Amino Acids, Peptides And Proteins In Organic Chemistry 3: Building Blocks, Catalysis And Coupling Chemistry (amino Acids, Peptides And Proteins In Organic Chemistry (vch))

Edited by Andrew B. Hughes Amino Acids, Peptides and Proteins in Organic Chemistry Further Reading Drauz, K., Gröger, H., May, O. (eds.) Lutz, S., Bornscheuer, U. T. (eds.) Enzyme Catalysis in Organic Synthesis Protein Engineering Handbook Third completely revised and enlarged edition 2009 2 Volume Set ISBN: 978-3-527-31850-6 3 Volumes 2011 ISBN: 978-3-527-32547-4 Fessner, W.-D., Anthonsen, T. Modern Biocatalysis Stereoselective and Environmentally Friendly Reactions 2009 ISBN: 978-3-527-32071-4 Sewald, N., Jakubke, H.-D. Peptides: Chemistry and Biology 2009 ISBN: 978-3-527-31867-4 Jakubke, H.-D., Sewald, N. Peptides from A to Z A Concise Encyclopedia Pignataro, B. (ed.) Ideas in Chemistry and Molecular Sciences 2008 ISBN: 978-3-527-31722-6 Royer, J. (ed.) Advances in Synthetic Chemistry 2010 ISBN: 978-3-527-32539-9 Asymmetric Synthesis of Nitrogen Heterocycles 2009 Reek, J. N. H., Otto, S. ISBN: 978-3-527-32036-3 Dynamic Combinatorial Chemistry Hecht, S., Huc, I. (eds.) 2010 Foldamers ISBN: 978-3-527-32122-3 Structure, Properties, and Applications 2007 ISBN: 978-3-527-31563-5 Edited by Andrew B. Hughes Amino Acids, Peptides and Proteins in Organic Chemistry Volume 3 - Building Blocks, Catalysis and Coupling Chemistry The Editor Andrew B. Hughes La Trobe University Department of Chemistry Victoria 3086 Australia All books published by Wiley-VCH are carefully produced. Nevertheless, authors, editors, and publisher do not warrant the information contained in these books, including this book, to be free of errors. Readers are advised to keep in mind that statements, data, illustrations, procedural details or other items may inadvertently be inaccurate. Library of Congress Card No.: applied for British Library Cataloguing-in-Publication Data A catalogue record for this book is available from the British Library. Bibliographic information published by the Deutsche Nationalbibliothek The Deutsche Nationalbibliothek lists this publication in the Deutsche Nationalbibliografie; detailed bibliographic data are available on the Internet at http://dnb.d-nb.de. # 2011 WILEY-VCH Verlag & Co. KGaA, Boschstr. 12, 69469 Weinheim, Germany All rights reserved (including those of translation into other languages). No part of this book may be reproduced in any form – by photoprinting, microfilm, or any other means – nor transmitted or translated into a machine language without written permission from the publishers. Registered names, trademarks, etc. used in this book, even when not specifically marked as such, are not to be considered unprotected by law. Composition Thomson Digital, Noida, India Printing and Bookbinding betz-druck GmbH, Darmstadt Cover Design Schulz Grafik Design, Fußgönheim Printed in the Federal Republic of Germany Printed on acid-free paper ISBN: 978-3-527-32102-5 V Contents List of Contributors XVII Part One Amino Acids as Building Blocks 1 1.1 1.2 1.2.1 1.3 1.3.1 1.3.2 1.3.3 1.4 1.4.1 1.4.2 1.4.3 1.4.3.1 1.4.3.2 1.4.3.3 1.5 1.5.1 1 Amino Acid Biosynthesis 3 Emily J. Parker and Andrew J. Pratt Introduction 3 Glutamate and Glutamine: Gateways to Amino Acid Biosynthesis 5 Case Study: GOGAT: GATs and Multifunctional Enzymes in Amino Acid Biosynthesis 6 Other Amino Acids from Ubiquitous Metabolites: Pyridoxal Phosphate-Dependent Routes to Aspartate, Alanine, and Glycine 8 Pyridoxal Phosphate: A Critical Cofactor of Amino Acid Metabolism 8 Case Study: Dual Substrate Specificity of Families of Aminotransferase Enzymes 10 PLP and the Biosynthesis of Alanine and Glycine 15 Routes to Functionalized Three-Carbon Amino Acids: Serine,