The Biosynthesis of Secondary Metabolites
This is a book about experiments and results of experiments. The results described are the fruit of thirty years' labour in the field of secondary metabolism. Secondary metabolism, more than any other part of the chemistry of life, has been the special pr
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THE BIOSYNTHESIS OF SECONDARY METABOLITES
R. B. Herbert
Department of Organic Chemistry University of Leeds
LONDON NEW YORK
CHAPMAN AND HALL
First published 1981 by Chapman and Hall Ltd 11 New Fetter Lane, London EC4P 4EE Published in the USA by Chapman and Hall in association with Methuen, Inc. 733 Third Avenue, New York, NY 10017 © 1981 R. B. Herbert So/tcover reprint o/the hardcover 1st edition 1981
This title is available in both hardbound and paperback editions. The paperback edition is sold subject to the condition that it shall not, by way of trade or otherwise, be lent, re-sold, hired out, or otherwise circulated without the publisher's prior consent in any form of binding or cover other than that in which it is published and without a similar condition including this condition being imposed on the subsequent purchaser. All rights reserved. No part of this book may be reprinted, or reproduced or utilized in any form or by any electronic, mechanical or other means, now known or hereafter invented, including photocopying and recording, or in any information storage and retrieval system, without permission in writing from the Publisher.
British Library Cataloguing in Publication Data Herbert, R. B. The biosynthesis of secondary metabolites. 1. Metabolism, Secondary 2. Biosynthesis 3. Natural products I. Title 574.19'29 QH521 80-41868 ISBN-13: 978-94-009-5835-7 e-ISBN-13: 978-94-009-5833-3 DOl: 10.lO07/978-94-009-5833-3
Contents
Preface
1 1.1
1.2
l.3
IX
Introduction 1 1 Primary and secondary metabolism 1 1.1.1 Introduction 1.1.2 Fatty acid biosynthesis 2 1.1.3 The biosynthesis of polyacetylenes and prostaglandins 4 Stereochemistry and biosynthesis 5 5 1.2.1 Chirality and prochirality 1.2.2 Chiral methyl groups 7 1.2.3 Hydroxylation at saturated carbon atoms 9 Some reactions of general importance in secondary metabolism 10 1.3.1 Oxidative coupling of phenols 10 1.3.2 Hydroxylation of aromatic substrates 11 1.3.3 Methylation 12
Techniques for biosynthesis Introduction Isotopic labelling 2.2.1 Radioactive isotopes 2.2.2 Stable isotopes 2.3 Enzymes and mutants
15 15 17 18 20 25
3
28 28 30 30 31 34 38 39 40 41
2
2.1 2.2
3.1 3.2 3.3 3.4 3.5 3.6 3.7
Polyketides Introduction Formation of poly-fJ-keto-acyl-CoA's 3.2.1 Acetate and malonate 3.2.2 Assembly of poly-fJ-keto-acyl-CoA's Tetraketides Pen take tides Hexaketides Heptaketides Octaketides v
VI
CONTENTS
3.8 Nona- and deca-ketides 3.9 Polyketides with mixed origins
42 44
4 4.1 4.2 4.3 4.4 4.5 4.6 4.7 4.8 4.9
Terpenes and steroids Introduction Steroids Pentacyclic triterpenes Squalene Monoterpenes Sesq ui terpenes Diterpenes Sesterpenes Carotenoids and vitamin A
50 50 52 58 60 62 63 70 72 72
5
The shikimic acid pathway Introduction Quinones Coumarins Flavonoids
80 80 84 89 89
5.1 5.2 5.3 5.4
Alkaloids 6 6.1 Introduction 6.2 Piperidine and pyrrolidine alkaloids 6.2.1 Piperidine alkaloids 6.2.2 Pyrrolidine alkaloids 6.3 Isoquinoline and related alkaloids 6.3.1 Phenethylamines and simple isoquinolines 6.3.2 Aporphines 6.3.3 Erythrina
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