The Porphyrin Handbook. Chlorophylls and Bilins: Biosynthesis, Synthesis and Degradation

307 Pages·2003·52.133 MB·English

by  Karl Kadish, Kevin M. Smith and Roger Guilard (Eds.)

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 13 / Chlorophylls and Bilins:
Biosynthesis, Synthesis, 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
@
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First edition 2003
ISBN: 0-12-393220-3 (Set ofVolumes11-20)
0-12-393221-1 (Volume 11)
0-12-393222-X (Volume 12)
0-12-393223-8 (Volume 13)
0-12-393224-6 (Volume 14)
0-12-393225-4 (Volume 15)
0-12-393226-2 (Volume 16)
0-12-393227-0(Volume 17)
0-12-393228-9 (Volume 18)
0-12-393229-7 (Volume 19)
0-12-393230-0 (Volume 20)
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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 awarded the Oursequel, in ten more volumes (11-20), builds upon
1999Chemistryawardby the 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 "expand the work and fillin 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 BI2. 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-l) took place in Dijon, France (June 2000), well as the transformation ofhemes into bile pigments,
hosted by one of the three editors ofthe 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 of Porphyrins and Phthalocyanines (JPP) from spectroscopy ofphthalocyanines.
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 contracted authors provided us with chapters in a timely
of our field. Our new series ofHandbook 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 scientific enrichment ofthe porphyrin and their specific areas for another fifteen years.
phthalocyanine research areas. We sincerely hopethatourreaders willappreciatethis
However, even before publication of Volumes 1-10, new treatise as much as they liked our first venture. The
we were becoming aware of the great interest and tetrapyrrolefieldcontinuesto expandinto newareasand
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)isawonderful thing, 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
Department of 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 75
[email protected] Lucia Banci
Chapter77 CERMand Department of Chemistry
University of Florence
Karl E.Anderson
50019 SestoFiorentino (Florence), Italy
Departments of Preventive Medicine and
[email protected]
Community Health Internal Medicine
l
Chapter39
and Pharmacology and Toxicology
The University of TexasMedical Branch at Galveston Jean-Michel Barbe
Texas77555-1109, USA Laboratoire dlngenicric Moleculaire
[email protected] pour la Separation et lesApplications desGaz
Chapter 94 L1MSAG (UMR 5633)
Universite de Bourgogne
John Arnold
Faculte desSciences "Gabriel"
Department of Chemistry
6, BdGabriel 21000 Dijon, France
University of California, Berkeley
jean-michel.barbe@u-bourgogneJr
Berkeley, California 94720-1460, USA
Chapters 79 776
[email protected] 1
Chapter 77 Pierrette Battioni
Universite ReneDescartes
Laboratoire de Chimie et Biochimie
Pharmacologiques etToxicologiques UMR 8061
75270 Paris,France
[email protected]
Chapter26
xi
xii Contributors to Volumes 1-20
Carl E.Bauer Sylvia S.Bottomley
Department of Biology Department of Medicine
Indiana University University of Oklahoma College of Medicine and
Bloomington, Indiana 47405, USA Department of Veterans Affairs Medical Center
[email protected] Hematology-Oncology Section (111J)
Chapter 80 921 N.E.13th Street
Oklahoma City
Marc Benard
Oklahoma 73104-5007, USA
Laboratoire de Chimie Quantique UMR 7551
[email protected]
Universite Louis Pasteur
Chapter85
67000 Strasbourg, France
[email protected] Roman Boulatov
Chapter48 Department of Chemistry
Stanford University
EhudBen-Hur
Stanford, California 94305-5080, USA
Consultant in Photomedicine
[email protected]
160 West EndAvenue # 24P, New York, NY 10023, USA
Chapter62
[email protected]
Chapter 117 Marcel Bouvet
Laboratoire de Chimie Inorganique et Materiaux Moleculaires
JeanBernadou
CNRS- UMR7071
Laboratoire de Chimie de Coordination du CNRS
Universite Pierreet Marie Curie
31077 Toulouse, France
4, place lussieu, CaseCourrier 42
[email protected]
75252 Pariscedex OS,France
Chapter31
[email protected]
Ivano Bertini
Chapter 118
CERMand Department of Chemistry
JohannW. Buchler
University of Florence
Institutfur Anorganische Chemie
50019 SestoFiorentino (Florence), Italy
Darmstadt University of Technology
[email protected]
0-64287 Darmstadt, Germany
Chapter39
[email protected]
David W. Bollivar
[email protected]
Department of Biology
Chapter20
Illinois Wesleyan University
Henry J.Callot
P.O. Box 2900, Bloomington, Illinois 61702-2900, USA
Faculte de Chimie
[email protected]
Universite Louis Pasteur
Chapter 78
F-67000 Strasbourg, France
Arnaud Bondon
[email protected]
UMR 6509, Organornetallique et Catalyse,
Chapter 7
Chimie et Hectrochimie Moleculaires
Isabelle Chambrier
Universite de RennesI
Wolfson Materials & Catalysis Centre
35042 Rennes,France
School of Chemical Sciencesand Pharmacy
[email protected]
University of EastAnglia
Chapter 38
Norwich NR4 7TJ, UK
[email protected]
Chapter 108
Contributors to Volumes 1-20 xiii
Jean-ClaudeChambron Anne Corrigall
Laboratoire de Chimie Organo-Minerale Lennox EalesPorphyria Laboratories
Universite Louis Pasteur Department of Medicine
Institut LeBel University of Cape Town Medical School
67070 Strasbourg, France Observatory, South Africa 7925
[email protected] [email protected]
Chapter 40 Chapter 89
Wai-Shun Chan Timothy M. Cox
Progenitor Cell Therapy, L.L.C. Department of Medicine
Park80 West, Plaza II, Suite 200 University of Cambridge, Box 157
Saddle Brook, NewJersey07663, USA Addenbrooke's Hospital, Cambridge CB2 200, UK
[email protected] [email protected]
Chapter 117 Chapter 90
JenniferCheek
Claudia Crestini
School of Medicine
Dipartimento di Scienze eTecnologie Chimiche
University of South Carolina
Tor Vergata University
Columbia, South Carolina 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, Texas 77204-5003, USA
School of Chemical Sciences [email protected]
University of Illinois at Urbana-Champaign Chapter52
Urbana, Illinois 61801, USA
Harry A. Dailey
Chapter 41
Biomedical and Health Sciences Institute
Zoe Clyde-Watson
Department of Microbiology, and
University Chemical Laboratory Department of Biochemistry & Molecular Biology
Cambridge University A220 Life Sciences Building
Cambridge, CB2 1EW, UK University of Georgia
Chapter 15 Athens, Georgia 30602-7229, USA
James P.Collman [email protected]
Department of Chemistry Chapter72
Stanford University Tamara A. Dailey
Stanford, California 94305-5080, USA
Biomedical and Health Sciences Institute
[email protected]
Department of Microbiology, and
Chapter62
Department of Biochemistry & Molecular Biology
Michael J.Cook A220 Life Sciences Building
Wolfson Materials & Catalysis Centre University of Georgia
School of Chemical Sciences and Pharmacy Athens, Georgia 30602-7229, USA
University of EastAnglia [email protected]
Norwich NR4 7TJ, UK Chapter72
[email protected]
Chapter 108
xiv Contributors to Volumes 1-20
Scott L. Darling Jean-CharlesDeybach
University Chemical Laboratory Centre Francaisdes Porphyries, INSERMU409
Cambridge University 178 rue des Renouillers
Cambridge, CB2 1EW, UK 92701 Colombes Cedex, France;
Chapter 15 andFaculte de Medecine Xavier Bichat
Universite ParisVII
JohnDawson
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]
Chapter53 Danilo Dini
Institut fur Organische Chemie
Cerna de la Torre
UniversitatTUbingen
Departamento de Qufmica Organica
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
Felix W. M. de Rooij
Universita degli Studi di Roma "La Sapienza"
Department of Internal Medicine, Erasmus MC
P.IeAldo Moro 5, 1-00185Roma, Italy
University Medical Center Rotterdam
[email protected]
P.B.2040, 3000 CA Rotterdam
Chapter 112
The Netherlands
[email protected] Annie Edixhoven
Chapters 93, 95 Department of Internal Medicine, Erasmus MC
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]
Chapter37 C. H. Elder
Department of Medical Biochemistry
Hubert de Verneuil
University of Wales College of Medicine
Laboratoirede Pathologie
Heath Park,CardiffCF14 4XN, UK
Moleculaire etTherapie Genique, INSERME0217
[email protected]
Universite V Segalen Bordeaux 2
Chapter 88
146 rue LeoSaignat
33076 Bordeaux cedex, France Michael KlausEngel
[email protected] 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, NewJersey07974, 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 Studi di 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 Shields Avenue
Davis, California 95616, USA
Peter Erk
[email protected]
Performance Chemicals Research
Chapter83
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
Chapter80
Institut Ie Bel
Universite Louis Pasteurde Strasbourg Shunichi Fukuzumi
4, rue Blaise Pascal,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 ResearchLaboratory
Chapter56
Washington, DC 20375-5338, USA
[email protected] Philip A. Gale
Chapter 121 Department of Chemistry
University of Southampton
Carlo Floriani
Southampton, S017 1BJ, UK
Institut de Chimie Minerale et Analytique, BCH
[email protected]
Universite de Lausanne
Chapter45
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 Coulon-Cinet
Laboratoire de Pathologie European Synchrotron Radiation Facility
Moleculaire et Therapie Genique F-38043 Grenoble, France; and
INSERME0217 Faculte de Pharmacie, Universite de Grenoble I
Universite V Segalen Bordeaux 2 F-38700 LaTronche, France
146 rue Leo Saignat [email protected]
33076 Bordeaux cedex, France Chapter49
[email protected]
Harry B.Cray
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]
Trornso, Norway; Chapter 63
andSanDiego 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
Chapter47
D 10099 Berlin, Germany
Avram Cold [email protected]
Department of Environmental Science and Engineering Chapter69
The University of North Carolina atChapel Hill
John T. Groves
Chapel Hill, North Carolina 27599-7400, USA
Department of Chemistry
[email protected]
Princeton University
Chapter29
Princeton, NewJersey08544-1009, USA
Albert Cossauer [email protected]
Department of Chemistry Chapter27
University of Fribourg
LenaGueletti
Route du Musee 9
Department of Chemistry
CH-1700 Fribourg, Switzerland
University of Houston
[email protected]
Houston, Texas 77204-5003, USA
Chapter84
Chapter59
Vincent Cotte
RogerGuilard
European Synchrotron Radiation Facility
Laboratoire d'lngenierie Moleculaire
F-38043 Grenoble, France
pour la Separation et lesApplications desGaz
Chapter49
LIMSAG (UMR 5633)
Jose Coulon Universite de Bourgogne
European Synchrotron Radiation Facility Faculte desSciences"Gabriel"
F-38043 Grenoble, France 6, BdGabriel 21000 Dijon, France
[email protected] [email protected]
Chapter49 Chapters 19, 21, 116