Chemical Synthesis of Gangliosides

Akihiro Imamura; Hiromune Ando; Hideharu Ishida

doi:10.1007/978-1-0716-2910-9_8

Chemical Synthesis of Gangliosides

Methods Mol Biol. 2023:2613:89-100. doi: 10.1007/978-1-0716-2910-9_8.

Authors

Akihiro Imamura¹, Hiromune Ando², Hideharu Ishida³

Affiliations

¹ Department of Applied Bioorganic Chemistry, Gifu University, Gifu, Japan. aimamura@gifu-u.ac.jp.
² Institute for Glyco-core Research (iGCORE), Gifu University, Gifu, Japan.
³ Department of Applied Bioorganic Chemistry, Gifu University, Gifu, Japan.

PMID: 36587073
DOI: 10.1007/978-1-0716-2910-9_8

Abstract

Synthetic methodologies for gangliosides have evolved over the past three decades. The strategies for constructing ganglioside skeletons can generally be classified as late-stage ceramide coupling, the glucosyl ceramide cassette strategy, or late-stage sialylation. Using these synthetic strategies, numerous natural gangliosides and their structural analogs, including functional probes, have been synthesized. This chapter describes the synthetic strategies for gangliosides and provides examples of the total synthesis of several gangliosides using each strategy.

Keywords: Ganglioside; Glycolipid; Glycosylation; Sialylation; Total synthesis.

MeSH terms

Ceramides / chemistry
Gangliosides* / chemistry
Glucosylceramides*

Substances

Gangliosides
Glucosylceramides
Ceramides