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THE PEPTIDES Analysis, Synthesis, Biology Treatise Editors S. UDENFRIEND AND J. MEIENHOFER Volume 1 Major Methods of Peptide Bond Formation Volume 2 Special Methods in Peptide Synthesis, Part A Volume 3 Protection of Functional Groups in Peptide Synthesis Volume 4 Modern Techniques of Conformational, Structural, and Configurational Analysis Volume 5 Special Methods in Peptide Synthesis, Part B Volume 6 Opioid Peptides: Biology, Chemistry, and Genetics The Peptides Analysis, Synthesis, Biology VOLUME 6 Opioid Peptides: Biology, Chemistry, and Genetics Edited by SIDNEY UDENFRIEND Roche Institute Of Molecular Biology Nutley, New Jersey JOHANNES MEIENHOFER Hoffmann-La Roche Inc. Nutley, New Jersey 1984 ACADEMIC PRESS, INC. (Harcourt Brace Jovanovich, Publishers) Orlando San Diego New York London Toronto Montreal Sydney Tokyo COPYRIGHT © 1984, BY ACADEMIC PRESS, INC. ALL RIGHTS RESERVED. NO PART OF THIS PUBLICATION MAY BE REPRODUCED OR TRANSMITTED IN ANY FORM OR BY ANY MEANS, ELECTRONIC OR MECHANICAL, INCLUDING PHOTOCOPY, RECORDING, OR ANY INFORMATION STORAGE AND RETRIEVAL SYSTEM, WITHOUT PERMISSION IN WRITING FROM THE PUBLISHER. ACADEMIC PRESS, INC. Orlando, Florida 3 2 8 8 7 United Kingdom Edition published by ACADEMIC PRESS, INC. (LONDON) LTD. 24/28 Oval Road, London NW1 7DX Library of Congress Cataloging in Publication Data Main entry under title: The Peptides : analysis, synthesis, biology· Vol. edited by Sidney Udenfriend, Johannes Meienhofer. Includes bibliographies and indexes. Contents: v. 1. Major methods of peptide bond formation.--v. 2. Special methods in peptide synthesis, part A. --[etc.]—v. 6. Physical methods in peptide conformational studies. 1. Peptides. I. Gross, Erhard. II. Meienhofer, Johannes. III. Title. [DNLM: 1. Peptides. QU68 P424] QP552.P4P47 574. Γ 92456 78-31958 ISBN 0-12-304206-2 (v. 6) PRINTED IN THE UNITED STATES OF AMERICA 84 85 86 87 9 8 7 6 5 4 3 2 1 Contributors Numbers in parentheses indicate the pages on which the author's contributions begin. G.M. Besser (323), Department of Endocrinology, St. Bartholomew's Hospital, London EC1A 7BE, United Kingdom Olivier Civelli (69), Department of Chemistry, University of Oregon, Eugene, Oregon 97403 Vicky Clement-Jones (323), Department of Endocrinology, St. Bartholomew's Hospital, London EC1A 7BE, United Kingdom James Douglass (69), Department of Chemistry, University of Oregon, Eugene, Oregon 97403 Avram Goldstein (95), Addiction Research Foundation and Stanford University, Palo Alto, California 94304 Philip E. Hansen (269), Sterling-Winthrop Research Institute, Rensselaer, New York 12144 Edward Herbert (69), Department of Chemistry, University of Oregon, Eugene, Oregon 97403 Daniel L. Kilpatrick (25), Roche Institute of Molecular Biology, Roche Research Center, Nutley, New Jersey 07110 Hans W. Kosterlitz (147), Unit for Research on Addictive Drugs, University of Aberdeen, Marischal College, Aberdeen AB9 IAS, Scotland, United Kingdom Choh Hao Li (191), Laboratory of Molecular Endocrinology, University of California, San Francisco, San Francisco, California 94143 Barry A. Morgan (269), Sterling-Winthrop Research Institute, Rensselaer, New York 12144 Shosaku Numa (1), Department of Medical Chemistry, Kyoto University Faculty of Medicine, Kyoto 606, Japan Stewart J. Paterson (147), Unit for Research on Addictive Drugs, University of Aberdeen, Marischal College, Aberdeen AB9 IAS, Scotland, United Kingdom IX X Contributors Linda E. Robson (147), Unit for Research on Addictive Drugs, University of Aberdeen, Marischal College, Aberdeen AB9 IAS, Scotland, United Kingdom Peter W. Schiller (219), Laboratory of Chemical Biology and Peptide Research, Clinical Research Institute of Montreal, Montreal, Quebec H2W 1R7, Canada Si