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Файл:Ординатура / Хирургия / Библиотека им академика М.И. Перельмана / Книга_5478_Библиотеки_им_академика_М_И_Перельмана
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Biomedical Applications of Peptide-, Glyco-
and Glycopeptide Dendrimers,
and Analogous Dendrimeric Structures
•
Jaroslav
ˇ
Sebest
´
ık
Milan Reini
ˇ
s
Jan Jeˇzek
Biomedical Applications
of Peptide-, Glyco-
and Glycopeptide
Dendrimers, and Analogous
Dendrimeric Structures
123
Jaroslav
ˇ
Sebest
´
ık
Department of Molecular Spectroscopy
Institute of Organic Chemistry
and Biochemistry, AS CR, vvi
Prague
Czech Republic
Milan Reini
ˇ
s
Institute of Molecular Genetics AS CR, vvi
Prague
Czech Republic
Jan Jeˇzek
Laboratory of Glycoconjugates
Institute of Organic Chemistry
and Biochemistry, AS CR, vvi
Prague
Czech Republic
ISBN 978-3-7091-1205-2 ISBN 978-3-7091-1206-9 (eBook)
DOI 10.1007/978-3-7091-1206-9
Springer Wien Heidelberg New York Dordrecht London
Library of Congress Control Number: 2012954529
This work is subject to copyright. All rights are reserved by the Publisher, whether the whole or part of
the material is concerned, specifically the rights of translation, reprinting, reuse of illustrations, recitation,
broadcasting, reproduction on microfilms or in any other physical way, and transmission or information
storage and retrieval, electronic adaptation, computer software, or by similar or dissimilar methodology
now known or hereafter developed. Exempted from this legal reservation are brief excerpts in connection
with reviews or scholarly analysis or material supplied specifically for the purpose of being entered
and executed on a computer system, for exclusive use by the purchaser of the work. Duplication of
this publication or parts thereof is permitted only under the provisions of the Copyright Law of the
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Permissions for use may be obtained through RightsLink at the Copyright Clearance Center. Violations
are liable to prosecution under the respective Copyright Law.
The use ofgeneral descriptive names, registered names, trademarks, service marks, etc. in this publication
does not imply, even in the absence of a specific statement, that such names are exempt from the relevant
protective laws and regulations and therefore free for general use.
While the advice and information in this book are believed to be true and accurate at the date of
publication, neither the authors nor the editors nor the publisher can accept any legal responsibility for
any errors or omissions that may be made. The publisher makes no warranty, express or implied, with
respect to the material contained herein.
Printed on acid-free paper
Springer is part of Springer Science+Business Media (www.springer.com)
© Springer-Verlag Wien 2012
Preface
The purpose of this book is to show the progress in the field of synthesis and
biomedical applications of peptide-,glyco-, glycopeptidedendrimers and analogous
dendrimeric structures. This booklet is intended to graduate students, advanced
undergraduates, and scientists working in the area of organic chemistry, biochem-
istry, nanoscience, biology, medicinal chemistry, and biomedical applications.
Dendrimers and dendritic macromolecules were pioneered in the 1980s. They
represent a dynamically expanding field spreading from physics, chemistry, and
biology to a broad area of biomedical applications. Dendrimers penetrate to till now
isolated areas of science and create an interconnected, logical, mutually influencing
scientific network, the dendrimer science (dendrimerology).
The reader will be introduced to a very diverse group of methodologiesspanning
from chemistry, physics, bioengineering,materials science, biomedical applications,
and beyond.
Many problems, when seen from the “dendrimeric point of view,” could be
overcome if people would use the broad scale of dendrimeric properties and
applications. The “cluster effect” (“multivalency”) plays a key role and serves as
a connecting glue between different structures.
During the last years the number of papers about dendrimers and their appli-
cations reached about 1,600 annually, i.e., twice so much in comparison with 2001.
That means thatthe informationwave isat the top. Due to space limitation, this book
could not cover all papers and reviews and we apologize to researchers involved in
the field whose works have not been covered herein. More references can be found
in our earlier reviews (2005; 2008a,b,c; 2011).
Prague, Czech Republic Jan Jeˇzek
September 2012 Milan Reini
ˇ
s
Jaroslav
ˇ
Sebest
´
ık
v
•
Acknowledgements
This work was supported by grant of the Czech Science Foundation (GA CR) Nos.
203/07/1517 and P208/11/0105; by grants from the Ministry of Education, Youth
and Sports (MSMT) No. LH11033; and Research Projects Z40550506 and RVO
61388963. Our thanks are due to Dr. Lenka
ˇ
Sebest
´
ıkov
´
a, Dr. Petr Niederhafner, and
Dr. Anna Fi
ˇ
serov
´
a for a critical reading of the manuscript.
vii
•
Contents
1 Introduction ................................................................. 1
References.................................................................... 4
Part I Chemistry and Structure of Dendrimers
2 Definition of Terms and Nomenclature................................... 9
2.1 Dendriplexes and Dendrisomes...................................... 11
2.2 Dendrigraft ........................................................... 12
2.3 Glycotope............................................................. 12
2.4 Glycocluster .......................................................... 13
2.5 Glycocluster–Cluster ................................................. 13
2.6 Cluster Effect and Multivalency ..................................... 13
2.7 Macromolecular Effect............................................... 14
2.8 Sugar Ball............................................................. 15
2.9 “Smart” Glycodendrimers ........................................... 15
References.................................................................... 15
3 Sugar Code (Glycocode) ................................................... 23
References.................................................................... 25
4 Classes of Peptide-, Glyco-, and Glycopeptide Dendrimers............ 29
References.................................................................... 34
5 The Dendritic State and Dendritic Effects ............................... 45
References.................................................................... 51
6 Synthesis of Dendrimers: Convergent and Divergent Approaches.... 55
6.1 Divergent ............................................................. 57
6.2 Convergent............................................................ 58
6.3 Lego Chemistry ...................................................... 58
6.4 Ligations .............................................................. 60
6.5 Click Chemistry ...................................................... 64
References.................................................................... 70
ix
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