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Bioinorganic Chemistry: Inorganic Elements in the Chemistry of Life an Introduction and Guide WOLFGANG KAIM BRIGITTE SCHWEDERSKI AXEL KLEIN SECOND EDITION BIOINORGANIC CHEMISTRY: INORGANIC ELEMENTS IN THE CHEMISTRY OF LIFE AN INTRODUCTION AND GUIDE INORGANIC CHEMISTRY A WILEY TEXTBOOK SERIES Bioinorganic Chemistry: Inorganic Elements in the Chemistry of Life Inorganic Chemistry A Wiley Series of Advanced Textbooks ISSN: 1939-5175 Editorial Board David Atwood, University of Kentucky, USA Bob Crabtree, Yale University, USA Gerd Meyer, University of Cologne, Germany Derek Woollins, University of St. Andrews, UK Previously Published Books in this Series Structural Methods in Molecular Inorganic Chemistry David W. H. Rankin, Norbert W. Mitzel & Carole A. Morrison; ISBN: 978-0-470-97278-6 Introduction to Coordination Chemistry Geoffrey Alan Lawrance; ISBN: 978-0-470-51931-8 Chirality in Transition Metal Chemistry Hani Amouri & Michel Gruselle; ISBN: 978-0-470-06054-4 Bioinorganic Vanadium Chemistry Dieter Rehder; ISBN: 978-0-470-06516-7 Inorganic Structural Chemistry 2nd Edition Ulrich Muller;¨ ISBN: 978-0-470-01865-1 Lanthanide and Actinide Chemistry Simon Cotton; ISBN: 978-0-470-01006-8 Mass Spectrometry of Inorganic and Organometallic Compounds: Tools-Techniques-Tips William Henderson & J. Scott McIndoe; ISBN: 978-0-470-85016-9 Main Group Chemistry, Second Edition A.G. Massey; ISBN: 978-0-471-19039-5 Synthesis of Organometallic Compounds: A Practical Guide Sanshiro Komiya; ISBN: 978-0-471-97195-5 Chemical Bonds: A Dialog Jeremy Burdett; ISBN: 978-0-471-97130-6 The Molecular Chemistry of the Transition Elements: An Introductory Course Francois Mathey & Alain Sevin; ISBN: 978-0-471-95687-7 Stereochemistry of Coordination Compounds Alexander von Zelewsky; ISBN: 978-0-471-95599-3 For more information on this series see: www.wiley.com/go/inorganic Bioinorganic Chemistry: Inorganic Elements in the Chemistry of Life An Introduction and Guide Second Edition Written and Translated by Wolfgang Kaim University of Stuttgart, Institute of Inorganic Chemistry, Stuttgart, Germany Brigitte Schwederski University of Stuttgart, Institute of Inorganic Chemistry, Stuttgart, Germany Axel Klein University of Cologne, Institute of Inorganic Chemistry, Cologne, Germany Originally published in the German language by Vieweg+Teubner, 65189 Wiesbaden, Germany, as “Wolfgang Kaim and Brigitte Schwederski: Bioanorganische Chemie. 4. Auflage (4th Edition)”. © Vieweg+Teubner/Springer Fachmedien Wiesbaden GmbH 2005. Springer Fachmedien is part of Springer Science+Business Media This edition first published 2013 © 2013 John Wiley & Sons, Ltd First English language edition published 1994 Registered office John Wiley & Sons Ltd, The Atrium, Southern Gate, Chichester, West Sussex, PO19 8SQ, United Kingdom For details of our global editorial offices, for customer services and for information about how to apply for permission to reuse the copyright materialin this book please see our website at www.wiley.com. The right of the author to be identified as the author of this work has been asserted in accordance with the Copyright, Designs and Patents Act 1988. All rights reserved. No part of this publication may be reproduced, stored in a retrieval system, or transmitted, in any form or by any means, electronic, mechanical, photocopying, recording or otherwise, except as permitted by the UK Copyright, Designs and Patents Act 1988, without the prior permission of the publisher. Wiley also publishes its books in a variety of electronic formats. Some content that appears in print may not be available in electronic books. Designations used by companies to distinguish their products are often claimed as trademarks. All brand names and product names used in this book are trade names, service marks, trademarks or registered trademarks of their respective owners. The publisher is not associated with any product or vendor mentioned in this book. Limit of Liability/Disclaimer of Warranty: While the publisher and author have used their best efforts in preparing this book, they make no representations or warranties with respect to the accuracy or completeness of the contents of this book and specifically disclaim any implied warranties of merchantability or fitness for a particular purpose. It is sold on the understanding that the publisher is not engaged in rendering professional services and neither the publisher nor the author shall be liable for damages arising herefrom. If professional advice or other expert assistance is required, the services of a competent professional should be sought The advice and strategies contained herein may not be suitable for every situation. In view of ongoing research, equipment modifications, changes in governmental regulations, and the constant flow of information relating to the use of experimental reagents, equipment, and devices, the reader is urged to review and evaluate the information provided in the package insert or instructions for each chemical, piece of equipment, reagent, or device for, among other things, any changes in the instructions or indication of usage and for added warnings and precautions. The fact that an organization or Website is referred to in this work as a citation and/or a potential source of further information does not mean that the author or the publisher endorses the information the organization or Website may provide or recommendations it may make. Further, readers should be aware that Internet Websites listed in this work may have changed or disappeared between when this work was written and when it is read. No warranty may be created or extended by any promotional statements for this work. Neither the publisher nor the author shall be liable for any damages arising herefrom. Library of Congress Cataloging-in-Publication Data Kaim, Wolfgang, 1951– [Bioanorganische Chemie. English] Bioinorganic chemistry : inorganic elements in the chemistry of life : an introduction and guide / written and translated by Wolfgang Kaim, Brigitte Schwederski, Axel Klein. – Second edition. pages cm Translation of: Bioanorganische Chemie. Includes bibliographical references and index. ISBN 978-0-470-97524-4 (cloth) – ISBN 978-0-470-97523-7 (paper) 1. Bioinorganic chemistry. I. Schwederski, Brigitte, 1959– II. Klein, Axel, 1964– III. Title. QP531.K3513 2013 572.51–dc23 2013011894 A catalogue record for this book is available from the British Library. HB ISBN: 9780470975244 PB ISBN: 9780470975237 Typeset in 10/12pt Times by Aptara Inc., New Delhi, India 1 2013 Contents Preface to the Second Edition ................................. xi Preface to the First Edition .................................. xiii 1 Historical Background, Current Relevance and Perspectives ............... 1 References ..................................... 6 2 Some General Principles ................................. 7 2.1 Occurrence and Availability of Inorganic Elements in Organisms ........... 7 Insertion: The Chelate Effect ............................ 14 Insertion: “Hard” and “Soft” Coordination Centers .................. 14 2.2 Biological Functions of Inorganic Elements ..................... 14 2.3 Biological Ligands for Metal Ions .......................... 16 2.3.1 Coordination by Proteins-Comments on Enzymatic Catalysis ........ 17 Insertion: The “Entatic State” in Enzymatic Catalysis ................ 20 2.3.2 Tetrapyrrole Ligands and Other Macrocycles ................ 22 Insertion: Electron Spin States in Transition Metal Ions ................ 28 2.3.3 Nucleobases, Nucleotides and Nucleic Acids (RNA, DNA) as Ligands .... 31 Insertion: Secondary Bonding ............................ 32 2.4 Relevance of Model Compounds .......................... 34 References ..................................... 34 3 Cobalamins, Including Vitamin and Coenzyme B12 ................... 37 3.1 History and Structural Characterization ....................... 37 Insertion: Bioorganometallics I ........................... 38 3.2 General Reactions of Alkylcobalamins ....................... 41 3.2.1 One-electron Reduction and Oxidation ................... 41 3.2.2 Co–C Bond Cleavage ........................... 42 Insertion: Electron Paramagnetic Resonance I .................... 43 3.3 Enzyme Functions of Cobalamins .......................... 45 3.3.1 Adenosylcobalamin (AdoCbl)-dependent Isomerases ............ 45 Insertion: Organic Redox Coenzymes ........................ 48 3.3.2 Alkylation Reactions of Methylcobalamin (MeCbl)-dependent Alkyl Transferases ................................ 51 3.4 Model Systems and the Enzymatic Activation of the Co–C Bond ........... 52 References ..................................... 53 4 Metals at the Center of Photosynthesis: Magnesium and Manganese ........... 57 4.1 Volume and Efficiency of Photosynthesis ...................... 57 4.2 Primary Processes in Photosynthesis ......................... 59 vi Contents 4.2.1 Light Absorption (Energy Acquisition) ................... 59 4.2.2 Exciton Transport (Directed Energy Transfer) ................ 59 4.2.3 Charge Separation and Electron Transport .................. 62 Insertion: Structure Determination by X-ray Diffraction ............... 65 4.3 Manganese-catalyzed Oxidation of Water to O2 ................... 67 Insertion: Spin–Spin Coupling ........................... 73 References ..................................... 74 5 The Dioxygen Molecule, O2: Uptake, Transport and Storage of an Inorganic Natural Product ..................................... 77 5.1 Molecular and Chemical Properties of Dioxygen, O2 ................. 77 5.2 Oxygen Transport and Storage through Hemoglobin and Myoglobin ........
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