rotterdam NMR Facility The Netherlands University of California, Davis [email protected] Davis, California 95616, USA Chapter 93 [email protected] Chapter 37 G. H. Elder Department of Medical Biochemistry Hubert de Verneuil University of Wales College of Medicine Laboratoire de Pathologie Heath Park,CardiffCF14 4XN, UK Moleculaire etTherapie Genique, INSERME0217 [email protected] Universite V Segalen Bordeaux 2 Chapter 88 146 rue Leo Saignat 33076 Bordeaux cedex, France Michael KlausEngel verneuil@u-bordeaux2Jr Dainippon Ink and Chemicals, Inc. Chapter 87 Central ResearchLaboratories 631 Sakado, Sakura-shi Chiba-ken 285-8668, Japan [email protected] Chapter 122 Contributors to Volumes 1-20 xv Christoph Erben Barbara Floris Lucent Technologies-Bell Laboratories Dipartimento di Scienze eTecnologie Chimiche Murray Hill, NewJersey 07974, USA Universita di Roma "Tor Vergata" [email protected] Via della Ricerca Scientifica Chapter 12 1-00133,Roma, Italy [email protected] Claudio Ercolani Chapter 112 Dipartimento di Chimica Universita degli Studidi Roma"La Sapienza" Nicole Frankenberg P.IeAldo Moro 5, 1-00185Roma, Italy Section of Molecular and Cellular Biology [email protected] University of California, Davis Chapters 101, 112 One ShieldsAvenue Davis, California 95616, USA Peter Erk [email protected] Performance Chemicals Research Chapter 83 GVP/C- J550, BASF AG 67056 Ludwigshafen/Rh, Germany Yuichi Fujita [email protected] Graduate School of Bioagricultural Sciences Chapter 119 Nagoya University Nagoya 464-8601, Japan JeanFischer [email protected] Laboratoire de Chimie Organornetallique et de Catalyse Chapter 80 Institut IeBel Universite Louis Pasteurde Strasbourg Shunichi Fukuzumi 4, rue BlaisePascal,67070 Strasbourg,France Department of Material and Life Sciences [email protected] Graduate School of Engineering Chapter 105 Osaka University Suita,Osaka 565-0871, Japan Steven R. Flom [email protected] Code 5613, Naval Research Laboratory Chapter 56 Washington, DC 20375-5338, USA [email protected] Philip A. Gale Chapter 121 Departmentof Chemistry University of Southampton Carlo Floriani Southampton, S017 1BJ, UK Institut de Chimie Minerale et Analytique, BCH [email protected] Universite de Lausanne Chapter 45 LausanneCH-l015, Switzerland Chapters24, 25 Andreas Gebauer Department of Chemistry Rita Floriani-Moro University of California at Berkeley Institut de Chimie Minerale et Analytique, BCH Berkeley, California 94720, USA Universite de Lausanne [email protected] LausanneCH-l015, Switzerland Chapters8, 9 Chapters24, 25 xvi Contributors to Volumes 1-20 Cecile Ged Chantal Goulon-Ginet Laboratoire de Pathologie EuropeanSynchrotron Radiation Facility Moleculaire etTherapie Genique F-38043 Grenoble, France;and INSERME0217 Faculte de Pharmacie, Universite de Grenoble I Universite V SegalenBordeaux 2 F-38700 LaTronche, France 146 rue LeoSaignat cgoulon@esrfJr 33076 Bordeaux cedex, France Chapter 49 [email protected] Harry B.Gray Chapter 87 Beckman Institute, MC 139-74 Abhik Ghosh California Institute of Technology Institute of Chemistry, Faculty of Science Pasadena,California 91125, USA University of Tr0mS0 [email protected] Trernse, Norway; Chapter 63 and SanDiego Supercomputer Center Bernhard Grimm University of California at SanDiego Institute of Biology/Plant Physiology LaJolla, California 92093-0505, USA Humboldt University [email protected] Unter den Linden 6 Chapter 47 D 10099 Berlin, Germany Avram Gold [email protected] Department of Environmental Science and Engineering Chapter 69 The University of North Carolina atChapel Hill JohnT. Groves Chapel Hill, North Carolina 27599-7400, USA Department of Chemistry [email protected] Princeton University Chapter 29 Princeton, NewJersey 08544-1009, USA Albert Gossauer [email protected] Department of Chemistry Chapter 27 University of Fribourg LenaGueletti Routedu Musee 9 Department of Chemistry CH-1700 Fribourg, Switzerland University of Houston [email protected] Houston, Texas77204-5003, USA Chapter 84 Chapter 59 Vincent Gotte RogerGuilard EuropeanSynchrotron Radiation Facility Laboratoire d'Ingenierie Moleculaire F-38043 Grenoble, France pour la Separation et lesApplications desGaz Chapter 49 LIMSAG (UMR 5633) Jose Goulon Universite de Bourgogne EuropeanSynchrotron Radiation Facility Faculte desSciences"Gabriel" F-38043 Grenoble, France 6, BdGabriel 21000 Dijon, France [email protected] [email protected] Chapter 49 Chapters 19, 21, 116
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