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Published in:
Structure and Conformation of Carbohydrates Read chapter Read first chapter

2008 | OriginalPaper | Chapter

31. Selective α-Sialylation

Authors : Hiromune Ando, Makoto Kiso

Published in: Glycoscience

Publisher: Springer Berlin Heidelberg

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Abstract

Chemical construction of a α‑glycoside of sialic acid is a demanding subject due to the structural disadvantages of sialic acid: the carboxylate group at C1, the deoxy moiety adjacent to the anomeric center, and the glycerol branch from C6. This chapter will provide an overview of sialic acid chemistry and show how the disadvantages can be surmounted and it will also cover the cutting‐edge methodology used for α‑selective sialylation. In this chapter, the forty‐year history of sialylation is compartmentalized into three periods. The first period represents the use of 2‑halogeno sialy donors. The second period covers the use of C3‑appended sialyl donors and a set of thioglycoside donors, including also the acetonitrile effect, and third is the period of C5‑modified sialy donors. While following this division, the chemistry of α‑selective sialylation is discussed, and some examples of the stereoselective syntheses of sialyl oligosaccharides are described. Furthermore, the synthesis of the homopolymer of sialic acid and artificial sialyl S- and C‑glycosides is discussed.

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previous chapter Stereoselective Synthesis of β-manno-Glycosides
next chapter Enzymatic Glycosylation by Transferases
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Metadata
Title
Selective α-Sialylation
Authors
Hiromune Ando
Makoto Kiso
Copyright Year
2008
Publisher
Springer Berlin Heidelberg
Book
Glycoscience

Print ISBN: 978-3-540-36154-1

Electronic ISBN: 978-3-540-30429-6

Copyright Year: 2008

DOI
https://doi.org/10.1007/978-3-540-30429-6_31