Synthesis and Biological Applications of Glycoconjugates


by

Olivier Renaudet, Nicolas Spinelli

DOI: 10.2174/97816080527761110101
eISBN: 978-1-60805-277-6, 2011
ISBN: 978-1-60805-537-1

  
  


Indexed in: Chemical Abstracts, Scopus

The interactions between carbohydrates and proteins have been extensively explored in a wide range of physiological and pathological p...[view complete introduction]
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Table of Contents

Foreword , Pp. i

Ben Davis

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Preface , Pp. ii

Olivier Renaudet and Nicolas Spinelli

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List of Contributors , Pp. iii-iv (2)

Olivier Renaudet and Nicolas Spinelli

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Bacterial Lectins and Adhesins: Structures, Ligands and Functions , Pp. 3-11 (9)

Anne Imberty

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Ligands for FimH , Pp. 12-35 (24)

Thisbe K. Lindhorst

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Multivalent Glycocalixarenes , Pp. 36-63 (28)

Francesco Sansone, Gabriele Rispoli, Alessandro Casnati and Rocco Ungaro

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Solving Promiscuous Protein Carbohydrate Recognition Domains with Multivalent Glycofullerenes , Pp. 64-77 (14)

Yoann M. Chabre and Rene Roy

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Monovalent and Multivalent Inhibitors of Bacterial Toxins , Pp. 78-91 (14)

Edward D. Hayes and W. Bruce Turnbull

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Monovalent and Multivalent Glycoconjugates as High Affinity Ligands for Galectins , Pp. 92-115 (24)

Sebastien Vidal

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Combinatorial Libraries of Dendritic Glycoclusters , Pp. 116-128 (13)

Jean-Louis Reymond and Tamis Darbre

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Cyclopeptide-Based Glycoclusters , Pp. 129-144 (16)

Olivier Renaudet, Didier Boturyn and Pascal Dumy

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Oligonucleotide-Carbohydrate Conjugates , Pp. 145-163 (19)

Nicolas Spinelli and Eric Defrancq

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Glycoliposomes and Metallic Glyconanoparticles in Glycoscience , Pp. 164-202 (39)

Marco Marradi, Fabrizio Chiodo, Isabel Garcia and Soledad Penades

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Chemoselective Glycosylation Techniques for the Synthesis of Bioactive Neoglycoconjugates, Glyconanoparticles and Glycoarrays , Pp. 203-225 (23)

Francesco Peri

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Glycosidases in Synthesis of Glycomimetics and Unnatural Carbohydrates , Pp. 226-239 (14)

Vladimir Kren

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Diels-Alder Based Synthesis of Glycomimetics , Pp. 240-254 (15)

Cristina Nativi, Elisa Dragoni, Barbara Richichi and Stefano Roelens

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Analytical Tools for Protein-Carbohydrate Interaction Studies , Pp. 255-266 (12)

Cedric Goyer and Pierre Labbe

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Index , Pp. 267-276 (10)

Olivier Renaudet and Nicolas Spinelli

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Foreword

Attachment of carbohydrates in all its forms is a strategy exploited by both nature and those that study nature. Since the first reviews over 70 years ago the importance of this critically modulating and even defining role has long been recognized by who those study them. The very presence of carbohydrate units in naturally occurring structures and their mimetics has a dramatic effect on their physical, chemical and biological properties. Glycoscience is by necessity broad in the range of techniques that it encompasses and I have argued for over ten years that in this context the sometimes-applied and somewhat artificial distinction between "chemical" and "biological" techniques is unhelpful.

This has never been the case – we are reaching a stage in the field where remarkable techniques are able to make even some very large naturally relevant glycoconjugates. Moreover, through these methods and the design of some remarkable molecular experimental approaches, we are using these glycoconjugates to unpick the many dazzling and exciting roles that carbohydrates play in Biology and Medicine.

This book highlights this superbly. Drs Renaudet and Spinelli have assembled an outstanding collection of excellent and relevant reviews written by leading protagonists in the field that complement each other superbly. Together they provide a wonderful account of the current state-of-the-art.

Vital current targets illustrate what might and will be achieved through both analysis and understanding. Many pathogens exploit the display of carbohydrates on host cell surfaces to gain entry. Imberty and Lindhorst, in their chapters, have described some of the most current and relevant examples. Integral to the approaches they have analyzed is a fundamental molecular analysis of the binding of sugars to proteins. This has been excellently amplified by the chapter of Goyer and Labbé, which describes some of the most pertinent quantitative techniques in current use, and by the several chapters that show how this understanding can be directly related to application. These include the design of inhibitors of bacterial toxins, superbly analyzed by Turnbull and Hayes, and ligands for the important mammalian galectins, the study of which Vidal summarizes superbly.

Use of well-defined scaffolds is an essential element if this study and exploitation is to be precise. Various platforms have been analyzed here: fullerenes (Roy and Chabre), dendritic clusters (Reymond and Darbre), calixarenes (Casnati et al.), cyclic peptides (Renaudet et al.) and even nucleic acids (Spinelli and Defrancq). All highlight longer-term applications, especially in applications that may allow probing of interactions in whole organisms, and these are especially elegantly drawn out in the chapter by Penadés et al. that consider particles of many relevant types.

Typically syntheses of glycoconjugates adopt one of two strategies. The first strategy is the formation of the glycan-aglycone link early, to form, for example, glycosylated building blocks such as glycosides, glycopeptides or glycosylated dendritic wedges, that may then be assembled. While, of course, chemical methods can create glycosidic bonds in a number of ways, the use of biocatalysts can bring with it advantages of selectivity and efficiency; Křen’s chapter highlights this utility well. The second strategy is formation of the link later on in the synthesis once the scaffold for its presentation is in place. Given the instability that may be associated with the link and the requirements for protection that need to be considered in the use of glycosylated building blocks, it is clear why the latter has often seemed the most attractive option. Peri has deftly summarized a broad range of methods for this late stage approach as applied to many useful platform types. Nativi et al. have delineated an emerging area that could allow access to glycomimetics based on the use of glycals in cycloadditions.

Together, these chapters give a powerful insight into the elucidation of the mechanism by which sugar-binding takes place, the tools used to probe into it and its consequences. This science has driven and continues to drive the synthesis and technology of glycoconjugates. These are the new tools of the glycobiology trade and I believe only the very start of an era of emerging diagnostics and therapeutics.

Prof. Ben Davis
University of Oxford
UK


Preface

The interactions between carbohydrates and proteins are involved in major physiological and pathological events. With the recent emergence of glycomics, an increasing number of sophisticated glycosylated structures capable of mimicking the multivalent display of the cell surface glycocalix has been reported. Besides giving precious guidelines on the binding parameters that govern these complex biological processes, synthetic glycoconjugates often revealed considerable interests for diagnostic and therapeutic applications.

Our main motivation to edit Synthesis and biological applications of glycoconjugates was to update the major advancements in this field through several chapters written by renowned experts who have largely contributed to the recent progresses. Illustrated with more than 200 colour figures and including literature citations mostly from the last decade, this book covers the recent chemical methods of glycoconjugates and clearly highlights their diverse biological properties. Chapter 1 analyzes the structure of lectins from pathogenic bacteria and gives structure/function relationships that are crucial for the development of high affinity ligands. In Chapter 2 carbohydrate binding by FimH is discussed and modern means for its investigation including photoaffinity labelling are described. Very recent crystallographic work is also documented that provides an explanation for shear-enhanced binding of type 1 fimbriated E. coli. Chapter 3 summarizes the most convenient methodologies for the synthesis of glycocalixarenes and describes their impressive aggregation properties and many other biological applications. Chapter 4 illustrates examples of bacterial and human lectins together with bacterial toxins having varied number of carbohydrate recognition domains that necessitated multivalent glycoconjugates. It focuses on glycofullerenes that have been used to describe novel synthetic strategies and possible fit with concomitant lectins. In Chapter 5 the structures of the cholera and E. coli heat-labile toxins are described. The authors also summarize the main strategies that have led to the development of monovalent and multivalent inhibitors of these toxins and they discuss the importance of chelation and protein aggregation as mechanisms of multivalent inhibition. Chapter 6 focuses on the design of high affinity ligands for galectins and provides a better knowledge of the implications of these proteins in biology. Chapter 7 demonstrates that combinatorial chemistry led to the discovery of glycopeptide dendrimers as strong ligands for lectins or drug-delivery systems and shows how the amino acid composition of the dendrimer branches can influence their biological activity. Chapter 8 focuses on the synthesis of a recent class of glycoclusters displayed on a cyclopeptide platform and highlights their promising biological properties, in particular as inhibitors or synthetic vaccines. Chapter 9 shows that the cellular delivery and bioavailability of oligonucleotides can be improved by their conjugation with carbohydrates and also describes the construction of carbohydrate biochips or glycoclusters using these conjugates. Chapter 10 focuses on glycoliposomes and covalently-functionalized glyconanoparticles which make use of the “glyco-code” to address specifically pathogens or pathological-related problems. Chapter 11 focuses on the synthesis of glycoproteins, glycopeptides, glycosylated natural compounds, carbohydrate-functionalized surfaces and nanoparticles using chemoselective glycosylation. In Chapter 12 the recent developments in glycosidase-catalyzed synthesis of unnatural semi-synthetic carbohydrate structures are presented. Chapter 13 reports the synthesis of glycomimetics and glycopeptidomimetics using hetero-Diels Alder reactions between α,α'-dioxothiones and glycals. Chapter 14 aims at describing the usual methods to characterize protein-carbohydrate interactions, namely inhibition of hemagglutination assay, enzyme-linked lectin assays, isothermal titration calorimetry, surface plasmon resonance and the more recent atomic force microscopy.

We believe that this Ebook will be of particular interest to a large community of graduate students, researchers and professionals in academia or industry involved in Glycoscience. We would like to express our sincerest gratitude to all of the authors who accepted to contribute to this exciting project, by sharing their strong experiences and knowledge in this research area.

Olivier Renaudet
Nicolas Spinelli
University of Grenoble
France


List of Contributors

Editor(s):
Olivier Renaudet
University of Grenoble
France


Nicolas Spinelli
University of Grenoble
France




Contributor(s):
Didier Boturyn
Département de Chimie Moléculaire
UMR-CNRS 5250 & ICMG FR 2607
Université Joseph Fourier
Grenoble Cedex 9, 38041
France


Alessandro Casnati
Dip.to di Chimica Organica e Industriale
Università degli Studi
Parco Area delle Scienze 17/A
Parma, 43124
Italy


Yoann M. Chabre
Pharmaqam – Groupe de Recherche en Chimie Thérapeutique
Université du Québec à Montréal
P.O. Box 8888, Succ. Centre-ville
Montréal
Québec
Canada H3C 3P8


Fabrizio Chiodo
Laboratory of GlycoNanotechnology
Biofunctional Nanomaterials Unit
CIC biomaGUNE, Parque Tecnológico de San Sebastián
Pº de Miramón 182
San Sebastián, 20009
Spain


Tamis Darbre
Department of Chemistry and Biochemistry
University of Berne
Freiestrasse 3, CH-3012
Berne
Switzerland


Eric Defrancq
Département de Chimie Moléculaire
UMR-CNRS 5250 & ICMG FR 2607
Université Joseph Fourier
Grenoble Cedex 9, 38041
France


Elisa Dragoni
ProtEra, Polo Scientifico Universita' di Firenze
viale delle Idee
Sesto F.no (FI), 22 I-50019
Italy


Pascal Dumy
Département de Chimie Moléculaire
UMR-CNRS 5250 & ICMG FR 2607
Université Joseph Fourier
Grenoble Cedex 9, 38041
France


Isabel García
Laboratory of GlycoNanotechnology
Biofunctional Nanomaterials Unit
Biomaterials and Nanomedicine (CIBER-BBN)
CIC biomaGUNE and Biomedical Research Networking Center in Bioengineering
Parque Tecnológico de San Sebastián
Pº de Miramón 182
San Sebastián, 20009
Spain


Cédric Goyer
Département de Chimie Moléculaire
UMR-CNRS 5250 & ICMG FR 2607
Université Joseph Fourier
Grenoble Cedex 9, 38041
France


Edward D. Hayes
School of Chemistry and Astbury Centre for Structural Molecular Biology
University of Leeds
Leeds LS2 9JT
UK


Anne Imberty
CERMAV-CNRS (affiliated to Université Joseph Fourier and ICMG)
BP 53
Grenoble cedex 9, 38041
France


Vladimír Křen
Institute of Microbiology
Centre of Biocatalysis and Biotransformation
Academy of Sciences of the Czech Republic
Vídeňská 1083
Prague 4 , CZ 142 20
Czech Republic


Pierre Labbé
Département de Chimie Moléculaire
UMR-CNRS 5250 & ICMG FR 2607
Université Joseph Fourier
Grenoble Cedex 9, 38041
France


Thisbe K. Lindhorst
Otto Diels Institute of Organic Chemistry
Christiana Albertina University of Kiel
Kiel, D-24098
Germany


Marco Marradi
Laboratory of GlycoNanotechnology
Biofunctional Nanomaterials Unit
Biomaterials and Nanomedicine (CIBER-BBN)
Parque Tecnológico de San Sebastián
Pº de Miramón 182
CIC biomaGUNE and Biomedical Research Networking Center in Bioengineering
San Sebastián, 20009
Spain


Cristina Nativi
Dipartimento di Chimica
Universita' di Firenze
via della Lastruccia, 3
Sesto F.no (FI), 13 I-50019
Italy


Soledad Penadés
Laboratory of GlycoNanotechnology
Biofunctional Nanomaterials Unit
Biomaterials and Nanomedicine (CIBER-BBN)
Parque Tecnológico de San Sebastián
Pº de Miramón 182
CIC biomaGUNE and Biomedical Research Networking Center in Bioengineering
San Sebastián, 20009
Spain


Francesco Peri
Department of Biotechnology and Biosciences
University of Milano-Bicocca
Piazza della Scienza, 2
Milano, 20126
Italy


Olivier Renaudet
Département de Chimie Moléculaire
UMR-CNRS 5250 & ICMG FR 2607
Université Joseph Fourier
Grenoble Cedex 9, 38041
France


Jean-Louis Reymond
Department of Chemistry and Biochemistry
University of Berne
Freiestrasse 3, CH-3012
Berne
Switzerland


Barbara Richichi
Dipartimento di Chimica
Universita’ di Firenze
via della Lastruccia, 3
Sesto F.no (FI), 13 I-50019
Italy


Stefano Roelens
Istituto Metodologie Chimiche (IMC)
CNR, Dipartimento di Chimica
Universita' di Firenze
via della Lastruccia, 3
Sesto F.no (FI), 13 I-50019
Italy


René Roy
Pharmaqam – Groupe de Recherche en Chimie Thérapeutique
Université du Québec à Montréal
P.O. Box 8888, Succ. Centre-ville
Montréal
Québec
Canada H3C 3P8


Francesco Sansone
Dip.to di Chimica Organica e Industriale
Università degli Studi
Parco Area delle Scienze 17/A
Parma, 43124
Italy


W. Bruce Turnbull
School of Chemistry and Astbury Centre for Structural Molecular Biology
University of Leeds

Leeds LS2 9JT
UK


Nicolas Spinelli
Département de Chimie Moléculaire
UMR-CNRS 5250 & ICMG FR 2607
Université Joseph Fourier
Grenoble Cedex 9, 38041
France


Rocco Ungaro
Dip.to di Chimica Organica e Industriale
Università degli Studi
Parco Area delle Scienze 17/A
Parma, 43124
Italy


Sébastien Vidal
Institut de Chimie et Biochimie Moléculaires et Supramoléculaires
Laboratoire de Chimie Organique 2
UMR 5246, Université Lyon 1 and CNRS
Villeurbanne, F 69622
France




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