Anionic oligosaccharides: synthesis and applications - Carbohydrate Chemistry: Chemical and Biological Approaches - page 195

Anionic oligosaccharides: synthesis and
applications
Eric Grand, Jos ´ Kovensky,* Gwladys Pourceau,
Sylvestre Toumieux and Anne Wadouachi
DOI: 10.1039/9781849739986-00195
Anionic oligosaccharides are largely involved in physiological and pathological processes.
The controlled production of these biomolecules is crucial for the comprehension of the
biological mechanisms in which they are involved, but it is still challenging and trouble-
some. This chapter reviews the recent protocols (since 2008) described in literature for
the obtaining of anionic oligosaccharides by de novo synthesis and by polysaccharide
depolymerisation. An overview on recent applications is also presented.
1 Introduction
Anionic oligosaccharides display an important role in biological pro-
cesses. They bind proteins through interactions mediated by highly
specific sequences or by electrostatic interactions between negatively
charged groups and cationic sites of proteins. Anionic polysaccharides
and oligosaccharides occur naturally in the form of polysialic acids (PSA),
glycosaminoglycans (GAG), such as heparin and heparan sulfate (HS),
dermatan sulphate (DS), chondroitin sulphate (CS), hyaluronic acid (HA)
and the like. Negatively charged oligosaccharides are involved in bio-
logical events as protein localisation at cell surfaces, control of prote-
olysis, modulation of angiogenesis and metastasis of tumours,
oligomerisation of cell growth factors, prevention of coagulation, and
virus infection. 1 The anionic character of most known N-linked oligo-
saccharides is due to the presence of sialic acids, however negative charge
in such molecules can also be due to sulphate esters or uronic acids.
This paper reviews recent progresses (2008-2013) concerning the ob-
tention and the applications of anionic oligosaccharides. First, chemical
synthesis of anionic oligosaccharides will be treated in part 2. For better
comprehension, chemical synthesis of oligosaccharides containing
carboxylic groups, sulphate groups, or both are discussed in three dis-
tinct sections (2.1; 2.2 and 2.3 respectively). Then production of anionic
oligosaccharides by depolymerisation of natural polysaccharides will be
dealt with in part 3. Finally, part 4 will cover applications of these com-
pounds. This chapter aims to exhaustively overview the recent research
on the anionic oligosaccharides synthesis and applications. Given the
wideness of this field, we invite readers to refer to citations for more
details. Sialic acid-containing oligosaccharides have been excluded of
this review as the specific strategies for their synthesis have extensively