Topics in Current Chemistry
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1 209 Topics in Current Chemistry Editorial Board: A. de Meijere K.N. Houk. H. Kessler J.-M. Lehn. S.V. Ley. S.L. Schreiber J. Thiem B. M. Trost F. V6gtle H. Yamamoto
2 Springer Berlin Heidelberg New York Barcelona Hong Kong London Milan Paris Singapore Tokyo
3 Biosynthesis Aromatic Polyketides, Isoprenoids, Alkaloids Volume Editors: Finian J. Leeper, John C. Vederas With contributions by R. Croteau, E.M. Davis, T. Hartmann, T. Hemscheidt, D. Ober, ]. E Sanz-Cervera, B. Shen, E. M. Stocking, R. M. Williams ~ Springer
4 The series Topics in Current Chemistry presents critical reviews of the present and future trends in modern chemical research. The scope of coverage includes all areas of chemical science including the interfaces with related disciplines such as biology, medicine and materials science. The goal of each thematic volume is to give the nonspecialist reader, whether at the university or in industry, a comprehensive overview of an area where new insights are emerging that are of interest to a larger scientific audience. As a rule, contributions are specially commissioned. The editors and publishers will, however, always be pleased to receive suggestions and supplementary information. Papers are accepted for Topics in Current Chemistry in English. In references Topics in Current Chemistry is abbreviated Top. Curr. Chem. and is cited as a journal. Springer WWW home page: Visit the TCC home page at or ISSN ISBN Springer-Verlag Berlin Heidelberg New York Library of Congress Catalog Card Number This work is subject to copyright. All rights are reserved, whether the whole or part of the material is concerned, specifically the rights of translation, reprinting reuse of illustrations, recitation, broadcasting, reproduction on microfilm or in any other ways, and storage in data banks. Duplication of this publication or parts thereof is only permitted under the provisions of the German Copyright Law of September 9,1965, in its current version, and permission for use must always be obtained from Springer- Verlag.Violations are liable for prosecution under the German Copyright Law. Springer-Verlag is a company in the BertelsmannSpringer publishing group Springer-Verlag Berlin Heidelberg 2000 Printed in Germany The use of general descriptive names, registered names, trademarks, etc. in this publication does not imply, even in the absence of a specific statement, that such names are exempt from the relevant protective laws and regulations and therefore free for general use. Cover design: Friedhelm Steinen-Broo, Barcelona; MEDIO, Berlin Typesetting: Fotosatz-Service K6hler GmbH, Wiirzburg SPIN: /3020 ra Printed on acid-free paper
5 Volume Editor Dr. Finian J. Leeper Department of Chemistry University of Cambridge Lensfield Road Cambridge CB2 1EW, Great Britain E-maih Prof. Dr. John C. Vederas Department of Chemistry University of Alberta Edmonton, Alberta Canada T6G 2G2 E-maih john. ca Editorial Board Prof. Dr. Armin de Meijere Institut ffir Organische Chemie der Georg-August-Universit/it Tammannstrat]e G6ttingen, Germany E-maih Prof. Dr. Horst Kessler Institnt ffir Organische Chemie TU MiJnchen Lichtenbergstrat~e Garching, Germany E-maih kessler@ch.tum.de Prof. Steven V. Ley University Chemical Laboratory Lensfield Road Cambridge CB2 1EW, Great Britain E-maih svll OOO@cus.cam.ac.uk Prof. Dr. Joachim Thiem Institut ffir Organische Chemie Universit~it Hamburg Martin-Luther-King-Platz Hamburg, Germany E-maih thiem@chemie.uni-hamburg.de Prof. Dr. Fritz V6gtle Kekul4-Institut ftir Organische Chemie und Biochemie der Universit~it Bonn Gerhard-Domagk-Strat~e Bonn, Germany E-maih voegtle@uni-bonn.de Prof. Kendall N. Houk Department of Chemistry and Biochemistry University of California 405 Higard Avenue Los Angeles, CA , USA houk@chem, ucla.edu Prof. Jean-Marie Lehn Institut de Chimie Universit~ de Strasbourg 1 rue Blaise Pascal, B.P.Z 296/R Strasbourg Cedex, France E-maih lehn@chimie.u-strasbg.fr Prof. Stuart L. Schreiber Chemical Laboratories Harvard University 12 Oxford Street Cambridge, MA , USA E-maih sls@slsiris.harvard.edu Prof. Barry M. Trost Department of Chemistry Stanford University Stanford, CA , USA E-maih bmtrost@leland.stanford.edu Prof. Hisashi Yamamoto School of Engineering Nagoya University Chikusa, Nagoya , Japan E-maih j45988a@nucc.cc.nagoya-u.ac.jp
6 - Editorial Topics in Current Chemistry Now Also Available Electronically For all customers with a standing order for Topics in Current Chemistry we offer the electronic form via LINK free of charge. Please contact your librarian who can receive a password for free access to the full articles by registration at: If you do not have a standing order you can nevertheless browse through the table of contents of the volumes and the abstracts of each article at: There you will also find information about the Board - Aims and Scope - Instructions for Authors
7 Preface The present book is the second of two volumes that provide state of the art expert reviews of central topics in modern natural products chemistry and secondary metabolism. Using specific examples, the previous volume emphasized two revolutions in experimental techniques that completely transformed the field of natural products chemistry from what it was in the 1950s. These were the use of stable isotopes in conjunction with modern NMR and mass spectrometry, and more recently, the development of molecular biological techniques to identify, purify and manipulate the enzymes responsible for the intricate series of steps to complex natural compounds. The previous volume specifically covered the use of isotopes in biosynthetic research and the formation of enzyme cofactors, vitamin B12 and reduced polyketides. This second volume describes the application of the same approaches (isotope methodology and molecular biology) to the biosynthesis of aromatic (unreduced) polyketides, enzymes responsible for cyclization of terpenoids (isoprenoids), and biochemical generation of selected classes of alkaloids (prenylated tryptophan, tropane, pyrrolizidine). The knowledge of the metabolic pathways and the techniques to elucidate them opens the door to combinatorial biosynthesis as well as to the production of targeted pharmaceutical agents utilizing a combination of chemistry, molecular biology and protein biochemistry. Recent advances suggest that it may soon be possible to rationally manipulate biochemical pathways to produce any target molecule, including non-natural variants, in substantial quantity. Genetically modified organisms containing mix-and-match combinations of biosynthetic enzymes (natural and/or mutated) will allow formation of large numbers of new compounds for biological evaluation. In addition, the availability of vast arrays of specialized enzymes in pure form may provide new reagents for combinatorial chemistry and parallel synthesis in drug discovery programs. In the current volume, Ben Shen begins with a review of the assembly of unreduced polyketides leading to aromatic compounds. The current understanding of the functions and interactions of the enzymes involved is gradually providing the rules for designing new compounds of this class as well as affording a basis for biosynthesis of flavonoids via chalcone synthases. In chapter 2, Edward Davis and Rodney Croteau describe the terpenoid synthases responsible for formation of the huge array of mono-, sesqui- and diterpenes (over 30,000 terpene derivatives are known). In particular, detailed structural and functional evaluation of four representative terpene synthases is provided. In the third
8 VIII Preface chapter, Robert Williams, Emily Stocking and Juan Sanz-Cervera review the biosynthesis of prenylated indole alkaloids and related substances derived from tryptophan. Many of these compounds are potent mycotoxins that contaminate food, but some, such as the ergot alkaloids (e.g. ergotamine, ergonovine) see extensive application in medicine. In chapter 4 Thomas Hemscheidt describes the current state of knowledge on the biosynthesis of tropane and related alkaloids, including cocaine. This well illustrates the difficulties that can be faced in elucidating the sequence of reactions involved in a biosynthetic pathway, especially when the intermediates are unstable and produced in very low amounts. The last chapter, by Thomas Hartmann covers the pyrrolizidine alkaloids. It not only describes the chemistry of the biosynthetic pathway but also gives an account of the physiology and ecology involved in the distribution and elaboration of the alkaloids within the producing plant, in the insects which eat the plants, and even in the animals which eat the insects. This shows us that for many natural products an understanding of how they are made is only a part of the whole story. Cambridge, January 2000 Finian J. Leeper John C. Vederas
9 Contents Biosynthesis of Aromatic Polyketides B. Shen... Cyclization Enzymes in the Biosynthesis of Monoterpenes, Sesquiterpenes, and Diterpenes E. M. Davis, R. Croteau... Biosynthesis of Prenylated Alkaloids Derived from Tryptophan R. M. Williams, E. M. Stocking, J. F. Sanz-Cervera... Tropane and Related Alkaloids T. Hemscheidt... Biosynthesis and Metabolism of Pyrrolizidine Alkaloids in Plants and Specialized Insect Herbivores T. Hartmann, D. Ober... Author Index Volumes
10 Contents of Volume 195 Biosynthesis - Polyketides and Vitamins Volume Editors: Finian J. Leeper, John C. Vederas ISBN Application of Isotopic Methods to Secondary Metabolic Pathways T.J. Simpson The Biosynthesis of Aliphatic Polyketides J. Staunton, B. Wilkinson Cofactor Biosynthesis: A Mechanistic Perspective T. P. Begley, C. Kinsland, S. Taylor, M. Tandon, R. Nicewonger, M. Wu, H.-J. Chiu, N. Kelleher, N. Campobasso, Y. Zhang Biosynthesis of Vitamin B:2 A.R. Battersby, E J. Leeper
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