Synthesis of the Tripeptide l -Trp-l -Ser-l -Glu Comparison of its b
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Synthesis of the tripeptide L-Trp-L-Ser-L-Glu Comparison of its biological activity with that of the Delta-Sleep-Inducing-Peptide (DSIP)
Vincent M. Monnier Dr. med. and Dip!. Chem.
1977
Springer Basel AG
CIP-Kurztitelaufnahme der Deutschen Bibliothek Monnier, Vincent M. Synthesis of the tripeptide L-Trp-L-Ser-L-Glu: comparison of its biolog. activity with that of the Delta-Sleep-Inducing-Peptide (DSIP). - l. Aufl. (Experientia: Suppl.; 29) ISBN 978-3-7643-0915-2 ISBN 978-3-0348-5577-8 (eBook) DOI 10.1007/978-3-0348-5577-8
All rights reserved No part of this book may be reproduced in any form, by photostat, microfilm, or any other means, without written permission from the publishers. © Springer Basel AG 1977
Originally published by Birkhauser Verlag Basel in 1977 ISBN 978-3-7643-0915-2
Table of contents
I II III
IV V
Abbreviations . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . Introduction... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . Schema of synthesis . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . Material and methods ........................ . . . . . . . . . 1.1 H-Glu(OBZL)-OBZL benzosulfonate and hydrochloride. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1.2 H-Glu(OBZL)-OBZL p-toluene sulfonate and hydrochloride . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2 Z-Trp . .. . . . . . . . . . . . . . . . ... .. . .. . .. .. .. . . . . . . . .. 3 BOC-Ser(BZL)-Glu(OBZL)-OBZL . . . . . . . . . . . . . . . . . 4 Ser(BZL)-Glu(OBZL)-OBZL trifiuoroacetate . . . . . . . . . 5 Z-Trp-Ser(BZL)-Glu(OBZL)-OBZL. . . . . . . . . . . . . . . . 6 Ser-Glu. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 7 Trp-Ser-Glu. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . Results............................................. Discussion.. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . (a) Chemical part. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . (b) Biological part . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . References .......................................... Abstract. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
8 9 11 12 12 13 13 13 14 14 15 15 16 19 19 21 25 27
5
Preface
The present work was done, as concerns the chemical-synthetical part, at the Institute for Organic Chemistry of the University Basel under the supervision of Prof. Dr. M. Brenner, as concerns the biological part, at the Laboratory for Sleep Research of the Physiological Institute of the University under the supervision of Prof. Dr. M. Monnier. I should like to express my gratitude to PD Dr. G.A. Schoenenberger who suggested the subject of this thesis and provided precious advice for its realization. I am very much indebted to Prof. Dr. M. Brenner who directed the synthetic work of the tripeptide. I am also grate
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