Carbohydrate chemistry: chemical and biological approaches

276 Pages·2018·10.118 MB·English

by  Amelia Pilar Rauter, Thisbe Lindhorst, Yves Queneau, Laurence Mulard, Richard Daniellou, Yanlong Gu, Vincent Ferrieres, Thierry Benvegnu, Alberto Marra, Paula Videira, Angelina Palmer

Carbohydrate Chemistry
Chemical and Biological Approaches Volume 43
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A Specialist Periodical Report
Carbohydrate Chemistry
Chemical and Biological Approaches
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10 Amelia Pilar Rauter, Universidade de Lisboa, Portugal
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1 Thisbe K. Lindhorst, Christiana Albertina University of Kiel,
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org | Yves Queneau, Universite´ de Lyon, France
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p://p Ana Lu´ısa Carvalho, Universidade Nova De Lisboa, Portugal
htt Thierry Benvegnu, Ecole Nationale Supe´rieure de Chimie de Rennes and
on Universite´ Bretagne Loire, France
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01 Richard Daniellou, University of Orle´ans, France
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er Vincent Ferrie`res, Ecole Nationale Supe´rieure de Chimie de Rennes,
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ec Ravneet Kaur Grewal, Sri Guru Granth Sahib World University, India
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1 Yanlong Gu, Huazhong University of Science and Technology, China
. on 1 Pierre Lafite, University of Orle´ans, France
ed Laurent Legentil, Ecole Nationale Supe´rieure de Chimie de Rennes,
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blis France
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P Lo¨ıc Lemie`gre, Ecole Nationale Supe´rieure de Chimie de Rennes and
Universite´ de Bretagne Loire, France
Filipa Marcelo, Universidade Nova De Lisboa, Portugal
Alberto Marra, Institut des Biomole´cules Max Mousseron, France
Laurence A. Mulard, Institut Pasteur, France
Angelina S. Palma, Universidade Nova De Lisboa, Portugal
Freddy Pessel, Ecole Nationale Supe´rieure de Chimie de Rennes and
Universite´ Bretagne Loire, France
Ce´dric Peyrot, University of Orle´ans, Ecole Nationale Supe´rieure de
Chimie de Rennes and Universite´ de Bretagne Loire, France
Benedita A. Pinheiro, Universidade Nova De Lisboa, Portugal
Palanisamy Ravichandiran, Huazhong University of Science and
Technology, China
View Online
Louise Renault, Ecole Nationale Supe´rieure de Chimie de Rennes and
Universite´ Bretagne Loire, France
Diana O. Ribeiro, Universidade Nova De Lisboa, Portugal
Paula Alexandra Videira, Universidade Nova De Lisboa, Portugal
Renaud Zelli, Universite´ Grenoble Alpes, France
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ISBN: 978-1-78801-003-0
PDF ISBN: 978-1-78801-064-1
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6 DOI: 10.1039/9781788010641
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39/ r The Royal Society of Chemistry 2018
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or Apart from fair dealing for the purposes of research for non-commercial
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ub Copyright, Designs and Patents Act 1988 and the Copyright and Related
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p:// Rights Regulations 2003, this publication may not be reproduced, stored or
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Preface
DOI: 10.1039/9781788010641-FP007
This volume, 43 of the series Carbohydrate Chemistry, illustrates the
diversity of the field of the glycosciences, encompassing chemical and
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00 biological approaches towards a wide range of applications, from
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1-F potential novel therapeutic strategies to novel chemical products and
64 processes for everyday life.
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01 In Chapter 1, Alberto Marra and Renaud Zelli provide a rich and
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78 complete overview of iminodisaccharides and iminooligosaccharides.
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78 They cover O-, S-, N-, and C-linked iminodisaccharides for which they
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9/ have reviewed the chemical and enzymatic synthetic strategies. These
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1 compounds are mostly studied for their glycosidases or glycosyl-
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oi:1 transferases inhibition properties. The authors finally provide a useful
g | d listingofalltypesofenzymeswhichhavebeenaddressedintheliterature
or related to iminooligosaccharides since 1985.
c.
s Laurence Mulard, in Chapter 2, addresses the tremendous structural
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htt patternofmicrobialpolysaccharides,inrelationtotheirpropertiestoact
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01 the host. The chapter is illustrated with structures that are part of pre-
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er clinical programs for vaccine development or components of marketed
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1 Chapter3,VincentFerrieresandLaurentLegentillookatbothenzymatic
. on 1 andchemicalstrategies.Theauthorsfirstdiscussthebenefitsoftheuse
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he ofglycosyltransferases,glycosylhydrolasesandglycosylphosphorylasesas
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With respect to the chemical approaches, the authors address the key
issues, namely the reactivity order of various hydroxy groups, the
importance of hydrogen bonding, armed/disarmed character of donors
or their partial protection, covering the essentials of this fundamental
reaction in carbohydrate chemistry.
Chapter4givesacompleteoverviewofglycosyltransferasesinhibitors,
a topic with considerable importance to provide novel strategies for
fighting abnormal glycosylation diseases. In their review, Paula Videira,
Filipa Marcelo and Ravneet Grewal discuss the conventional specific
inhibitors, notably those designed as mimics of donor, acceptor or
transition state. Recently proposed alternative chemotype designs, not
substrate like, are also discussed, illustrated with promising examples
that could lead to therapeutic developments.
Carbohydrate microarrays are high-throughput and sensitive tools
which can uncover complex carbohydrate structures and protein-
carbohydrate interactions. In Chapter 5, Angelina Palma, together with
Diana Ribeiro, Benedita Pinheiro and Ana Luisa Carvalho, beautifully
Carbohydr.Chem.,2018,43,vii–viii | vii
(cid:2)c TheRoyalSocietyofChemistry2018
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illustratethepowerofthesetoolsforthedeterminationofplantcellwall
structure and degradation pathways. The chapter reviews nicely the
literature on cell wall structure and degradation, offers a complete
overview on glycan microarrays and on the existing platforms and
specific chemical modifications required for the grafting of the carbo-
hydrates on the surfaces. The authors illustrate the efficiency of
the method with numerous examples, including efficient coupling
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6 In the search for cleaner chemical processes, the solvent is a critical
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7 that carbohydrates can be useful components of novel media for
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7 chemical reactions. They review particularly the properties and uses of
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39/ combinations of carbohydrates and organic or inorganic salts leading
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0.1 to low-melting mixtures which can then be used as the medium for
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oi: various organic reactions showing specific chemical activation abilities.
g | d Following the same philosophy which is to develop innovative eco-
or friendlychemicalsandprocessesfromcarbohydrates,ThierryBenvegnu,
c.
s.rs together with Louise Renault and Freddy Pessel, have reviewed in
ub Chapter 7 the field of carbohydrate-based surfactants. After an overview
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htt with uronic building blocks widely available from marine resources,
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01 addressothernovelbuildingblocks,suchasisosorbideandtrehalose,as
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er well as more elaborate systems which comprise a spacer between the
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. n 11 starch, xylan or alginates to various types of surfactants (alkylpolyglyco-
o sides or glycuronamides), or even directly from lignocellulose to lig-
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he nocellulosic hydrolysate fatty esters.
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Peyrot, Pierre Lafiteand Lo¨ıc Lemi`egre address the field of formationof
hydrogels using low molecular weight hydrogelators. They give an over-
view of the main types of monosaccharidic or disaccharidic hydro-
gelators, as well as bolaamphiphilic systems, discussing their syntheses
and some of their properties in relation to their structure.
Wehopethatreaderswillenjoythisvolume,andthatthewidescopeof
contributions, arising from synthetic, biological, structural, and applied
motivations, will stimulate transdisciplinary approaches towards novel
developments in the glycosciences.
Yves Queneau
Am´elia P. Rauter
Thisbe K. Lindhorst
viii | Carbohydr.Chem.,2018,43,vii–viii
CONTENTS
Cover
Frontcoverimagecourtesyof
AnaMartadeMatos.
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e Synthesis and biological properties of imino-disaccharides 1
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De and -oligosaccharides
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. n 1 Alberto Marra and Renaud Zelli
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he 1 Introduction 1
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3 Synthesis of imino-S-disaccharides 30
4 Synthesis of imino-N-oligosaccharides 31
5 Synthesis of imino-C-disaccharides 36
6 Glycosidase inhibition properties 60
7 Conclusions 66
References 66
Bacterial polysaccharides as major surface antigens: 71
interest in O-acetyl substitutions
Laurence A. Mulard
1 Introduction 71
2 PS O-acetylation: a widespread modification 72
3 On the role of CPS O-acetylation on the host-pathogen 76
crosstalk
Carbohydr.Chem.,2018,43,ix–xi | ix
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4 O-Acetylated CPSs from pathogenic bacteria: 81
implication in vaccine development
5 Conclusion 97
References 97
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0 Regioselective glycosylation: What’s new? 104
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88 2 Tackling the regioselectivity problem using biocatalysts 105
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c.or Glycosyltransferase inhibitors: a promising strategy to pave a 135
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htt 1 Glycan biosynthesis and glycan processing enzymes 135
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ber 3 Glycosyltransferase inhibitors 138
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. n 1 6 Glycomimetics 145
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References 154
Targeting protein-carbohydrate interactions in plant cell-wall 159
biodegradation: the power of carbohydrate microarrays
Diana O. Ribeiro, Benedita A. Pinheiro, Ana Lu´ısa Carvalho and
Angelina S. Palma
1 Structural diversity of plant cell-wall polysaccharides 159
2 Cellulolytic microorganisms express proteomes highly 162
efficient in plant cell-wall biodegradation
3 Carbohydrate microarrays 166
4 Conclusions 172
Acknowledgements 173
References 173
x | Carbohydr.Chem.,2018,43,ix–xi