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These Proceedings of the 1st International Peptide Symposium, held in Kyoto, Japan, in December 1997, represent a high point of international cooperation in the field of peptide science. Recently, science and technology in this area have advanced considerably, allowing traditional peptide chemists to expand into areas of peptide science encompassing physics, biology and medicine. Furthermore, improvements in procedures for chemical and bio-syntheses, purification, analysis and related areas, have removed barriers with respect to the size of molecules. These Proceedings include plenary lectures and oral and poster presentations collected from a wide diversity of topics providing a truly comprehensive and up-to-date overview of the field of peptide science. This publication contains essential reference information for researchers active in peptide science.
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PEPTIDE
SCIENCE – PRESENT AND FUTURE
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PEPTIDE SCIENCE – PRESENT AND FUTURE Proceedings of the 1st International Peptide Symposium
Edited by
YASUTSUGU SHIMONISHI Osaka University, Japan
KLUWER ACADEMIC PUBLISHERS N E W Y O R K , B O S T O N , D O R D R E C H T, LONDON , MOSCOW
eBook ISBN
0-306-46864-6
Print ISBN
0-792-35271-8
©2002 Kluwer Academic Publishers New York, Boston, Dordrecht, London, Moscow
All rights reserved
No part of this eBook may be reproduced or transmitted in any form or by any means, electronic, mechanical, recording, or otherwise, without written consent from the Publisher
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Contents
xxxv
Preface First International Peptide Symposium
xxxvii
Acknowledgements
xxxix
Abbreviations
xli
Plenary lectures 1.
2.
From big molecules to smaller ones J.A. Wells, B.C. Cunningham, A. Braisted, S. Atwell, W. DeLano, M. Ultsch, M.A. Starovasnik and A.M. de Vos
1
Directions for solving the remaining problems in the synthesis of large peptides S. Sakakibara
6
General lectures 3. 4.
Peptide science: past, present and future D. Brandenburg
15
Quo vadis? Where is peptide chemistry headed? T. Shiba
21
Session A: Peptide mimetics and de novo design 5.
6.
7.
8.
Designing peptidomimetic antagonists for peptide receptors: topochemical differences of agonists and antagonists V.J. Hruby, S. Liao, G. Han, G. Bonner, M. Shenderovich, J. Slaninova, F. Porreca, H.I. Yamamura and M.E. Hadley
26
Self-assembling homopolymeric peptide tapes in aqueous solution A. Aggeli, M. Bell, A. Strong, S. Radford and N. Boden
30
Peptides containing nonnatural amino acids with functional side groups M. Sisido
34
Active carbonates of N-protected amino alcohols for synthesis of carbamate pseudopeptides J.B. Halstrøm
39
v
vi 9.
10.
11.
12.
13.
14.
15.
16.
17.
18.
Contents Convenient one-pot synthesis of cystine-containing peptides from protected peptidyl resins and its application to the synthesis of bifunctional anti-HIV compounds H. Tamamura, T. Ishihara, H. Oyake, A. Otaka and N. Fujii
41
Stereoselective synthesis of two type (E)-alkene dipeptide isosteres from a single substrate of β -aziridinyl- α,β -enoate H. Tamamura, M. Yamashita, H. Muramatsu, T. Ibuka, A. Otaka and N. Fujii
44
Design and synthesis of conformationally constrained dipeptide containin