Fortschritte der Chemie organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products
- PDF / 11,912,518 Bytes
- 303 Pages / 439.37 x 666.142 pts Page_size
- 60 Downloads / 196 Views
Progress in the Chemistl7 of Organic Natural Products
40 Founded ~ L Zeehmeister Edited ~ W. Hen, H. Grisellaeh, G. W. Ki~
Authors: P. A. Cad.", R. G. Cooke, J. M. Edwards, W. Heller, C.W. Jefford, E. Lederer, P. Lefraneier, Sukh Dev, Ch. Tamm
Springer-Verlag Men New Yor"
1981
Dr. W. HERZ, Professor of Chemistry, Department of Chemistry, The Florida State University, Tallahassee, Florida, U. S. A. Prof. Dr. H. GRISEBACH, Biologisches Institut II, Lehrstuhl fur Biochemie der Pflanzen, Albert-Ludwigs-Universitiit, Freiburg i. Br., Federal Republic of Germany G. W.
KIRBY,
Sc. D., Regius Professor of Chemistry, Chemistry Department, The University, Glasgow, Scotland
With 21 Figures
This work is subject to copyright All rights are reserved, whether the whole or part of the material is concerned, specifically those of translation, reprinting, re-use of illustrations, hroadcasting, reproduction by photocopying machine or similar means, and storage in data banks
© 1981 hy Springer-Verlag/Wien Softcover reprint of the hardcover 1st edition 1981 Library of Congress Catalog Card Number AC 39-1015
ISSN 0071-7886 ISBN-13: 978-3-7091-8613-8 DOl: 10.1007/978-3-7091-8611-4
e-ISBN-13: 978-3-7091-8611-4
Contents List of Contributors . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ..
IX
Chemistry of Synthetic Immunomodulant Muramyl Peptides. By P. LEFRANCIER and E. LEDERER ........................................................... .
I. From Freund's Adjuvant to MDP . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
2
II. Synthesis of N-acetyl-muramyl-L-alanyl-D-isoglutamine (MDP) ..... . . . . . . . . 1. Protected Dipeptide Derivatives . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2. Protected N-acetyl-muramyl Derivatives. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
4 4 5
3. Coupling of Protected Muramic Acid and Dipeptide Derivatives ......... 4. Deprotecting Procedures ........................................ ... 5. Synthesis of Labelled MDP . . .. . . . . . . . . . . . . . . . . .. . . . . . . . . . . . . . . . . . . . .
7 7 9
III. Synthesis of Other N-acetyl-muramyl-dipeptides, Analogues and Derivatives of MDP ................................................................
9
1. Modifications of the Peptide Moiety. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2. Modifications of the Carbohydrate Moiety .... . . . . . . . . . . . . . . . . . . . . . . . .
9 13
IV. Synthesis of N-acetyl-muramyl-tri-, tetra-, and -pentapeptides, and of Some Analogs Bearing a Lipophilic Group at the C-terminal End. . . . . . . . . . . . . . . . 1. Substitution of the (X-amide Group of MDP by a Free or Amidated Amino Acid.............................................................. 2. Lengthening of the Peptide Chain at the Carboxyl Function of MDP ... 3. Lipophilic Derivatives of N-acetyl-muramyl-L-alanyl-D-isoglutaminyl-Lalanine....... ......... .....................
Data Loading...
